Basic Info

Common NameSimetryn(F05831)
2D Structure
FRCD IDF05831
CAS Number1014-70-6
PubChem CID13905
FormulaC8H15N5S
IUPAC Name

2-N,4-N-diethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine

InChI Key

MGLWZSOBALDPEK-UHFFFAOYSA-N

InChI

InChI=1S/C8H15N5S/c1-4-9-6-11-7(10-5-2)13-8(12-6)14-3/h4-5H2,1-3H3,(H2,9,10,11,12,13)

Canonical SMILES

CCNC1=NC(=NC(=N1)SC)NCC

Isomeric SMILES

CCNC1=NC(=NC(=N1)SC)NCC

Synonyms
        
            2,4-Bis(ethylamino)-6-methylthio-1,3,5-triazine
        
            Simetryn
        
            1014-70-6
        
            GY-Bon
        
            Symetryne
        
            SIMETRYNE
        
            Cymetrin
        
            2,4-Bis(ethylamino)-6-(methylthio)-s-triazine
        
            2-Methylthio-4,6-bis(ethylamino)-s-triazine
        
            Caswell No. 094B
        
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 - Alkyl-2-thio-s-triazine - Aryl thioether - Alkylarylthioether - Heteroaromatic compound - Azacycle - Sulfenyl compound - Thioether - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organosulfur compound - Organonitrogen 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 Weight213.303
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity143
Monoisotopic Mass213.105
Exact Mass213.105
XLogP2.5
Formal Charge0
Heavy Atom Count14
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+0.8393
Human Intestinal AbsorptionHIA+0.7702
Caco-2 PermeabilityCaco2-0.5164
P-glycoprotein SubstrateNon-substrate0.6606
P-glycoprotein InhibitorNon-inhibitor0.8377
Non-inhibitor0.8150
Renal Organic Cation TransporterNon-inhibitor0.7539
Distribution
Subcellular localizationLysosome0.5192
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8683
CYP450 2D6 SubstrateNon-substrate0.7724
CYP450 3A4 SubstrateNon-substrate0.7371
CYP450 1A2 InhibitorInhibitor0.8611
CYP450 2C9 InhibitorNon-inhibitor0.6241
CYP450 2D6 InhibitorNon-inhibitor0.8473
CYP450 2C19 InhibitorInhibitor0.8445
CYP450 3A4 InhibitorNon-inhibitor0.8810
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5897
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9306
Non-inhibitor0.8022
AMES ToxicityNon AMES toxic0.8132
CarcinogensNon-carcinogens0.8803
Fish ToxicityLow FHMT0.8063
Tetrahymena Pyriformis ToxicityHigh TPT0.8815
Honey Bee ToxicityLow HBT0.6435
BiodegradationNot ready biodegradable0.9954
Acute Oral ToxicityIII0.8093
Carcinogenicity (Three-class)Danger0.3550

Model Value Unit
Absorption
Aqueous solubility-3.3174LogS
Caco-2 Permeability1.4040LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4231LD50, mol/kg
Fish Toxicity2.3091pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.3548pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Rice(Brown Rice)Japan0.05ppm
RiceKorea0.05ppm

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
Balance between herbicidal activity and toxicity effect: a case study of thejoint effects of triazine and phenylurea herbicides on Selenastrum capricornutum and Photobacterium phosphoreum.Aquat Toxicol2014 May24681700
Pesticides in water, fish and shellfish from littoral area of Lake Biwa.Bull Environ Contam Toxicol2009 Jun19277442
Biodegradation of methylthio-s-triazines by Rhodococcus sp. strain FJ1117YT, and production of the corresponding methylsulfinyl, methylsulfonyl and hydroxyanalogues.Pest Manag Sci2007 Mar17245693
Molecular and immunochemical characteristics of monoclonal and recombinantantibodies selective for the triazine herbicide simetryn and application toenvironmental analysis.J Agric Food Chem2005 Jun 2915969481
Effects of the triazine herbicide, simetryn, on freshwater plankton communities in experimental ponds.Environ Pollut199515091533