Lenacil

Lenacil

Skeletal formula of Lenacil
Names
Preferred IUPAC name 3-cyclohexyl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione
Identifiers
CAS Number	2164-08-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:6407
ChEMBL	ChEMBL1522462
ChemSpider	15699
ECHA InfoCard	100.016.818
EC Number	218-499-0
KEGG	C11200
PubChem CID	16559
UNII	X58DK6S8KX
CompTox Dashboard (EPA)	DTXSID9042093
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−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)
Solubility in water	6 mg/L (25 °C)
Hazards
GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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. "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.