Bitertanol

Basic Info

Common NameBitertanol(F06107)
2D Structure
FRCD IDF06107
CAS Number55179-31-2
PubChem CID91656
FormulaC20H23N3O2
IUPAC Name

3,3-dimethyl-1-(4-phenylphenoxy)-1-(1,2,4-triazol-1-yl)butan-2-ol

InChI Key

VGPIBGGRCVEHQZ-UHFFFAOYSA-N

InChI

InChI=1S/C20H23N3O2/c1-20(2,3)18(24)19(23-14-21-13-22-23)25-17-11-9-16(10-12-17)15-7-5-4-6-8-15/h4-14,18-19,24H,1-3H3

Canonical SMILES

CC(C)(C)C(C(N1C=NC=N1)OC2=CC=C(C=C2)C3=CC=CC=C3)O

Isomeric SMILES

CC(C)(C)C(C(N1C=NC=N1)OC2=CC=C(C=C2)C3=CC=CC=C3)O

Synonyms
        
            Bitertanol [BSI:ISO]
        
            Bitertanol
        
            55179-31-2
        
            Biloxazol
        
            Baycor
        
            Sibutol
        
            Baymat-spray
        
            Baycor 25 WP
        
            Bay KWG 0599
        
            KWG 0599
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBiphenyls and derivatives
Intermediate Tree NodesNot available
Direct ParentBiphenyls and derivatives
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsBiphenyl - Phenoxy compound - Phenol ether - Azole - Heteroaromatic compound - 1,2,4-triazole - Secondary alcohol - Azacycle - Organoheterocyclic compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Properties

Property NameProperty Value
Molecular Weight337.423
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Complexity398
Monoisotopic Mass337.179
Exact Mass337.179
XLogP4.2
Formal Charge0
Heavy Atom Count25
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9288
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5126
P-glycoprotein SubstrateNon-substrate0.7005
P-glycoprotein InhibitorInhibitor0.5365
Non-inhibitor0.5472
Renal Organic Cation TransporterNon-inhibitor0.8617
Distribution
Subcellular localizationMitochondria0.7624
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6615
CYP450 2D6 SubstrateNon-substrate0.7677
CYP450 3A4 SubstrateSubstrate0.6605
CYP450 1A2 InhibitorNon-inhibitor0.7118
CYP450 2C9 InhibitorInhibitor0.5851
CYP450 2D6 InhibitorNon-inhibitor0.8395
CYP450 2C19 InhibitorInhibitor0.6932
CYP450 3A4 InhibitorNon-inhibitor0.6884
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.8261
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9947
Non-inhibitor0.7296
AMES ToxicityNon AMES toxic0.7251
CarcinogensNon-carcinogens0.8189
Fish ToxicityHigh FHMT0.9476
Tetrahymena Pyriformis ToxicityHigh TPT0.8697
Honey Bee ToxicityLow HBT0.7519
BiodegradationNot ready biodegradable0.9970
Acute Oral ToxicityIII0.7898
Carcinogenicity (Three-class)Non-required0.4197
Model Value Unit
Absorption
Aqueous solubility-3.5174LogS
Caco-2 Permeability1.3052LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8608LD50, mol/kg
Fish Toxicity1.1084pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7613pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Citrus fruits0110000European Union0.01*03/11/2017
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*03/11/2017
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*03/11/2017
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*03/11/2017
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*03/11/2017
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*03/11/2017
Others (2)0110990European Union0.01*03/11/2017
Tree nuts0120000European Union0.02*03/11/2017
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*03/11/2017
Brazil nuts0120020European Union0.02*03/11/2017
Cashew nuts0120030European Union0.02*03/11/2017
Chestnuts0120040European Union0.02*03/11/2017
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*03/11/2017
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*03/11/2017
Macadamias0120070European Union0.02*03/11/2017
Pecans (Hickory nuts,)0120080European Union0.02*03/11/2017
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 ...0120090European Union0.02*03/11/2017
Pistachios0120100European Union0.02*03/11/2017
Walnuts0120110European Union0.02*03/11/2017
Others (2)0120990European Union0.02*03/11/2017

References

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In vitro-in vivo correlations for endocrine activity of a mixture of currentlyused pesticides.Toxicol Appl Pharmacol2013 Nov 123954766
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Desorption electrospray ionization mass spectrometry for trace analysis of agrochemicals in food.Anal Chem2009 Jan 1519090743
Fungicide seed treatment efficacy against Microdochium nivale and M. majus invitro and in vivo.Pest Manag Sci2008 Aug18338339
Induction and inhibition of cytochrome P450-dependent monooxygenases of rats byfungicide bitertanol.Food Chem Toxicol2006 Dec16971034
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Evaluation of a method based on liquid chromatography/electrospray tandem massspectrometry for analyzing eight triazolic and pyrimidine fungicides in extracts of processed fruits and vegetables.J AOAC Int2004 Jul-Aug15295895
Determination of tridemorph and other fungicide residues in fruit samples byliquid chromatography-electrospray tandem mass spectrometry.J Chromatogr A2004 Aug 615378888
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells bysynthetic chemicals].Shokuhin Eiseigaku Zasshi2004 Apr15272608
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Assessment of the stability of pesticides during cryogenic sample processing. 1. Apples.J Agric Food Chem2002 Jan 3011804510
Multiresidue determination of 19 fungicides in processed fruits and vegetables bycapillary gas chromatography after gel permeation chromatography.J AOAC Int1999 Sep-Oct10513021
Determination of bitertanol residues in strawberries by liquid chromatographywith fluorescence detection and confirmation by gas chromatography/massspectrometry.J AOAC Int1998 Nov-Dec9850587