17090-44-7

Usage

Herbicide

Used for controlling weeds in rice crops 2,2-dichloro-N-(3,4-dichlorophenyl)acetamide is primarily employed as a herbicide to manage weeds in rice fields, ensuring the healthy growth of the crop.

Mode of action

Inhibits acetolactate synthase enzyme activity The compound works by inhibiting the activity of the enzyme acetolactate synthase, which plays a crucial role in plant growth and development.

Disruption of amino acid biosynthesis

Essential amino acids By inhibiting acetolactate synthase, 2,2-dichloro-N-(3,4-dichlorophenyl)acetamide ultimately disrupts the biosynthesis of essential amino acids in plants, leading to their death.

Environmental concerns

Persistence and bioaccumulation The compound's persistence in the environment and potential for bioaccumulation raise concerns about its long-term effects on ecosystems.

Upstream product

• 79-43-6 dichloro-acetic acid 
• 95-76-1 m,p-dichloroaniline 
• 79-36-7 dichloroacethyl chloride 

Relevant academic research and scientific papers

Novel N-phenyl dichloroacetamide derivatives as anticancer reagents: Design, synthesis and biological evaluation

A current study shows that sodium dichloroacetate (DCA) can induce cancer cell apoptosis and inhibit tumor growth, but its cytotoxic activity is low (IC50 > 1000 μM for A549). In this paper, a variety of DCA derivatives were synthesized, and their cytotoxic activities were evaluated. The result showed that the N-phenyl-2,2-dichloroacetamide analogues had satisfactory potencies. Among them, N-(3-iodophenyl)-2,2-dichloroacetamide (3e), an optimized lead compound, has an IC50 against A549 as low as 4.76 μM. Furthermore, it can induce cancer cell apoptosis and has a low toxicity in mice (LD50 = 1117 mg/kg). N-phenyl-2,2-dichloroacetamide analogues has higher cytotoxic activity and N-(3-iodophenyl)-2,2-dichloroacetamide (3e) is an optimized lead compound.

Substituent effect on the infrared and Raman spectra of N-(substituted-phenyl)-2,2-dichloroacetamides, XyC6H 5-yNHCOCHCl2 (X = o/m/p-CH3 or Cl; y = 1, 2 or 3)

Several substituted N-(phenyl)-2,2-dichloroacetamides of the configuration XyC6H5-yNHCOCHCl2 (where, X = H, CH3 or Cl and y = 1, 2 or 3) have been synthesized and their infrared and Raman spectra measured in the solid state with the objective of correlating CO and NH frequencies of these substituted phenyldichloroacetamides with those of substituted phenylchloroacetamides and trichloroacetamides. The study reveals that there is no systematic variation in the frequencies with the substitution. The effect of substitution in the phenyl ring in terms of electron-donating and electron-withdrawing groups could not be generalized. The same trend is observed even with disubstituted phenyl-2,2-dichloroacetamides, which may be due to the varying crystalline states of the amides as the spectra are measured in the solid state. The infrared and Raman frequencies of the amides of the configuration XyC6H5-yNHCOR (where, X = H, CH3 or Cl and y = 1, 2 or 3 and R = CH2Cl, CHCl2, CCl3) have also been examined for comparison purpose. The entire data indicate that neither the infrared CO or NH absorption frequencies nor the Raman scattered CO or NH frequencies show regular trends in all these compounds for the stated above.