| Identification | More | [Name]
Lenacil | [CAS]
2164-08-1 | [Synonyms]
3-CYCLOHEXYL-5,6-TRIMETHYLENEURACIL
3-CYCLOHEXYL-6,7-DIHYDRO-1H-CYCLOPENTAPYRIMIDINE-2,4-(3H,5H)-DIONE
ADOL
Cyclohexyl-5,6-trimethyleneuracil
cyclohexyl-6,7-dihydro-1h-cyclopentapyrimidine-2,4(3h,5h)-dione
LABOTEST-BB LT00134853
LENACIL
VENZAR
VENZAR(R)
1H-Cyclopentapyrimidine-2,4(3H,5H)-dione, 3-cyclohexyl-6,7-dihydro-
1H-Cyclopentapyrimidine-2,4(3H,5H)-dione, 6,7-dihydro-3-cyclohexyl-
3-Cyclohexyl-1,5,6,7-tetrahydo-2H-cyclopentapyrimidine-2,4(3H)-dione
3-Cyclohexyl-1,5,6,7-tetrahydrocyclopentapyrimidine-2,4(3H)-dione
3-Cyclohexyl-2-hydroxy-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one
3-Cyclohexyl-5,6-trimethylenuracil
5h)-dione,6,7-dihydro-3-cyclohexyl-1h-cyclopentapyrimidine-4(3h
6,7-dihydro-3-cyclohexyl-1h-cyclopentapyrimidine-2,4(3h,5h)-dione
buracyl
Du Pont 634
dupont634 | [EINECS(EC#)]
218-499-0 | [Molecular Formula]
C13H18N2O2 | [MDL Number]
MFCD00055395 | [Molecular Weight]
234.29 | [MOL File]
2164-08-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
316-326°C | [Boiling point ]
376.62°C (rough estimate) | [density ]
d20 1.32 kg/l | [refractive index ]
1.6450 (estimate) | [storage temp. ]
0-6°C | [form ]
Solid | [pka]
10.66±0.20(Predicted) | [color ]
White to off-white | [Water Solubility ]
6mg/L(25 ºC) | [Merck ]
13,5455 | [Henry's Law Constant]
1.3×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [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) | [InChIKey]
ZTMKADLOSYKWCA-UHFFFAOYSA-N | [SMILES]
O=C1NC2=C(CCC2)C(=O)N1C3CCCCC3 | [LogP]
2.860 (est) | [CAS DataBase Reference]
2164-08-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Lenacil(2164-08-1) | [EPA Substance Registry System]
2164-08-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
N | [Risk Statements ]
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 | [WGK Germany ]
WGK 2 | [RTECS ]
GY5875000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1
Carc. 2 | [Toxicity]
LD50 (80% wettable powder) orally in rats: >11,000 mg/kg; LC50 96 hr in bluegill sunfish; rainbow trout: 100-1000; 135 mg/l; LC50 8 day in bobwhite quail, Peking duck (mg/kg): 2300, >5620. (DuPont technical data sheet) |
| Hazard Information | Back Directory | [Description]
Lenacil is an uracil herbicide for selective weed control. It has a low solubility in water, has a high risk of leaching to groundwater based on its chemical properties and is semi-volatile. It is moderately persistent in soil and will persist in aquatic systems. It is not greatly toxic to mammals and is a known irritant, but no other significant human health issues have been identified. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms. | [Uses]
Herbicide. | [Uses]
Lenacil acts similarly in weed control. It is used preplanting
by soil incorporation or as a preemergence treatment of
fodder, red beets, and sugar beets. The chemical is also used
on spinach, strawberries, and various ornamentals. Usage
rates range from 0.4 to 1.2 kg/ha depending on the crop and
soil type. | [Definition]
ChEBI: A cyclopentapyrimidine that is 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione substituted by a cyclohexyl group at position 3. | [Production Methods]
The industrial synthesis of Lenacil begins with the preparation of cyclohexylamine, which undergoes condensation with malonic acid derivatives and urea to form the fused pyrimidine ring system. This reaction typically involves heating under reflux in a polar solvent, with acid or base catalysis to facilitate ring closure and ensure high yield. The resulting compound is then purified through crystallisation or solvent extraction to remove impurities and unreacted precursors. | [Agricultural Uses]
Herbicide: Systemic herbicide that attacks roots. | [Trade name]
LENAZAR FLO®; SAFARI LITE®;
VENZAR Flowable® | [Mechanism of action]
Selective, systemic absorbed by roots and having residual effect. Inhibits photosynthesis (photosystem II). | [Pesticide Type]
Herbicide |
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