72802-46-1

Usage

Function

Herbicide and algicide

Mechanism of Action

Inhibits photosynthesis in plants and algae

Application

Used in agriculture for weed control and in aquatic environments for managing algal blooms

Physical Properties

Appearance: White, crystalline solid
Solubility: Sparingly soluble in water
Volatility: Low

Toxicity

Mammalian Toxicity: Low acute toxicity
Environmental Impact: Persistence in the environment, potential for water source contamination, harm to non-target organisms

Importance of Proper Use

Essential to minimize environmental impacts

InChI:InChI=1/C13H17ClN2O/c14-10-6-8-12(9-7-10)16-13(17)15-11-4-2-1-3-5-11/h6-9,11H,1-5H2,(H2,15,16,17)

Upstream product

• 21368-28-5 4-chlorobenzoyl azide 
• 108-91-8 cyclohexylamine 
• 186353-04-8 chloromethyl N-(4-chlorophenyl) carbamate 
• 106-47-8 4-chloro-aniline 
• 3173-53-3 Cyclohexyl isocyanate 
• 931-53-3 Cyclohexyl isocyanide 
• 74-11-3 para-chlorobenzoic acid 
• 76345-27-2 N-(4-chlorophenyl)-N'-cyclohexylmethanediimine 
• 2131-55-7 4-Chlorophenyl isothiocyanate 

Relevant academic research and scientific papers

Visible-light-promoted oxidative desulphurisation: A strategy for the preparation of unsymmetrical ureas from isothiocyanates and amines using molecular oxygen

A green and efficient visible-light promoted oxidative desulphurisation protocol has been proposed for the construction of unsymmetrical ureas under mild conditions with broad substrate scope and good functional group tolerance. Most appealingly, the reaction can proceed smoothly without adding any strong oxidants. Control experiments and computational studies support a mechanism involving water-assisted in situ generation of thioureas and photocatalytic oxidative desulphurisation. The present method provides a promising synthesis strategy for the formation of diverse and useful unsymmetrical urea derivatives in the fields of pharmaceutical and synthetic chemistry.

Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides

This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted into unsymmetrical ureas in moderate to good yields using an electricity ON-OFF strategy.

CaI2-Catalyzed direct transformation of: N -Alloc-, N -Troc-, and N -Cbz-protected amines to asymmetrical ureas

A novel and facile CaI2-catalyzed direct synthesis of asymmetrical ureas from N-Alloc-, N-Troc-, and N-Cbz-protected amines is developed. In this study, the efficient reaction of Alloc-, Troc-, and Cbz-carbamates with amines in the presence of catalytic CaI2 successfully generated various asymmetrical ureas. This catalytic synthetic procedure provided the desired ureas via reactions of these protected aromatic and aliphatic amines with various amines in high yields without side products. This suggests that novel direct synthesis of ureas from Alloc-, Troc-, and Cbz-carbamates can be a promising approach for the synthesis of useful ureas.

Scalable, One-Pot, Microwave-Accelerated Tandem Synthesis of Unsymmetrical Urea Derivatives

We report a facile, microwave-accelerated, one-pot tandem synthesis of unsymmetrical ureas via a Curtius rearrangement. In this method, one-pot microwave irradiation of commercially available (hetero)aromatic acids and amines in the presence of diphenylphosphoryl azide enabled extremely rapid (1-5 min) construction of an array of unsymmetrical ureas in good to excellent yields. We demonstrate the utility of our method in the efficient, gram-scale synthesis of key biologically active compounds targeting the cannabinoid 1 and α7 nicotinic acetylcholine receptors.

Oximes as reusable templates for the synthesis of ureas and carbamates by an: In situ generation of carbamoyl oximes

Oximes have been identified as reusable templates for the synthesis of ureas and carbamates by an in situ generation of carbamoyl oximes under metal-free conditions. The recovered oxime has been utilised for three trials in the synthesis of urea derivatives without any loss in the yield and efficiency. In addition, this template approach could override the usage of hazardous and less stable isocyanates as substrates.

Cobalt(II)-catalyzed isocyanide insertion reaction with amines under ultrasonic conditions: A divergent synthesis of ureas, thioureas and azaheterocycles

Cobalt(II) acetylacetonate-catalyzed isocyanide insertion reactions with amines utilizing tert-butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2-aminoben

QSAR and classification of murine and human soluble epoxide hydrolase inhibition by urea-like compounds

A data set of 348 urea-like compounds that inhibit the soluble epoxide hydrolase enzyme in mice and humans is examined. Compounds having IC50 values ranging from 0.06 to >500 μM (murine) and 0.10 to >500 μM (human) are categorized as active or

Structural refinement of inhibitors of urea-based soluble epoxide hydrolases

The soluble epoxide hydrolase (sEH) is involved in the metabolism of arachidonic, linoleic, and other fatty acid epoxides, endogenous chemical mediators that play an important role in blood pressure regulation and inflammation. 1,3-Disubstituted ureas, carbamates, and amides are new potent and stable inhibitors of sEH. However, the poor solubility of the lead compounds limits their use. Inhibitor structure-activity relationships were investigated to better define the structural requirements for inhibition and to identify points in the molecular topography that could accept polar groups without diminishing inhibition potency. Results indicate that lipophilicity is an important factor controlling inhibitor potency. Polar groups could be incorporated into one of the alkyl groups without loss of activity if they were placed at a sufficient distance from the urea function. The resulting compounds had a 2-fold higher water solubility. These findings will facilitate the rational design and optimization of sEH inhibitors with better physical properties.

α-Haloalkyl Haloformates and Related Compounds 3.1 A Facile Synthesis of Symmetrical and Unsymmetrical Ureas via Chloromethyl Carbamates

Chloromethyl carbamates were prepared by the reaction of chloromethyl chloroformates with amines and found to produce mono-, symmetrically or unsymmetrically di- and trisubstituted ureas including their N-hydroxy and N-alkoxy derivatives in moderate to good yield.