Basic Info

Common NameHexaconazole(F05422)
2D Structure
Description

Hexaconazole is a systemic conazole (imidazole) fungicide used for the control of many seed-borne and soil-borne diseases and fungi particularly Ascomycetes and Basidiomycetes. It is commonly used in the control of apple, coffee and peanut diseases. It has a broad spectrum of action, being systemic with protective and curative action. It is known to disrupt membrane function.

FRCD IDF05422
CAS Number79983-71-4
PubChem CID66461
FormulaC14H17Cl2N3O
IUPAC Name

2-(2,4-dichlorophenyl)-1-(1,2,4-triazol-1-yl)hexan-2-ol

InChI Key

STMIIPIFODONDC-UHFFFAOYSA-N

InChI

InChI=1S/C14H17Cl2N3O/c1-2-3-6-14(20,8-19-10-17-9-18-19)12-5-4-11(15)7-13(12)16/h4-5,7,9-10,20H,2-3,6,8H2,1H3

Canonical SMILES

CCCCC(CN1C=NC=N1)(C2=C(C=C(C=C2)Cl)Cl)O

Isomeric SMILES

CCCCC(CN1C=NC=N1)(C2=C(C=C(C=C2)Cl)Cl)O

Synonyms
        
            Anvil (fungicide)
        
            Hexaconazole
        
            79983-71-4
        
            Contaf
        
            Sitara
        
            Anvil
        
            Anvil L
        
            Contaf 5EC
        
            Chlortriafol
        
            Anvil Liquid
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassHalobenzenes
Intermediate Tree NodesChlorobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
Substituents1,3-dichlorobenzene - Aryl chloride - Aryl halide - Azole - Tertiary alcohol - 1,2,4-triazole - Heteroaromatic compound - Organoheterocyclic compound - Azacycle - Aromatic alcohol - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Organochloride - Organohalogen compound - Organopnictogen compound - Alcohol - Organic oxygen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.

Properties

Property NameProperty Value
Molecular Weight314.21
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Complexity308
Monoisotopic Mass313.075
Exact Mass313.075
XLogP3.7
Formal Charge0
Heavy Atom Count20
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+0.6831
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5155
P-glycoprotein SubstrateSubstrate0.6612
P-glycoprotein InhibitorNon-inhibitor0.7727
Non-inhibitor0.7517
Renal Organic Cation TransporterNon-inhibitor0.6097
Distribution
Subcellular localizationMitochondria0.7030
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7369
CYP450 2D6 SubstrateNon-substrate0.8451
CYP450 3A4 SubstrateSubstrate0.5561
CYP450 1A2 InhibitorNon-inhibitor0.6849
CYP450 2C9 InhibitorNon-inhibitor0.6772
CYP450 2D6 InhibitorNon-inhibitor0.8339
CYP450 2C19 InhibitorNon-inhibitor0.5303
CYP450 3A4 InhibitorInhibitor0.7352
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6949
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.6715
Non-inhibitor0.6097
AMES ToxicityNon AMES toxic0.6588
CarcinogensNon-carcinogens0.7607
Fish ToxicityHigh FHMT0.9942
Tetrahymena Pyriformis ToxicityHigh TPT0.9861
Honey Bee ToxicityLow HBT0.8919
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7951
Carcinogenicity (Three-class)Non-required0.5519

Model Value Unit
Absorption
Aqueous solubility-3.1817LogS
Caco-2 Permeability1.0895LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1883LD50, mol/kg
Fish Toxicity1.2467pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6344pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Beans (with pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, ...0260010European Union0.01*26/04/2013
Beans (without pods) (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap bean...0260020European Union0.01*26/04/2013
Oil palms kernels (Argan nuts, Babassu palm nuts, Jojoba nuts, Shea nuts,)0402020European Union0.02*26/04/2013
Buckwheat and other pseudocereals (Amaranth/kiwicha, Amaranth/kiwicha, Amaranth/kiwicha, Kaniwa/canihua, Quinoa, Chia seeds,)0500020European Union0.01*26/04/2013
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.05*26/04/2013
Citrus fruits0110000European Union0.01*26/04/2013
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*26/04/2013
Rosemary (Santolina/green lavander cotton, Green santolina,)0256060European Union0.02*26/04/2013
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*26/04/2013
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*26/04/2013
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*26/04/2013
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*26/04/2013
Others (2)0110990European Union0.01*26/04/2013
Tree nuts0120000European Union0.02*26/04/2013
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*26/04/2013
Brazil nuts0120020European Union0.02*26/04/2013
Cashew nuts0120030European Union0.02*26/04/2013
Chestnuts0120040European Union0.02*26/04/2013
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*26/04/2013
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*26/04/2013

References

TitleJournalDatePubmed ID
Nanohexaconazole: synthesis, characterisation and efficacy of a novel fungicidal nanodispersion.IET Nanobiotechnol2018 Sep30104464
Synthesis of (Hexaconazole-Zinc/Aluminum-Layered Double Hydroxide Nanocomposite) Fungicide Nanodelivery System for Controlling Ganoderma Disease in Oil Palm.J Agric Food Chem2018 Jan 3129281878
Factors Affecting the Bioaccessibility and Intestinal Transport ofDifenoconazole, Hexaconazole, and Spirodiclofen in Human Caco-2 Cells Followingin Vitro Digestion.J Agric Food Chem2017 Oct 1828915046
Pesticide pollution of multiple drinking water sources in the Mekong Delta,Vietnam: evidence from two provinces.Environ Sci Pollut Res Int2015 Jun25572267
Pesticide residue analysis of soil, water, and grain of IPM basmati rice.Environ Monit Assess2014 Dec25213562
Analysis of isobaric pesticides in pepper with high-resolution liquidchromatography and mass spectrometry: complementary or redundant?J Agric Food Chem2013 Mar 1323305249
Studies of enantiomeric degradation of the triazole fungicide hexaconazole intomato, cucumber, and field soil by chiral liquid chromatography-tandem massspectrometry.Chirality2013 Mar23335346
Monitoring of pesticide residues in South Indian tea.Environ Monit Assess2013 Aug23341056
Enantioselective residue dissipation of hexaconazole in cucumber (Cucumis sativusL.), head cabbage (Brassica oleracea L. var. caulorapa DC.), and soils.J Agric Food Chem2012 Mar 722309697
The decline and residues of hexaconazole in tomato and soil.Environ Monit Assess2012 Mar21533586
Monitoring and risk assessment of pesticides in fresh omija (Schizandra chinensisBaillon) fruit and juice.Food Chem Toxicol2012 Feb22079148
Survey on the pesticide residues in tea in south India.Environ Monit Assess2011 May20640937
Reducing the impact of pesticides on biological control in Australian vineyards: pesticide mortality and fecundity effects on an indicator species, the predatory mite Euseius victoriensis (Acari: Phytoseiidae).J Econ Entomol2010 Dec21309226
Development of monoclonal immunoassays for the determination of triazolefungicides in fruit juices.J Agric Food Chem2008 Oct 818783243
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
Sorption behavior of triazole fungicides in Indian soils and its correlation withsoil properties.J Agric Food Chem2002 Oct 2312381130
Pesticide residues in grapes, wine, and their processing products.J Agric Food Chem2000 Apr10775335
Application of solid-phase partition cartridges in the determination of fungicideresidues in vegetable samples.J Chromatogr1993 Jul 238360304

Targets

General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 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:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 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:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 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:
Scaffold protein binding
Specific Function:
Receptor for extracellular adenine nucleotides such as ATP and ADP. In platelets binding to ADP leads to mobilization of intracellular calcium ions via activation of phospholipase C, a change in platelet shape, and probably to platelet aggregation.
Gene Name:
P2RY1
Uniprot ID:
P47900
Molecular Weight:
42071.08 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.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 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:
Zinc ion binding
Specific Function:
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
Gene Name:
NR1I2
Uniprot ID:
O75469
Molecular Weight:
49761.245 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:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 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:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 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:
Oxygen binding
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:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 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 d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 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 ]