Lenacil
Herbicide
From Wikipedia, the free encyclopedia
Lenacil is a uracil-derived chemical herbicide used to control broadleaf weeds.
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| Names | |
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| Preferred IUPAC name
3-cyclohexyl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.016.818 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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: | |
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| 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).
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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]