Isoxaflutole
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Basic Info
| Common Name | Isoxaflutole(F05093) |
| 2D Structure | |
| Description | Isoxaflutole is an isoxazole herbicide that is approved for use on field corn. It demonstrates developmental toxicity and has been classified as a Group B2 carcinogen (probable human carcinogen). |
| FRCD ID | F05093 |
| CAS Number | 141112-29-0 |
| PubChem CID | 84098 |
| Formula | C15H12F3NO4S |
| IUPAC Name | (5-cyclopropyl-1,2-oxazol-4-yl)-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]methanone |
| InChI Key | OYIKARCXOQLFHF-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H12F3NO4S/c1-24(21,22)12-6-9(15(16,17)18)4-5-10(12)13(20)11-7-19-23-14(11)8-2-3-8/h4-8H,2-3H2,1H3 |
| Canonical SMILES | CS(=O)(=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C2=C(ON=C2)C3CC3 |
| Isomeric SMILES | CS(=O)(=O)C1=C(C=CC(=C1)C(F)(F)F)C(=O)C2=C(ON=C2)C3CC3 |
| Synonyms |
UNII-0T9R0O0EYT
(5-Cyclopropylisoxazol-4-yl)(2-(methylsulfonyl)-4-(trifluoromethyl)phenyl)methanone
Isoxaflutole
141112-29-0
Merlin
0T9R0O0EYT
(5-cyclopropyl-1,2-oxazol-4-yl)-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]methanone
IFT cpd
Isoxaflutole [ISO]
HSDB 7275
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Ketones - Aryl ketones - Phenylketones |
| Direct Parent | Aryl-phenylketones |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aryl-phenylketone - Trifluoromethylbenzene - Benzenesulfonyl group - Benzoyl - 5-cyclopropylisoxazole - Cyclopropylisoxazole - Monocyclic benzene moiety - Benzenoid - Azole - Heteroaromatic compound - Isoxazole - Sulfonyl - Sulfone - Oxacycle - Azacycle - Organoheterocyclic compound - Organic oxide - Organosulfur compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Alkyl halide - Organic nitrogen compound - Alkyl fluoride - Hydrocarbon derivative - Organopnictogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 359.319 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 4 |
| Complexity | 597 |
| Monoisotopic Mass | 359.044 |
| Exact Mass | 359.044 |
| XLogP | 2.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| 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+ | 0.8997 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5309 |
| P-glycoprotein Substrate | Non-substrate | 0.8780 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8246 |
| Non-inhibitor | 0.9433 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8875 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5782 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7264 |
| CYP450 2D6 Substrate | Non-substrate | 0.7358 |
| CYP450 3A4 Substrate | Non-substrate | 0.5990 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5487 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5792 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5731 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7319 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.6064 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9772 |
| Non-inhibitor | 0.9088 | |
| AMES Toxicity | Non AMES toxic | 0.6215 |
| Carcinogens | Non-carcinogens | 0.5601 |
| Fish Toxicity | High FHMT | 0.9702 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8969 |
| Honey Bee Toxicity | Low HBT | 0.7115 |
| Biodegradation | Not ready biodegradable | 0.8761 |
| Acute Oral Toxicity | III | 0.5021 |
| Carcinogenicity (Three-class) | Non-required | 0.5956 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2854 | LogS |
| Caco-2 Permeability | 1.1379 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6308 | LD50, mol/kg |
| Fish Toxicity | 1.4194 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6880 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Fruit spices | 0820000 | European Union | 0.1* | 24/06/2015 | |
| Allspice/pimento | 0820010 | European Union | 0.1* | 24/06/2015 | |
| (a) lettuces and salad plants | 0251000 | European Union | 0.02* | 24/06/2015 | |
| Lamb's lettuces/corn salads (Italian corn salads,) | 0251010 | European Union | 0.02* | 24/06/2015 | |
| Escaroles/broad-leaved endives (Curly endives/ frisée endives, Dandelions, Puntarelle, Radicchio/red-leaved chicories, Sugar loaf chicories, Wild chicories/common chicories,) | 0251030 | European Union | 0.02* | 24/06/2015 | |
| Florence fennels | 0270040 | European Union | 0.02* | 24/06/2015 | |
| Land cresses | 0251050 | European Union | 0.02* | 24/06/2015 | |
| Roman rocket/rucola (Wall rocket,) | 0251060 | European Union | 0.02* | 24/06/2015 | |
| Red mustards | 0251070 | European Union | 0.02* | 24/06/2015 | |
| Baby leaf crops (including brassica species) (Chards/beet leaves, Escaroles/broad-leaved endives, Indian mustards/mustard greens, Lettuces, Spinaches, Other species harvested at baby leaf stage,) | 0251080 | European Union | 0.02* | 24/06/2015 | |
| Others (2) | 0251990 | European Union | 0.02* | 24/06/2015 | |
| (b) spinaches and similar leaves | 0252000 | European Union | 0.02* | 24/06/2015 | |
| Spinaches (Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-kh... | 0252010 | European Union | 0.02* | 24/06/2015 | |
| Purslanes (Agretti, Glassworts/samphires, Rock samphires, Sea asters, Sea lavenders, Winter purslanes/miner's lettuces, Karkallas/Hottentot figs/Iceplant leaves,) | 0252020 | European Union | 0.02* | 24/06/2015 | |
| Chards/beet leaves (Beetroot leaves, Swiss chards,) | 0252030 | European Union | 0.02* | 24/06/2015 | |
| Others (2) | 0252990 | European Union | 0.02* | 24/06/2015 | |
| (c) grape leaves and similar species (Climbing wattle/acacia shoots, Malabar nightshades,) | 0253000 | European Union | 0.02* | 24/06/2015 | |
| (d) watercresses (Morning glory/Chinese convolvolus/water convolvolus/kangkung, Water clovers, Water mimosas,) | 0254000 | European Union | 0.02* | 24/06/2015 | |
| (e) witloofs/Belgian endives (Dandelion leaves (forced),) | 0255000 | European Union | 0.02* | 24/06/2015 | |
| (f) herbs and edible flowers | 0256000 | European Union | 0.05* | 24/06/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Leaching of S-metolachlor, terbuthylazine, desethyl-terbuthylazine, mesotrione,flufenacet, isoxaflutole, and diketonitrile in field lysimeters as affected bythe time elapsed between spraying and first leaching event. | J Environ Sci Health B | 2015 | 26252079 |
| Water pressure head and temperature impact on isoxaflutole degradation in cropresidues and loamy surface soil under conventional and conservation tillagemanagement. | Chemosphere | 2012 Aug | 22677522 |
| [Screening method of pesticides in meat using cleanup with GPC and mini-column]. | Shokuhin Eiseigaku Zasshi | 2009 Apr | 19436160 |
| Processes affecting the dissipation of the herbicide isoxaflutole and itsdiketonitrile metabolite in agricultural soils under field conditions. | J Agric Food Chem | 2007 Oct 17 | 17880161 |
| Influence of rainfall distribution on simulations of atrazine, metolachlor, andisoxaflutole/metabolite transport in subsurface drained fields. | J Agric Food Chem | 2007 Jul 11 | 17552537 |
| Characterization of fate and transport of isoxaflutole, a soil-applied cornherbicide, in surface water using a watershed model. | J Agric Food Chem | 2005 Nov 2 | 16248595 |
| Effects of moisture, temperature, and biological activity on the degradation ofisoxaflutole in soil. | J Agric Food Chem | 2002 Sep 25 | 12236689 |
Targets
- 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:
- Zinc ion binding
- Specific Function:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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:
- Primary amine oxidase activity
- Specific Function:
- Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and signal transduction. The VCAM1/ITGA4/ITGB1 interaction may play a pathophysiologic role both in immune responses and in leukocyte emigration to sites of inflammation.
- Gene Name:
- VCAM1
- Uniprot ID:
- P19320
- Molecular Weight:
- 81275.43 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:
- 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 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 ]