Prothioconazole

Basic Info

Common NameProthioconazole(F05759)
2D Structure
FRCD IDF05759
CAS Number178928-70-6
PubChem CID6451142
FormulaC14H15Cl2N3OS
IUPAC Name

2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1H-1,2,4-triazole-3-thione

InChI Key

MNHVNIJQQRJYDH-UHFFFAOYSA-N

InChI

InChI=1S/C14H15Cl2N3OS/c15-11-4-2-1-3-10(11)7-14(20,13(16)5-6-13)8-19-12(21)17-9-18-19/h1-4,9,20H,5-8H2,(H,17,18,21)

Canonical SMILES

C1CC1(C(CC2=CC=CC=C2Cl)(CN3C(=S)N=CN3)O)Cl

Isomeric SMILES

C1CC1(C(CC2=CC=CC=C2Cl)(CN3C(=S)N=CN3)O)Cl

Synonyms
        
            Prothioconazole
        
            178928-70-6
        
            2-(2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1H-1,2,4-triazole-3(2H)-thione
        
            2-[2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione
        
            CHEBI:84008
        
            MNHVNIJQQRJYDH-UHFFFAOYSA-N
        
            2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1H-1,2,4-triazole-3-thione
        
            2-(2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl)-1,2-dihydro-3H-1,2,4-triazole-3-thione
        
            Prothioconazole [ISO:BSI]
        
            PROLINE 480 SC Fungicide
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassHalobenzenes
Intermediate Tree NodesNot available
Direct ParentChlorobenzenes
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsChlorobenzene - Aryl chloride - Aryl halide - Azole - Triazoline - Heteroaromatic compound - 1,2,4-triazole - Tertiary alcohol - Chlorohydrin - Halohydrin - Azacycle - Organoheterocyclic compound - Organonitrogen compound - Organochloride - Organohalogen compound - Alkyl chloride - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Alkyl halide - Organooxygen compound - Organosulfur compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.

Properties

Property NameProperty Value
Molecular Weight344.254
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Complexity458
Monoisotopic Mass343.031
Exact Mass343.031
XLogP2.7
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.5599
Human Intestinal AbsorptionHIA+0.9229
Caco-2 PermeabilityCaco2-0.5406
P-glycoprotein SubstrateNon-substrate0.5999
P-glycoprotein InhibitorNon-inhibitor0.7352
Non-inhibitor0.7484
Renal Organic Cation TransporterNon-inhibitor0.6718
Distribution
Subcellular localizationMitochondria0.7366
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7565
CYP450 2D6 SubstrateNon-substrate0.8224
CYP450 3A4 SubstrateNon-substrate0.5495
CYP450 1A2 InhibitorNon-inhibitor0.5677
CYP450 2C9 InhibitorNon-inhibitor0.6053
CYP450 2D6 InhibitorNon-inhibitor0.8089
CYP450 2C19 InhibitorNon-inhibitor0.5398
CYP450 3A4 InhibitorInhibitor0.6506
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5069
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7215
Non-inhibitor0.5376
AMES ToxicityNon AMES toxic0.5785
CarcinogensNon-carcinogens0.7273
Fish ToxicityHigh FHMT0.9954
Tetrahymena Pyriformis ToxicityHigh TPT0.9495
Honey Bee ToxicityLow HBT0.7944
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5999
Carcinogenicity (Three-class)Non-required0.4706
Model Value Unit
Absorption
Aqueous solubility-3.5009LogS
Caco-2 Permeability1.0002LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5653LD50, mol/kg
Fish Toxicity1.4364pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5978pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
BarleyBritain0.05mg/kg
RyeBritain0.01mg/kg
WheatBritain0.01mg/kg
Rape SeedBritain0.05mg/kg
BarleyCanada0. 35mg/kg
Dry ChickpeasCanada0. 9mg/kg
Dry LentilsCanada0. 9mg/kg
Fat Of CattleCanada0.1mg/kg
Fat Of GoatsCanada0.1mg/kg
Fat Of HorsesCanada0.1mg/kg
Fat Of SheepCanada0.1mg/kg
Meat Byproducts Of CattleCanada0. 2mg/kg
Meat Byproducts Of GoatsCanada0. 2mg/kg
Meat Byproducts Of HogsCanada0.05mg/kg
Meat Byproducts Of HorsesCanada0. 2mg/kg
Meat Byproducts Of SheepCanada0. 2mg/kg
Meat Of CattleCanada0.02mg/kg
Meat Of GoatsCanada0.02mg/kg
Meat Of HorsesCanada0.02mg/kg
Meat Of SheepCanada0.02mg/kg

References

TitleJournalDatePubmed ID
Effect of Prothioconazole Application Timing on Fusarium Mycotoxin Content in Maize Grain.J Agric Food Chem2018 May 1629681149
Simultaneous determination of 124 pesticide residues in Chinese liquor andliquor-making raw materials (sorghum and rice hull) by rapid Multi-plugFiltration Cleanup and gas chromatography-tandem mass spectrometry.Food Chem2018 Feb 1528958527
Simultaneous Enantioselective Determination of the Chiral FungicideProthioconazole and Its Major Chiral Metabolite Prothioconazole-Desthio in Foodand Environmental Samples by Ultraperformance Liquid Chromatography-Tandem MassSpectrometry.J Agric Food Chem2017 Sep 2028844143
Antifungal metabolites from Schinopsis balansae Engl (Anacardiaceae): isolation, identification and evidences of their mode of action on Fusarium graminearumSchwabe.Nat Prod Res2017 Jun27806649
Occurrence of mycotoxins in wheat grains exposed to fungicides on fusarium head blight control in southern Brazil.J Environ Sci Health B2017 Apr 328080216
Expression of catalase, alcohol dehydrogenase, and malate dehydrogenase in rotgrains upon fungicide use on maize hybrids grown at different spacings.Genet Mol Res2017 Apr 2028437557
Quantification of potential exposure of gray partridge (Perdix perdix) topesticide active substances in farmlands.Sci Total Environ2015 Jul 1525847175
Impact of post-anthesis rainfall, fungicide and harvesting time on the concentration of deoxynivalenol and zearalenone in wheat.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201526361223
Currently used pesticides and their mixtures affect the function of sex hormonereceptors and aromatase enzyme activity.Toxicol Appl Pharmacol2013 Oct 1523871939
Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions.Int J Food Microbiol2012 Oct 122947301
Role of fungicides, application of nozzle types, and the resistance level of wheat varieties in the control of Fusarium head blight and deoxynivalenol.Toxins (Basel)2011 Nov22174980
Reduction of Fusarium head blight and deoxynivalenol in wheat with earlyfungicide applications of prothioconazole.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2010May20349372
Meta-analysis of the effects of triazole-based fungicides on wheat yield and testweight as influenced by Fusarium head blight intensity.Phytopathology2010 Feb20055650