Rimsulfuron
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Basic Info
| Common Name | Rimsulfuron(F05440) |
| 2D Structure | |
| Description | Rimsulfuron is a herbicide for annual grass and annual broad-leaved weed control in maize, potatoes and other crops. It is selective, systemic, and absorbed through foliage and roots and translocated into the plant. It is an acetolactate synthase (ALS) inhibitor. |
| FRCD ID | F05440 |
| CAS Number | 122931-48-0 |
| PubChem CID | 91779 |
| Formula | C14H17N5O7S2 |
| IUPAC Name | 1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonylpyridin-2-yl)sulfonylurea |
| InChI Key | MEFOUWRMVYJCQC-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H17N5O7S2/c1-4-27(21,22)9-6-5-7-15-12(9)28(23,24)19-14(20)18-13-16-10(25-2)8-11(17-13)26-3/h5-8H,4H2,1-3H3,(H2,16,17,18,19,20) |
| Canonical SMILES | CCS(=O)(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC |
| Isomeric SMILES | CCS(=O)(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC |
| Synonyms |
122931-48-0
UNII-462J071RD7
Rimsulfuron
Titus
Matrix
Tarot
Rimsulfuron [ANSI]
DPX-E9636
DPX-E 9636
CHEBI:8866
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyridinesulfonamides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridinesulfonamides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyridine-2-sulfonamide - Alkyl aryl ether - Sulfonylurea - Pyrimidine - Sulfone - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Heteroaromatic compound - Ether - Carboximidic acid derivative - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Azacycle - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Organosulfur compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyridinesulfonamides. These are heterocyclic compounds containing a pyridine ring substituted by one or more sulfonamide groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 431.438 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 7 |
| Complexity | 722 |
| Monoisotopic Mass | 431.057 |
| Exact Mass | 431.057 |
| XLogP | 0.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 28 |
| 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- | 0.6968 |
| Human Intestinal Absorption | HIA+ | 0.7647 |
| Caco-2 Permeability | Caco2- | 0.6406 |
| P-glycoprotein Substrate | Non-substrate | 0.6735 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7159 |
| Non-inhibitor | 0.9751 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9021 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6552 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6096 |
| CYP450 2D6 Substrate | Non-substrate | 0.8594 |
| CYP450 3A4 Substrate | Non-substrate | 0.6237 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7827 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5990 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9112 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6440 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8938 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6983 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9695 |
| Non-inhibitor | 0.7897 | |
| AMES Toxicity | Non AMES toxic | 0.6692 |
| Carcinogens | Non-carcinogens | 0.7000 |
| Fish Toxicity | High FHMT | 0.8655 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8538 |
| Honey Bee Toxicity | Low HBT | 0.8344 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7913 |
| Carcinogenicity (Three-class) | Non-required | 0.5908 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.6760 | LogS |
| Caco-2 Permeability | 0.3637 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9564 | LD50, mol/kg |
| Fish Toxicity | 1.6306 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4378 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Blueberry | Japan | 0.05ppm | |||
| Tomato | Japan | 0.05ppm | |||
| Potato | Japan | 0.1ppm | |||
| Corn(Maize) | Japan | 0.1ppm | |||
| Tomato | Australia | 0.05mg/kg | |||
| Blueberries | Canada | 0.05mg/kg | |||
| Tomatoes | Canada | 0.05mg/kg | |||
| Field Corn | Canada | 0.1mg/kg | |||
| Potatoes | Canada | 0.1mg/kg |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Nicosulfuron Biodegradation by a Novel Cold-Adapted Strain Oceanisphaerapsychrotolerans LAM-WHM-ZC. | J Agric Food Chem | 2017 Nov 29 | 29111703 |
| Isoxadifen safening mechanism in sweet corn genotypes with differential response to P450-metabolized herbicides. | Pestic Biochem Physiol | 2017 May | 28456300 |
| Degradation Processes of Pesticides Used in Potato Cultivations. | Rev Environ Contam Toxicol | 2017 | 27718007 |
| 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 |
| Method validation and dissipation kinetics of four herbicides in maize and soilusing QuEChERS sample preparation and liquid chromatography tandem massspectrometry. | Food Chem | 2016 Jan 1 | 26213040 |
| Sulfonylurea herbicides in an agricultural catchment basin and its adjacent wetland in the St. Lawrence River basin. | Sci Total Environ | 2014 May 1 | 24534695 |
| Dissipation and residues of rimsulfuron in potato and soil under fieldconditions. | Bull Environ Contam Toxicol | 2012 Dec | 23076614 |
| 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 |
| N-methylimidazolium ionic liquid-functionalized silica as a sorbent for selectivesolid-phase extraction of 12 sulfonylurea herbicides in environmental water andsoil samples. | J Chromatogr A | 2010 Mar 5 | 20116796 |
| Trace level determination of selected sulfonylurea herbicides in wetland sedimentby liquid chromatography electrospray tandem mass spectrometry. | J Environ Sci Health B | 2010 Jan | 20390926 |
| Leaching of three sulfonylurea herbicides during sprinkler irrigation. | J Environ Qual | 2009 Dec 30 | 20048324 |
| Flazasulfuron: alcoholysis, chemical hydrolysis, and degradation on variousminerals. | J Agric Food Chem | 2003 Dec 17 | 14664534 |
| Dissipation of nicosulfuron and rimsulfuron in surface soil. | J Agric Food Chem | 2002 Jul 31 | 12137479 |
| Nicosulfuron: alcoholysis, chemical hydrolysis, and degradation on variousminerals. | J Agric Food Chem | 2002 Jan 30 | 11804524 |
| Determination of sulfonylurea herbicides in grains by capillary electrophoresis. | J AOAC Int | 1995 Jul-Aug | 7580322 |
Targets
- General Function:
- Glutathione transferase activity
- Specific Function:
- Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
- Gene Name:
- GSTA2
- Uniprot ID:
- P09210
- Molecular Weight:
- 25663.675 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 d 24-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.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 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:
- 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:
- Serine-type endopeptidase inhibitor activity
- Specific Function:
- Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
- Gene Name:
- SERPINE1
- Uniprot ID:
- P05121
- Molecular Weight:
- 45059.695 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:
- Serine-type endopeptidase activity
- Specific Function:
- Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
- Gene Name:
- PLAU
- Uniprot ID:
- P00749
- Molecular Weight:
- 48507.09 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:
- Tumor necrosis factor receptor binding
- Specific Function:
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Upregulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:22517918).The TNF intracellular domain (ICD) form induces IL12 production in dendritic cells.
- Gene Name:
- TNF
- Uniprot ID:
- P01375
- Molecular Weight:
- 25644.15 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:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 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 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Cytokine that plays an essential role in the regulation of survival, proliferation and differentiation of hematopoietic precursor cells, especially mononuclear phagocytes, such as macrophages and monocytes. Promotes the release of proinflammatory chemokines, and thereby plays an important role in innate immunity and in inflammatory processes. Plays an important role in the regulation of osteoclast proliferation and differentiation, the regulation of bone resorption, and is required for normal bone development. Required for normal male and female fertility. Promotes reorganization of the actin cytoskeleton, regulates formation of membrane ruffles, cell adhesion and cell migration. Plays a role in lipoprotein clearance.
- Gene Name:
- CSF1
- Uniprot ID:
- P09603
- Molecular Weight:
- 60178.885 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 ]