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(±)-Diclofop

certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

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Synonym(s):
(RS)-2-[4-(2,4-Dichlorophenoxy)phenoxy]propionic acid
Empirical Formula (Hill Notation):
C15H12Cl2O4
CAS Number:
40843-25-2
Molecular Weight:
327.16
Beilstein:
2338390
MDL number:
MFCD00152216

grade

certified reference material
TraceCERT®

Quality Level

300

product line

TraceCERT®

shelf life

limited shelf life, expiry date on the label

manufacturer/tradename

Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

format

neat

storage temp.

2-8°C

SMILES string

CC(Oc1ccc(Oc2ccc(Cl)cc2Cl)cc1)C(O)=O

InChI

1S/C15H12Cl2O4/c1-9(15(18)19)20-11-3-5-12(6-4-11)21-14-7-2-10(16)8-13(14)17/h2-9H,1H3,(H,18,19)

InChI key

OOLBCHYXZDXLDS-UHFFFAOYSA-N

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General description

This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO 17034. The CRM is traceable to primary material from an NMI, e.g. NIST or NMIJ.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com
(+/–)-Diclofop is a chiral herbicide that belongs to the chemical class of chiral aryloxyphenoxypropionate compounds. The actual herbicidal active ingredient― carboxylic acid, is released after application through hydrolysis of the ester. It is absorbed mainly through leaves and inhibits the biosynthesis of fatty acids by suppressing the activity of acetyl CoA carboxylase (ACCase). It is used for the post-emergence control of wild oats, wild millets, and other annual grass weeds commonly occurring in wheat, barley, rye, red fescue, and broad-leaved crops.
It was included on 1st June 2011 in Annex I of Directive 91/414/EEC by the European Commission Directive 2011/45/EU. It is authorized for use under EC Regulation No 1107/2009, as per the Commission Implementing Regulation (EU) No 540/2011, however it is a candidate for substitution.

Application

It is intended to be used as a certified reference material (CRM) for calibration in chromatography and other analytical techniques.
The (+/–)-Diclofop CRM can also be used as following:
  • To evaluate the likely enantioselective oxidative stress produced in Microcystis aeruginosa by diclofop acid
  • For analyzing the phytotoxic effects of diclofop acid enantiomers on the plant Arabidopsis thaliana
  • To study the enantioselective toxicity of diclofop acid on the non-target rice Xiushui 63 seedlings
  • In the chiral separation of diclofop-acid using one- and two- dimensional HPLC methods
  • To determine the enantioselective toxicity and degradation of diclofop in three algal cultures

Recommended products

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Legal Information

TraceCERT is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Qiong Zhang et al.
Environmental science & technology, 46(15), 8405-8412 (2012-07-10)
Diclofop-methyl (DM) is a widely used chiral herbicide, which rapidly hydrolyzes to its major metabolite diclofop acid (DC) after application. With a carbon chiral center, DC not only is an important ingredient of herbicidal activity, but also has a long
Jing Ye et al.
Aquatic toxicology (Amsterdam, Netherlands), 146, 12-19 (2013-11-19)
Enantioselective oxidative stress and toxin release from Microcystis aeruginosa after exposure to the chiral herbicide diclofop acid were investigated. Racemic diclofop acid, R-diclofop acid and S-diclofop acid induced reactive oxygen species (ROS) generation, increased the concentration of malondialdehyde (MDA), enhanced
Xiyun Cai et al.
Journal of agricultural and food chemistry, 56(6), 2139-2146 (2008-03-06)
Aryloxyphenoxypropanoates are a class of chiral herbicides. They have a pair of enantiomers, only the R(+) form of which is herbicidally active. Diclofop, the model compound of these herbicides, is commercialized as the racemate of the ester form, diclofop-methyl, consisting
Vanesa Guillén-Casla et al.
Journal of agricultural and food chemistry, 56(7), 2303-2309 (2008-03-15)
Simple one- and two-dimensional high-performance liquid chromatography (HPLC) methods for the simultaneous enantiomeric determination of alkyloxyphenoxypropionic acid herbicides is presented. Compounds studied were ( R, S)-2-[4-(2,4-dichlorophenoxy)phenoxy]propionic acid (diclofop-acid) and ( R, S)-2-[4-(2,4-dichlorophenoxy)]methyl propionate (diclofop-methyl). Mobile phases necessary to separate their
Review of the existing maximum residue levels for diclofop (considered variant diclofop-methyl) according to Article 12 of Regulation (EC) No 396/2005
European Food Safety Authority (EFSA), et al.
EFSA Journal, e05981 null
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