Bentazon
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Basic Info
| Common Name | Bentazon(F05390) |
| 2D Structure | |
| Description | Bentazon is a chemical manufactured by BASF Chemicals for use in herbicides. It is categorized under the thiadiazine group of chemicals. Sodium bentazon is available commercially and appears slightly brown in colour. Bentazon has been classified by the EPA as a Group E chemical, because it is believed to be non-carcinogenic to humans (as based on testing conducted on animals). However, there are no studies or experiments that can determine toxic and/or carcinogenic effects of bentazon on humans. |
| FRCD ID | F05390 |
| CAS Number | 25057-89-0 |
| PubChem CID | 2328 |
| Formula | C10H12N2O3S |
| IUPAC Name | 2,2-dioxo-3-propan-2-yl-1H-2$l^{6},1,3-benzothiadiazin-4-one |
| InChI Key | ZOMSMJKLGFBRBS-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H12N2O3S/c1-7(2)12-10(13)8-5-3-4-6-9(8)11-16(12,14)15/h3-7,11H,1-2H3 |
| Canonical SMILES | CC(C)N1C(=O)C2=CC=CC=C2NS1(=O)=O |
| Isomeric SMILES | CC(C)N1C(=O)C2=CC=CC=C2NS1(=O)=O |
| Wikipedia | Bentazon |
| Synonyms |
Bentazone
bentazon
Basagran
25057-89-0
Bendioxide
Leader
Basagran 480
Pentazone
Laddok
Pledge
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Not available |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzenoids |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Benzenoid - Vinylogous amide - Organic sulfuric acid or derivatives - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzenoids. These are aromatic compounds containing one or more benzene rings. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 240.277 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 385 |
| Monoisotopic Mass | 240.057 |
| Exact Mass | 240.057 |
| XLogP | 2.8 |
| 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+ | 0.8664 |
| Human Intestinal Absorption | HIA+ | 0.9936 |
| Caco-2 Permeability | Caco2- | 0.5306 |
| P-glycoprotein Substrate | Non-substrate | 0.6768 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6472 |
| Non-inhibitor | 0.9555 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9227 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7435 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.5824 |
| CYP450 2D6 Substrate | Non-substrate | 0.8480 |
| CYP450 3A4 Substrate | Non-substrate | 0.6057 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7932 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6739 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9119 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7348 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9254 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7750 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9871 |
| Non-inhibitor | 0.8970 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.7725 |
| Fish Toxicity | High FHMT | 0.9155 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7744 |
| Honey Bee Toxicity | Low HBT | 0.8359 |
| Biodegradation | Not ready biodegradable | 0.8325 |
| Acute Oral Toxicity | III | 0.7684 |
| Carcinogenicity (Three-class) | Non-required | 0.6425 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.7428 | LogS |
| Caco-2 Permeability | 1.4815 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3704 | LD50, mol/kg |
| Fish Toxicity | 2.2830 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4253 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.03* | 18/05/2015 | |
| Citrus fruits | 0110000 | European Union | 0.03* | 18/05/2015 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.03* | 18/05/2015 | |
| 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* | 18/05/2015 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.03* | 18/05/2015 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.03* | 18/05/2015 | |
| 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* | 18/05/2015 | |
| Others (2) | 0110990 | European Union | 0.03* | 18/05/2015 | |
| Tree nuts | 0120000 | European Union | 0.03* | 18/05/2015 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.03* | 18/05/2015 | |
| Brazil nuts | 0120020 | European Union | 0.03* | 18/05/2015 | |
| Cashew nuts | 0120030 | European Union | 0.03* | 18/05/2015 | |
| Chestnuts | 0120040 | European Union | 0.03* | 18/05/2015 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.03* | 18/05/2015 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.03* | 18/05/2015 | |
| Macadamias | 0120070 | European Union | 0.03* | 18/05/2015 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.03* | 18/05/2015 | |
| Pistachios | 0120100 | European Union | 0.03* | 18/05/2015 | |
| Walnuts | 0120110 | European Union | 0.03* | 18/05/2015 | |
| Others (2) | 0120990 | European Union | 0.03* | 18/05/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Ecological risk analysis of pesticides used on irrigated rice crops in southernBrazil. | Chemosphere | 2016 Nov | 27479455 |
| Organomineral Interactions and Herbicide Sorption in Brazilian Tropical andSubtropical Oxisols under No-Tillage. | J Agric Food Chem | 2016 May 25 | 26666375 |
| A double built-in containment strategy for production of recombinant proteins in transgenic rice. | PLoS One | 2014 Dec 22 | 25531447 |
| Determination and occurrence of phenoxyacetic acid herbicides and theirtransformation products in groundwater using ultra high performance liquidchromatography coupled to tandem mass spectrometry. | Molecules | 2014 Dec 10 | 25514054 |
| Expression and purification of recombinant human serum albumin from selectivelyterminable transgenic rice. | J Zhejiang Univ Sci B | 2013 Oct | 24101203 |
| Preparation of mesoporous activated carbon from palm-date pits: optimizationstudy on removal of bentazon, carbofuran, and 2,4-D using response surfacemethodology. | Water Sci Technol | 2013 | 24135098 |
| Before the curtain falls: endocrine-active pesticides--a German contaminationlegacy. | Rev Environ Contam Toxicol | 2011 | 21541850 |
| 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 |
| A selectively terminable transgenic rice line expressing human lactoferrin. | Protein Expr Purif | 2010 Nov | 20433928 |
| The influence of small- and large-scale composting on the dissipation ofpesticide residues in a biopurification matrix. | J Sci Food Agric | 2010 May | 20393991 |
| Photodegradation of bentazon, clopyralid, and triclopyr on model leaves:importance of a systematic evaluation of pesticide photostability on crops. | J Agric Food Chem | 2009 Mar 11 | 19222158 |
| A strategy to provide long-term control of weedy rice while mitigating herbicide resistance transgene flow, and its potential use for other crops with relatedweeds. | Pest Manag Sci | 2009 Jul | 19367567 |
| Germination behaviour of seeds from herbicide treated plants of Chenopodium albumL. | An Acad Bras Cienc | 2009 Dec | 19893909 |
| Influence of surfactants on the leaching of bentazone in a sandy loam soil. | Pest Manag Sci | 2009 Aug | 19365877 |
| In-situ microcosms, a tool for assessment of pesticide impacts on oyster spat(Crassostrea gigas). | Ecotoxicology | 2008 May | 18236155 |
| Lysimeter experiment to investigate the potential influence of diffusion-limited sorption on pesticide availability for leaching. | J Agric Food Chem | 2006 Nov 29 | 17117804 |
| Physiological and biochemical characterization of quinclorac resistance in afalse cleavers (Galium spurium L.) biotype. | J Agric Food Chem | 2005 Feb 23 | 15713032 |
| Salicylate activity. 2. Potentiation of atrazine. | J Agric Food Chem | 2005 Dec 14 | 16332129 |
| Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds ofglyphosate-treated, glyphosate-resistant soybean. | J Agric Food Chem | 2003 Jan 1 | 12502430 |
| Influence of organic matter and pH on bentazone sorption in soils. | J Agric Food Chem | 2003 Aug 27 | 12926884 |
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:
- 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:
- Serine-type endopeptidase inhibitor activity
- Specific Function:
- Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
- Gene Name:
- SERPINE1
- Uniprot ID:
- P05121
- Molecular Weight:
- 45059.695 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:
- Cytokine activity
- Specific Function:
- Cytokine that affects the growth, movement, or activation state of cells that participate in immune and inflammatory response. Chemotactic for activated T-cells. Binds to CXCR3.
- Gene Name:
- CXCL9
- Uniprot ID:
- Q07325
- Molecular Weight:
- 14018.72 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:
- Platelet-derived growth factor binding
- Specific Function:
- Collagen type III occurs in most soft connective tissues along with type I collagen. Involved in regulation of cortical development. Is the major ligand of GPR56 in the developing brain and binding to GPR56 inhibits neuronal migration and activates the RhoA pathway by coupling GPR56 to GNA13 and possibly GNA12.
- Gene Name:
- COL3A1
- Uniprot ID:
- P02461
- Molecular Weight:
- 138564.005 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 ]