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Lenacil
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Name

Lenacil

 EINECS 218-499-0
CAS No. 2164-08-1 Density 1.32
PSA 54.86000 LogP 1.53050
Solubility 6mg/l in water; 4g/kg in cyclohexanone; 8g/kg in DMF; 6g/kg in DMSO; 2g/kg in toluene. Aqueous solution is stable at ≤316°C. Decomposes in hot alkaline solution. Melting Point 316-326 ºC
Formula C13H18 N2 O2 Boiling Point 411°Cat760mmHg
Molecular Weight 234.298 Flash Point 202.4°C
Transport Information UN 3077 Appearance Colorless crystals
Safety Low toxicity by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NOx. Risk Codes R50/53   
Molecular Structure Molecular Structure of 2164-08-1 (Lenacil) Hazard Symbols
Synonyms

3-Cyclohexyl-5,6-trimethyleneuracil;3-Cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidine-2,4(3H,5H)-dione;5-Cyclohexyl-5,7-diaza-2,3,4,5,6,7-hexahydroindene-4,6-dione; Adol; Adol(pesticide); Adol 80WP; Buracyl; Du Pont 634; Elbatan; Experimental Herbicide634; Herbicide 634; Hexilure; Lenacil; Lenacil 80WP; Uracil 634; Venzar

Article Data 9

Lenacil Synthetic route

54010-15-0

butyl 5-(cyclohexylureido)-cyclopent-1-ene-1-carboxylate

2164-08-1

lenacil

Conditions
ConditionsYield
With sodium butanolate In butan-1-ol
32315-10-9

bis(trichloromethyl) carbonate

2-amino-1-cyclopentenecarboxylic acid

108-91-8

cyclohexylamine

2164-08-1

lenacil

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 2-amino-1-cyclopentenecarboxylic acid In 1,2-dichloro-ethane for 6h; Reflux; Large scale;
Stage #2: cyclohexylamine In 1,2-dichloro-ethane for 6h; Solvent; Reflux; Large scale;
2164-08-1

lenacil

5-oxolenacil

Conditions
ConditionsYield
With chromium(VI) oxide; acetic acid In dichloromethane at 20℃; for 4h; Oxidation;16%
2164-08-1

lenacil

7-bromo-3-cyclohexyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); acetic acid In tetrachloromethane for 4h; Bromination; Heating;
2164-08-1

lenacil

7-hydroxylenacil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-bromosuccinimide; AcOH; AIBN / CCl4 / 4 h / Heating
2: AcOH / 8 h / 100 °C
3: CH3ONa / methanol / 2 h / 20 °C
View Scheme
2164-08-1

lenacil

5-hydroxylenacil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 16 percent / CrO3; AcOH / CH2Cl2 / 4 h / 20 °C
2: 33 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 20 °C
View Scheme
2164-08-1

lenacil

acetic acid 3-cyclohexyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopentapyrimidin-7-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-bromosuccinimide; AcOH; AIBN / CCl4 / 4 h / Heating
2: AcOH / 8 h / 100 °C
View Scheme

Lenacil Chemical Properties

Molecular Structure of Lenacil (2164-08-1):

EINECS: 218-499-0
IUPAC Name: 3-Cyclohexyl-1,5,6,7-tetrahydrocyclopenta[d]pyrimidine-2,4-dione  
Molecular Formula: C13H18N2O2
Molecular Weight: 234.294220 g/mol
XLogP3-AA: 1.7
H-Bond Donor: 1
H-Bond Acceptor: 2
Canonical SMILES: C1CCC(CC1)N2C(=O)C3=C(CCC3)NC2=O
InChI: 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
Index of Refraction: 1.584
Molar Refractivity: 63.3 cm3
Molar Volume: 188.9 cm3
Surface Tension: 51.1 dyne/cm
Density: 1.24 g/cm3
Flash Point: 202.4 °C
Melting Point: 316-326 °C
Enthalpy of Vaporization: 76.66 kJ/mol
Boiling Point: 411 °C at 760 mmHg
Vapour Pressure: 1.79E-08 mmHg at 25 °C
Water Solubility: 66.64 mg/L at 25 °C
Storage Temp.: 0-6 °C
BRN: 0751331

Lenacil Toxicity Data With Reference

1.    

orl-rat LD50:11,000 mg/kg

     85ARAE    Agricultural Chemicals. 2 (1977),159.
2.    

skn-rbt LD50:>5 g/kg

     PEMNDP    Pesticide Manual. 9 (1991),518.

Lenacil Safety Profile

Safety Information of Lenacil (2164-08-1):
Hazard Codes: N
Risk Statements: 50/53
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 60-61
60: This material and/or its container must be disposed of as hazardous waste
61: Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR: UN 3077
RTECS: GY5875000
Low toxicity by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NOx.

Lenacil Specification

  Lenacil (2164-08-1) is also known as Lenacil [ANSI:BSI:ISO] ; 1H-Cyclopentapyrimidine-2,4(3H,5H)-dione, 3-cyclohexyl-6,7-dihydro-(7CI)(8CI)(9CI) ; 3-Cyclohexyl-1,5,6,7-tetrahydrocyclopentapyrimidine-2,4(3H)-dione ; 3-Cyclohexyl-5,6-trimethyleneuracil ; 3-Cyclohexyl-5,6-trimethylenuracil ; 3-Cyclohexyl-5,6-trimethylenuracil [German] ; 3-Cyclohexyl-6,7-dihydro-1H-cyclopentapyrimidine-2,4(3H,5H)-dione ; 5-24-07-00375 (Beilstein Handbook Reference) ; 6,7-Dihydro-3-cyclohexyl-1H-cyclopentapyrimidine-2,4(3H,5H)-dione ; Adol ; Adol (pesticide) ; Buracyl ; CCRIS 1936 ; Caswell No. 525A ; Du Pont 634 ; EPA Pesticide Chemical Code 525200 ; Elbatan ; Experimental herbicide 634 ; Herbicide 634 ; Hexilure ; Lenacile ; Lenacile [ISO-French] ; Uracil 634 ; Venzar ; 1H-Cyclopentapyrimidine-2,4(3H,5H)-dione, 3-cyclohexyl-6,7-dihydro- ; 1H-Cyclopentapyrimidine-2,4(3H,5H)-dione, 6,7-dihydro-3-cyclohexyl- . It is used to deal with mixed soil and bud for control in fodder radish, red radish and beet in the weeds.

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