lenacil
{{Short description|Chemical compound}}
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{{Use mdy dates|date=January 2025}}
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| Name = Lenacil
| ImageFile = Lenacil structuur.png
| ImageSize = 200px
| ImageName = Skeletal formula of Lenacil
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| PIN = 3-cyclohexyl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione
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| ChEBI = 6407
| SMILES = C1CCC(CC1)N2C(=O)C3=C(CCC3)NC2=O
| ChemSpiderID = 15699
| KEGG = C11200
| PubChem = 16559
| UNII = X58DK6S8KX
| StdInChI = 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)
| StdInChIKey = ZTMKADLOSYKWCA-UHFFFAOYSA-N
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| ChEMBL = 1522462
| CASNo = 2164-08-1
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| EINECS = 218-499-0
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| Section2={{Chembox Properties
| C=13 | H=18 | O=2 | N=2
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| GHSSignalWord = Warning
| HPhrases = {{H-phrases|H351|H410}}
| PPhrases = {{P-phrases|P203| P273| P280| P318| P391| P405| P501}}
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Lenacil is a uracil-derived chemical herbicide used to control dicotyledons. Its formula is {{chem2|C13H18N2O2}}.
Production and synthesis
Lenacil was first patented and manufactured by DuPont{{Cite book | first1=Müfit |last1=Bahadir |first2=Harun |last2=Parlar |first3=Michael |last3=Spiteller | title = Springer Umweltlexikon | publisher = Springer | isbn = 978-3-540-63561-1 | year = 2000 |url=https://books.google.com/books?id=MbM211w450IC&pg=PA702| page = 702 |language=de}}{{Cite book | first1= Terence Robert |last1=Roberts |first2=D. H. |last2=Hutson | title = Metabolic pathways of agrochemicals |volume= 2 | publisher = Royal Soc of Chemistry | isbn = 978-0-85404-499-3 | year = 1999 | url=https://books.google.com/books?id=uC2-Ocob_MMC&pg=PA699| page = 699 }} in the 1960s.[https://patents.google.com/patent/US3235360 U.S. Patent 3235360, "Control of undesirable vegetation" van 15 februari 1966 aan E.I. Du Pont de Nemours and Company]. [https://web.archive.org/web/20230909153455/https://patents.google.com/patent/US3235360 Gearchiveerd] op 9 september 2023.
The compound can be produced via a condensation reaction between ethyl-2-oxocyclopentanecarboxylate and cyclohexylurea under an environment of phosphoric acid:{{Cite book | title = Ullmann's Agrochemicals |volume= 1 | publisher = Wiley-VCH | isbn = 978-3-527-31604-5 | year = 2007 | url=https://books.google.com/books?id=cItuoO9zSjkC&pg=PA809FF | page = 809ff }}{{dead url|date=January 2025}}{{Cite book |first1 = Thomas A. |last1=Unger | title = Pesticide synthesis handbook | isbn = 978-0-81551401-5 | year = 1996 | url=https://books.google.com/books?id=WGDtttLgQBwC&pg=PA569 |page=569 |publisher=Elsevier Science }}
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.{{Cite journal |last1=Andres |first1=S. |last2=Dulio |first2=V. |date=2024 |title=List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 (NORMAN-SLE-S109.0.1.0) [Data set] |journal=Zenodo |doi=10.5281/zenodo.10944199}} 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.{{Cite journal |date=2009-10-07 |title=Peer review of the pesticide risk assessment of the active substance lenacil {{!}} EFSA |url=https://www.efsa.europa.eu/en/efsajournal/pub/1326 |access-date=2025-01-09 |website=www.efsa.europa.eu |language=en |doi=10.2903/j.efsa.2009.1326}}