Sulfentrazone
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Basic Info
| Common Name | Sulfentrazone(F05138) |
| 2D Structure | |
| Description | Sulfentrazone is a chemical used as a herbicide. It is the active ingredient in Dismiss as well as Solitare herbicides. It is effective for controlling sedges in turfgrass. |
| FRCD ID | F05138 |
| CAS Number | 122836-35-5 |
| PubChem CID | 86369 |
| Formula | C11H10Cl2F2N4O3S |
| IUPAC Name | N-[2,4-dichloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]phenyl]methanesulfonamide |
| InChI Key | OORLZFUTLGXMEF-UHFFFAOYSA-N |
| InChI | InChI=1S/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3 |
| Canonical SMILES | CC1=NN(C(=O)N1C(F)F)C2=CC(=C(C=C2Cl)Cl)NS(=O)(=O)C |
| Isomeric SMILES | CC1=NN(C(=O)N1C(F)F)C2=CC(=C(C=C2Cl)Cl)NS(=O)(=O)C |
| Synonyms |
Sulfentrazone
122836-35-5
Authority
Sulfentrazone [ISO]
F 6285
UNII-7TY7WT1599
HSDB 7014
CHEBI:9339
7TY7WT1599
FMC 97285
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Azoles |
| Subclass | Triazoles |
| Intermediate Tree Nodes | Phenyltriazoles |
| Direct Parent | Phenyl-1,2,4-triazoles |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Phenyl-1,2,4-triazole - Sulfanilide - 1,3-dichlorobenzene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Organic sulfonic acid amide - Organosulfonic acid amide - Heteroaromatic compound - Organic sulfonic acid or derivatives - Aminosulfonyl compound - Organosulfonic acid or derivatives - Sulfonyl - Azacycle - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Organofluoride - Organochloride - Organohalogen compound - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Alkyl fluoride - Alkyl halide - Organopnictogen compound - Organic oxide - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 387.183 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Complexity | 613 |
| Monoisotopic Mass | 385.982 |
| Exact Mass | 385.982 |
| 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+ | 0.8544 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5583 |
| P-glycoprotein Substrate | Non-substrate | 0.8633 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9008 |
| Non-inhibitor | 0.9721 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9318 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6444 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.5753 |
| CYP450 2D6 Substrate | Non-substrate | 0.7907 |
| CYP450 3A4 Substrate | Non-substrate | 0.5513 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7709 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6103 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9221 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8171 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7336 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8494 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8691 |
| Non-inhibitor | 0.7810 | |
| AMES Toxicity | Non AMES toxic | 0.6021 |
| Carcinogens | Non-carcinogens | 0.6194 |
| Fish Toxicity | High FHMT | 0.9353 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9288 |
| Honey Bee Toxicity | Low HBT | 0.9091 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7709 |
| Carcinogenicity (Three-class) | Non-required | 0.6304 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.3318 | LogS |
| Caco-2 Permeability | 0.9817 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2045 | LD50, mol/kg |
| Fish Toxicity | 1.6631 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4802 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Effect of herbicides in the oxidative stress in crop winter species. | An Acad Bras Cienc | 2018 Apr-Jun | 29898110 |
| Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl-pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors. | J Agric Food Chem | 2016 Jan 27 | 26728549 |
| A quick, easy, cheap, effective, rugged, and safe method for the simultaneousdetection of four triazolone herbicides in cereals combined with ultrahighperformance liquid chromatography with tandem mass spectrometry. | J Sep Sci | 2014 Sep | 24923624 |
| Herbicide solubilization in micelle-clay composites as a basis for controlledrelease sulfentrazone and metolachlor formulations. | J Agric Food Chem | 2008 Oct 8 | 18781765 |
| Syntheses and herbicidal activities of novel triazolinone derivatives. | J Agric Food Chem | 2008 Mar 26 | 18298068 |
| Water purification from organic pollutants by optimized micelle-clay systems. | Environ Sci Technol | 2005 Apr 1 | 15871274 |
| Sulfentrazone adsorbed on micelle-montmorillonite complexes for slow release insoil. | J Agric Food Chem | 2003 May 21 | 12744675 |
| Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds ofglyphosate-treated, glyphosate-resistant soybean. | J Agric Food Chem | 2003 Jan 1 | 12502430 |
Targets
- General Function:
- Transmembrane signaling receptor activity
- Specific Function:
- Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in capillary morphogenesis.
- Gene Name:
- SELE
- Uniprot ID:
- P16581
- Molecular Weight:
- 66654.575 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 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor for TNFSF5/CD40LG. Transduces TRAF6- and MAP3K8-mediated signals that activate ERK in macrophages and B cells, leading to induction of immunoglobulin secretion.
- Gene Name:
- CD40
- Uniprot ID:
- P25942
- Molecular Weight:
- 30618.76 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:
- 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:
- 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:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 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:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 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:
- 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 ]
- 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 binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 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 ]