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Lenacil

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Lenacil
Skeletal formula of Lenacil
Names
Preferred IUPAC name 3-cyclohexyl-1,5,6,7-tetrahydrocyclopentapyrimidine-2,4-dione
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.818 Edit this at Wikidata
EC Number
  • 218-499-0
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H18N2O2/c16-12-10-7-4-8-11(10)14-13(17)15(12)9-5-2-1-3-6-9/h9H,1-8H2,(H,14,17)Key: ZTMKADLOSYKWCA-UHFFFAOYSA-N
SMILES
  • C1CCC(CC1)N2C(=O)C3=C(CCC3)NC2=O
Properties
Chemical formula C13H18N2O2
Molar mass 234.299 g·mol
Hazards
GHS labelling:
Pictograms GHS08: Health hazard GHS09: Environmental hazard
Signal word Warning
Hazard statements H351, H410
Precautionary statements P203, P273, P280, P318, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Lenacil is a uracil-derived chemical herbicide used to control dicotyledons. Its formula is C13H18N2O2.

Production and synthesis

Lenacil was first patented and manufactured by DuPont in the 1960s.

The compound can be produced via a condensation reaction between ethyl-2-oxocyclopentanecarboxylate and cyclohexylurea under an environment of phosphoric acid.

Uses

Lenacil is used in the agricultural industry as a selective herbicide to protect sugar and fodder beets.

Toxicity

Lenacil is noted as a potential endocrine disrupting compound. It is not acutely toxic or genotoxic to mammals, though there is limited evidence the compound is carcinogenic. Lenacil is noted as particularly damaging to algae and aquatic plants, which is a concern if the compound leaches into groundwater when used as a pesticide.

References

  1. Bahadir M, Parlar H, Spiteller M (2000). Springer Umweltlexikon (in German). Springer. p. 702. ISBN 978-3-540-63561-1.
  2. Roberts TR, Hutson DH (1999). Metabolic pathways of agrochemicals. Vol. 2. Royal Soc of Chemistry. p. 699. ISBN 978-0-85404-499-3.
  3. U.S. Patent 3235360, "Control of undesirable vegetation" van 15 februari 1966 aan E.I. Du Pont de Nemours and Company. Gearchiveerd op 9 september 2023.
  4. Ullmann's Agrochemicals. Vol. 1. Wiley-VCH. 2007. p. 809ff. ISBN 978-3-527-31604-5.
  5. Unger TA (1996). Pesticide synthesis handbook. p. 569. ISBN 978-0-81551401-5.
  6. ^ "Peer review of the pesticide risk assessment of the active substance lenacil | EFSA". www.efsa.europa.eu. October 7, 2009. doi:10.2903/j.efsa.2009.1326. Retrieved January 9, 2025.
  7. Andres S, Dulio V (2024). "List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 (NORMAN-SLE-S109.0.1.0) ". Zenodo. doi:10.5281/zenodo.10944199.

Category:Pesticides