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Fluazifop-P-butyl

PubChem CID
3033674
Structure
Fluazifop-P-butyl_small.png
Fluazifop-P-butyl_3D_Structure.png
Molecular Formula
Synonyms
  • FLUAZIFOP-P-BUTYL
  • 79241-46-6
  • Fusilade II
  • Fusilade super
  • Fusilade 2000
Molecular Weight
383.4 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-11
Description
Fluazifop-P-butyl is a butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate that has R configutation. The active enantiomer of the herbicide fluazifop-butyl, it is used as a post-emergence herbicide for the control grass weeds in various broad-leaved crops. It has a role as an agrochemical, a herbicide and an EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor. It is functionally related to a fluazifop-P. It is an enantiomer of a (S)-fluazifop-butyl.
Fluazifop-p-butyl is a selective phenoxy herbicide used for postemergence control of annual and perennial grass weeds. It is used on soybeans and other broad-leaved crops such as carrots, spinach, potatoes, and ornamentals. Fluazifop-p-butyl is a general use pesticide. Fluazifop-p-butyl is a different compound than either fluazifop or fluazifop butyl. Both the chemical structures and the toxicities of these compounds are different. Fluazifop-p-butyl formulations can contain some fluazifop-butyl. Fluazifop-p-butyl is a slightly toxic compound. A single ingested dose can cause severe stomach and intestine disturbance. Ingestion of large quantities may cause problems in the central nervous system such as drowsiness, dizziness, loss of coordination and fatigue. Breathing small amounts of the product may cause vomiting and severe lung congestion.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Fluazifop-P-butyl.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

butyl (2R)-2-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C19H20F3NO4/c1-3-4-11-25-18(24)13(2)26-15-6-8-16(9-7-15)27-17-10-5-14(12-23-17)19(20,21)22/h5-10,12-13H,3-4,11H2,1-2H3/t13-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

VAIZTNZGPYBOGF-CYBMUJFWSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CCCCOC(=O)[C@@H](C)OC1=CC=C(C=C1)OC2=NC=C(C=C2)C(F)(F)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C19H20F3NO4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

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 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 Nikkaji Number

2.3.8 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
383.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
4.5
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
383.13444261 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
383.13444261 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
57.7 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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
453
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
1
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 Collision Cross Section

194.8 Ų [M+H]+ [CCS Type: TW]

196.88 Ų [M+H]+

194.26 Ų [M+Na]+

S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.3 Chemical Classes

3.3.1 Pesticides

Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pesticide (Fluazifop-P-butyl) -> USDA PDB

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 9
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
19.276 min
Precursor m/z
384.1417
Precursor Adduct
[M+H]+
Top 5 Peaks

384.1417 999

328.0791 329

282.0736 266

310.0686 3

57.0699 1

Thumbnail
Thumbnail
License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).
2 of 9
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
19.276 min
Precursor m/z
384.1417
Precursor Adduct
[M+H]+
Top 5 Peaks

282.0736 999

328.0792 355

254.0788 95

91.0543 71

255.0502 50

Thumbnail
Thumbnail
License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Herbicide

7.2 Agrochemical Transformations

Fluazifop-P-butyl has known environmental transformation products that include Fluazifop-P, 4-[[5-(trifluoromethyl)-2-pyridyl]oxy]phenol, 2-Hydroxy-5-(trifluoromethyl)pyridine, and AE F020686.
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

7.3 USDA Pesticide Data Program

8 Pharmacology and Biochemistry

8.1 Transformations

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
This is a man-made compound that is used as a pesticide.

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

9.1.2 Household Products

Household & Commercial/Institutional Products

Information on 22 consumer products that contain Fluazifop-p-butyl in the following categories is provided:

• Landscaping/Yard

• Pesticides

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

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

H226 (21.6%): Flammable liquid and vapor [Warning Flammable liquids]

H317 (15.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H361 (34.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H361d (65.3%): Suspected of damaging the unborn child [Warning Reproductive toxicity]

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

P203, P210, P233, P240, P241, P242, P243, P261, P272, P273, P280, P302+P352, P303+P361+P353, P318, P321, P333+P317, P362+P364, P370+P378, P391, P403+P235, 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 176 reports by companies from 8 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

Flam. Liq. 3 (21.6%)

Skin Sens. 1 (15.9%)

Repr. 2 (34.7%)

Repr. 2 (65.3%)

Aquatic Acute 1 (100%)

Aquatic Chronic 1 (100%)

Reproductive toxicity - category 2

Hazardous to the aquatic environment (acute) - category 1

Hazardous to the aquatic environment (chronic) - category 1

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Fluazifop-P-butyl: 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.

11 Toxicity

11.1 Toxicological Information

11.1.1 RAIS Toxicity Values

Oral Acute Reference Dose (RfDoa)(mg/kg-day)
0.5
Oral Acute Reference Dose Reference
OPP
Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.0051
Oral Chronic Reference Dose Reference
OPP

11.1.2 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Acute or One Day PAD (RfD) [mg/kg/day]
0.5
Acute or One Day HHBPs [ppb]
3000
Acute HHBP Sensitive Lifestage/Population
Children
Chronic or One Day PAD (RfD) [mg/kg/day]
0.0051
Chronic or One Day HHBPs [ppb]
30
Chronic HHBP Sensitive Lifestage/Population
General Population

11.1.3 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

11.1.4 Acute Effects

11.2 Ecological Information

11.2.1 EPA Ecotoxicity

Pesticide Ecotoxicity Data from EPA

12 Literature

12.1 Consolidated References

12.2 Springer Nature References

12.3 Chemical Co-Occurrences in Literature

12.4 Chemical-Gene Co-Occurrences in Literature

12.5 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 ChEBI Ontology

16.2 ChemIDplus

16.3 UN GHS Classification

16.4 EPA CPDat Classification

16.5 NORMAN Suspect List Exchange Classification

16.6 CCSBase Classification

16.7 EPA DSSTox Classification

16.8 Consumer Product Information Database Classification

16.9 PFAS and Fluorinated Organic Compounds in PubChem

16.10 MolGenie Organic Chemistry Ontology

17 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. EPA Safe Drinking Water Act (SDWA)
  5. 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
    butyl (R)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.123.086
    butyl (R)-2-[4-(5-trifluoromethyl-2-pyridyloxy)phenoxy]propionate (EC: 616-669-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/83747
  6. 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
  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. 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/
    Fluazifop-P-butyl
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  11. ChEBI
  12. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  13. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  14. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  15. EPA Chemical and Products Database (CPDat)
  16. EPA Pesticide Ecotoxicity Database
  17. Hazardous Chemical Information System (HCIS), Safe Work Australia
  18. 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
    fluazifop-P-butyl (ISO); butyl...
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  19. Japan Chemical Substance Dictionary (Nikkaji)
  20. MassBank Europe
  21. 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
  22. USDA Pesticide Data Program
  23. Springer Nature
  24. Wikidata
  25. PubChem
  26. GHS Classification (UNECE)
  27. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  28. PATENTSCOPE (WIPO)
CONTENTS