Oxadiazon
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Oxadiazon(F05115) |
| 2D Structure | |
| Description | Oxadiazon is used as pre-emergence and post-emergence herbicide. It is mainly used for cotton, rice, soybean and sunflower and acts by inhibiting protoporphyrinogen oxidase (PPO). |
| FRCD ID | F05115 |
| CAS Number | 19666-30-9 |
| PubChem CID | 29732 |
| Formula | C15H18Cl2N2O3 |
| IUPAC Name | 5-tert-butyl-3-(2,4-dichloro-5-propan-2-yloxyphenyl)-1,3,4-oxadiazol-2-one |
| InChI Key | CHNUNORXWHYHNE-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H18Cl2N2O3/c1-8(2)21-12-7-11(9(16)6-10(12)17)19-14(20)22-13(18-19)15(3,4)5/h6-8H,1-5H3 |
| Canonical SMILES | CC(C)OC1=C(C=C(C(=C1)N2C(=O)OC(=N2)C(C)(C)C)Cl)Cl |
| Isomeric SMILES | CC(C)OC1=C(C=C(C(=C1)N2C(=O)OC(=N2)C(C)(C)C)Cl)Cl |
| Synonyms |
Oxadiazon [ANSI:BSI:ISO]
OXADIAZON
19666-30-9
Ronstar
Oxadiazone
Oxydiazon
Caswell No. 624A
RP 17623
UNII-C6U0E0YTP6
HSDB 6936
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Halobenzenes |
| Intermediate Tree Nodes | Chlorobenzenes |
| Direct Parent | Dichlorobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Phenoxy compound - 1,3-dichlorobenzene - Phenol ether - Alkyl aryl ether - Aryl chloride - Aryl halide - 1,3,4-oxadiazole - Azole - Oxadiazole - Heteroaromatic compound - Ether - Organoheterocyclic compound - Azacycle - Oxacycle - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxide - Organic nitrogen compound - Organopnictogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 345.22 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 462 |
| Monoisotopic Mass | 344.069 |
| Exact Mass | 344.069 |
| XLogP | 4.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| 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+ | 0.9472 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5093 |
| P-glycoprotein Substrate | Non-substrate | 0.8710 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6925 |
| Non-inhibitor | 0.7401 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9478 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7369 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7038 |
| CYP450 2D6 Substrate | Non-substrate | 0.8157 |
| CYP450 3A4 Substrate | Substrate | 0.7208 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5663 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5900 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9196 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8671 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8681 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8202 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9869 |
| Non-inhibitor | 0.8278 | |
| AMES Toxicity | Non AMES toxic | 0.7397 |
| Carcinogens | Non-carcinogens | 0.7230 |
| Fish Toxicity | High FHMT | 0.9995 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9221 |
| Honey Bee Toxicity | Low HBT | 0.7644 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7858 |
| Carcinogenicity (Three-class) | Non-required | 0.4459 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -5.6279 | LogS |
| Caco-2 Permeability | 1.4002 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0254 | LD50, mol/kg |
| Fish Toxicity | 0.6814 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7512 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Rice (African rice, Hybrid Nerica®, Indian rice/wild rice,) | 0500060 | European Union | 0.05* | 01/09/2008 | |
| Wheat (Durum wheat, Einkorn wheat/small spelt/one-grain wheat, Emmer wheat, Khorasan wheat, Spelt, Triticale, Other species of genus Triticum, not elsewhere mentioned,) | 0500090 | European Union | 0.05* | 01/09/2008 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 01/09/2008 | |
| 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 | 0.05* | 01/09/2008 | |
| (d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark... | 0639000 | European Union | 0.05* | 01/09/2008 | |
| Edible offals (other than liver and kidney) | 1014050 | European Union | 0.05* | 01/09/2008 | |
| Edible offals (other than liver and kidney) | 1015050 | European Union | 0.05* | 01/09/2008 | |
| (f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo... | 1016000 | European Union | 0.05* | 01/09/2008 | |
| Rye | 0500070 | European Union | 0.05* | 01/09/2008 | |
| Sorghum (Durra/jowari/milo, Sudan grass, Other species of genus Sorghum, not elsewhere mentioned,) | 0500080 | European Union | 0.05* | 01/09/2008 | |
| Others (2) | 0500990 | European Union | 0.05* | 01/09/2008 | |
| TEAS, COFFEE, HERBAL INFUSIONS, COCOA AND CAROBS | 0600000 | European Union | 0.05* | 01/09/2008 | |
| Teas | 0610000 | European Union | 0.05* | 01/09/2008 | |
| Coffee beans | 0620000 | European Union | 0.05* | 01/09/2008 | |
| Herbal infusions from | 0630000 | European Union | 0.05* | 01/09/2008 | |
| (a) flowers | 0631000 | European Union | 0.05* | 01/09/2008 | |
| Chamomile | 0631010 | European Union | 0.05* | 01/09/2008 | |
| Hibiscus/roselle | 0631020 | European Union | 0.05* | 01/09/2008 | |
| Jasmine | 0631040 | European Union | 0.05* | 01/09/2008 | |
| Lime/linden | 0631050 | European Union | 0.05* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of magnetic dispersive solid phase extraction using toner powder asan efficient and economic sorbent in combination with dispersive liquid-liquidmicroextraction for extraction of some widely used pesticides in fruit juices. | J Chromatogr A | 2018 Jan 12 | 29174132 |
| β-catenin Mutations Are Not Involved in Early-stage Hepatocarcinogenesis Induced by Protoporphyrinogen Oxidase Inhibitors in Mice. | Toxicol Pathol | 2017 Jun | 28580885 |
| Occurrence and removal of organic micropollutants: An overview of the watch list of EU Decision 2015/495. | Water Res | 2016 May 1 | 26967909 |
| Influence of Environmental Factors, Cultural Practices, and Herbicide Applicationon Seed Germination and Emergence Ecology of Ischaemum rugosum Salisb. | PLoS One | 2015 Sep 14 | 26368808 |
| Metabonomic strategy for the investigation of the mode of action of thephytotoxin (5S,8R,13S,16R)-(-)-pyrenophorol using 1H nuclear magnetic resonancefingerprinting. | J Agric Food Chem | 2006 Mar 8 | 16506820 |
| [Determination of oxadiazon residues in cereals by gas chromatography-massspectrometry]. | Se Pu | 2002 Mar | 12541984 |
Targets
- General Function:
- Oxygen-dependent protoporphyrinogen oxidase activity
- Specific Function:
- Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX.
- Gene Name:
- PPOX
- Uniprot ID:
- P50336
- Molecular Weight:
- 50764.8 Da
References
- Zuo Y, Yang SG, Jiang LL, Hao GF, Wang ZF, Wu QY, Xi Z, Yang GF: Quantitative structure-activity relationships of 1,3,4-thiadiazol-2(3H)-ones and 1,3,4-oxadiazol-2(3H)-ones as human protoporphyrinogen oxidase inhibitors. Bioorg Med Chem. 2012 Jan 1;20(1):296-304. doi: 10.1016/j.bmc.2011.10.079. Epub 2011 Nov 10. [22130420 ]
- 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 ]
- 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:
- 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 ]
- 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:
- 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:
- 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:
- Zinc ion binding
- Specific Function:
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
- Gene Name:
- RARA
- Uniprot ID:
- P10276
- Molecular Weight:
- 50770.805 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 ]