13558-77-5

Usage

Uses

Used in Agricultural Industry:
1-(2-chloroacetyl)-3-p-tolylurea is used as a herbicide and plant growth regulator for its ability to prevent sprouting in potatoes and other crops. This application helps to extend the shelf life of these produce items and reduce losses due to sprouting, which can negatively impact the quality and marketability of the crops.
Used in Regulatory Measures:
Due to its classification as a possible human carcinogen, 1-(2-chloroacetyl)-3-p-tolylurea is subject to scrutiny and control in many countries. Its use in agriculture is regulated to mitigate potential health and environmental impacts, ensuring that exposure levels are kept within safe limits for both humans and the ecosystem.

InChI:InChI=1/C10H11ClN2O2/c1-7-2-4-8(5-3-7)12-10(15)13-9(14)6-11/h2-5H,6H2,1H3,(H2,12,13,14,15)

Upstream product

• 4461-30-7 2-chloroacetylisocyanate 
• 106-49-0 p-toluidine 
• 79-37-8 oxalyl dichloride 
• 79-07-2 Chloroacetamide 
• 471-46-5 Oxalamide 
• 622-51-5 p-tolylurea 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 68195-19-7 2-[5-(4-chloro-phenoxymethyl)-[1,3,4]oxadiazol-2-ylsulfanyl]-N-p-tolylcarbamoyl-acetamide 
• 86538-76-3 2-(1H-benzoimidazol-2-ylsulfanyl)-N-p-tolylcarbamoyl-acetamide 
• 89174-60-7 1-[2-(5,6-Diphenyl-[1,2,4]triazin-3-ylsulfanyl)-acetyl]-3-p-tolyl-urea 
• 84325-91-7 1-{2-[4-(4-Oxo-2-phenyl-4H-quinazolin-3-yl)-phenoxy]-acetyl}-3-p-tolyl-urea 
• 76427-16-2 1-(2-{N'-[1-(4-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazino}-acetyl)-3-p-tolyl-urea 
• 76427-15-1 1-(2-{N'-[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-hydrazino}-acetyl)-3-p-tolyl-urea 
• 76427-14-0 1-(2-{N'-[1-(2-Hydroxy-phenyl)-meth-(E)-ylidene]-hydrazino}-acetyl)-3-p-tolyl-urea 
• 76427-49-1 1-(2-Hydrazino-acetyl)-3-p-tolyl-urea 

Relevant academic research and scientific papers

A concise approach to n-substituted rhodanines through a base-assisted one-pot coupling and cyclization process

An efficient approach to obtain functionalized rhodanines was developed through a base-assisted one-pot coupling and continuous cyclization of a primary amine, carbon disulfide, and methyl (2-chloroacetyl)carbamate. This conversion tolerates a broad range of functional groups and can be used to scale the preparation of N-substituted rhodanines in excellent yields.

Synthesis and biological evaluation of novel L-homoserine lactone analogs as quorum sensing inhibitors of pseudomonas aeruginosa

In this study, we synthesized four series of novel L-homoserine lactone analogs and evaluated their in vitro quorum sensing (QS) inhibitory activity against two biomonitor strains, Chromobacterium violaceum CV026 and Pseudomonas aeruginosa PAO1. Studies of the structure–activity relationships of the set of L-homoserine lactone analogs indicated that phenylurea-containing N-dithiocarbamated homoserine lactones are more potent than (Z)-4-bromo-5-(bromomethylene)-2(5H)-furanone (C30), a positive control for biofilm formation. In particular, compared with C30, QS inhibitor 11f significantly reduced the production of virulence factors (pyocyanin, elastase and rhamnolipid), swarming motility, the formation of biofilm and the mRNA level of QS-related genes regulated by the QS system of PAO1. These results reveal 11f as a potential lead compound for developing novel antibacterial quorum sensing inhibitors.

Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress

We prepared a series of quinoxalin-2-mercapto-acetyl-urea analogs and evaluated them for their ability to inhibit viral egress in our Marburg and Ebola VP40 VLP budding assays in HEK293T cells. We also evaluated selected compounds in our bimolecular complementation assay (BiMC) to detect and visualize a Marburg mVP40–Nedd4 interaction in live mammalian cells. Antiviral activity was assessed for selected compounds using a live recombinant vesicular stomatitis virus (VSV) (M40 virus) that expresses the EBOV VP40 PPxY L-domain. Finally selected compounds were evaluated in several ADME assays to have an early assessment of their drug properties. Our compounds had low nM potency in these assays (e.g., compounds 21, 24, 26, 39), and had good human liver microsome stability, as well as little or no inhibition of P450 3A4.

Alkylation potency and protein specificity of aromatic urea derivatives and bioisosteres as potential irreversible antagonists of the colchicine-binding site

A number of N-phenyl-N′-(2-chloroethyl)ureas (CEUs) have been shown to be potent antimitotics through their covalent binding to the colchicine-binding site on intracellular β-tubulin. The present communication aimed to evaluate the role of the electrophilic 2-chloroethyl amino moiety of CEU on cell growth inhibition and the specificity of the drugs as irreversible antagonists of the colchicine-binding site. To that end, several N-phenyl-N′-(2-ethyl)urea (EU), N-phenyl-N′-(2-chloroethyl)urea (CEU), N-aryl amino-2-oxazoline (OXA), and N-phenyl-N′-(2-chloroacetyl)urea (CAU) derivatives were prepared and tested for their antiproliferative activity, their effect on the cell cycle, and their irreversible binding to β-tubulin. EU derivatives were devoid of antiproliferative activity. CEUs (2h-2i, 2k, 2l, OXA 3e, 3h, 3i, 3k, 3l, tBCEU, and ICEU), OXA (3h, 3i, 3k, 3l, tBOXA, and IOXA), and CAU (4a-4m, tBCAU, and ICAU) had GI50 between 1.7 and 10 μM on three tumor cell lines. Cytotoxic CEU and OXA arrested the cell cycle in G2/M phase, while the corresponding CAU were not phase specific. Finally, Western blot analysis clearly showed that only CEUs 2h, 2k, 2l, tBCEU, ICEU and OXA 3h, 3i, 3k, 3l, tBOXA,and IOXA were able to bind irreversibly to the colchicine-binding site. Our results suggest that increasing the potency of the electrophilic moiety of the aromatic ureas enhances their antiproliferative activity but decreases significantly their capacity to covalently bind to the colchicine-binding site.