Triasulfuron
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Basic Info
| Common Name | Triasulfuron(F05148) |
| 2D Structure | |
| Description | Triasulfuron is a selective sulfonylurea herbicide, which is absorbed by the leaves and the roots and is distributed through the plant to the meristems. It inhibits the biosynthesis of essential branched-chain amino acids valine and isoleucine, which prevents cell division and the plant growth is stopped. It is used as a herbicide in the cultivation of cereals (wheat, barley and triticale ) and can be applied before or after the emergence of the weeds. |
| FRCD ID | F05148 |
| CAS Number | 82097-50-5 |
| PubChem CID | 73282 |
| Formula | C14H16ClN5O5S |
| IUPAC Name | 1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea |
| InChI Key | XOPFESVZMSQIKC-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H16ClN5O5S/c1-9-16-12(19-14(17-9)24-2)18-13(21)20-26(22,23)11-6-4-3-5-10(11)25-8-7-15/h3-6H,7-8H2,1-2H3,(H2,16,17,18,19,20,21) |
| Canonical SMILES | CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2OCCCl |
| Isomeric SMILES | CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2OCCCl |
| Synonyms |
EPA Pesticide Chemical Code 128969
Triasulfuron
82097-50-5
Logran
Triasulfuron [ISO]
CGA 131036
UNII-299LHF498M
1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea
CHEBI:9673
299LHF498M
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzenesulfonamides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzenesulfonamides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Benzenesulfonamide - Benzenesulfonyl group - Phenoxy compound - 2-methoxy-1,3,5-triazine - Alkoxy-s-triazine - Phenol ether - Alkyl aryl ether - Triazine - 1,3,5-triazine - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Heteroaromatic compound - Ether - Organoheterocyclic compound - Azacycle - Organic oxide - Alkyl halide - Alkyl chloride - Organic nitrogen compound - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxygen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 401.822 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 7 |
| Complexity | 560 |
| Monoisotopic Mass | 401.056 |
| Exact Mass | 401.056 |
| XLogP | 2.3 |
| 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+ | 0.5638 |
| Human Intestinal Absorption | HIA+ | 0.9672 |
| Caco-2 Permeability | Caco2- | 0.6477 |
| P-glycoprotein Substrate | Non-substrate | 0.7492 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7593 |
| Non-inhibitor | 0.7942 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7650 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6356 |
| Metabolism | ||
| CYP450 2C9 Substrate | Substrate | 0.5073 |
| CYP450 2D6 Substrate | Non-substrate | 0.8483 |
| CYP450 3A4 Substrate | Non-substrate | 0.5339 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6472 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5080 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8584 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5879 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6830 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7207 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8798 |
| Non-inhibitor | 0.6871 | |
| AMES Toxicity | Non AMES toxic | 0.6571 |
| Carcinogens | Non-carcinogens | 0.7723 |
| Fish Toxicity | Low FHMT | 0.5156 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9370 |
| Honey Bee Toxicity | Low HBT | 0.8392 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | IV | 0.6193 |
| Carcinogenicity (Three-class) | Non-required | 0.5443 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6118 | LogS |
| Caco-2 Permeability | 0.4672 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9320 | LD50, mol/kg |
| Fish Toxicity | 1.4403 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5413 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.05* | 01/01/2012 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 01/01/2012 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 01/01/2012 | |
| 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* | 01/01/2012 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 01/01/2012 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 01/01/2012 | |
| 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* | 01/01/2012 | |
| Others (2) | 0110990 | European Union | 0.05* | 01/01/2012 | |
| Tree nuts | 0120000 | European Union | 0.05* | 01/01/2012 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 01/01/2012 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 01/01/2012 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 01/01/2012 | |
| Chestnuts | 0120040 | European Union | 0.05* | 01/01/2012 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 01/01/2012 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 01/01/2012 | |
| Macadamias | 0120070 | European Union | 0.05* | 01/01/2012 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 01/01/2012 | |
| Pistachios | 0120100 | European Union | 0.05* | 01/01/2012 | |
| Walnuts | 0120110 | European Union | 0.05* | 01/01/2012 | |
| Others (2) | 0120990 | European Union | 0.05* | 01/01/2012 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Recycling organic residues in soils as amendments: Effect on the mobility of two herbicides under different management practices. | J Environ Manage | 2018 Oct 15 | 30041096 |
| 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 |
| Trace determination of sulfonylurea herbicides in water and grape samples bycapillary zone electrophoresis using large volume sample stacking. | Anal Bioanal Chem | 2010 Jul | 20496055 |
| Effects of a municipal sewage sludge amendment on triasulfuron soil sorption and wheat growth. | J Agric Food Chem | 2009 Dec 9 | 19891476 |
Targets
- General Function:
- Hydroxymethylglutaryl-coa synthase activity
- Specific Function:
- This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
- Gene Name:
- HMGCS2
- Uniprot ID:
- P54868
- Molecular Weight:
- 56634.915 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:
- 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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:
- 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:
- 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 ]
- 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:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 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 ]