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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=CC(=CC(=C1O)[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
Endpoints of spermatotoxicity in the rat after short duration exposures to fourteen reproductive toxicants.
1992
Overview of studies on rat sperm motion analysis using a Hamilton-Thorne Sperm Analyzer--collaborative working study.
2001 Dec
Spectroscopic study of nitroaromatic-smectite sorption mechanisms.
2001 Dec 15
The Quinone-binding sites of the Saccharomyces cerevisiae succinate-ubiquinone oxidoreductase.
2001 May 18
Analysis of acidic pesticides using in situ derivatization with alkylchloroformate and solid-phase microextraction (SPME) for GC-MS.
2001 Sep
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 Apr
Spectroscopic study of dinitrophenol herbicide sorption on smectite.
2002 Dec 1
Differential pulse adsorptive stripping voltammetric determination of dinoseb and dinoterb at a modified electrode.
2003 Apr
Chemically induced supernumerary lumbar ribs in CD-1 mice: size distribution and dose response.
2004 Feb
Comparative studies on the spermatotoxic effects of dinoseb and its structurally related chemicals.
2004 Jun
Quantitative analysis of six pesticides in fruits by capillary electrophoresis-electrospray-mass spectrometry.
2005 Apr
Adsorption kinetics and isotherms of pesticides onto activated carbon-cloth.
2005 Sep
Inhibition of PSII in atrazine-tolerant tobacco cells by barbatic acid, a lichen-derived depside.
2006 Jan
Toxic actions of dinoseb in medaka (Oryzias latipes) embryos as determined by in vivo 31P NMR, HPLC-UV and 1H NMR metabolomics.
2006 Mar 10
Evidence for a novel quinone-binding site in the photosystem II (PS II) complex that regulates the redox potential of cytochrome b559.
2007 Jan 30
Flow-injection determination of carbaryl and carbofuran based on KMnO(4)-Na(2)SO(3) chemiluminescence detection.
2007 Jul-Aug
On-line preconcentration strategies for analyzing pesticides in fruits and vegetables by micellar electrokinetic chromatography.
2007 Jun 15
Effects of dinoseb on energy reserves in the soil arthropod Folsomia candida.
2007 Oct
Review of developmental toxicity of nitrophenolic herbicide dinoseb, 2-sec-butyl-4,6-dinitrophenol.
2008 Apr
Combined repeated dose and reproductive/developmental toxicity screening test of the nitrophenolic herbicide dinoseb, 2-sec-butyl-4,6-dinitrophenol, in rats.
2008 Apr
Cost-effective experimental design to support modeling of concentration-response functions.
2008 Jun
'Systems toxicology' approach identifies coordinated metabolic responses to copper in a terrestrial non-model invertebrate, the earthworm Lumbricus rubellus.
2008 Jun 3
MetaboMiner--semi-automated identification of metabolites from 2D NMR spectra of complex biofluids.
2008 Nov 28
Review of testicular toxicity of dinitrophenolic compounds, 2-sec-butyl-4,6-dinitrophenol, 4,6-dinitro-o-cresol and 2,4-dinitrophenol.
2008 Nov-Dec
(RS)-Dimethyl-ammonium 2-sec-butyl-4,6-dinitro-phenolate.
2009 Oct 3
Remediating dinoseb-contaminated soil with zerovalent iron.
2009 Sep 15
Study of mass transfer in a dynamic hollow-fibre liquid phase microextraction system.
2010 Jan
Prenatal developmental toxicity of gavage or feeding doses of 2-sec-butyl-4,6-dinitrophenol in rats.
2010 Jun
Study on the treatment of 2-sec-butyl-4,6-dinitrophenol (DNBP) wastewater by ClO2 in the presence of aluminum oxide as catalyst.
2010 Nov 15
A high-throughput screen for teratogens using human pluripotent stem cells.
2014 Jan
In vitro neurotoxic hazard characterisation of dinitrophenolic herbicides.
2016 Jun 11
Distribution, lipid-bilayer affinity and kinetics of the metabolic effects of dinoseb in the liver.
2017 Aug 15
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:22:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:27 GMT 2023
Record UNII
YD44ZEM22M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
NSC-202753
Code 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 Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
Code System Code Type Description
WIKIPEDIA
DINOSEB
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-861-7
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
FDA UNII
YD44ZEM22M
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
CHEBI
34719
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID3020207
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
ALANWOOD
dinoseb
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
HSDB
1445
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
CAS
88-85-7
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
PUBCHEM
6950
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
NSC
202753
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY
MERCK INDEX
m4585
Created by admin on Fri Dec 15 15:22:27 GMT 2023 , Edited by admin on Fri Dec 15 15:22:27 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT