Chemistry:Lenacil
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]
Toxicity
Lenacil is noted as a potential endocrine disrupting compound.[8] 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
- ↑ Bahadir, Müfit; Parlar, Harun; Spiteller, Michael (2000) (in de). Springer Umweltlexikon. Springer. p. 702. ISBN 978-3-540-63561-1. https://books.google.com/books?id=MbM211w450IC&pg=PA702.
- ↑ Roberts, Terence Robert; Hutson, D. H. (1999). Metabolic pathways of agrochemicals. 2. Royal Soc of Chemistry. p. 699. ISBN 978-0-85404-499-3. https://books.google.com/books?id=uC2-Ocob_MMC&pg=PA699.
- ↑ 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.
- ↑ Ullmann's Agrochemicals. 1. Wiley-VCH. 2007. p. 809ff. ISBN 978-3-527-31604-5. https://books.google.com/books?id=cItuoO9zSjkC&pg=PA809FF.Template:Dead url
- ↑ Unger, Thomas A. (1996). Pesticide synthesis handbook. Elsevier Science. p. 569. ISBN 978-0-81551401-5. https://books.google.com/books?id=WGDtttLgQBwC&pg=PA569.
- ↑ Melnikov, N. N. (1971). Chemistry of Pesticides. Springer-Verlag. p. 422. ISBN 978-1-4684-6253-1. https://doi.org/10.1007/978-1-4684-6251-7.
- ↑ 7.0 7.1 (in en) Peer review of the pesticide risk assessment of the active substance lenacil | EFSA. 2009-10-07. doi:10.2903/j.efsa.2009.1326. https://www.efsa.europa.eu/en/efsajournal/pub/1326. Retrieved 2025-01-09.
- ↑ 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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