Metsulfuron-Methyl
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Basic Info
Common Name | Metsulfuron-Methyl(F05106) |
2D Structure | |
Description | Metsulfuron-methyl is a residual sulfonylurea herbicide that kills broadleaf weeds and some annual grasses. It is a systemic compound with foliar and soil activity, that inhibits cell division in shoots and roots. It has residual activity in soils, allowing it to be used infrequently but requiring up to 22 months before planting certain crops (sunflowers, flax, corn, or safflower). It has very low toxicity to mammals, birds, fish, and insects, but is a moderate eye irritant. |
FRCD ID | F05106 |
CAS Number | 74223-64-6 |
PubChem CID | 52999 |
Formula | C14H15N5O6S |
IUPAC Name | methyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate |
InChI Key | RSMUVYRMZCOLBH-UHFFFAOYSA-N |
InChI | InChI=1S/C14H15N5O6S/c1-8-15-12(18-14(16-8)25-3)17-13(21)19-26(22,23)10-7-5-4-6-9(10)11(20)24-2/h4-7H,1-3H3,(H2,15,16,17,18,19,21) |
Canonical SMILES | CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC |
Isomeric SMILES | CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC |
Synonyms | Granstar Gropper Escort (pesticide) METSULFURON-METHYL Metsulfuron methyl 74223-64-6 Escort ALLY Allie Brush-off |
Classifies | Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Benzoic acids and derivatives |
Intermediate Tree Nodes | Not available |
Direct Parent | Benzoic acid esters |
Alternative Parents |
|
Molecular Framework | Aromatic heteromonocyclic compounds |
Substituents | Benzenesulfonamide - Benzoate ester - Benzenesulfonyl group - 2-methoxy-1,3,5-triazine - Alkoxy-s-triazine - Benzoyl - Alkyl aryl ether - 1,3,5-triazine - Triazine - Heteroaromatic compound - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Methyl ester - Sulfonyl - Carboxylic acid ester - Carboxylic acid derivative - Ether - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organopnictogen compound - Organic oxide - Aromatic heteromonocyclic compound |
Description | This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 381.363 |
Hydrogen Bond Donor Count | 2 |
Hydrogen Bond Acceptor Count | 9 |
Rotatable Bond Count | 6 |
Complexity | 609 |
Monoisotopic Mass | 381.074 |
Exact Mass | 381.074 |
XLogP | 1.5 |
Formal Charge | 0 |
Heavy Atom Count | 26 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB- | 0.5142 |
Human Intestinal Absorption | HIA+ | 0.8804 |
Caco-2 Permeability | Caco2- | 0.6159 |
P-glycoprotein Substrate | Non-substrate | 0.8006 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.8218 |
Non-inhibitor | 0.9445 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.9123 |
Distribution | ||
Subcellular localization | Mitochondria | 0.5893 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.5000 |
CYP450 2D6 Substrate | Non-substrate | 0.8810 |
CYP450 3A4 Substrate | Non-substrate | 0.7103 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8685 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.6616 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9233 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8152 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.6991 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8009 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9834 |
Non-inhibitor | 0.8342 | |
AMES Toxicity | Non AMES toxic | 0.7652 |
Carcinogens | Non-carcinogens | 0.8047 |
Fish Toxicity | High FHMT | 0.8766 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.7089 |
Honey Bee Toxicity | Low HBT | 0.8575 |
Biodegradation | Not ready biodegradable | 1.0000 |
Acute Oral Toxicity | III | 0.8199 |
Carcinogenicity (Three-class) | Non-required | 0.5462 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -3.4245 | LogS |
Caco-2 Permeability | 0.4787 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.8508 | LD50, mol/kg |
Fish Toxicity | 1.6825 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.4715 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Muscle | 1013010 | European Union | 0.01* | 02/01/2015 | |
Others (2) | 1015990 | European Union | 0.01* | 02/01/2015 | |
Muscle | 1016010 | European Union | 0.01* | 02/01/2015 | |
Edible offals (other than liver and kidney) | 1015050 | European Union | 0.01* | 02/01/2015 | |
FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 02/01/2015 | |
Citrus fruits | 0110000 | European Union | 0.01* | 02/01/2015 | |
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 02/01/2015 | |
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 02/01/2015 | |
Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 02/01/2015 | |
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 02/01/2015 | |
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 02/01/2015 | |
Others (2) | 0110990 | European Union | 0.01* | 02/01/2015 | |
Muscle | 1015010 | European Union | 0.01* | 02/01/2015 | |
Fat | 1015020 | European Union | 0.01* | 02/01/2015 | |
Liver | 1015030 | European Union | 0.01* | 02/01/2015 | |
Kidney | 1015040 | European Union | 0.01* | 02/01/2015 | |
Fat | 1013020 | European Union | 0.01* | 02/01/2015 | |
Liver | 1013030 | European Union | 0.01* | 02/01/2015 | |
Kidney | 1013040 | European Union | 0.01* | 02/01/2015 | |
Others (2) | 1013990 | European Union | 0.01* | 02/01/2015 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Effects of grazing different ergovaline concentrations on vasoactivity of bovine lateral saphenous vein. | J Anim Sci | 2018 Jun 29 | 29701794 |
Simple, cost-effective and sensitive liquid chromatography diode array detectormethod for simultaneous determination of eight sulfonylurea herbicides in soyamilk samples. | J Chromatogr A | 2016 Nov 18 | 28314393 |
Metsulfuron-methyl-based herbicidal ionic liquids. | J Agric Food Chem | 2015 Apr 8 | 25734891 |
Currently used pesticides and their mixtures affect the function of sex hormonereceptors and aromatase enzyme activity. | Toxicol Appl Pharmacol | 2013 Oct 15 | 23871939 |
Joint ecotoxicology of cadmium and metsulfuron-methyl in wheat (Triticum aestivum). | Environ Monit Assess | 2013 Apr | 22773146 |
The nutritive value of grasspea (Lathyrus sativus) and allied species, their toxicity to animals and the role of malnutrition in neurolathyrism. | Food Chem Toxicol | 2011 Mar | 21112364 |
Trace determination of sulfonylurea herbicides in water and grape samples bycapillary zone electrophoresis using large volume sample stacking. | Anal Bioanal Chem | 2010 Jul | 20496055 |
Trace level determination of selected sulfonylurea herbicides in wetland sedimentby liquid chromatography electrospray tandem mass spectrometry. | J Environ Sci Health B | 2010 Jan | 20390926 |
Persistence of metsulfuron-methyl in paddy field and detection of its residues incrop produce. | Bull Environ Contam Toxicol | 2009 Dec | 19609477 |
Preparation of molecularly imprinted solid phase extraction usingbensulfuron-methyl imprinted polymer and clean-up for the sulfonylurea-herbicidesin soybean. | Anal Chim Acta | 2008 Apr 28 | 18405688 |
Factors influencing degradation of pesticides in soil. | J Agric Food Chem | 2007 May 30 | 17488087 |
Effects of soil storage on the microbial community and degradation ofmetsulfuron-methyl. | J Agric Food Chem | 2006 Jan 11 | 16390191 |
Effect of different soil textures on leaching potential and degradation ofpesticides in biobeds. | J Agric Food Chem | 2004 Sep 8 | 15373405 |
[Simultaneous determination of ten sulfonylurea herbicide residues in soybeans byhigh performance liquid chromatography]. | Se Pu | 2004 Nov | 15807119 |
A comparison of crop and non-crop plants as sensitive indicator species forregulatory testing. | Pest Manag Sci | 2002 Dec | 12476989 |
Ion chromatographic analysis of selected free amino acids and cations toinvestigate the change of nitrogen metabolism by herbicide stress in soybean(glycine max). | J Agric Food Chem | 2001 Jan | 11305252 |
Analysis of metsulfuron-methyl in soil by liquid chromatography/tandem massspectrometry. Application to a field dissipation study. | J Agric Food Chem | 1999 Oct | 10552834 |