15737-37-8

Usage

Uses

Used in Agricultural Industry:
3-(4-chlorophenyl)-1,1-diethylurea is used as a herbicide for controlling the growth of unwanted plants and weeds. It inhibits the photosynthesis process in plants, leading to their eventual death, thus providing an effective solution for managing unwanted vegetation in agricultural settings.
However, due to its persistence in the environment and potential impact on non-target organisms and ecosystems, the use of 3-(4-chlorophenyl)-1,1-diethylurea has been restricted or banned in several countries to mitigate the associated environmental and health risks.

Upstream product

• 104-12-1 p-chlorphenylisocyanate 
• 109-89-7 diethylamine 
• 201230-82-2 carbon monoxide 
• 106-47-8 4-chloro-aniline 
• 103-71-9 phenyl isocyanate 
• 100-00-5 4-chlorobenzonitrile 
• 13939-06-5 molybdenum hexacarbonyl 
• 2131-55-7 4-Chlorophenyl isothiocyanate 
• 1014-72-8 1-phenyl-3,3-diethylurea 
• 84784-24-7 3-(4-chlorophenyl)-1-(4-tolyl)-1-nitrosourea 
• 88-10-8 N,N-diethylcarbamyl chloride 

Downstream Products

• 1783-39-7 N-(p-Chlorphenyl)-N'.N'-diaethyl-formamidin 
• 30085-34-8 N-(4-chlorophenyl)-N'-hydroxyurea 
• 105363-76-6 C₂₂H₂₈Cl₂N₄O 
• 111669-89-7 1-(4-chlorophenyl)-3,3-diethyl-1-nitrosourea 
• 43013-74-7 N¹,N¹-Diethyl-N²-(p-chlorphenyl)-chlorformamidin 

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.

Efficient Direct Halogenation of Unsymmetrical N -Benzyl- and N -Phenylureas with Trihaloisocyanuric Acids

A simple and efficient methodology for the direct halogenation of N -phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N -phenylureas with different patterns of substitution. Additionally, less reactive N -benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature.

Pd/C-catalyzed reductive carbonylation of nitroaromatics for the synthesis of unsymmetrical ureas: One-step synthesis of neburon

A Pd/C catalyzed reductive carbonylation of nitroarenes for the synthesis of unsymmetrical ureas has been developed. Using inexpensive and stable nitroarenes as the substrates, a series of unsymmetrical ureas were produced in moderate to good yields. A range of functional groups including thioethers, halides and vinyl were compatible with this reaction. As a heterogeneous catalyst, Pd/C was recycled and reused four times without losing activity. Notably, urea-based herbicide neburon was prepared in 64% yield under our standard conditions.

2-Picolylamino(diphenylphosphinoselenoic)amide supported zinc complexes: Efficient catalyst for insertion of N–H bond into carbodiimides, isocyanates, and isothiocyanate

We report here the hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by zinc complexes supported by the ligand 2-picolylamino-(diphenylphosphinoselenoic)amide [{(Ph2P-(?Se)}2NCH2(C5H4N)] (1). A series of zinc complexes [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnX2] [(X?Cl (2), Br (3a), I (4)] were prepared from ligand 1 and the corresponding zinc dihalide in a 1:1 molar ratio at 60°C in a chloroform solvent. The reaction of ligand 1 and ZnBr2 in methanol yielded another zinc complex [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnBr2(CH3OH)] (3b). The molecular structures of compounds 3a, 3b, and 4 were established through single-crystal X-ray diffraction analyses. The solid-state structures of all the complexes revealed a κ2- chelation through pyridine nitrogen and selenium atoms of ligand 1 to the zinc ion. Complex 2 proved to be a competent pre-catalyst for the addition of the amine N–H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanate and phenylisothiocyanate in toluene solvents, which proceeded rapidly at room temperature with 5 mol% catalyst loading to yield (up to 99%) the corresponding derivatives of urea and thio-urea. However, a temperature of 90°C was needed for the hydroamination of N,N′ dicyclohexylcarbodiimide. We also report the most plausible mechanism of the hydroamination reaction.

Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex

The hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(iv) complex as a precatalyst is reported here. The titanium(iv) complex [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(iv) [Ti(NMe2)4] with [{Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of an amine N-H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanates and phenylisothiocyanates in toluene solvents proceeding rapidly at room temperature with 5 mol% catalyst loadings to yield the corresponding urea and thio-urea derivatives up to 99%. However, ambient temperature was needed for hydroamination of 1,3-dicyclohexylcarbodiimide. The amine addition reactions with isocyanates showed first order kinetics with respect to catalyst 1 as well as substrates. The most plausible mechanism for the hydroamination reaction was established by isolating 1,1-dimethylphenyl urea as a side product.

Antidepressant activity of carbamates and urea derivatives

Thirteen (13) compounds of N-phenyl-O-alkyl carbamates (1 and 3), N,N-diethyl-N′-alkyl/aryl/phenylpiperazinoureas (4-6, 8-12), N-phenyl-N′-phenylpiperazino/imidazoureas (2, 7), and N-ethyl-(N′- phenylpiperazino) thioureas 13 were synthesized and tested for their antidepressant-like activity in mice. It was found that compound N-phenyl-O-heptyl carbamate 1 and N-phenyl-N′-phenylpiperazinourea 2 showed 32.5 and 27.7% antidepressant activity in the forced swim test in mice, respectively. Considering other carbamates it was found that a decrease in alkyl chain length caused a marked decline in the antidepressant activity. Compounds 1-4 show even higher activities in the forced swim test than the standard phenelzine. Springer Science+Business Media, LLC 2011.

Synthesis of carbamate derivatives of biological interest

A number of carbamates derivatives 1-12 were synthesized and evaluated for their antioxidant, urease inhibition, anticancer, antibacterial, and antifungal activities. N-Ethylamine-N′, N′-diethyl carbamate (4), showed remarkable metal chelating capability

Synthesis of unsymmetrical ureas by sulfur-assisted carbonylation with carbon monoxide and oxidation with molecular oxygen under mild conditions

With ambient pressure of carbon monoxide and oxygen at room temperature, N,N-dialkyl-N′-arylureas were selectively accessible from secondary amines, aromatic amines, and sulfur in good to excellent yields. For example, N-butyl-N-methyl-N′-(3,4-dichlorophenyl)urea, which is used as a herbicide (neburon), was afforded successfully from butylmethylamine (2 equiv), 3,4-dichloroaniline (1 equiv) and sulfur (1 equiv) in 79% (21.8 g) yield using carbon monoxide (0.1 MPa) and oxygen (0.1 MPa) at 20°C in DMF. Georg Thieme Verlag Stuttgart.

Synthesis of 2,4-diaminoquinazoline derivatives

A series of 6- and 7-substituted derivatives of 2-(N,N-diethylamino)-4-(N,N-dimethylamino)quinazoline have been synthesized. The synthesis consists in converting N-phenyl-N',N'-diethylurea into chloroamidines which are treated with N,N-dimethylcyanamide t