Metribuzin
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Basic Info
| Common Name | Metribuzin(F05105) |
| 2D Structure | |
| Description | Metribuzin (4-amino-6-tert-butyl-3-(methylthio)-as-triazin-5 (4H)-one) is a herbicide used both pre- and post-emergence in crops including soy bean, potatoes, tomatoes and sugar cane. It acts by inhibiting photosynthesis by disrupting photosystem II. It is widely used in agriculture and has been found to contaminate groundwater. |
| FRCD ID | F05105 |
| CAS Number | 21087-64-9 |
| PubChem CID | 30479 |
| Formula | C8H14N4OS |
| IUPAC Name | 4-amino-6-tert-butyl-3-methylsulfanyl-1,2,4-triazin-5-one |
| InChI Key | FOXFZRUHNHCZPX-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H14N4OS/c1-8(2,3)5-6(13)12(9)7(14-4)11-10-5/h9H2,1-4H3 |
| Canonical SMILES | CC(C)(C)C1=NN=C(N(C1=O)N)SC |
| Isomeric SMILES | CC(C)(C)C1=NN=C(N(C1=O)N)SC |
| Synonyms |
METRIBUZIN
21087-64-9
Lexone
Sencor
Metribuzine
Zenkor
Sencorex
Senkor
Lexone DF
Sencor DF
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organosulfur compounds |
| Class | Thioethers |
| Subclass | Aryl thioethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aryl thioethers |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aryl thioether - Alkylarylthioether - Triazine - 1,2,4-triazine - Heteroaromatic compound - Lactam - Azacycle - Organoheterocyclic compound - Sulfenyl compound - Organic oxide - Hydrocarbon derivative - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 214.287 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Complexity | 316 |
| Monoisotopic Mass | 214.089 |
| Exact Mass | 214.089 |
| XLogP | 1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| 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+ | 0.8927 |
| Human Intestinal Absorption | HIA+ | 0.8096 |
| Caco-2 Permeability | Caco2+ | 0.5106 |
| P-glycoprotein Substrate | Non-substrate | 0.7758 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8539 |
| Non-inhibitor | 0.9960 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9299 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7173 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7357 |
| CYP450 2D6 Substrate | Non-substrate | 0.7968 |
| CYP450 3A4 Substrate | Substrate | 0.5125 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5595 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.5724 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9527 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6499 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8751 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7369 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9854 |
| Non-inhibitor | 0.8007 | |
| AMES Toxicity | Non AMES toxic | 0.6237 |
| Carcinogens | Non-carcinogens | 0.9057 |
| Fish Toxicity | High FHMT | 0.9700 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6267 |
| Honey Bee Toxicity | Low HBT | 0.7329 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7852 |
| Carcinogenicity (Three-class) | Non-required | 0.4987 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3125 | LogS |
| Caco-2 Permeability | 1.2156 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.2588 | LD50, mol/kg |
| Fish Toxicity | 1.6252 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3095 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Celery | Japan | 0.5ppm | |||
| Carrot | Japan | 0.5ppm | |||
| Artichoke | Japan | 0.1ppm | |||
| Kale | Japan | 0.5ppm | |||
| Cashew nuts | 0120030 | European Union | 0.1* | 26/04/2017 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.1* | 26/04/2017 | |
| Citrus fruits | 0110000 | European Union | 0.1* | 26/04/2017 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.1* | 26/04/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.1* | 26/04/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.1* | 26/04/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.1* | 26/04/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.1* | 26/04/2017 | |
| Others (2) | 0110990 | European Union | 0.1* | 26/04/2017 | |
| Tree nuts | 0120000 | European Union | 0.1* | 26/04/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 26/04/2017 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 26/04/2017 | |
| Chestnuts | 0120040 | European Union | 0.1* | 26/04/2017 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 26/04/2017 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 26/04/2017 | |
| Macadamias | 0120070 | European Union | 0.1* | 26/04/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Constructing Slow-Release Formulations of Metribuzin Based on DegradablePoly(3-hydroxybutyrate). | J Agric Food Chem | 2016 Jul 20 | 27356030 |
| De-oiled two-phase olive mill waste may reduce water contamination by metribuzin. | Sci Total Environ | 2016 Jan 15 | 26437341 |
| Aptamer-based Resonance Light Scattering for Sensitive Detection of Acetamiprid. | Anal Sci | 2016 | 27396657 |
| Pesticide application and detection in variable agricultural intensity watershedsand their river systems in the maritime region of Canada. | Arch Environ Contam Toxicol | 2012 Nov | 22903630 |
| The origin of metamitron resistant Chenopodium album populations in sugar beet. | Commun Agric Appl Biol Sci | 2012 | 23878988 |
| Degradation and adsorption of pesticides in compost-based biomixtures aspotential substrates for biobeds in southern Europe. | J Agric Food Chem | 2010 Aug 25 | 20666446 |
| Synthesis and structure--activity relationships of substituted cinnamic acids andamide analogues: a new class of herbicides. | J Agric Food Chem | 2009 Apr 22 | 19368353 |
| Biocompost from sugar distillery effluent: effect on metribuzin degradation,sorption and mobility. | Pest Manag Sci | 2008 Oct | 18454433 |
| A rapid multi-residue determination method of herbicides in grain by GC-MS-SIM. | J Chromatogr Sci | 2008 May-Jun | 18492353 |
| Novel system for reducing leaching of the herbicide metribuzin usingclay-gel-based formulations. | J Agric Food Chem | 2008 Dec 24 | 19053382 |
| Factors influencing degradation of pesticides in soil. | J Agric Food Chem | 2007 May 30 | 17488087 |
| Accelerators increase permeability of cuticles for the lipophilic solutesmetribuzin and iprovalicarb but not for hydrophilic methyl glucose. | J Agric Food Chem | 2005 Apr 6 | 15796601 |
| Runoff and drainage losses of atrazine, metribuzin, and metolachlor in threewater management systems. | J Environ Qual | 2002 Jan-Feb | 11841063 |
| Determination of triazine herbicides in foods with liquid chromatography massspectrometry. | Analyst | 2000 Nov | 11193084 |
| Bioavailability in rats of bound pesticide residues from tolerant or susceptible varieties of soybean and canola treated with metribuzin or atrazine. | Chemosphere | 1998 Feb | 9451811 |
| Assessment of the reproductive and developmental toxicity of pesticide/fertilizermixtures based on confirmed pesticide contamination in California and Iowagroundwater. | Fundam Appl Toxicol | 1994 May | 8056207 |
| Influence of metribuzin on the Rhizobium leguminosarum--lentil (Lens culinaris)symbiosis. | Can J Microbiol | 1992 Apr | 1611561 |
| Triazine and chloroacetamide herbicides in Sydenham River water and municipaldrinking water, Dresden, Ontario, Canada, 1981-1987. | Arch Environ Contam Toxicol | 1990 May-Jun | 2353833 |
| Analysis of triazine herbicides residues in butter and pasteurized milk. | Z Lebensm Unters Forsch | 1988 Apr | 3381593 |
Targets
- 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:
- 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:
- 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:
- 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:
- 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor for TNFSF5/CD40LG. Transduces TRAF6- and MAP3K8-mediated signals that activate ERK in macrophages and B cells, leading to induction of immunoglobulin secretion.
- Gene Name:
- CD40
- Uniprot ID:
- P25942
- Molecular Weight:
- 30618.76 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:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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:
- 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:
- Virus receptor activity
- Specific Function:
- Binds LDL, the major cholesterol-carrying lipoprotein of plasma, and transports it into cells by endocytosis. In order to be internalized, the receptor-ligand complexes must first cluster into clathrin-coated pits.(Microbial infection) Acts as a receptor for hepatitis C virus in hepatocytes, but not through a direct interaction with viral proteins (PubMed:10535997, PubMed:12615904). Acts as a receptor for vesicular stomatitis virus (PubMed:23589850). In case of HIV-1 infection, may function as a receptor for extracellular Tat in neurons, mediating its internalization in uninfected cells (PubMed:11100124).
- Gene Name:
- LDLR
- Uniprot ID:
- P01130
- Molecular Weight:
- 95375.105 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 ]