Chlorsulfuron
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Chlorsulfuron(F05042) |
| 2D Structure | |
| Description | Chlorsulfuron is a triazine herbicide that is recommended for selective control of weeds in wheat (pre- and/or postemergent to crop) and barley (postemergent to crop) as well as reduced tillage fallow preceding wheat. Controls most broadleaf and some grass weeds. |
| FRCD ID | F05042 |
| CAS Number | 64902-72-3 |
| PubChem CID | 47491 |
| Formula | C12H12ClN5O4S |
| IUPAC Name | 1-(2-chlorophenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea |
| InChI Key | VJYIFXVZLXQVHO-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H12ClN5O4S/c1-7-14-10(17-12(15-7)22-2)16-11(19)18-23(20,21)9-6-4-3-5-8(9)13/h3-6H,1-2H3,(H2,14,15,16,17,18,19) |
| Canonical SMILES | CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2Cl |
| Isomeric SMILES | CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2Cl |
| Synonyms |
CHLORSULFURON
2-Chlorsulfuron
64902-72-3
Chlorsulfon
Glean
Chlorosulfuron
Trilixon
Telar
Finesse
Glean C
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Sulfonylureas |
| Intermediate Tree Nodes | Not available |
| Direct Parent | S-triazinyl-2-sulfonylureas |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | S-triazinyl-2-sulfonylurea - Benzenesulfonamide - Benzenesulfonyl group - 2-methoxy-1,3,5-triazine - Alkoxy-s-triazine - Alkyl aryl ether - Amino-1,3,5-triazine - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - 1,3,5-triazine - Benzenoid - Triazine - Heteroaromatic compound - Aminosulfonyl compound - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Carbonic acid derivative - Ether - Organoheterocyclic compound - Azacycle - Organochloride - Organohalogen compound - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organooxygen compound - Organosulfur compound - Organic oxide - Hydrocarbon derivative - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as s-triazinyl-2-sulfonylureas. These are aromatic heterocyclic compounds containing a s-triazine ring which is substituted with a urea at the ring 2-position. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 357.769 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Complexity | 514 |
| Monoisotopic Mass | 357.03 |
| Exact Mass | 357.03 |
| XLogP | 2.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| 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- | 0.7050 |
| Human Intestinal Absorption | HIA+ | 0.9687 |
| Caco-2 Permeability | Caco2- | 0.5911 |
| P-glycoprotein Substrate | Non-substrate | 0.7770 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8447 |
| Non-inhibitor | 0.9631 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8868 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5693 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.5242 |
| CYP450 2D6 Substrate | Non-substrate | 0.8615 |
| CYP450 3A4 Substrate | Non-substrate | 0.6518 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8347 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5789 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8902 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7893 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7457 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6119 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9702 |
| Non-inhibitor | 0.8679 | |
| AMES Toxicity | Non AMES toxic | 0.7917 |
| Carcinogens | Non-carcinogens | 0.7714 |
| Fish Toxicity | High FHMT | 0.9397 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9209 |
| Honey Bee Toxicity | Low HBT | 0.8842 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | IV | 0.6257 |
| Carcinogenicity (Three-class) | Non-required | 0.5508 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6581 | LogS |
| Caco-2 Permeability | 0.7531 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8413 | LD50, mol/kg |
| Fish Toxicity | 1.5902 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6268 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 01/09/2008 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 01/09/2008 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.05* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.05* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.05* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.05* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 01/09/2008 | |
| Pistachios | 0120100 | European Union | 0.05* | 01/09/2008 | |
| Walnuts | 0120110 | European Union | 0.05* | 01/09/2008 | |
| Others (2) | 0120990 | European Union | 0.05* | 01/09/2008 | |
| Pome fruits | 0130000 | European Union | 0.05* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Multiplex highly sensitive immunochromatographic assay based on the use ofnonprocessed antisera. | Anal Bioanal Chem | 2018 Mar | 29353430 |
| Nicosulfuron Biodegradation by a Novel Cold-Adapted Strain Oceanisphaerapsychrotolerans LAM-WHM-ZC. | J Agric Food Chem | 2017 Nov 29 | 29111703 |
| Somatic cell selection for chlorsulfuron-resistant mutants in potato:identification of point mutations in the acetohydroxyacid synthase gene. | BMC Biotechnol | 2017 Jun 6 | 28587679 |
| 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 |
| Inheritance of resistance to 2,4-D and chlorsulfuron in a multiple-resistantpopulation of Sisymbrium orientale. | Pest Manag Sci | 2015 Nov | 25476820 |
| Determination of four sulfonylurea herbicides in tea by matrix solid-phasedispersion cleanup followed by dispersive liquid-liquid microextraction. | J Sep Sci | 2014 Sep | 24956010 |
| Determination of sulfonylureas in cereal samples with electrophoretic methodusing ionic liquid with dispersed carbon nanotubes as electrophoretic buffer. | Food Chem | 2014 Jan 15 | 24054250 |
| Mechanisms of resistance to acetolactate synthase-inhibiting herbicides inpopulations of Apera spica-venti from the Czech Republic. | Pest Manag Sci | 2014 Apr | 23893862 |
| Transformation of apple (Malus × domestica) using mutants of apple acetolactatesynthase as a selectable marker and analysis of the T-DNA integration sites. | Plant Cell Rep | 2013 May | 23494389 |
| Ammonium chloride salting out extraction/cleanup for trace-level quantitativeanalysis in food and biological matrices by flow injection tandem massspectrometry. | Anal Chim Acta | 2013 Mar 20 | 23473245 |
| Pleiotropic effects of herbicide-resistance genes on crop yield: a review. | Pest Manag Sci | 2013 Aug | 23457026 |
| Preparation and evaluation of molecularly imprinted ionic liquids polymer assorbent for on-line solid-phase extraction of chlorsulfuron in environmentalwater samples. | J Chromatogr A | 2011 Sep 16 | 21807367 |
| Development and validation of a solid-phase extraction method coupled tohigh-performance liquid chromatography with ultraviolet-diode array detection forthe determination of sulfonylurea herbicide residues in bovine milk samples. | J Chromatogr A | 2011 Mar 4 | 21277578 |
| Fast extraction and dilution flow injection mass spectrometry method forquantitative chemical residue screening in food. | J Agric Food Chem | 2011 Jul 27 | 21388127 |
| Isolation and characterization of a rice glutathione S-transferase gene promoter regulated by herbicides and hormones. | Plant Cell Rep | 2011 Apr | 21153026 |
| Trace determination of sulfonylurea herbicides in water and grape samples bycapillary zone electrophoresis using large volume sample stacking. | Anal Bioanal Chem | 2010 Jul | 20496055 |
| Crops with target-site herbicide resistance for Orobanche and Striga control. | Pest Manag Sci | 2009 May | 19280593 |
| Use of ethylcellulose to control chlorsulfuron leaching in a calcareous soil. | J Agric Food Chem | 2009 Apr 8 | 19334760 |
| Influence of long-term used herbicides on resistance development in Aperaspica-venti L. to sulfonylureas. | Commun Agric Appl Biol Sci | 2009 | 20222609 |
| Organic amendments from olive cake as a strategy to modify the degradation ofsulfonylurea herbicides in soil. | J Agric Food Chem | 2007 Jul 25 | 17608500 |
Targets
- General Function:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments. Degrades fibronectin but not laminin or Pz-peptide.
- Gene Name:
- MMP9
- Uniprot ID:
- P14780
- Molecular Weight:
- 78457.51 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Type iii transforming growth factor beta receptor binding
- Specific Function:
- Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
- Gene Name:
- TGFB1
- Uniprot ID:
- P01137
- Molecular Weight:
- 44340.685 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]