Lenacil
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| Preferred IUPAC name
3-cyclohexyl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione | |
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| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
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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: | |
| GHS08: Health hazard GHS09: Environmental hazard | |
| 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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Lenacil is a uracil-derived chemical herbicide used to control broadleaf weeds.
Production and synthesis
[edit | edit source]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
[edit | edit source]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
[edit | edit source]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
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- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ 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.
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