Page last updated: 2024-12-07

2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile, also known as **dichlorophenoxynitrobenzonitrile (DCNB)**, is a **herbicide** that belongs to the **nitrophenol** family.

Here's why it's important for research:

**1. Mode of Action:**

* DCNB is a **photosynthetic inhibitor**. It interferes with the **electron transport chain** in photosynthesis, specifically at the **photosystem II complex**. This disruption disrupts plant growth and ultimately leads to death.
* Research on DCNB's mode of action can help understand the mechanisms of photosynthesis and develop new herbicides with improved efficacy and specificity.

**2. Environmental Impact:**

* DCNB has been used as a **herbicide** in various agricultural settings.
* Research on DCNB focuses on its **environmental fate and persistence**. It's essential to understand how it breaks down in the environment, its potential for soil and water contamination, and its impact on non-target organisms.

**3. Resistance Mechanisms:**

* Plants can develop resistance to DCNB.
* Research on DCNB resistance mechanisms can help identify the genetic and biochemical changes involved and develop strategies to manage resistance.

**4. Chemical Synthesis and Structure-Activity Relationships:**

* Research on DCNB involves the **synthesis and modification of its structure**.
* Studying these changes can lead to the development of new analogs with improved herbicidal activity or reduced environmental impact.

**5. Agricultural Applications:**

* DCNB has been used to control weeds in various crops.
* Research can explore its potential for sustainable agriculture, such as its use in **integrated pest management (IPM)** strategies.

**6. Chemical Biology:**

* DCNB's interactions with specific cellular components, such as the photosynthetic apparatus, are of interest in **chemical biology**.
* This research can help understand fundamental biological processes and identify new drug targets.

**Overall, research on 2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile is essential to address various issues related to its environmental impact, development of new herbicides, understanding plant resistance, and its potential for agricultural applications.**

Cross-References

ID SourceID
PubMed CID133143
CHEMBL ID343131
SCHEMBL ID3487806
MeSH IDM0110976

Synonyms (13)

Synonym
benzonitrile, 2-(3,4-dichlorophenoxy)-5-nitro-
2-(3,4-dichlorophenoxy)-5-nitro-benzonitrile
mdl-860
78940-62-2
mdl 860
CHEMBL343131
2-(3,4-dichlorophenoxy)-5-nitrobenzonitrile
AKOS017261835
SCHEMBL3487806
QAYKDRUKUZJJSO-UHFFFAOYSA-N
mdl-860, >=98% (hplc)
A902356
DTXSID601000150
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (63)

Assay IDTitleYearJournalArticle
AID167257Antiviral activity against rhinovirus RV-741986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387026Antiviral activity against Coxsackievirus B1 in african green monkey Vero cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID108206Antiviral activity against mengo1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167389Antiviral activity against rhinovirus RV-891986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID199880Ratio of the MIC50 of 6-(4-Nitro-phenoxy)-nicotinonitrile compared to compound obtained in the same test for Rhinovirus (RV)-21986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167244Antiviral activity against rhinovirus RV-1B1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167251Antiviral activity against rhinovirus RV-441986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID29738Cytotoxicity concentration in HeLa cells1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID199879Lowest concentration to reduce viral effect by 50% or more against Rhinovirus (RV)-21986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID54330Lowest concentration to reduce viral effect by 50% or more against coxsackie virus A211986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID199877Lowest concentration to reduce viral effect by 50% or more against Rhinovirus (RV)-1A1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464162Antiviral activity against Coxsackievirus B1 infected in new born ICR mouse assessed as protection index at 75 mg/kg, sc administered for 12 days (Rvb = 0%)2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID167250Antiviral activity against rhinovirus RV-41986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387028Antiviral activity against Coxsackievirus B4 in african green monkey Vero cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID167247Antiviral activity against rhinovirus RV-321986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387029Antiviral activity against Coxsackievirus B5 in african green monkey Vero cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID387031Antiviral activity against Coxsackievirus A24 in human MRC5 cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID1464159Antiviral activity against Coxsackievirus B1 infected in new born ICR mouse assessed as mortality at 75 mg/kg, sc administered for 12 days (Rvb = 100%)2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID167256Antiviral activity against rhinovirus RV-681986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167396Antiviral activity against rhinovirus RV-Hanks1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID199878Ratio of the MIC50 of 6-(4-Nitro-phenoxy)-nicotinonitrile compared to compound obtained in the same test for Rhinovirus (RV)-1A1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464147Cytotoxicity against human Hep2 cells assessed as decrease in cell viability after 48 hrs by neutral red uptake assay2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID167248Antiviral activity against rhinovirus RV-331986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167242Antiviral activity against rhinovirus RV-131986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167243Antiviral activity against rhinovirus RV-141986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387027Antiviral activity against Coxsackievirus B2 in african green monkey Vero cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID167255Antiviral activity against rhinovirus RV-641986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167254Antiviral activity against rhinovirus RV-551986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464156Antiviral activity against Coxsackievirus B1 infected in new born ICR mouse assessed as increase in mean survival time at 75 mg/kg, sc administered for 12 days2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID387034Antiviral activity against Enterovirus 68 in human MRC5 cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID1464153Selectivity index, ratio of CC50 for human Hep2 cells to IC50 for Coxsackievirus B3 Nancy infected in human Hep2 cells2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID1679148Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 cultured in GAS media assessed as reduction in bacterial growth incubated for 7 days by resazurin dye fluorescence based assay2021RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1
Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds.
AID387033Antiviral activity against Echovirus 11 in human MRC5 cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID167241Antiviral activity against rhinovirus RV-101986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167391Compound was evaluated for inhibition of rhinovirus RV-Hanks 75%1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID106696Compound was evaluated for oral activity in Coxsackievirus A21 infected mice; survival/total = 27/381986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464152Selectivity index, ratio of CC50 for human Hep2 cells to IC50 for Coxsackievirus B1 Connecticut 5 infected in human Hep2 cells2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID167249Antiviral activity against rhinovirus RV-391986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167395Compound was evaluated for inhibition of rhinovirus RV-Hanks at a dose of 50 ug/mL by by 50-75%1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167245Antiviral activity against rhinovirus RV-211986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464150Antiviral activity against Coxsackievirus B1 Connecticut 5 infected in human Hep2 cells assessed as inhibition of virus-induced cytopathic effect after 48 hrs by neutral red uptake assay2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID1679147Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 cultured in 7H12 media assessed as reduction in bacterial growth incubated for 7 days by resazurin dye fluorescence based assay2021RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1
Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds.
AID246229Effective concentration required to inhibit Coxsackie B3 virus induced cytopathicity in vero cells2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides.
AID68428Antiviral activity against Echo 121986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID54480Antiviral activity against rhinovirus Coxsackie B31986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1679146Cytotoxicity against African green monkey Vero cells assessed by reduction in cell viability incubated for 72 hrs by resazurin dye fluorescence based assay2021RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1
Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds.
AID167246Antiviral activity against rhinovirus RV-291986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID106683Compound was evaluated for oral activity in Coxsackievirus A21 infected mice; survival/total = 2/301986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387025Antiviral activity against Coxsackievirus B3 assessed as reduction of virus-induced cytopathogenicity after 3 days by MTS assay2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID167390Antiviral activity against rhinovirus RV-91986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387030Antiviral activity against Coxsackievirus B6 in african green monkey Vero cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID167393Compound was evaluated for inhibition of rhinovirus RV-Hanks at a dose of 50 ug/mL by < 50%1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID167253Antiviral activity against rhinovirus RV-51986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464148Antiviral activity against Poliovirus 1 LSc-2ab infected in human Hep2 cells assessed as inhibition of virus-induced cytopathic effect after 48 hrs by neutral red uptake assay2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID54472Ratio of the MIC50 of 6-(4-Nitro-phenoxy)-nicotinonitrile compared to compound obtained in the same test for coxsackie A211986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID246485Effective concentration required to inhibit herpes simplex virus type 1 Kos strain induced cytopathicity in Hel cells; not determined2005Journal of medicinal chemistry, Jan-27, Volume: 48, Issue:2
Synthesis and antiviral evaluation of cis-substituted cyclohexenyl and cyclohexanyl nucleosides.
AID220032Antiviral activity against coxsackie B41986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID200037Antiviral activity against rhinovirus Polio 21986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID387032Antiviral activity against Echovirus 9 in human MRC5 cells2008Bioorganic & medicinal chemistry letters, Sep-15, Volume: 18, Issue:18
Synthesis and anti-CVB 3 evaluation of substituted 5-nitro-2-phenoxybenzonitriles.
AID1464149Selectivity index, ratio of CC50 for human Hep2 cells to IC50 for Poliovirus 1 infected in human Hep2 cells2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID167252Antiviral activity against rhinovirus RV-491986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
AID1464151Antiviral activity against Coxsackievirus B3 Nancy infected in human Hep2 cells assessed as inhibition of virus-induced cytopathic effect after 48 hrs by neutral red uptake assay2017Bioorganic & medicinal chemistry letters, 10-01, Volume: 27, Issue:19
Synthesis and anti-enterovirus activity of new analogues of MDL-860.
AID167258Antiviral activity against rhinovirus RV-81986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Antipicornavirus activity of substituted phenoxybenzenes and phenoxypyridines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (25.00)18.7374
1990's0 (0.00)18.2507
2000's3 (25.00)29.6817
2010's4 (33.33)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.93

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.93 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]