Page last updated: 2024-12-10

2-(2,3,3-trichloro-1-nitroprop-2-enylidene)-1,3-dihydrobenzimidazole

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

The compound you're describing, **2-(2,3,3-trichloro-1-nitroprop-2-enylidene)-1,3-dihydrobenzimidazole**, is more commonly known as **nitrofen**, a fungicide. Its importance in research stems from its **biological activity** and **potential environmental concerns**.

Here's a breakdown:

**Chemical Structure and Properties:**

* **Structure:** Nitrofen consists of a benzimidazole ring system attached to a nitro-substituted allyl group. The allyl group has three chlorine atoms and a nitro group.
* **Properties:** It's a solid at room temperature and is sparingly soluble in water.

**Biological Activity:**

* **Fungicide:** Nitrofen was primarily used as a fungicide in agriculture, particularly for controlling diseases in cereal crops and vegetables.
* **Mechanism of Action:** It disrupts the growth of fungi by inhibiting their ability to produce energy through mitochondrial respiration. This action makes it an effective broad-spectrum fungicide.

**Research Significance:**

1. **Environmental Impact:** Nitrofen has been found to persist in the environment and to accumulate in soil and water. Its potential for soil and water contamination has raised concerns, particularly for aquatic ecosystems.
2. **Human Health Effects:** Studies have shown that nitrofen can be toxic to aquatic organisms and may have adverse effects on human health, especially with prolonged exposure.
3. **Alternative Fungicides:** The research focuses on finding alternative fungicides that are more environmentally friendly and have reduced toxicity.
4. **Bioremediation:** Researchers are exploring the use of microorganisms and enzymes to degrade nitrofen in contaminated environments.
5. **Ecotoxicology:** Nitrofen serves as a model compound for studying the fate and effects of organic pollutants in the environment.

**Current Status:**

* **Banned in Several Countries:** Due to environmental concerns, nitrofen has been banned in many countries, including the European Union and the United States.

In summary, 2-(2,3,3-trichloro-1-nitroprop-2-enylidene)-1,3-dihydrobenzimidazole (nitrofen) is a fungicide that, despite its past use, has been the subject of extensive research due to its environmental and health implications. Research on nitrofen helps scientists understand the potential risks of chemical pollutants and develop safer alternatives for agriculture and human health.

Cross-References

ID SourceID
PubMed CID3106764
CHEMBL ID1323364
CHEBI ID115526
SCHEMBL ID14513386

Synonyms (21)

Synonym
2-(2,3,3-trichloro-1-(hydroxy(oxido)amino)-2-propenylidene)-2,3-dihydro-1h-benzimidazole
2-(2,3,3-trichloro-1-nitro-prop-2-enylidene)-1,3-dihydrobenzimidazole
NCI60_022446
nsc-665105
nsc665105
MLS000713016
smr000282783
CBDIVE_006924
2-(2,3,3-trichloro-1-nitro-allylidene)-2,3-dihydro-1h-benzoimidazole
CHEBI:115526
AKOS000669248
HMS2684G04
2-(2,3,3-trichloro-1-nitroprop-2-enylidene)-1,3-dihydrobenzimidazole
SCHEMBL14513386
CHEMBL1323364
2-(2,3,3-trichloro-1-nitroprop-2-en-1-ylidene)-2,3-dihydro-1h-1,3-benzodiazole
Q27197379
2-(2,3,3-trichloro-1-nitro-2-propen-1-ylidene)-2,3-dihydro-1h-benzimidazole
70265-24-6
2-(2,3,3-trichloro-1-nitroprop-2-en-1-ylidene)-2,3-dihydro-1h-benzimidazole
STL580864
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzimidazolesAn organic heterocyclic compound containing a benzene ring fused to an imidazole ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (26)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency3.54810.003245.467312,589.2998AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency8.91250.004023.8416100.0000AID485290
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency17.74070.140911.194039.8107AID2451
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency50.11870.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
Nrf2Homo sapiens (human)Potency11.22020.09208.222223.1093AID624171
thioredoxin reductaseRattus norvegicus (Norway rat)Potency11.22020.100020.879379.4328AID588453
phosphopantetheinyl transferaseBacillus subtilisPotency89.12510.141337.9142100.0000AID1490
ATAD5 protein, partialHomo sapiens (human)Potency16.35350.004110.890331.5287AID504467
TDP1 proteinHomo sapiens (human)Potency22.72650.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency11.46420.180013.557439.8107AID1460; AID1468
thioredoxin glutathione reductaseSchistosoma mansoniPotency3.16230.100022.9075100.0000AID485364
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency6.30960.011212.4002100.0000AID1030
regulator of G-protein signaling 4Homo sapiens (human)Potency17.78280.531815.435837.6858AID504845
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency39.81070.707936.904389.1251AID504333
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency56.23410.354828.065989.1251AID504847
parathyroid hormone/parathyroid hormone-related peptide receptor precursorHomo sapiens (human)Potency158.48903.548119.542744.6684AID743266
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency14.12540.425612.059128.1838AID504891
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency50.11870.050127.073689.1251AID588590
urokinase-type plasminogen activator precursorMus musculus (house mouse)Potency6.30960.15855.287912.5893AID540303
plasminogen precursorMus musculus (house mouse)Potency6.30960.15855.287912.5893AID540303
urokinase plasminogen activator surface receptor precursorMus musculus (house mouse)Potency6.30960.15855.287912.5893AID540303
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency23.35070.00798.23321,122.0200AID2546; AID2551
gemininHomo sapiens (human)Potency0.81990.004611.374133.4983AID624296
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency29.20430.251215.843239.8107AID504327; AID588347
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
calpain II, partialSus scrofa (pig)IC50 (µMol)27.79271.77424.93387.7087AID1420
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (14.29)29.6817
2010's4 (57.14)24.3611
2020's2 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.22

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 Index12.22 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.22)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]