Terbumeton

Basic Info

Common NameTerbumeton(F06137)
2D Structure
FRCD IDF06137
CAS Number33693-04-8
PubChem CID36584
FormulaC10H19N5O
IUPAC Name

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

InChI Key

BCQMBFHBDZVHKU-UHFFFAOYSA-N

InChI

InChI=1S/C10H19N5O/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)OC)NC(C)(C)C

Isomeric SMILES

CCNC1=NC(=NC(=N1)OC)NC(C)(C)C

Synonyms
        
            TERBUMETON
        
            Terbuthylon
        
            Caragard
        
            Karagard
        
            Terbutone
        
            33693-04-8
        
            Tribunil G 14259
        
            Terbumeton [BSI:ISO]
        
            GS 14259
        
            EINECS 251-637-8
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassTriazines
SubclassAminotriazines
Intermediate Tree NodesNot available
Direct Parent1,3,5-triazine-2,4-diamines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents2,4-diamine-s-triazine - 2-methoxy-1,3,5-triazine - Alkoxy-s-triazine - Alkyl aryl ether - Secondary aliphatic/aromatic amine - N-aliphatic s-triazine - 1,3,5-triazine - Heteroaromatic compound - Ether - Secondary amine - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Amine - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as 1,3,5-triazine-2,4-diamines. These are aromatic compounds containing a 1,3,5-triazine ring which is 2,4-disusbtituted wit amine groups.

Properties

Property NameProperty Value
Molecular Weight225.296
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity206
Monoisotopic Mass225.159
Exact Mass225.159
XLogP3.1
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+0.8999
Human Intestinal AbsorptionHIA+0.9807
Caco-2 PermeabilityCaco2-0.5671
P-glycoprotein SubstrateNon-substrate0.5728
P-glycoprotein InhibitorNon-inhibitor0.7855
Non-inhibitor0.9606
Renal Organic Cation TransporterNon-inhibitor0.8608
Distribution
Subcellular localizationMitochondria0.6380
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8053
CYP450 2D6 SubstrateNon-substrate0.7513
CYP450 3A4 SubstrateNon-substrate0.5117
CYP450 1A2 InhibitorInhibitor0.7334
CYP450 2C9 InhibitorNon-inhibitor0.7572
CYP450 2D6 InhibitorNon-inhibitor0.9147
CYP450 2C19 InhibitorNon-inhibitor0.5832
CYP450 3A4 InhibitorNon-inhibitor0.8430
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8019
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9140
Non-inhibitor0.7840
AMES ToxicityNon AMES toxic0.8221
CarcinogensNon-carcinogens0.8968
Fish ToxicityLow FHMT0.9234
Tetrahymena Pyriformis ToxicityHigh TPT0.7859
Honey Bee ToxicityLow HBT0.5792
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityII0.7417
Carcinogenicity (Three-class)Non-required0.4256
Model Value Unit
Absorption
Aqueous solubility-3.1773LogS
Caco-2 Permeability1.1652LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6846LD50, mol/kg
Fish Toxicity2.0351pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1317pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
FruitAustria0.1mg/kg
StrawberrySwitzerland0.1mg/kg
GrapeSwitzerland0.1mg/kg
GrapeFrance0.1mg/kg
Citrus FruitsIsrael0.01mg/kg
Citrus FruitsItaly0.02mg/kg
PersimmonIsrael0.01mg/kg
GrapeItaly0.02mg/kg
GrapesGermany0.1mg/kg
VegetablesGermany0.01mg/kg
FruitGermany0.01mg/kg

References

TitleJournalDatePubmed ID
Enhanced degradation of prometryn and other s-triazine herbicides in purecultures and wastewater by polyvinyl alcohol-sodium alginate immobilizedLeucobacter sp. JW-1.Sci Total Environ2018 Feb 1528963898
An Improved Pneumatic Nebulization Gas-Solid Microextraction Device Used toDetect Triazine Herbicides in White Spirit.Anal Sci201626860563
Ionic-liquid-impregnated resin for the microwave-assisted solid-liquid extractionof triazine herbicides in honey.J Sep Sci2015 Sep26082329
Assessment of two extraction methods to determine pesticides in soils, sediments and sludges. Application to the Túria River Basin.J Chromatogr A2015 Jan 2325573188
Determination of triazine herbicides in fresh vegetables by dynamicmicrowave-assisted extraction coupled with homogeneous ionic liquidmicroextraction high performance liquid chromatography.Anal Bioanal Chem2015 Feb25542578
Ionic liquid-based foam flotation followed by solid phase extraction to determinetriazine herbicides in corn.Talanta2014 May24720960
Determination of triazine herbicides in vegetables by ionic liquid foamfloatation solid phase extraction high performance liquid chromatography.J Chromatogr B Analyt Technol Biomed Life Sci2014 Mar 1524607694
Multiresidue analysis of pesticides in urine of healthy adult companion dogs.Environ Sci Technol2014 Dec 1625365583
Aqueous two-phase extraction for determination of triazine herbicides in milk by high-performance liquid chromatography.J Chromatogr B Analyt Technol Biomed Life Sci2014 Dec 125444545