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1-[(6-Chloropyridin-3-YL)methyl]imidazolidin-2-one

PubChem CID
15390532
Structure
1-[(6-Chloropyridin-3-YL)methyl]imidazolidin-2-one_small.png
1-[(6-Chloropyridin-3-YL)methyl]imidazolidin-2-one_3D_Structure.png
1-[(6-Chloropyridin-3-YL)methyl]imidazolidin-2-one__Crystal_Structure.png
Molecular Formula
Synonyms
  • imidacloprid-urea
  • 120868-66-8
  • 1-[(6-CHLOROPYRIDIN-3-YL)METHYL]IMIDAZOLIDIN-2-ONE
  • Imidacloprid urea
  • 1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one
Molecular Weight
211.65 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2007-02-09
  • Modify:
    2025-01-18
Description
Imidacloprid-urea is a imidazolidinone that is imidazolidin-2-one substituted by a (6-chloropyridin-3-yl)methyl group at position 1. It is a metabolite of the insecticide imidacloprid. It has a role as a marine xenobiotic metabolite. It is a monochloropyridine, an imidazolidinone and a member of ureas.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1-[(6-Chloropyridin-3-YL)methyl]imidazolidin-2-one.png

1.2 3D Conformer

1.3 Crystal Structures

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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C9H10ClN3O/c10-8-2-1-7(5-12-8)6-13-4-3-11-9(13)14/h1-2,5H,3-4,6H2,(H,11,14)
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

ADWTYURAFSWNSU-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

C1CN(C(=O)N1)CC2=CN=C(C=C2)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H10ClN3O
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 ChEBI ID

2.3.4 ChEMBL 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
211.65 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
211.0512396 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
211.0512396 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
45.2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
224
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
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 2010.01.29)

3.2 Chemical Classes

3.2.1 Pesticides

Pesticides -> Insecticides -> Transformation products
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
Environmental transformation -> Pesticide transformation products (metabolite, successor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Pesticide (Imidacloprid urea) -> USDA PDB

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

Source of Spectrum
O1-55-52-12
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 LC-MS

1 of 36
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Authors
Nikiforos Alygizakis, 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
4.6 min
Precursor m/z
212.0585
Precursor Adduct
[M+H]+
Top 5 Peaks

212.0575 999

214.0548 201

213.0604 66

128.025 28

130.022 9

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License
CC BY-SA
2 of 36
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Authors
Nikiforos Alygizakis, 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
4.5 min
Precursor m/z
212.0585
Precursor Adduct
[M+H]+
Top 5 Peaks

212.0578 999

128.0253 883

214.0548 248

130.022 224

126.0096 174

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License
CC BY-SA

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Pesticides -> Insecticides -> Transformation products
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

7.2 Agrochemical Transformations

NTN33893-urea is a known environmental transformation product of Imidacloprid.
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759
Imidacloprid-urea is a known environmental transformation product of Imidacloprid.
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

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

9.1.1 Use Classification

Transformation products
S69 | LUXPEST | Pesticide Screening List for Luxembourg | DOI:10.5281/zenodo.3862688
Pesticides -> Insecticides -> Transformation products
S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448
Environmental transformation -> Pesticide transformation products (metabolite, successor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Literature

11.1 Consolidated References

11.2 Springer Nature References

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Gene Co-Occurrences in Literature

11.5 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 ChEBI Ontology

14.2 ChemIDplus

14.3 ChEMBL Target Tree

14.4 EPA CPDat Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 EPA DSSTox Classification

14.7 EPA Substance Registry Services Tree

14.8 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. 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
  5. ChEBI
  6. 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
  7. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  8. The Cambridge Structural Database
  9. EPA Chemical and Products Database (CPDat)
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. MassBank Europe
  12. 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
  13. NMRShiftDB
  14. 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/
    Imidacloprid urea
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  15. USDA Pesticide Data Program
  16. SpectraBase
    1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-one
    https://spectrabase.com/spectrum/GYCo2QLPCug
    1-[(6-chloranylpyridin-3-yl)methyl]imidazolidin-2-one
    https://spectrabase.com/spectrum/JmGxzMAc2eF
  17. Springer Nature
  18. Wikidata
  19. PubChem
  20. EPA Substance Registry Services
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS