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Lenacil

Lenacil
Skeletal formula of Lenacil
Skeletal formula of Lenacil
Names
Preferred IUPAC name
3-cyclohexyl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.016.818 Edit this at Wikidata
EC Number
  • 218-499-0
KEGG
UNII
  • 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
  • C1CCC(CC1)N2C(=O)C3=C(CCC3)NC2=O
Properties
C13H18N2O2
Molar mass 234.299 g·mol−1
Density 1.32 g/cm3
Melting point 315.6 to 316.8 °C (600.1 to 602.2 °F; 588.8 to 590.0 K)
6 mg/L (25 °C)
Hazards
GHS labelling:
GHS08: Health hazard GHS09: Environmental hazard
Warning
H351, H410
P203, P273, P280, P318, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lenacil is a uracil-derived chemical herbicide used to control broadleaf weeds.

Production and synthesis

Lenacil was first patented and manufactured by DuPont[1][2] in the 1960s.[3]

The compound can be produced via a condensation reaction between ethyl-2-oxocyclopentanecarboxylate (the Dieckmann condensation product of diethyl adipate) and cyclohexylurea under an environment of phosphoric acid:[4][5][6]

Uses

Lenacil is used in the agricultural industry as a selective herbicide to protect sugar and fodder beets.[7]

Lenacil's HRAC classification is Group C1, Group C (global, Australia) or Group 5 (numeric), as it inhibits photosynthesis at photosystem II.[8]

Toxicity

Lenacil is noted as a potential endocrine disrupting compound.[9] 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.[7]

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.[dead link]
  5. ^ Unger TA (1996). Pesticide synthesis handbook. Elsevier Science. p. 569. ISBN 978-0-81551401-5.
  6. ^ Melnikov NN (1971). Chemistry of Pesticides. Springer-Verlag. p. 422. ISBN 978-1-4684-6253-1.
  7. ^ a b "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.
  8. ^ "Classification of Herbicides According to Site of Action". Retrieved July 19, 2025.
  9. ^ Andres S, Dulio V (2024). "List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 (NORMAN-SLE-S109.0.1.0) [Data set]". Zenodo. doi:10.5281/zenodo.10944199.

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