Terbutylazine
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Basic Info
| Common Name | Terbutylazine(F06008) |
| 2D Structure | |
| FRCD ID | F06008 |
| CAS Number | 5915-41-3 |
| PubChem CID | 22206 |
| Formula | C9H16ClN5 |
| IUPAC Name | 2-N-tert-butyl-6-chloro-4-N-ethyl-1,3,5-triazine-2,4-diamine |
| InChI Key | FZXISNSWEXTPMF-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H16ClN5/c1-5-11-7-12-6(10)13-8(14-7)15-9(2,3)4/h5H2,1-4H3,(H2,11,12,13,14,15) |
| Canonical SMILES | CCNC1=NC(=NC(=N1)Cl)NC(C)(C)C |
| Isomeric SMILES | CCNC1=NC(=NC(=N1)Cl)NC(C)(C)C |
| Synonyms |
TERBUTYLETHYLAZINE
Terbuthylazine
5915-41-3
Terbutylazine
Gardoprim
Terbutazine
ChlorCaragard
Primatol M
Sorgoprim
Gardeprim A 1862
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Triazines |
| Subclass | Aminotriazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aminotriazines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Amino-1,3,5-triazine - Chloro-s-triazine - Halo-s-triazine - Aminotriazine - Secondary aliphatic/aromatic amine - Aryl chloride - Aryl halide - 1,3,5-triazine - Heteroaromatic compound - Secondary amine - Azacycle - Hydrocarbon derivative - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Amine - Organopnictogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aminotriazines. These are organic compounds containing an amino group attached to a triazine ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 229.712 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 193 |
| Monoisotopic Mass | 229.109 |
| Exact Mass | 229.109 |
| XLogP | 3.1 |
| 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+ | 0.8743 |
| Human Intestinal Absorption | HIA+ | 0.9891 |
| Caco-2 Permeability | Caco2- | 0.5070 |
| P-glycoprotein Substrate | Non-substrate | 0.5531 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8203 |
| Non-inhibitor | 0.7166 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8004 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4797 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8704 |
| CYP450 2D6 Substrate | Non-substrate | 0.7623 |
| CYP450 3A4 Substrate | Non-substrate | 0.5406 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8182 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8469 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7689 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.5409 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8240 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6361 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9325 |
| Non-inhibitor | 0.8045 | |
| AMES Toxicity | Non AMES toxic | 0.9108 |
| Carcinogens | Non-carcinogens | 0.8287 |
| Fish Toxicity | Low FHMT | 0.7691 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9919 |
| Honey Bee Toxicity | Low HBT | 0.8094 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.8015 |
| Carcinogenicity (Three-class) | Danger | 0.4196 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.9843 | LogS |
| Caco-2 Permeability | 1.2993 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3703 | LD50, mol/kg |
| Fish Toxicity | 1.8807 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3873 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Citrus fruits | 0110000 | 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 | 0.05* | 01/09/2008 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 01/09/2008 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 01/09/2008 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 01/09/2008 | |
| Chestnuts | 0120040 | European Union | 0.05* | 01/09/2008 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 01/09/2008 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 01/09/2008 | |
| Macadamias | 0120070 | European Union | 0.05* | 01/09/2008 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 01/09/2008 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.05* | 01/09/2008 | |
| Pistachios | 0120100 | European Union | 0.05* | 01/09/2008 | |
| Walnuts | 0120110 | European Union | 0.05* | 01/09/2008 | |
| Others (2) | 0120990 | European Union | 0.05* | 01/09/2008 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Oxidative stress in triazine pesticide toxicity: a review of the main biomarker findings. | Arh Hig Rada Toksikol | 2018 Jun 1 | 29990300 |
| Enhanced degradation of prometryn and other s-triazine herbicides in purecultures and wastewater by polyvinyl alcohol-sodium alginate immobilizedLeucobacter sp. JW-1. | Sci Total Environ | 2018 Feb 15 | 28963898 |
| Toxicity prediction and assessment of an environmentally realistic pesticidemixture to Daphnia magna and Raphidocelis subcapitata. | Ecotoxicology | 2018 Apr 26 | 29700712 |
| Environmental and human health risk indicators for agricultural pesticides inestuaries. | Ecotoxicol Environ Saf | 2018 Apr 15 | 29288903 |
| Toxicity of environmentally realistic concentrations of chlorpyrifos and terbuthylazine in indoor microcosms. | Chemosphere | 2017 Sep | 28505576 |
| Contaminants of emerging concern in the open sea waters of the Western Mediterranean. | Environ Pollut | 2017 Oct | 28781184 |
| Quantification of the fate of mesotrione applied alone or in a herbicide mixture in two Brazilian arable soils. | Environ Sci Pollut Res Int | 2017 Mar | 28188550 |
| Use of two grasses for the phytoremediation of aqueous solutions polluted withterbuthylazine. | Int J Phytoremediation | 2016 Sep | 26934386 |
| Multivariate approach to gill pathology in European sea bass after experimental exposure to cadmium and terbuthylazine. | Ecotoxicol Environ Saf | 2016 Jul | 27057996 |
| Dual-layer solid-phase extraction based on molecular imprinting technology:Seeking a route to enhance selectivity for trace analysis of pesticide residuesin olive oil. | Electrophoresis | 2016 Jul | 27062483 |
| Soil spreading of liquid olive mill processing wastes impacts leaching ofadsorbed terbuthylazine. | Chemosphere | 2016 Aug | 27179239 |
| An Improved Pneumatic Nebulization Gas-Solid Microextraction Device Used toDetect Triazine Herbicides in White Spirit. | Anal Sci | 2016 | 26860563 |
| Aquatic risk assessment of priority and other river basin specific pesticides in surface waters of Mediterranean river basins. | Chemosphere | 2015 Sep | 26002046 |
| Ionic-liquid-impregnated resin for the microwave-assisted solid-liquid extractionof triazine herbicides in honey. | J Sep Sci | 2015 Sep | 26082329 |
| Filtration of triazine herbicides by polymer-clay sorbents: coupling anexperimental mechanistic approach with empirical modeling. | Water Res | 2015 Mar 1 | 25506764 |
| Assessment of two extraction methods to determine pesticides in soils, sediments and sludges. Application to the Túria River Basin. | J Chromatogr A | 2015 Jan 23 | 25573188 |
| Determination of triazine herbicides in fresh vegetables by dynamicmicrowave-assisted extraction coupled with homogeneous ionic liquidmicroextraction high performance liquid chromatography. | Anal Bioanal Chem | 2015 Feb | 25542578 |
| Development of a selective sorbent for the solid-phase extraction ofterbuthylazine in olive oil samples: a molecular imprinting strategy. | J Sep Sci | 2015 Apr | 25655132 |
| Leaching of S-metolachlor, terbuthylazine, desethyl-terbuthylazine, mesotrione,flufenacet, isoxaflutole, and diketonitrile in field lysimeters as affected bythe time elapsed between spraying and first leaching event. | J Environ Sci Health B | 2015 | 26252079 |
| Influence of soil biochar aging on sorption of the herbicides MCPA, nicosulfuron,terbuthylazine, indaziflam, and fluoroethyldiaminotriazine. | J Agric Food Chem | 2014 Nov 12 | 25338136 |