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Details

Stereochemistry RACEMIC
Molecular Formula C10H12N2O5
Molecular Weight 240.2127
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DINOSEB

SMILES

CCC(C)C1=C(O)C(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O

InChI

InChIKey=OWZPCEFYPSAJFR-UHFFFAOYSA-N
InChI=1S/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C10H12N2O5
Molecular Weight 240.2127
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Dinoseb, a herbicide that was widely used for weed-control when producing crops like soybeans, vegetables, fruits, and nuts, or citrus. It also killed insects in grapes and was used to dry seed crops. It was banned because it possessed dangers of birth defects and sterility for farm workers. However, it’s still used in some countries, e.g., China, evidenced by the fact that it is found in rain- and drinking water.

Approval Year

PubMed

PubMed

TitleDatePubMed
Distribution, lipid-bilayer affinity and kinetics of the metabolic effects of dinoseb in the liver.
2017-08-15
In vitro neurotoxic hazard characterisation of dinitrophenolic herbicides.
2016-06-11
A high-throughput screen for teratogens using human pluripotent stem cells.
2014-01
Study on the treatment of 2-sec-butyl-4,6-dinitrophenol (DNBP) wastewater by ClO2 in the presence of aluminum oxide as catalyst.
2010-11-15
Protein biomarkers for in vitro testing of embryotoxicity.
2010-11-05
Effects of olive oil and its fractions on oxidative stress and the liver's fatty acid composition in 2,4-Dichlorophenoxyacetic acid-treated rats.
2010-10-29
Dietary olive oil effect on antioxidant status and fatty acid profile in the erythrocyte of 2,4-D- exposed rats.
2010-08-25
Prenatal developmental toxicity of gavage or feeding doses of 2-sec-butyl-4,6-dinitrophenol in rats.
2010-06
Oxidative degradation of dinitro butyl phenol (DNBP) utilizing hydrogen peroxide and solar light over a Al2O3-supported Fe(III)-5-sulfosalicylic acid (ssal) catalyst.
2010-04-15
Study of mass transfer in a dynamic hollow-fibre liquid phase microextraction system.
2010-01
(RS)-Dimethyl-ammonium 2-sec-butyl-4,6-dinitro-phenolate.
2009-10-03
Preparation and application of sustained release microcapsules of potassium ferrate(VI) for dinitro butyl phenol (DNBP) wastewater treatment.
2009-09-30
Remediating dinoseb-contaminated soil with zerovalent iron.
2009-09-15
Evaluation of a TiO2 photocatalysis treatment on nitrophenols and nitramines contaminated plant wastewaters by solid-phase extraction coupled with ESI HPLC-MS.
2009-07-15
MetaboMiner--semi-automated identification of metabolites from 2D NMR spectra of complex biofluids.
2008-11-28
Atmospheric pressure glow discharge desorption mass spectrometry for rapid screening of pesticides in food.
2008-09
Small-scale spatial variability of atrazine and dinoseb adsorption parameters in an alluvial soil.
2008-08-12
Review of testicular toxicity of dinitrophenolic compounds, 2-sec-butyl-4,6-dinitrophenol, 4,6-dinitro-o-cresol and 2,4-dinitrophenol.
2008-06-11
'Systems toxicology' approach identifies coordinated metabolic responses to copper in a terrestrial non-model invertebrate, the earthworm Lumbricus rubellus.
2008-06-03
Cost-effective experimental design to support modeling of concentration-response functions.
2008-06
Review of developmental toxicity of nitrophenolic herbicide dinoseb, 2-sec-butyl-4,6-dinitrophenol.
2008-04
Combined repeated dose and reproductive/developmental toxicity screening test of the nitrophenolic herbicide dinoseb, 2-sec-butyl-4,6-dinitrophenol, in rats.
2008-04
Effects of dinoseb on energy reserves in the soil arthropod Folsomia candida.
2007-10
On-line preconcentration strategies for analyzing pesticides in fruits and vegetables by micellar electrokinetic chromatography.
2007-06-15
Flow-injection determination of carbaryl and carbofuran based on KMnO(4)-Na(2)SO(3) chemiluminescence detection.
2007-05-02
Establishing the feasibility of coupled solid-phase extraction-solid-phase derivatization for acidic herbicides.
2007-03-02
Evidence for a novel quinone-binding site in the photosystem II (PS II) complex that regulates the redox potential of cytochrome b559.
2007-01-30
Potentiating effect of the ATP-sensitive potassium channel blocker glibenclamide on complex I inhibitor neurotoxicity in vitro and in vivo.
2006-09
[Expression of drgA gene encoding NAD(P)H:quinone-oxidoreductase in cells of the cyanobacterium Synechocystis sp. PCC 6803].
2006-08
Origin and health impacts of emissions of toxic by-products and fine particles from combustion and thermal treatment of hazardous wastes and materials.
2006-06
Metabolic effects of dinoseb, diazinon and esfenvalerate in eyed eggs and alevins of Chinook salmon (Oncorhynchus tshawytscha) determined by 1H NMR metabolomics.
2006-05-25
Toxic actions of dinoseb in medaka (Oryzias latipes) embryos as determined by in vivo 31P NMR, HPLC-UV and 1H NMR metabolomics.
2006-03-10
Spatial and geographical variations of urban, suburban and rural atmospheric concentrations of phenols and nitrophenols.
2006-03
Inhibition of PSII in atrazine-tolerant tobacco cells by barbatic acid, a lichen-derived depside.
2006-01
Adsorption kinetics and isotherms of pesticides onto activated carbon-cloth.
2005-09
Modeling the concentration-response function of the herbicide dinoseb on Daphnia magna (survival time, reproduction) and Pseudokirchneriella subcapitata (growth rate).
2005-09
Quantitative analysis of six pesticides in fruits by capillary electrophoresis-electrospray-mass spectrometry.
2005-04
Comparative studies on the spermatotoxic effects of dinoseb and its structurally related chemicals.
2004-06
Chemically induced supernumerary lumbar ribs in CD-1 mice: size distribution and dose response.
2004-02
Acceptor and donor-side interactions of phenolic inhibitors in Photosystem II.
2003-04-18
Differential pulse adsorptive stripping voltammetric determination of dinoseb and dinoterb at a modified electrode.
2003-04
Effects of dinoseb, 4,6-dinitro-o-cresol, and 2,4-dinitrophenol on rat Sertoli-germ cell co-cultures.
2003-03-19
Spectroscopic study of dinitrophenol herbicide sorption on smectite.
2002-12-01
Hsp70 instability and induction by a pesticide in Folsomia candida.
2002-07-10
Effects of dinoseb on the life cycle of Daphnia magna: modeling survival time and a proposal for an alternative to the no-observed-effect concentration.
2002-04
Spectroscopic study of nitroaromatic-smectite sorption mechanisms.
2001-12-15
Overview of studies on rat sperm motion analysis using a Hamilton-Thorne Sperm Analyzer--collaborative working study.
2001-12
Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS.
2001-09
The Quinone-binding sites of the Saccharomyces cerevisiae succinate-ubiquinone oxidoreductase.
2001-05-18
Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants.
1992
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 17:55:33 GMT 2025
Edited
by admin
on Mon Mar 31 17:55:33 GMT 2025
Record UNII
YD44ZEM22M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-202753
Preferred Name English
DINOSEB
HSDB   ISO   MI  
Common Name English
(RS)-2-SEC-BUTYL-4,6-DINITROPHENOL
Systematic Name English
DINOSEB [HSDB]
Common Name English
DINOSEB [ISO]
Common Name English
DINOSEB [MI]
Common Name English
2-(1-METHYLPROPYL)-4,6-DINITROPHENOL
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 37505
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
Code System Code Type Description
WIKIPEDIA
DINOSEB
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-861-7
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
FDA UNII
YD44ZEM22M
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
CHEBI
34719
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID3020207
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
SMS_ID
300000053276
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
ALANWOOD
dinoseb
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
HSDB
1445
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
CAS
88-85-7
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
PUBCHEM
6950
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
NSC
202753
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY
MERCK INDEX
m4585
Created by admin on Mon Mar 31 17:55:33 GMT 2025 , Edited by admin on Mon Mar 31 17:55:33 GMT 2025
PRIMARY Merck Index
Related Record Type Details
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