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Picolinafen

PubChem CID
3294375
Structure
Picolinafen_small.png
Picolinafen_3D_Structure.png
Molecular Formula
Synonyms
  • Picolinafen
  • 137641-05-5
  • Picolinafen [ISO]
  • UNII-VJE2EX3SNN
  • VJE2EX3SNN
Molecular Weight
376.3 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-09-06
  • Modify:
    2025-01-18
Description
Picolinafen is a pyridinecarboxamide resulting from the formal condensation of the carboxy group of 6-(m-trifluoromethylphenoxy)picolinic acid with the amino group of p-fluoroaniline. A carotenoid biosynthesis inhibitor, it is used as a herbicide for the control of broad-leaved weeds in cereal crops. It has a role as a herbicide, an agrochemical and a carotenoid biosynthesis inhibitor. It is a pyridinecarboxamide, a member of (trifluoromethyl)benzenes, an aromatic ether and a member of monofluorobenzenes.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Picolinafen.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]pyridine-2-carboxamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C19H12F4N2O2/c20-13-7-9-14(10-8-13)24-18(26)16-5-2-6-17(25-16)27-15-4-1-3-12(11-15)19(21,22)23/h1-11H,(H,24,26)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

CWKFPEBMTGKLKX-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1=CC(=CC(=C1)OC2=CC=CC(=N2)C(=O)NC3=CC=C(C=C3)F)C(F)(F)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H12F4N2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
376.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
4.9
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
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
376.08349028 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
376.08349028 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
51.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
27
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
495
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
0
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 Kovats Retention Index

Semi-standard non-polar
2477 , 2483

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

3.3.2 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

3.3.3 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pesticide
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254
Herbicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticide (Picolinafen) -> 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. #37912
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.
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2 of 2
Source of Spectrum
Prof. L. Mondello (Chromaleont s.r.l./Univ. Messina, Italy)
Source of Sample
Sigma-Aldrich Cat. #37912
Copyright
Copyright © 2016-2024  John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 LC-MS

1 of 49
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
12.302 min
Precursor m/z
377.0908
Precursor Adduct
[M+H]+
Top 5 Peaks

377.0917 999

378.0948 155

379.0967 17

284.0528 14

359.0803 12

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License
CC BY
2 of 49
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
12.316 min
Precursor m/z
377.0908
Precursor Adduct
[M+H]+
Top 5 Peaks

377.0916 999

256.0582 991

284.0533 610

359.0808 604

378.0944 188

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License
CC BY

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Pesticide active substances
Herbicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

7.2 Agrochemical Transformations

Picolinafen has known environmental transformation products that include 2-3-trifluoromethylphenoxy-6-pyridine carboxylic acid and 4-fluoroanaline.
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Picolinafen has known environmental transformation products that include 6-(3-trifluoromethylphenoxy)-2-pyridine carboxylic acid and 4-fluoroaniline.
S78 | SLUPESTTPS | Pesticides and TPs from SLU, Sweden | DOI:10.5281/zenodo.4687924

7.3 EU Pesticides Data

Active Substance
picolinafen
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/11/2016 Expiration: 30/06/2031
Legislation
02/64/EC, 2010/77/EU, Reg. (EU) 2015/1885, Reg. (EU) 2016/1423, Reg. (EU) 2016/549, Reg. (EU) No 540/2011
ADI
0.014 mg/kg bw/day [02/64/EC, Reg. (EU) 2016/1423]
ARfD
0.05 mg/kg bw [02/64/EC, Reg. (EU) 2016/1423]
AOEL
0.03 mg/kg bw/day [02/64/EC, Reg. (EU) 2016/1423]

7.4 USDA Pesticide Data Program

8 Pharmacology and Biochemistry

8.1 Transformations

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
Herbicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 3
View All
Pictogram(s)
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P273, P391, 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 182 reports by companies from 4 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.

10.1.2 Hazard Classes and Categories

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

STOT RE 2

Aquatic Acute 1

Aquatic Chronic 1

10.2 Regulatory Information

Status Regulation (EC)
02/64/EC, 2010/77/EU, Reg. (EU) 2015/1885, Reg. (EU) 2016/1423, Reg. (EU) 2016/549, Reg. (EU) No 540/2011

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Wiley References

11.4 Chemical Co-Occurrences in Literature

11.5 Chemical-Gene Co-Occurrences in Literature

11.6 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Classification

13.1 ChEBI Ontology

13.2 ChemIDplus

13.3 UN GHS Classification

13.4 NORMAN Suspect List Exchange Classification

13.5 EPA DSSTox Classification

13.6 PFAS and Fluorinated Organic Compounds in PubChem

13.7 EPA Substance Registry Services Tree

13.8 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    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. 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
    picolinafen (ISO); N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]pyridine-2-carboxamide; 4′-fluoro-6-[(α,α,α-trifluoro-m-tolyl)oxy]picolinanilide
    https://echa.europa.eu/substance-information/-/substanceinfo/100.112.657
    picolinafen (ISO); N-(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]pyridine-2-carboxamide; 4′-fluoro-6-[(α,α,α-trifluoro-m-tolyl)oxy]picolinanilide (EC: 604-030-0)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/31269
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. ChEBI
  7. EU Pesticides Database
  8. 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/
    picolinafen
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  9. USDA Pesticide Data Program
  10. 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
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. MassBank Europe
  13. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  14. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  15. SpectraBase
  16. Springer Nature
  17. Wikidata
  18. Wiley
  19. PubChem
  20. GHS Classification (UNECE)
  21. EPA Substance Registry Services
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS