Basic Info

Common NameTerbacil(F05443)
2D Structure
Description

Terbacil is a herbicide for control of annual grasses, broad-leaved weeds and some perennial weeds that is used on a range of crops including top fruit, lucerne and some herbs. Its mode of action is selective and absorbed mainly through the roots.

FRCD IDF05443
CAS Number5902-51-2
PubChem CID22188
FormulaC9H13ClN2O2
IUPAC Name

3-tert-butyl-5-chloro-6-methyl-1H-pyrimidine-2,4-dione

InChI Key

NBQCNZYJJMBDKY-UHFFFAOYSA-N

InChI

InChI=1S/C9H13ClN2O2/c1-5-6(10)7(13)12(8(14)11-5)9(2,3)4/h1-4H3,(H,11,14)

Canonical SMILES

CC1=C(C(=O)N(C(=O)N1)C(C)(C)C)Cl

Isomeric SMILES

CC1=C(C(=O)N(C(=O)N1)C(C)(C)C)Cl

Synonyms
        
            Experimental herbicide 732
        
            TERBACIL
        
            Turbacil
        
            5902-51-2
        
            Geonter
        
            Sinbar
        
            3-tert-Butyl-5-chloro-6-methyluracil
        
            Compound 732
        
            Du Pont 732
        
            Du Pont herbicide 732
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassDiazines
SubclassPyrimidines and pyrimidine derivatives
Intermediate Tree NodesNot available
Direct ParentHalopyrimidines
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsHalopyrimidine - Pyrimidone - Aryl chloride - Aryl halide - Hydropyrimidine - Heteroaromatic compound - Vinylogous amide - Lactam - Urea - Azacycle - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Properties

Property NameProperty Value
Molecular Weight216.665
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Complexity328
Monoisotopic Mass216.067
Exact Mass216.067
XLogP1.9
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+0.9752
Human Intestinal AbsorptionHIA+0.9882
Caco-2 PermeabilityCaco2+0.5241
P-glycoprotein SubstrateNon-substrate0.7648
P-glycoprotein InhibitorNon-inhibitor0.8216
Non-inhibitor0.9755
Renal Organic Cation TransporterNon-inhibitor0.8951
Distribution
Subcellular localizationMitochondria0.6637
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7491
CYP450 2D6 SubstrateNon-substrate0.8430
CYP450 3A4 SubstrateSubstrate0.5372
CYP450 1A2 InhibitorNon-inhibitor0.7565
CYP450 2C9 InhibitorNon-inhibitor0.6721
CYP450 2D6 InhibitorNon-inhibitor0.9425
CYP450 2C19 InhibitorNon-inhibitor0.7452
CYP450 3A4 InhibitorNon-inhibitor0.9289
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9105
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9606
Non-inhibitor0.8402
AMES ToxicityNon AMES toxic0.8982
CarcinogensNon-carcinogens0.8020
Fish ToxicityLow FHMT0.5131
Tetrahymena Pyriformis ToxicityHigh TPT0.9295
Honey Bee ToxicityLow HBT0.8836
BiodegradationNot ready biodegradable0.9678
Acute Oral ToxicityIII0.7871
Carcinogenicity (Three-class)Non-required0.6198

Model Value Unit
Absorption
Aqueous solubility-2.5428LogS
Caco-2 Permeability1.4890LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1124LD50, mol/kg
Fish Toxicity1.8744pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.8142pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
LimeJapan0.1ppm
GrapefruitJapan0.1ppm
Other HerbsJapan0.05ppm
Other SpicesJapan0.1ppm
Other FruitsJapan0.1ppm
Passion FruitJapan0.1ppm
MangoJapan0.1ppm
GuavaJapan0.1ppm
PineappleJapan0.1ppm
AvocadoJapan0.1ppm
PapayaJapan0.1ppm
BananaJapan0.1ppm
Japanese PersimmonJapan0.1ppm
Water MelonJapan0.4ppm
AlmondJapan0.5ppm
PecanJapan0.1ppm
GrapeJapan0.1ppm
Other BerriesJapan0.1ppm
BlueberryJapan0.1ppm
BlackberryJapan0.1ppm

Targets

General Function:
Transmembrane signaling receptor activity
Specific Function:
Involved in lymphocyte proliferation and functions as a signal transmitting receptor in lymphocytes, natural killer (NK) cells, and platelets.
Gene Name:
CD69
Uniprot ID:
Q07108
Molecular Weight:
22559.25 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Transferase activity
Specific Function:
Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
Gene Name:
CD38
Uniprot ID:
P28907
Molecular Weight:
34328.145 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]