CRM18124
Mesotrion Metabolite AMBA
certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Synonym(s):
2-Amino-4-(methylsulfonyl)benzoic acid
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About This Item
Empirical Formula (Hill Notation):
C8H9NO4S
CAS Number:
Molecular Weight:
215.23
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.
−20°C
InChI
1S/C8H9NO4S/c1-14(12,13)5-2-3-6(8(10)11)7(9)4-5/h2-4H,9H2,1H3,(H,10,11)
InChI key
KFOGGDGNOLZBNY-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. This 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
AMBA (2-amino-4-methylsulfonylbenzoic acid) is one of the metabolites formed from biodegradation of parent Mesotrione. Mesotrione is a selective herbicide that belongs to the triketone family, developed for use in maize culture as a substitute for atrazine. It is used for pre- and post-emergence control of common broad-leaved weeds, primarily in corn (maize). It acts by inhibiting the p-hydroxyphenylpyruvate dioxygenase (HPPD) enzyme, thus, blocking the production of carotenoid pigments in susceptible plants.
Mesotrion is currently approved for its use in the European Union. Maximum residue levels (MRLs) have been set according to Reg (EU) 2017/626 for mesotrione for various products of plant and animal origin from 0.01 to 0.05 mg/kg. Compared to the parent compound, AMBA metabolite is more persistent in soil and possess greater toxicity in selected microorganisms.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com
AMBA (2-amino-4-methylsulfonylbenzoic acid) is one of the metabolites formed from biodegradation of parent Mesotrione. Mesotrione is a selective herbicide that belongs to the triketone family, developed for use in maize culture as a substitute for atrazine. It is used for pre- and post-emergence control of common broad-leaved weeds, primarily in corn (maize). It acts by inhibiting the p-hydroxyphenylpyruvate dioxygenase (HPPD) enzyme, thus, blocking the production of carotenoid pigments in susceptible plants.
Mesotrion is currently approved for its use in the European Union. Maximum residue levels (MRLs) have been set according to Reg (EU) 2017/626 for mesotrione for various products of plant and animal origin from 0.01 to 0.05 mg/kg. Compared to the parent compound, AMBA metabolite is more persistent in soil and possess greater toxicity in selected microorganisms.
Application
The certified reference material (CRM) is intended to be used as a calibrant for chromatography and other analytical techniques. The CRM may also find following uses:
- Study the biodegradation and toxicity of herbicide mixtures mesotrione, nicosulfuron, and S-metolachlor by a bacterial strain, Bacillus sp. Mes11
- Isolation and characterization of a Bacillus sp. from cloud water for rapid biotransformation of mesotrione herbicide
- Investigation of mesotrione biodegradation products by the bacterial strain Bacillus sp. 3B6 using liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry (LC/ESI-QTOF-MS)
- Qualitative and quantitative metabolic profiling of mesotrione, by the bacterial strain Bacillus sp. 3B6 using NMR, LC-NMR, and LC-MS
- Method development for the determination of the mesotrione and its two metabolites, MNBA and AMBA in rice, rice plants, rice hulls, water, and soil using UPLC and triple-quadrupole tandem mass spectrometry
Recommended products
Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
Legal Information
TraceCERT is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Stéphanie Durand et al.
Rapid communications in mass spectrometry : RCM, 20(17), 2603-2613 (2006-08-01)
The metabolic pathway involved in the biotransformation of the herbicide mesotrione by the bacterial strain Bacillus sp. 3B6 was investigated by a reliable liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry (LC/ESI-QTOF-MS) method. The LC/ESI-MS method, both in positive and negative
S Durand et al.
Letters in applied microbiology, 43(2), 222-228 (2006-07-28)
The aim of this study was to find and characterize a fungal or bacterial strain capable of metabolizing mesotrione, a new selective herbicide for control of broad-leaved weeds in maize. This strain was isolated from cloud water and showed close
Stéphanie Durand et al.
Chemosphere, 81(3), 372-380 (2010-08-10)
Enhanced knowledge of pesticide transformation products formed in the environment could lead to both accurate estimates of the overall effects of these compounds on environmental ecosystems and human health and improved removal processes. These compounds can present chemical and environmental
Isabelle Batisson et al.
Environmental pollution (Barking, Essex : 1987), 157(4), 1195-1201 (2009-01-06)
Dissipation kinetics of mesotrione, a new triketone herbicide, sprayed on soil from Limagne (Puy-de-Dôme, France) showed that the soil microflora were able to biotransform it. Bacteria from this soil were cultured in mineral salt solution supplemented with mesotrione as sole
Pengqiang Du et al.
Food chemistry, 229, 260-267 (2017-04-05)
In this study, an efficient and fast method for the determination of the herbicide mesotrione and its two metabolites [4-methylsulfonyl-2-nitrobenzoic acid (MNBA) and 2-amino-4-methylsulfonylbenzoic acid (AMBA)] in rice, rice plants, rice hulls, water, and soil was developed, using ultra performance
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