Metamitron
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Basic Info
| Common Name | Metamitron(F06132) |
| 2D Structure | |
| FRCD ID | F06132 |
| CAS Number | 41394-05-2 |
| PubChem CID | 38854 |
| Formula | C10H10N4O |
| IUPAC Name | 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5-one |
| InChI Key | VHCNQEUWZYOAEV-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3 |
| Canonical SMILES | CC1=NN=C(C(=O)N1N)C2=CC=CC=C2 |
| Isomeric SMILES | CC1=NN=C(C(=O)N1N)C2=CC=CC=C2 |
| Synonyms |
METAMITRON
Goltix
41394-05-2
Herbrak
Metamiton
4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5-one
Metamitron [German]
Methiamitron
4-Amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one
DRW 1139
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazines |
| Subclass | 1,2,4-triazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 1,2,4-triazines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | 1,2,4-triazine - Benzenoid - Monocyclic benzene moiety - Heteroaromatic compound - Lactam - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 1,2,4-triazines. These are compounds containing a triazine ring, which is a heterocyclic ring, similar to the six-member benzene ring but with three carbons replaced by nitrogen atoms, at ring positions 1, 2, and 4. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 202.217 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Complexity | 328 |
| Monoisotopic Mass | 202.085 |
| Exact Mass | 202.085 |
| XLogP | 0.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.9865 |
| Human Intestinal Absorption | HIA+ | 0.9972 |
| Caco-2 Permeability | Caco2+ | 0.6901 |
| P-glycoprotein Substrate | Non-substrate | 0.7526 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8587 |
| Non-inhibitor | 0.9924 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9155 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8962 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6432 |
| CYP450 2D6 Substrate | Non-substrate | 0.8497 |
| CYP450 3A4 Substrate | Non-substrate | 0.5053 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8058 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5736 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9522 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7191 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9476 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.5000 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9665 |
| Non-inhibitor | 0.8323 | |
| AMES Toxicity | Non AMES toxic | 0.5757 |
| Carcinogens | Non-carcinogens | 0.9016 |
| Fish Toxicity | High FHMT | 0.9301 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5000 |
| Honey Bee Toxicity | Low HBT | 0.9142 |
| Biodegradation | Not ready biodegradable | 0.9937 |
| Acute Oral Toxicity | III | 0.7841 |
| Carcinogenicity (Three-class) | Non-required | 0.4628 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.6526 | LogS |
| Caco-2 Permeability | 1.2379 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1762 | LD50, mol/kg |
| Fish Toxicity | 1.8621 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2034 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.1* | 01/09/2008 | |
| Citrus fruits | 0110000 | European Union | 0.1* | 01/09/2008 | |
| Fruiting vegetables | 0230000 | European Union | 0.1* | 01/09/2008 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.1* | 01/09/2008 | |
| 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* | 01/09/2008 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.1* | 01/09/2008 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.1* | 01/09/2008 | |
| 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* | 01/09/2008 | |
| Others (2) | 0110990 | European Union | 0.1* | 01/09/2008 | |
| Tree nuts | 0120000 | European Union | 0.1* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.1* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.1* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.1* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.1* | 01/09/2008 | |
| Quinces (Chinese quinces, Japanese quinces,) | 0130030 | European Union | 0.1* | 01/09/2008 | |
| Medlars | 0130040 | European Union | 0.1* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Field dissipation of metamitron in soil and sugar beet crop. | Bull Environ Contam Toxicol | 2013 Jan | 23135307 |
| Application of RP-HPLC-diode array detector after SPE to the determination ofpesticides in pepper samples. | J AOAC Int | 2012 Sep-Oct | 23175966 |
| The origin of metamitron resistant Chenopodium album populations in sugar beet. | Commun Agric Appl Biol Sci | 2012 | 23878988 |
| Effect of selected sugar beet herbicides on germination of various Chenopodiumalbum populations. | Commun Agric Appl Biol Sci | 2007 | 18399450 |
| Glyphosate adsorption in soils compared to herbicides replaced with theintroduction of glyphosate resistant crops. | Chemosphere | 2005 Nov | 15951002 |
| Aquatic risk assessment of a realistic exposure to pesticides used in bulb crops: a microcosm study. | Environ Toxicol Chem | 2004 Jun | 15376534 |
| Metabolism of metamitron in goat following a single oral administration of anontoxic dose level: a continued study. | J Agric Food Chem | 2004 Dec 1 | 15563222 |
| Toxicokinetics, recovery, and metabolism of metamitron in goat. | J Agric Food Chem | 2003 Sep 24 | 13129305 |
| Acid hydrolysis of 1,6-dihydro-4-amino-3-methyl-6-phenyl-1,2, 4-triazin-5(4H)-one(1,6-dihydrometamitron). | J Agric Food Chem | 1999 Sep | 10552738 |