Terbutryn

Basic Info

Common NameTerbutryn(F05959)
2D Structure
FRCD IDF05959
CAS Number886-50-0
PubChem CID13450
FormulaC10H19N5S
IUPAC Name

2-N-tert-butyl-4-N-ethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine

InChI Key

IROINLKCQGIITA-UHFFFAOYSA-N

InChI

InChI=1S/C10H19N5S/c1-6-11-7-12-8(15-10(2,3)4)14-9(13-7)16-5/h6H2,1-5H3,(H2,11,12,13,14,15)

Canonical SMILES

CCNC1=NC(=NC(=N1)SC)NC(C)(C)C

Isomeric SMILES

CCNC1=NC(=NC(=N1)SC)NC(C)(C)C

Synonyms
        
            Igran 50
        
            Terbutryn
        
            886-50-0
        
            TERBUTRYNE
        
            Clarosan
        
            Shortstop
        
            Prebane
        
            Terbutrex
        
            Igran
        
            Saterb
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTriazines
Subclass1,3,5-triazines
Intermediate Tree NodesNot available
Direct ParentMethylthio-s-triazines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsMethylthio-s-triazine - 2,4-diamine-s-triazine - Alkyl-2-thio-s-triazine - Aryl thioether - Amino-1,3,5-triazine - Aminotriazine - Secondary aliphatic/aromatic amine - Alkylarylthioether - N-aliphatic s-triazine - Heteroaromatic compound - Azacycle - Sulfenyl compound - Thioether - Secondary amine - Amine - Hydrocarbon derivative - Organosulfur compound - Organonitrogen compound - Organopnictogen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as methylthio-s-triazines. These are aromatic compounds containing a 1,3,5-triazine ring that is substituted at the 2-position with a methylthio group.

Properties

Property NameProperty Value
Molecular Weight241.357
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity206
Monoisotopic Mass241.136
Exact Mass241.136
XLogP3.7
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8296
Human Intestinal AbsorptionHIA+0.8445
Caco-2 PermeabilityCaco2-0.5433
P-glycoprotein SubstrateNon-substrate0.6094
P-glycoprotein InhibitorNon-inhibitor0.7183
Non-inhibitor0.7029
Renal Organic Cation TransporterNon-inhibitor0.7984
Distribution
Subcellular localizationMitochondria0.4740
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8618
CYP450 2D6 SubstrateNon-substrate0.7420
CYP450 3A4 SubstrateNon-substrate0.6422
CYP450 1A2 InhibitorInhibitor0.7549
CYP450 2C9 InhibitorNon-inhibitor0.5727
CYP450 2D6 InhibitorNon-inhibitor0.8623
CYP450 2C19 InhibitorInhibitor0.7353
CYP450 3A4 InhibitorNon-inhibitor0.7837
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6034
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9829
Non-inhibitor0.7993
AMES ToxicityNon AMES toxic0.8269
CarcinogensNon-carcinogens0.9016
Fish ToxicityLow FHMT0.7521
Tetrahymena Pyriformis ToxicityHigh TPT0.9049
Honey Bee ToxicityLow HBT0.6399
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7892
Carcinogenicity (Three-class)Danger0.4192
Model Value Unit
Absorption
Aqueous solubility-3.9372LogS
Caco-2 Permeability1.3604LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1037LD50, mol/kg
Fish Toxicity2.0818pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3325pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other Terrestrial Mammals,Edible OffalJapan3ppm
Other Poultry Animals,KidneyJapan0.05ppm
Peas,Immature(With Pods)Japan0.1ppm
PersimmonIsrael0. 2mg/kg
Other Poultry,EggsJapan0.05ppm
Chicken,EggsJapan0.05ppm
Other Poultry Animals,Edible OffalJapan0.05ppm
Chicken,Edible OffalJapan0.05ppm
Chicken,KidneyJapan0.05ppm
Other Poultry Animals,LiverJapan0.05ppm
Chicken,LiverJapan0.05ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
MilkJapan0.1ppm
Pig,Edible OffalJapan3ppm
Cattle,Edible OffalJapan3ppm
Other Terrestrial Mammals,KidneyJapan3ppm
Pig,KidneyJapan3ppm

References

TitleJournalDatePubmed ID
Spectrofluorimetric Method for Quantification of Triazine Herbicides inAgricultural Matrices.Anal Sci201626960611
An Improved Pneumatic Nebulization Gas-Solid Microextraction Device Used toDetect Triazine Herbicides in White Spirit.Anal Sci201626860563
Aquatic risk assessment of priority and other river basin specific pesticides in surface waters of Mediterranean river basins.Chemosphere2015 Sep26002046
Pesticide and trace metal occurrence and aquatic benchmark exceedances in surfacewaters and sediments of urban wetlands and retention ponds in Melbourne,Australia.Environ Sci Pollut Res Int2015 Jul25697552
Comprehensive two-dimensional liquid chromatography coupled to high resolutiontime of flight mass spectrometry for chemical characterization of sewagetreatment plant effluents.J Chromatogr A2015 Feb 625578044
Identification of photosynthesis inhibitors of pelagic marine algae using 96-wellplate microfractionation for enhanced throughput in effect-directed analysis.Environ Sci Technol2014 Jul 1524926900
Protocol for an electrospray ionization tandem mass spectral product ion library:development and application for identification of 240 pesticides in foods.Anal Chem2012 Jul 322686274
Atrazine and terbutryn degradation in deposits from groundwater environmentwithin the boreal region in Lahti, Finland.J Agric Food Chem2008 Dec 2419053391
Factors influencing degradation of pesticides in soil.J Agric Food Chem2007 May 3017488087
Prediction of the adsorption of ionizable pesticides in soils.J Agric Food Chem2007 Mar 2117295514
Bioconcentration, biomagnification and metabolism of 14C-terbutryn and14C-benzo[a]pyrene in Gammarus fossarum and Asellus aquaticus.Chemosphere2007 Jan16997349
Population growth study of the rotifer Brachionus sp. fed with triazine-exposed microalgae.Aquat Toxicol2007 Aug 117553575
Sorption-desorption behavior of triazine and phenylurea herbicides in Kishonriver sediments.Water Res2004 Dec15556213
Effects of terbutryn on aufwuchs and Lumbriculus variegatus in artificial indoor streams.Environ Toxicol Chem2001 Sep11521827
Analysis of triazine herbicides residues in butter and pasteurized milk.Z Lebensm Unters Forsch1988 Apr3381593