2164-08-1

Basic information

• Product Name: Lenacil
• Synonyms: 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
• CAS NO: 2164-08-1
• Molecular Formula: C₁₃H₁₈N₂O₂
• Molecular Weight: 234.29
• EINECS: 218-499-0
• Mol File: 2164-08-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 316-326°C
• Boiling Point: 376.62°C (rough estimate)
• Flash Point: 202.4°C
• Appearance: Colorless crystals
• Density: d20 1.32 kg/l
• Vapor Pressure: 1.79E-08mmHg at 25°C
• Refractive Index: 1.6450 (estimate)
• Storage Temp.: 0-6°C
• PKA: 10.66±0.20(Predicted)
• Water Solubility: 6mg/L(25 oC)
• Merck: 13,5455
• CAS DataBase Reference: Lenacil(CAS DataBase Reference)
• NIST Chemistry Reference: Lenacil(2164-08-1)
• EPA Substance Registry System: Lenacil(2164-08-1)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077
• RTECS: GY5875000
• Hazardous Substances Data: 2164-08-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 2164-08-1 differently. You can refer to the following data:
1. Herbicide.
2. 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.
3. Lenacil is an herbicide used in the protection of crops. Non-cytotoxic agent.

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.

Agricultural Uses

Herbicide: Systemic herbicide that attacks roots.

Trade name

LENAZAR FLO?; SAFARI LITE?; VENZAR Flowable?

InChI:InChI=1/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)

Synthetic route

butyl 5-(cyclohexylureido)-cyclopent-1-ene-1-carboxylate (54010-15-0) → lenacil (2164-08-1)

Conditions	Yield
With sodium butanolate In butan-1-ol

bis(trichloromethyl) carbonate (32315-10-9) + 2-amino-1-cyclopentenecarboxylic acid + cyclohexylamine (108-91-8) → lenacil (2164-08-1)

Conditions	Yield
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;

lenacil (2164-08-1) → 5-oxolenacil

Conditions	Yield
With chromium(VI) oxide; acetic acid In dichloromethane at 20℃; for 4h; Oxidation;	16%

lenacil (2164-08-1) → 7-bromo-3-cyclohexyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

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

lenacil (2164-08-1) → 7-hydroxylenacil

Conditions	Yield
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

lenacil (2164-08-1) → 5-hydroxylenacil

Conditions	Yield
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

lenacil (2164-08-1) → acetic acid 3-cyclohexyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopentapyrimidin-7-yl ester

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

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 773099-73-3 2-amino-1-cyclopentenecarboxylic acid 
• 108-91-8 cyclohexylamine 
• 54010-15-0 butyl 5-(cyclohexylureido)-cyclopent-1-ene-1-carboxylate 

Relevant articles and documents

Synthesis method of agricultural herbicide

The invention discloses a synthesis method of an agricultural herbicide. The method comprises the following steps of: adding a solvent X, a substrate and ammonium formate into a reaction kettle, carrying out reaction for 4h under 90DEG C, adding MOH, carrying out heat preservation reaction for 2 hours, carrying out reduced pressure distillation to remove the solvent X, performing cooling 25 DEG Cand adding hydrochloric acid to adjust the pH value to 7, adding ethyl acetate, performing stirring and liquid separation; adding ethyl acetate, performing stirring and extracting, merging organic phases, performing pressurized distillation, performing concentration to obtain 2-amino-1-cyclopentenecarboxylic acid; adding a solvent Y into another reaction kettle, then adding the 2-amino-1-cyclopentenecarboxylic acid and a carbonylation reagent, heating to react for 6h, absorbing tail gas, combining wastewater, concentrating the solvent Y until no liquid flows out, adding the solvent Y and cyclohexylamine, heating and refluxing for 6h, performing cooling and centrifugal filtering, adding a filter cake into the solvent Y, heating and stirring for 1h, performing cooling and centrifugal filtering, and performing drying in vacuum to obtain a product; and heating wastewater, performing reduced pressure distillation, adding methyl alcohol and performing stirring and filtering after solid precipitation, leaching a filter cake with methyl alcohol, and conducting vacuum drying so as to obtain white sandy solid of which the reaction general formula is described in the descriptions of the invention.

SIDE-REACTIONS IN THE INDUSTRIAL METHOD FOR THE PREPARATION OF BUTYL 5-(CYCLOHEXYLUREIDO)CYCLOPENT-1-ENE-1-CARBOXYLATE

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4,5-Dichloroimidazole-2-carboxylic acid derivatives

4,5-Dichloroimidazole-2-carboxylic acid derivatives of the formula STR1 in which the group STR2 represents a carbon atom which has three bonds to hetero-atoms, and their salts with bases, possess insecticidal, acaricidal, fungicidal, nematicidal and herbicidal properties.