Lenacil

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Contents

Lenacil
Lenacil structuur.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-499-0
KEGG
PubChem CID
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
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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 dicotyledons. Its formula is C13H18N2O2.

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 and cyclohexylurea under an environment of phosphoric acid: [4] [5]

Lenacil synthesis.svg

Uses

Lenacil is used in the agricultural industry as a selective herbicide to protect sugar and fodder beets. [6]

Toxicity

Lenacil is noted as a potential endocrine disrupting compound. [7] 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. [6]

Related Research Articles

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<span class="mw-page-title-main">Agrochemical</span> Any chemical used in agriculture

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<span class="mw-page-title-main">Phenoxy herbicide</span> Class of herbicide

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<span class="mw-page-title-main">Sulfentrazone</span> Chemical compound

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<span class="mw-page-title-main">Saflufenacil</span> Chemical compound

Saflufenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf weeds in crops including soybeans and corn.

<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

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<span class="mw-page-title-main">Linuron</span> Chemical compound

Linuron is a phenylurea herbicide that is used to control the growth of grass and weeds for the purpose of supporting the growth of crops like soybeans.

<span class="mw-page-title-main">Fomesafen</span> PPOi herbicide

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<span class="mw-page-title-main">Butafenacil</span> Chemical compound

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<span class="mw-page-title-main">Aclonifen</span> Chemical compound

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<span class="mw-page-title-main">Tribenuron</span> Chemical compound

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<span class="mw-page-title-main">Isoxaflutole</span> Chemical compound

Isoxaflutole is a selective herbicide used mainly in maize crops. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Balance and Merlin. It was first marketed by Rhône-Poulenc in 1996.

<span class="mw-page-title-main">Isoproturon</span> Weed control herbicide

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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. 1 2 "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) [Data set]". Zenodo. doi:10.5281/zenodo.10944199.