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(2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol

PubChem CID
158076
Structure
(2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol_small.png
(2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol_3D_Structure.png
Molecular Formula
Synonyms
  • Paclobutrazol
  • 76738-62-0
  • 82336-55-8
  • (2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol
  • Paclobutrazol 10 microg/mL in Isooctane
Molecular Weight
293.79 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-02-01
Description
(R,R)-paclobutrazol is a 1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol in which both stereocentres have R configuration. It is an enantiomer of a (S,S)-paclobutrazol.
See also: Paclobutrazol (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H20ClN3O/c1-15(2,3)14(20)13(19-10-17-9-18-19)8-11-4-6-12(16)7-5-11/h4-7,9-10,13-14,20H,8H2,1-3H3/t13-,14+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RMOGWMIKYWRTKW-KGLIPLIRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C)(C)[C@H]([C@@H](CC1=CC=C(C=C1)Cl)N2C=NC=N2)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H20ClN3O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

76738-62-0
82336-55-8

2.3.2 European Community (EC) Number

112-752-8

2.3.3 ChEBI ID

2.3.4 DSSTox Substance ID

2.3.5 Metabolomics Workbench ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.3.8 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol
  • paclobutrazol
  • paclobutrazol, (R*,S*)-(+-)-isomer
  • paclobutrazol, (R*,S*)-isomer
  • paclobutrazol, (R-(R*,R*))-isomer
  • paclobutrazol, (R-(R*,S*))-isomer
  • paclobutrazol, (S-(R*,R*))-isomer
  • paclobutrazol, (S-(R*,S*))-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
293.79 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
293.1294900 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
293.1294900 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
50.9 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
300
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Ionization Efficiency

Ionization mode
Positive
logIE
3.79
pH
2.7
Instrument
Agilent XCT
Ion source
Electrospray ionization
Additive
formic acid (5.3nM)
Organic modifier
MeCN (80%)

3.2.2 Collision Cross Section

170.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]

3.3 Chemical Classes

3.3.1 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

3.3.2 Pesticides

Plant Growth Regulators
Active substance -> EU Pesticides database: Approved
Fungicides, Plant growth regulators
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticide (Paclobutrazol) -> USDA PDB

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 2
Source of Spectrum
Prof. L. Mondello (Chromaleont s.r.l./Univ. Messina, Italy)
Source of Sample
Sigma-Aldrich Cat. #46046
Copyright
Database Compilation Copyright © 2023-2024 John Wiley and Sons, Inc. Copyright © 2023-2024 John Wiley and Sons, Inc., Portions Copyright Wiley-VCH GmbH, Adams Library under license from Diablo Analytical. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Prof. L. Mondello (Chromaleont s.r.l./Univ. Messina, Italy)
Source of Sample
Sigma-Aldrich Cat. #46046
Copyright
Copyright © 2016-2024  John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Growth Reg.
Pesticide active substances -> Plant Growth Regulators
Fungicides, Plant growth regulators
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

7.2 EU Pesticides Data

Active Substance
paclobutrazol
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/06/2011 Expiration: 31/08/2026
Legislation
2011/55/EU, Reg. (EU) 2018/155, Reg. (EU) 2023/918, Reg. (EU) No 2018/1266, Reg. (EU) No 540/2011
ADI
0.022 mg/kg bw/day [11/55/EU]
ARfD
0.1 mg/kg bw [11/55/EU]
AOEL
0.1 mg/kg bw/day [11/55/EU]

7.3 USDA Pesticide Data Program

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

Fungicides, Plant growth regulators
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Flammable
Irritant
Health Hazard
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H228 (49.6%): Flammable solid [Danger Flammable solids]

H302+H332 (24.3%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H312 (47.8%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H315 (13.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (13.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (45.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H332 (33.9%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H335 (13.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H361 (19.1%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H361d (26.1%): Suspected of damaging the unborn child [Warning Reproductive toxicity]

H400 (44.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (44.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P210, P240, P241, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 115 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Flam. Sol. 1 (49.6%)

Acute Tox. 4 (100%)

Acute Tox. 4 (47.8%)

Skin Irrit. 2 (13.9%)

Skin Sens. 1 (13.9%)

Eye Irrit. 2 (45.2%)

Acute Tox. 4 (33.9%)

STOT SE 3 (13.9%)

Repr. 2 (19.1%)

Repr. 2 (26.1%)

Aquatic Acute 1 (44.3%)

Aquatic Chronic 1 (44.3%)

Flam. Sol. 1 (100%)

Acute Tox. 4 (100%)

Eye Irrit. 2 (100%)

Acute Tox. 4 (100%)

Repr. 2 (100%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

9.2 Regulatory Information

Status Regulation (EC)
2011/55/EU, Reg. (EU) 2018/155, Reg. (EU) 2023/918, Reg. (EU) No 2018/1266, Reg. (EU) No 540/2011
New Zealand EPA Inventory of Chemical Status
Paclobutrazol: Does not have an individual approval but may be used under an appropriate group standard

9.3 Other Safety Information

Chemical Assessment

IMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-[(4-chlorophenyl)methyl]-.alpha.-(1,1-dimethylethyl)-, (R*,R*)-(.+-.)-: Environment tier I assessment

IMAP assessments - 1H-1,2,4-Triazole-1-ethanol, .beta.-[(4-chlorophenyl)methyl]-.alpha.-(1,1-dimethylethyl)-, (R*,R*)-(.+-.)-: Human health tier I assessment

10 Toxicity

10.1 Toxicological Information

10.1.1 EPA IRIS Information

Toxicity Summary
EPA IRIS Summary PDF (Update: Mar-31-1987 )
Critical Effect Systems
Hepatic
Reference Dose (RfD), chronic
1.3 x 10 ^-2 mg/kg-day

10.1.2 RAIS Toxicity Values

Oral Acute Reference Dose (RfDoa)(mg/kg-day)
0.3
Oral Acute Reference Dose Reference
OPP
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.013
Oral Chronic Reference Dose Reference
IRIS Current

10.1.3 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Acute or One Day PAD (RfD) [mg/kg/day]
0.3
Acute or One Day HHBPs [ppb]
2000
Acute HHBP Sensitive Lifestage/Population
Children
Chronic or One Day PAD (RfD) [mg/kg/day]
0.11
Chronic or One Day HHBPs [ppb]
650
Chronic HHBP Sensitive Lifestage/Population
General Population

10.1.4 Target Organs

Hepatic

10.2 Ecological Information

10.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

10.2.2 US EPA Regional Screening Levels for Chemical Contaminants

Resident Soil (mg/kg)
8.20e+02
Industrial Soil (mg/kg)
1.10e+04
Tapwater (ug/L)
2.30e+02
MCL (ug/L)
2.00e+02
Risk-based SSL (mg/kg)
4.60e-01
Chronic Oral Reference Dose (mg/kg-day)
1.30e-02
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

10.2.3 US EPA Regional Removal Management Levels for Chemical Contaminants

Resident Soil (mg/kg)
2.50e+03
Industrial Soil (mg/kg)
3.20e+04
Tapwater (ug/L)
6.80e+02
MCL (ug/L)
2.00e+02
Chronic Oral Reference Dose (mg/kg-day)
1.30e-02
Volatile
Volatile
Mutagen
Mutagen
Fraction of Contaminant Absorbed in Gastrointestinal Tract
1
Fraction of Contaminant Absorbed Dermally from Soil
0.1

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Wiley References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 ChEBI Ontology

14.3 ChemIDplus

14.4 UN GHS Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 CCSBase Classification

14.7 EPA DSSTox Classification

14.8 EPA Substance Registry Services Tree

14.9 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1H-1,2,4-Triazole-1-ethanol, .beta.-[(4-chlorophenyl)methyl]-.alpha.-(1,1-dimethylethyl)-, (R*,R*)-(.+-.)-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. ChemIDplus
    1H-1,2,4-Triazole-1-ethanol, beta-((4-chlorophenyl)methyl)-alpha-(1,1-dimethylethyl)-, (R-(R*,R*))-
    https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0082336558
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. EPA Integrated Risk Information System (IRIS)
  5. EPA Safe Drinking Water Act (SDWA)
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    paclobutrazol (ISO); (2RS,3RS)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol
    https://echa.europa.eu/substance-information/-/substanceinfo/100.121.374
    paclobutrazol (ISO); (2RS,3RS)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol (EC: 616-379-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/75261
    (2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol (EC: 112-752-8)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/398677
    (2R,3R)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol
    https://echa.europa.eu
  7. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  8. Risk Assessment Information System (RAIS)
    LICENSE
    This work has been sponsored by the U.S. Department of Energy (DOE), Office of Environmental Management, Oak Ridge Operations (ORO) Office through a joint collaboration between United Cleanup Oak Ridge LLC (UCOR), Oak Ridge National Laboratory (ORNL), and The University of Tennessee, Ecology and Evolutionary Biology, The Institute for Environmental Modeling (TIEM). All rights reserved.
    https://rais.ornl.gov/
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  10. ChEBI
  11. EPA Pesticide Ecotoxicity Database
  12. EU Pesticides Database
  13. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Paclobutrazol
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  14. EPA Regional Screening Levels for Chemical Contaminants at Superfund Sites
  15. USDA Pesticide Data Program
  16. Hazardous Chemical Information System (HCIS), Safe Work Australia
  17. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    paclobutrazol (ISO); (2RS,3RS)-1-(4-chloro­phenyl)-4,4-dimethyl-...
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  18. Japan Chemical Substance Dictionary (Nikkaji)
  19. Kruve Lab, Ionization & Mass Spectrometry, Stockholm University
    paclobutrazol
  20. Metabolomics Workbench
  21. SpectraBase
  22. Springer Nature
  23. Wikidata
    1H-1,2,4-Triazole-1-ethanol, beta-((4-chlorophenyl)methyl)-alpha-(1,1-dimethylethyl)-, (R-(R*,R*))-
    https://www.wikidata.org/wiki/Q83112630
  24. Wikipedia
  25. Wiley
  26. PubChem
  27. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  28. GHS Classification (UNECE)
  29. EPA Substance Registry Services
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
CONTENTS