2327-02-8

Usage

Uses

Used in Chemical Synthesis:
1-(3,4-Dichlorophenyl)urea is used as a reagent in the synthesis of hydatoin derivatives, which possess anticonvulsant properties. Its unique chemical structure allows it to participate in various chemical reactions, contributing to the development of new compounds with potential therapeutic applications.
Used in Agriculture:
In the agricultural industry, 1-(3,4-Dichlorophenyl)urea is used as a pre-emergent herbicide. Its application helps control the growth of unwanted plants, ensuring the healthy development of crops and increasing agricultural productivity.

InChI:InChI=1/C7H6Cl2N2O/c8-5-2-1-4(3-6(5)9)11-7(10)12/h1-3H,(H3,10,11,12)

Upstream product

• 102-36-3 3,4-dichlorophenylisocyanate 
• 132373-16-1 1-(3,4-Dichloro-phenyl)-3-[3,5,5-trimethyl-2-thioxo-thiazolidin-(4Z)-ylidene]-urea 
• 116121-36-9 C₁₃H₁₅Cl₂N₃O₂S₂ 
• 116121-34-7 C₁₃H₁₅Cl₂N₃O₂S₂ 
• 132408-12-9 4-(3,4-Dichloro-phenyl)-2-(3,5,5-trimethyl-2-thioxo-thiazolidin-4-yl)-[1,2,4]oxadiazolidine-3,5-dione 
• 132373-06-9 4-(3,4-Dichloro-phenyl)-2-(3,4,4-trimethyl-2-thioxo-thiazolidin-5-yl)-[1,2,4]oxadiazolidine-3,5-dione 
• 95-50-1 1,2-dichloro-benzene 
• 57-13-6 urea 
• 590-28-3 potassium cyanate 
• 95-76-1 m,p-dichloroaniline 
• 917-61-3 sodium isocyanate 
• 401797-02-2 2-(3,4-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 132373-08-1 1-(3,4-Dichloro-phenyl)-3-[3,4,4-trimethyl-2-thioxo-thiazolidin-(5Z)-ylidene]-urea 

Downstream Products

• 99514-61-1 N-(5-chloro-2-hydroxy-phenyl)-N'-(3,4-dichloro-phenyl)-urea 
• 95428-71-0 N-<3,4-Dichlor-phenyl>-N'-<2-(cyclohexen-(1)-yl)-cyclohexen-(1)-yl>-harnstoff 
• 126381-35-9 1-(2-Cyano-acetyl)-3-(3,4-dichloro-phenyl)-urea 
• 330-54-1 DCMU 
• 116121-50-7 1-(3,4-Dichloro-phenyl)-3-(3,5,5-trimethyl-2-thioxo-thiazolidin-4-yl)-urea 
• 126381-38-2 6-Amino-1-(3,4-dichloro-phenyl)-1H-pyrimidine-2,4-dione 
• 126381-41-7 6-Amino-1-(3,4-dichloro-phenyl)-5-nitroso-1H-pyrimidine-2,4-dione 
• 126381-36-0 1-{2-Cyano-2-[(E)-hydroxyimino]-acetyl}-3-(3,4-dichloro-phenyl)-urea 
• 13142-49-9 1-(3,4-dichlorophenyl)-3-(pyridin-2-yl)urea 
• 116121-40-5 1-(3,4-Dichloro-phenyl)-3-(3,5,5-trimethyl-2-oxo-thiazolidin-4-yl)-urea 

Relevant academic research and scientific papers

Fungal biodegradation of a phenylurea herbicide, diuron: Structure and toxicity of metabolites

Microbial degradation, organic synthesis and ecotoxicology were used to investigate the fate of diuron after spreading on soils. Quantitative biodegradation assays were performed with fungal strains, showing that diuron was degraded but not entirely mineralized. The modifications observed consisted in demethylation of the terminal nitrogen atom. The identified metabolites were synthesized in sufficient amounts to confirm their structures and determine their non-target toxicity using four biotests. The two metabolites exhibited higher effects than parent diuron. This limited biodegradability and potential aquatic toxicity suggest that diuron is of higher environmental concern than previously recognized. (C) 2000 Society of Chemical Industry.

A Cu-Promoted C-N Coupling of Boron Esters and Diaziridinone: An Approach to Aryl Ureas

A novel Cu-promoted C-N coupling between boron esters and di-tert-butyldiaziridinone is described. A wide variety of aryl ureas can be readily obtained under mild conditions with up to a 92% yield.

Disrupting the Conserved Salt Bridge in the Trimerization of Influenza A Nucleoprotein

Antiviral drug resistance in influenza infections has been a major threat to public health. To develop a broad-spectrum inhibitor of influenza to combat the problem of drug resistance, we previously identified the highly conserved E339?R416 salt bridge of the nucleoprotein trimer as a target and compound 1 as an inhibitor disrupting the salt bridge with an EC50 = 2.7 μM against influenza A (A/WSN/1933). We have further modified this compound via a structure-based approach and performed antiviral activity screening to identify compounds 29 and 30 with EC50 values of 110 and 120 nM, respectively, and without measurable host cell cytotoxicity. Compared to the clinically used neuraminidase inhibitors, these two compounds showed better activity profiles against drug-resistant influenza A strains, as well as influenza B, and improved survival of influenza-infected mice.

Chemical screening of novel strigolactone agonists that specifically interact with DWARF14 protein

Strigolactones (SLs) are a class of plant hormones that regulate shoot branching as well as being known as root-derived signals for parasitic and symbiotic interactions. The physical interaction between SLs and the DWARF14 (D14) receptor family can be examined by differential scanning fluorimetry (DSF) that monitors the changes in protein melting temperature (Tm). The Tm of D14 is lowered by bioactive SLs in DSF analysis. In this report, we screened the compounds that lower the Tm of Arabidopsis D14 (AtD14) as potential candidates for SL agonists using DSF analysis. Subsequent physiological analyzes revealed that 113D10 acts as a novel SL agonist in a D14-dependent manner. Intriguingly, 113D10 has a chemical structure different from natural SLs in that it does not possess an enol ether bond that connects to a methylbutenolide moiety. Moreover, 113D10 does not stimulate seed germination of root parasitic plants. Accordingly, 113D10 can be a useful tool for SL studies and agricultural applications.

A practically simple, catalyst free and scalable synthesis of: N -substituted ureas in water

A practically simple, mild and efficient method is developed for the synthesis of N-substituted ureas by nucleophilic addition of amines to potassium isocyanate in water without organic co-solvent. Using this methodology, a variety of N-substituted ureas (mono-, di- and cyclic-) were synthesized in good to excellent yields with high chemical purity by applying simple filtration or routine extraction procedures avoiding silica gel purification. The developed methodology was also found to be suitable for gram scale synthesis of molecules having commercial application in large volumes. The identified reaction conditions were found to promote a unique substrate selectivity from a mixture of two amines.

Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C?H Amination of Arenes with Carbamates, Urea, and N-Heterocycles

The C?H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH2 as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.

REACTION OF CARBAMOYL DERIVATIVES OF 4- AND 5-HYDROXYLAMINOTHIAZOLIDINE-2-THIONES AND 4-HYDROXYLAMINOIMIDAZOLIDIN-2-ONE WITH METHYL CHLOROFORMATE. PROPERTIES OF SUBSTITUTED 1,2,4-OXADIAZOLIDINE-3,5-DIONES.

Acylation with methyl chloroformate of N-monocarbamoyl derivatives of 4- and 5-hydroxylaminothiazolidin-2-thione and 4-hydroxylaminoimidazolidin-2-one, depending on their structure and the reaction conditions, leads either to N,O-bisacylhydroxylamines or to their intramolecular cyclization products, the substituted 1,2,4-oxadiazolidine-3,5-diones which, on decarboxylation, may convert into the corresponding 4- and 5-carbamoyliminothiazolidine-2-thiones.