Basic information
- CAS
125116-23-6- Standard SMILES
CC1(C)CCC(Cc2ccc(Cl)cc2)C1(O)Cn1cncn1- InChIKey
XWPZUHJBOLQNMN-UHFFFAOYSA-N- Molecular formula
- C17H22ClN3O
- Average molar mass
- 319.8 g/mol
- Monoisotopic mass
- 319.14514
Overview
Metconazole is a member of the class of cyclopentanols carrying 1,2,4-triazol-1-ylmethyl and 4-chlorobenzyl and geminal dimethyl substituents at positions 1, 2 and 5 respectively. Used to control a range of fungal infections including alternaria, rusts, fusarium and septoria diseases. It has a role as an EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor and an antifungal agrochemical. It is a member of cyclopentanols, a tertiary alcohol, a member of triazoles, a member of monochlorobenzenes, a conazole fungicide and a triazole fungicide.
Names & identifiers
- Preferred name
- Metconazole
- IUPAC
- 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol
- English name
- METCONAZOLE
- Molecular formula
- C17H22ClN3O
- Molecular weight
- 319.83
Names & synonyms
Metconazole125116-23-6DTXSID4034497CARAMBAQUASH5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-olDTXCID2014497CHEBI:81773A2F791945QCyclopentanol, 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-5-((4-chlorophenyl)methyl)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentan-1-olCYCLOPENTANOL, 5-((4-CHLOROPHENYL)METHYL)-2,2-DIMETHYL-1-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-
Show more names
(1RS,5RSmetaconazoleMetconazole 0Metconazole [iso][2H6]-MetconazoleC14955000 Metconazolemetconazole (bsi,pa iso)Metconazole@10 μg/mL in AcCN
RefChem:156825603-031-3cis-metconazoleMetconazole Solution in MethanolMetconazole Solution in AcetonitrileMetconazole 10 |Ig/mL in CyclohexaneMetconazole 10 microg/mL in CyclohexaneMetconazole 100 |Ig/mL in Acetonitrile
Database identifiers
- CAS
125116-23-6- PubChem CID
- 86210
- DTXSID
DTXSID4034497- ChEMBL
CHEMBL1883512- ChEBI
CHEBI:81773- EC Number
- 603-031-3
- Nikkaji
- J676.712E
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 50.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 384
Experimental & physicochemical properties
Pesticides
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
Pesticide (Metconazole) -> USDA PDB
Pesticide
LogP3.93
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
169.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID4034497]
168.62 Ų [M+H]+ [CCS Type: TW]
185.36 Ų [M+Cl]-
167.7 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]
Physicochemical properties
- Melting point
- 111.5 °C · 111.5°C
- Boiling point
- 285 °C · 285°C (rough estimate)
- Density
- 1.1888 · 1.1888 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)
- pka
- 13.82 · 13.82±0.60(Predicted)
- BRN
- 8333708 · 8333708
- Henry's Law Constant
- 3.8 · 3.8×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Major Application
- agricultureenvironmental
- InChI
- InChI=1S/C17H22ClN3O/c1-16(2)8-7-14(9-13-3-5-15(18)6-4-13)17(16,22)10-21-12-19-11-20-21/h3-6,11-12,14,22H,7-10H2,1-2H3
- InChIKey
- XWPZUHJBOLQNMN-UHFFFAOYSA-N
- SMILES
- C1(CN2C=NC=N2)(O)C(CC2=CC=C(Cl)C=C2)CCC1(C)C
- FDA UNII
- 2 F791945Q · A2F791945Q
- Pesticides Freedom of Information Act (FOIA)
- Metconazole
- EPA Substance Registry System
- Metconazole (125116-23-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS08,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H361d-H411
- Precautionary statements
- 201 · P201-P202-P264-P273-P301+P312-P308+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,N
- Risk Statements
- 22 · 22-51/53
- Safety Statements
- 60 · 60
- RIDADR
- 3077 · UN3077 9/PG 3
- WGK Germany
- 2 · 2
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Repr. 2
Safety & regulation
GHS classification
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)
Danger
H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Commission Regulation (EC) No 451/2000
Metconazole is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
2006/74/EC, Reg. (EU) 2018/524, Reg. (EU) 2019/168, Reg. (EU) 2020/421, Reg. (EU) 2021/566, Reg. (EU) 2022/378, Reg. (EU) 2023/689, Reg. (EU) 2024/1749, Reg. (EU) 2026/398, Reg. (EU) No 540/2011, Reg. (EU) No 878/2014
Cyclopentanol, 5-(4-chlorophenyl)methyl-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Acute Tox. 4 (98.4%)
Reproductive toxicity - category 2
Repr. 2
Toxicology
RAIS Toxicity Values
0.3
OPP
0.04
OPP
USGS Health-Based Screening Levels for Evaluating Water-Quality
Metconazole
66620
Pesticide
200
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
EPA Human Health Benchmarks for Pesticides
Metconazole
0.3
8000
Females 13-49 yrs
0.04
200
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- ridadr
- UN3077 9/PG 3
- risk_code
- 22-51/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- Xn,N
- safety_code
- 60
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H361d-H411
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Repr. 2
- Precautionary statements
- P201-P202-P264-P273-P301+P312-P308+P313
Chemistry & industry
Uses & manufacturing
Use Classification
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
Applications
UsesMetconazole is an conazole based fungicide used for the control of black sigatoka disease on banana. Metconazole acts primarily as an inhibitor of ergosterol biosynthesis which interferes with the syn thesis of fungal cell membranes.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
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Additional notes
DefinitionChEBI: A member of the class of cyclopentanols carrying 1,2,4-triazol-1-ylmethyl and 4-chlorobenzyl and geminal dimethyl substituents at positions 1, 2 and 5 respectively. Used to control a range of fungal infections including alternaria, rusts, fusarium and sept ria diseases.
Related reactions
5 records
Compound notes
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