Clomazone
(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 | Clomazone(F05398) |
| 2D Structure | |
| Description | Clomazone, a white solid compound, is an agricultural herbicide, and has been the active ingredient of products named. The molecule consists of a 2-chlorobenzyl group bound to a N-O heterocycle called Isoxazole. |
| FRCD ID | F05398 |
| CAS Number | 81777-89-1 |
| PubChem CID | 54778 |
| Formula | C12H14ClNO2 |
| IUPAC Name | 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-1,2-oxazolidin-3-one |
| InChI Key | KIEDNEWSYUYDSN-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H14ClNO2/c1-12(2)8-16-14(11(12)15)7-9-5-3-4-6-10(9)13/h3-6H,7-8H2,1-2H3 |
| Canonical SMILES | CC1(CON(C1=O)CC2=CC=CC=C2Cl)C |
| Isomeric SMILES | CC1(CON(C1=O)CC2=CC=CC=C2Cl)C |
| Synonyms |
2-(2-Chlorobenzyl)-4,4-dimethylisoxazolidin-3-one
Clomazone
Dimethazone
81777-89-1
Magister
Command
Gamit
UNII-570RAC03NF
HSDB 6614
FMC 57020
|
| 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 | Not available |
| Direct Parent | Chlorobenzenes |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Chlorobenzene - Aryl chloride - Aryl halide - Oxazolidinone - Isoxazolidine - Carboxylic acid derivative - Oxacycle - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 239.699 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 280 |
| Monoisotopic Mass | 239.071 |
| Exact Mass | 239.071 |
| XLogP | 2.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 16 |
| 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+ | 0.9701 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5212 |
| P-glycoprotein Substrate | Non-substrate | 0.6459 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7060 |
| Non-inhibitor | 0.8862 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7654 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5782 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8530 |
| CYP450 2D6 Substrate | Non-substrate | 0.8017 |
| CYP450 3A4 Substrate | Substrate | 0.7136 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6926 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6175 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7877 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5202 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8263 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6217 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9821 |
| Non-inhibitor | 0.7450 | |
| AMES Toxicity | Non AMES toxic | 0.5928 |
| Carcinogens | Non-carcinogens | 0.6823 |
| Fish Toxicity | High FHMT | 0.9751 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9919 |
| Honey Bee Toxicity | Low HBT | 0.8052 |
| Biodegradation | Not ready biodegradable | 0.9954 |
| Acute Oral Toxicity | III | 0.7811 |
| Carcinogenicity (Three-class) | Non-required | 0.4474 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4024 | LogS |
| Caco-2 Permeability | 1.2750 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2742 | LD50, mol/kg |
| Fish Toxicity | 1.3757 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5925 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Safflower Seeds | Japan | 0.02ppm | |||
| Sesame Seeds | Japan | 0.02ppm | |||
| Sunflower Seeds | Japan | 0.02ppm | |||
| Other Fruits | Japan | 0.02ppm | |||
| Date | Japan | 0.02ppm | |||
| Passion Fruit | Japan | 0.02ppm | |||
| Mango | Japan | 0.02ppm | |||
| Guava | Japan | 0.02ppm | |||
| Pineapple | Japan | 0.02ppm | |||
| Avocado | Japan | 0.02ppm | |||
| Papaya | Japan | 0.02ppm | |||
| Kiwifruit | Japan | 0.02ppm | |||
| Banana | Japan | 0.02ppm | |||
| Japanese Persimmon | Japan | 0.02ppm | |||
| Grape | Japan | 0.02ppm | |||
| Other Berries | Japan | 0.02ppm | |||
| Huckleberry | Japan | 0.02ppm | |||
| Japanese Pear | Japan | 0.02ppm | |||
| Kidney Beans,Immature(With Pods) | Japan | 0.05ppm | |||
| Other Liliaceous Vegetables | Japan | 0.02ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Can herbicide safeners allow selective control of weedy rice infesting ricecrops? | Pest Manag Sci | 2017 Jan | 27484802 |
| Removal of clomazone herbicide from a synthetic effluent by electrocoagulation. | Water Sci Technol | 2016 | 27332840 |
| Comparative study on effects of dietary with diphenyl diselenide on oxidativestress in carp (Cyprinus carpio) and silver catfish (Rhamdia sp.) exposed toherbicide clomazone. | Environ Toxicol Pharmacol | 2013 Sep | 23892285 |
| Biodegradation of clomazone in a California rice field soil: carbon allocationand community effects. | J Agric Food Chem | 2013 Mar 20 | 23432155 |
| Pesticide pressure and fish farming in barrage pond in Northeastern France. Part II: residues of 13 pesticides in water, sediments, edible fish and theirrelationships. | Environ Sci Pollut Res Int | 2013 Jan | 22961490 |
| Pesticide pressure and fish farming in barrage pond in northeastern France. Part III: how management can affect pesticide profiles in edible fish? | Environ Sci Pollut Res Int | 2013 Jan | 22467231 |
| Accumulation and half-lives of 13 pesticides in muscle tissue of freshwaterfishes through food exposure. | Chemosphere | 2013 Apr | 23374295 |
| Occurrence and distribution study of residues from pesticides applied undercontrolled conditions in the field during rice processing. | J Agric Food Chem | 2012 May 9 | 22497619 |
| On-farm bioremediation of dimethazone and trifluralin residues in runoff water from an agricultural field. | J Environ Sci Health B | 2012 | 22560023 |
| Evaluation of a modified QuEChERS extraction of multiple classes of pesticidesfrom a rice paddy soil by LC-APCI-MS/MS. | J Agric Food Chem | 2011 Nov 23 | 21978193 |
| Comparison of extraction solvents and conditions for herbicide residues in milledrice with liquid chromatography-diode array detection analysis (LC-DAD). | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2010Feb | 20013445 |
| Microbial degradation of clomazone under simulated California rice fieldconditions. | J Agric Food Chem | 2010 Mar 24 | 20178392 |
| Degradation of the herbicides clomazone, paraquat, and glyphosate by thermallyactivated peroxydisulfate. | J Agric Food Chem | 2010 Dec 22 | 21105654 |
| Carotenoid inhibitors reduce strigolactone production and Striga hermonthicainfection in rice. | Arch Biochem Biophys | 2010 Dec 1 | 20732294 |
| A clomazone immunoassay to study the environmental fate of the herbicide in rice (Oryza sativa) agriculture. | J Agric Food Chem | 2010 Apr 14 | 20302341 |
| Field dissipation and environmental hazard assessment of clomazone, molinate, andthiobencarb in Australian rice culture. | J Agric Food Chem | 2006 Sep 20 | 16968085 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Santi A, Menezes C, Duarte MM, Leitemperger J, Lopes T, Loro VL: Oxidative stress biomarkers and acetylcholinesterase activity in human erythrocytes exposed to clomazone (in vitro). Interdiscip Toxicol. 2011 Sep;4(3):149-53. doi: 10.2478/v10102-011-0023-9. [22058656 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element.
- Gene Name:
- NR1I3
- Uniprot ID:
- Q14994
- Molecular Weight:
- 39942.145 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:
- 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:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 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:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 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 ]