74011
(±)-Diclofop
certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Synonym(s):
(RS)-2-[4-(2,4-Dichlorophenoxy)phenoxy]propionic acid
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About This Item
Empirical Formula (Hill Notation):
C15H12Cl2O4
CAS Number:
Molecular Weight:
327.16
Beilstein:
2338390
MDL number:
UNSPSC Code:
41116107
NACRES:
NA.24
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grade
certified reference material
TraceCERT®
Quality Level
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.
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:
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
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Legal Information
TraceCERT is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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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
Jing Ye et al.
Bulletin of environmental contamination and toxicology, 83(1), 85-91 (2009-05-20)
In this study, the acute toxicity (72-h EC50 values) of chiral diclofop acid towards rice Xiushui 63 seedlings and its effects on the Hill reaction activities of chloroplasts were determined. Significant differences were observed between the two enantiomers in 72-h
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
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
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