Ethofumesate
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Basic Info
| Common Name | Ethofumesate(F05413) |
| 2D Structure | |
| Description | Ethofumesate is a pre- and post-emergence herbicide for grasses and broad-leaved weed control in various crops. |
| FRCD ID | F05413 |
| CAS Number | 26225-79-6 |
| PubChem CID | 33360 |
| Formula | C13H18O5S |
| IUPAC Name | (2-ethoxy-3,3-dimethyl-2H-1-benzofuran-5-yl) methanesulfonate |
| InChI Key | IRCMYGHHKLLGHV-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H18O5S/c1-5-16-12-13(2,3)10-8-9(18-19(4,14)15)6-7-11(10)17-12/h6-8,12H,5H2,1-4H3 |
| Canonical SMILES | CCOC1C(C2=C(O1)C=CC(=C2)OS(=O)(=O)C)(C)C |
| Isomeric SMILES | CCOC1C(C2=C(O1)C=CC(=C2)OS(=O)(=O)C)(C)C |
| Synonyms |
ETHOFUMESATE
26225-79-6
Progress
Tramat
NORTRON
Nortron (new)
Nortran
Caswell No. 427BB
NC 8438
Ethofumesate [ANSI:BSI:ISO]
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Coumarans |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Coumarans |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Coumaran - Benzenoid - Organosulfonic acid ester - Sulfonic acid ester - Methanesulfonate - Organic sulfonic acid or derivatives - Sulfonyl - Organosulfonic acid or derivatives - Acetal - Oxacycle - Organic oxygen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as coumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 286.342 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 411 |
| Monoisotopic Mass | 286.087 |
| Exact Mass | 286.087 |
| XLogP | 2.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.9203 |
| Human Intestinal Absorption | HIA+ | 0.9968 |
| Caco-2 Permeability | Caco2- | 0.6001 |
| P-glycoprotein Substrate | Non-substrate | 0.6788 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6622 |
| Non-inhibitor | 0.8834 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8818 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5347 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8334 |
| CYP450 2D6 Substrate | Non-substrate | 0.8165 |
| CYP450 3A4 Substrate | Substrate | 0.5705 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5489 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6855 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8956 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7064 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7156 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5323 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7035 |
| Non-inhibitor | 0.6990 | |
| AMES Toxicity | AMES toxic | 0.5358 |
| Carcinogens | Carcinogens | 0.6245 |
| Fish Toxicity | High FHMT | 0.9174 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5000 |
| Honey Bee Toxicity | High HBT | 0.8638 |
| Biodegradation | Ready biodegradable | 0.5956 |
| Acute Oral Toxicity | III | 0.7737 |
| Carcinogenicity (Three-class) | Non-required | 0.6003 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.4598 | LogS |
| Caco-2 Permeability | 0.5545 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4147 | LD50, mol/kg |
| Fish Toxicity | 1.0696 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1366 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 15 | 11/07/2017 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.03* | 11/07/2017 | |
| Citrus fruits | 0110000 | European Union | 0.03* | 11/07/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.03* | 11/07/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.03* | 11/07/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.03* | 11/07/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.03* | 11/07/2017 | |
| Others (2) | 0110990 | European Union | 0.03* | 11/07/2017 | |
| Tree nuts | 0120000 | European Union | 0.03* | 11/07/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.03* | 11/07/2017 | |
| Brazil nuts | 0120020 | European Union | 0.03* | 11/07/2017 | |
| Cashew nuts | 0120030 | European Union | 0.03* | 11/07/2017 | |
| Chestnuts | 0120040 | European Union | 0.03* | 11/07/2017 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.03* | 11/07/2017 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.03* | 11/07/2017 | |
| Macadamias | 0120070 | European Union | 0.03* | 11/07/2017 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.03* | 11/07/2017 | |
| Pistachios | 0120100 | European Union | 0.03* | 11/07/2017 | |
| Walnuts | 0120110 | European Union | 0.03* | 11/07/2017 | |
| Others (2) | 0120990 | European Union | 0.03* | 11/07/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicity and bioaccumulation of ethofumesate enantiomers in earthworm Eisenia fetida. | Chemosphere | 2014 Oct | 25048902 |
| Exposure assessment of pesticides in a shallow groundwater of the Tagusvulnerable zone (Portugal): a multivariate statistical approach (JCA). | Environ Sci Pollut Res Int | 2011 Aug | 22307895 |
| Enantiomeric resolution of chiral pesticides by high-performance liquidchromatography. | J Agric Food Chem | 2006 Mar 8 | 16506803 |
| Mobility and dissipation of ethofumesate and halofenozide in turfgrass and baresoil. | J Agric Food Chem | 2001 Jun | 11409984 |
| Method for the analysis of triadimefon and ethofumesate from dislodgeable foliar residues on turfgrass by solid-phase extraction and in-vial elution. | J Agric Food Chem | 1999 Aug | 10552640 |
Targets
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 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:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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:
- 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:
- 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 ]