An official website of the United States government

Valifenalate

PubChem CID
11338509
Structure
Valifenalate_small.png
Valifenalate_3D_Structure.png
Molecular Formula
Synonyms
  • Valifenalate
  • 283159-90-0
  • Valiphenal
  • Valifenalate [ISO]
  • S4BR27QQ5S
Molecular Weight
398.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-10-26
  • Modify:
    2025-01-18
Description
Valifenalate is a diastereoisomeric mixture of L-(R)- and L-(S)-valifenalate. An anti-peronosporic fungicide, it is used to control mildew in many crops including grapes, potatoes and tomatoes. It has a role as an antifungal agrochemical. It is a diastereoisomeric mixture and an acylamino acid fungicide. It contains a L-(R)-valifenalate and a L-(S)-valifenalate.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Valifenalate.png

1.2 3D Conformer

2 Biologic Description

SVG Image
SVG Image
Sequence
VX

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

methyl 3-(4-chlorophenyl)-3-[[(2S)-3-methyl-2-(propan-2-yloxycarbonylamino)butanoyl]amino]propanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C19H27ClN2O5/c1-11(2)17(22-19(25)27-12(3)4)18(24)21-15(10-16(23)26-5)13-6-8-14(20)9-7-13/h6-9,11-12,15,17H,10H2,1-5H3,(H,21,24)(H,22,25)/t15?,17-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

DBXFMOWZRXXBRN-LWKPJOBUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

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

3.2 Molecular Formula

C19H27ClN2O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

3.3.2 European Community (EC) Number

3.3.3 UNII

3.3.4 ChEBI ID

3.3.5 DSSTox Substance ID

3.3.6 Nikkaji Number

3.3.7 Wikidata

3.4 Synonyms

3.4.1 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
398.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
398.1608497 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
398.1608497 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
93.7 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
504
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
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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)

4.2 Experimental Properties

4.2.1 Collision Cross Section

208.43 Ų [M-H]-

208.51 Ų [M+HCOO]-

208.16 Ų [M+HCOO]-

207.08 Ų [M+Cl]-

206.93 Ų [M+Cl]-

208.44 Ų [M-H]-

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

4.3 Chemical Classes

4.3.1 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

4.3.2 Pesticides

Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Fungicides
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Environmental transformation -> Pesticides (parent, predecessor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pesticide (Valifenalate) -> USDA PDB

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

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

7.2 Agrochemical Transformations

Valifenalate has known environmental transformation products that include S3 (4-chlorobenzoic acid), Valifenalate metabolite Prop.2, Valifenalate metabolite Prop.1, and S2 (IR5885-acid).
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

7.3 EU Pesticides Data

Active Substance
valifenalate (formerly valiphenal)
Status
Approved [Reg. (EC) No 1107/2009]
Date
Approval: 01/07/2014 Expiration: 01/03/2027
Legislation
Dossier complete 06/586/EC, Reg. (EU) 2018/155, Reg. (EU) 2020/2007, Reg. (EU) 2024/1892, Reg. (EU) No 144/2014
ADI
0.07 mg/kg bw/day [EFSA 2013]
AOEL
0.07 mg/kg bw/day [EFSA 2013]

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
Fungicides
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 2
View All
Pictogram(s)
Health Hazard
Environmental Hazard
Signal
Warning
GHS Hazard Statements

H351 (98.9%): Suspected of causing cancer [Warning Carcinogenicity]

H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P203, P273, P280, P318, P391, 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 88 reports by companies from 2 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

Carc. 2 (98.9%)

Aquatic Chronic 2 (100%)

Carc. 2

Aquatic Chronic 2

10.2 Regulatory Information

Status Regulation (EC)
Dossier complete 06/586/EC, Reg. (EU) 2018/155, Reg. (EU) 2020/2007, Reg. (EU) 2024/1892, Reg. (EU) No 144/2014

11 Toxicity

11.1 Toxicological Information

11.1.1 RAIS Toxicity Values

Oral Chronic Reference Dose (RfDoc) (mg/kg-day)
0.22
Oral Chronic Reference Dose Reference
OPP

11.1.2 EPA Human Health Benchmarks for Pesticides

Chemical Substance
Chronic or One Day PAD (RfD) [mg/kg/day]
0.22
Chronic or One Day HHBPs [ppb]
1300
Chronic HHBP Sensitive Lifestage/Population
General Population

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

13.5 Chemical-Gene Co-Occurrences in Patents

14 Classification

14.1 ChEBI Ontology

14.2 ChemIDplus

14.3 UN GHS Classification

14.4 NORMAN Suspect List Exchange Classification

14.5 EPA DSSTox Classification

14.6 EPA Substance Registry Services Tree

14.7 MolGenie Organic Chemistry Ontology

15 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
    methyl N-(isopropoxycarbonyl)-L-valyl-(3RS)-3-(4-chlorophenyl)-β-alaninate; valifenalate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.125.911
    methyl N-(isopropoxycarbonyl)-L-valyl-(3RS)-3-(4-chlorophenyl)-β-alaninate; valifenalate (EC: 608-192-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/97947
  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. 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/
  8. ChEBI
  9. EPA Pesticide Ecotoxicity Database
  10. EU Pesticides Database
  11. 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/
    Valifenalate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  12. USDA Pesticide Data Program
  13. 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
    methyl N-(isopropoxycarbonyl)-L-valyl-(3RS)-3-(4-chlorophenyl)-β-alaninate;...
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. Springer Nature
  16. Wikidata
  17. PubChem
  18. GHS Classification (UNECE)
  19. EPA Substance Registry Services
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS