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.
ID Source | ID |
---|---|
PubMed CID | 3106764 |
CHEMBL ID | 1323364 |
CHEBI ID | 115526 |
SCHEMBL ID | 14513386 |
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 |
Class | Description |
---|---|
benzimidazoles | An 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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE | Homo sapiens (human) | Potency | 3.5481 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 8.9125 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
Chain A, Putative fructose-1,6-bisphosphate aldolase | Giardia intestinalis | Potency | 17.7407 | 0.1409 | 11.1940 | 39.8107 | AID2451 |
Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 50.1187 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 28.1838 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
Nrf2 | Homo sapiens (human) | Potency | 11.2202 | 0.0920 | 8.2222 | 23.1093 | AID624171 |
thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 11.2202 | 0.1000 | 20.8793 | 79.4328 | AID588453 |
phosphopantetheinyl transferase | Bacillus subtilis | Potency | 89.1251 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
ATAD5 protein, partial | Homo sapiens (human) | Potency | 16.3535 | 0.0041 | 10.8903 | 31.5287 | AID504467 |
TDP1 protein | Homo sapiens (human) | Potency | 22.7265 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
Microtubule-associated protein tau | Homo sapiens (human) | Potency | 11.4642 | 0.1800 | 13.5574 | 39.8107 | AID1460; AID1468 |
thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 3.1623 | 0.1000 | 22.9075 | 100.0000 | AID485364 |
aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 6.3096 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
regulator of G-protein signaling 4 | Homo sapiens (human) | Potency | 17.7828 | 0.5318 | 15.4358 | 37.6858 | AID504845 |
bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 39.8107 | 0.7079 | 36.9043 | 89.1251 | AID504333 |
vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 56.2341 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
parathyroid hormone/parathyroid hormone-related peptide receptor precursor | Homo sapiens (human) | Potency | 158.4890 | 3.5481 | 19.5427 | 44.6684 | AID743266 |
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | Homo sapiens (human) | Potency | 14.1254 | 0.4256 | 12.0591 | 28.1838 | AID504891 |
DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 50.1187 | 0.0501 | 27.0736 | 89.1251 | AID588590 |
urokinase-type plasminogen activator precursor | Mus musculus (house mouse) | Potency | 6.3096 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
plasminogen precursor | Mus musculus (house mouse) | Potency | 6.3096 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
urokinase plasminogen activator surface receptor precursor | Mus musculus (house mouse) | Potency | 6.3096 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 23.3507 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
geminin | Homo sapiens (human) | Potency | 0.8199 | 0.0046 | 11.3741 | 33.4983 | AID624296 |
histone acetyltransferase KAT2A isoform 1 | Homo sapiens (human) | Potency | 29.2043 | 0.2512 | 15.8432 | 39.8107 | AID504327; AID588347 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
calpain II, partial | Sus scrofa (pig) | IC50 (µMol) | 27.7927 | 1.7742 | 4.9338 | 7.7087 | AID1420 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. 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. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
AID1794808 | Fluorescence-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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (14.29) | 29.6817 |
2010's | 4 (57.14) | 24.3611 |
2020's | 2 (28.57) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (12.22) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 7 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |