Bentranil is a synthetic fungicide that belongs to the benzoylphenyl urea class. It acts as a chitin synthesis inhibitor, interfering with the formation of the chitinous exoskeletons of fungal pathogens. Bentranil is primarily used to control powdery mildew diseases in a variety of crops, including grapes, apples, and strawberries. Its effectiveness stems from its ability to penetrate the fungal cell wall and disrupt chitin synthesis. Research on bentranil focuses on its efficacy against specific fungal pathogens, its environmental impact, and the development of more sustainable alternatives. The compound has been studied for its potential to inhibit the growth of various fungi, including those responsible for plant diseases, human pathogens, and even those involved in bioremediation.'
bentranil : A benzoxazine that is 4H-3,1-benzoxazin-4-one substituted by a phenyl group at position 2. It is a postemergence herbicide used for the control of annual weeds in cereal crops, maize, and rice. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 13926 |
| CHEMBL ID | 24449 |
| CHEBI ID | 145402 |
| SCHEMBL ID | 272702 |
| Synonym |
|---|
| bdbm50077011 |
| 2-phenyl-benzo[d][1,3]oxazin-4-one |
| EU-0066816 |
| 1022-46-4 |
| wln: t66 bvo enj dr |
| linurotox |
| nsc16082 |
| 2-phenyl-3,1-benzoxazinone-(4) |
| nsc-16082 |
| 4h-3, 2-phenyl- |
| linarotox |
| h-170 |
| bentranil |
| 4h-3,1-benzoxazin-4-one, 2-phenyl- |
| CBDIVE_001429 |
| OPREA1_579311 |
| CHEMDIV2_003515 |
| MAYBRIDGE1_006945 |
| STK385092 |
| 2-phenyl-4h-3,1-benzoxazin-4-one |
| CHEMBL24449 , |
| AKOS000313370 |
| HMS1378P17 |
| HMS561D15 |
| CHEBI:145402 |
| 2-phenyl-3,1-benzoxazin-4-one |
| 2-phenyl-[3,1]benzoxazin-4-one |
| nsc 16082 |
| unii-f6r7d8ujo5 |
| ai3-61952 |
| f6r7d8ujo5 , |
| 2-phenylbenzo[d]1,3-oxazin-4-one |
| SR-01000389722-2 |
| sr-01000389722 |
| FT-0622748 |
| SCHEMBL272702 |
| 2-phenyl-4-[4h]-3,1-benzoxazinone |
| 3-phenyl-1h-2,4-benzoxazin-1-one |
| 3-phenyl-2,4-benzoxazin-1-one |
| DTXSID60144732 |
| J-000660 |
| mfcd00043598 |
| SR-01000389722-1 |
| bentranil, pestanal(r), analytical standard |
| JS-3012 |
| 2-phenylbenzo(d)(1,3)oxazin-4-one |
| 2-phenyl-4-oxo-3,1-benzoxazine |
| 2-phenyl-4h-benzo[d][1,3]oxazin-4-one |
| Z57177801 |
| T70020 |
| BAA02246 |
| CS-0086717 |
| B5739 |
| EN300-22840157 |
| PD127826 |
| Role | Description |
|---|---|
| herbicide | A substance used to destroy plant pests. |
| [role 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] | |
| Class | Description |
|---|---|
| benzoxazine | |
| [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 | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chymotrypsinogen A | Bos taurus (cattle) | IC50 (µMol) | 11.7000 | 0.9800 | 4.0560 | 7.2000 | AID1802581 |
| Chymotrypsinogen A | Bos taurus (cattle) | Ki | 8.7000 | 0.9000 | 4.0000 | 8.7000 | AID1802582 |
| Neutrophil elastase | Homo sapiens (human) | IC50 (µMol) | 17.0000 | 0.0063 | 2.0734 | 22.3780 | AID66497 |
| Neutrophil elastase | Homo sapiens (human) | Ki | 9.5499 | 0.0020 | 1.2866 | 9.5499 | AID67499; AID67501 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| protein binding | Chymotrypsinogen A | Bos taurus (cattle) |
| serpin family protein binding | Chymotrypsinogen A | Bos taurus (cattle) |
| protease binding | Neutrophil elastase | Homo sapiens (human) |
| transcription corepressor activity | Neutrophil elastase | Homo sapiens (human) |
| endopeptidase activity | Neutrophil elastase | Homo sapiens (human) |
| serine-type endopeptidase activity | Neutrophil elastase | Homo sapiens (human) |
| protein binding | Neutrophil elastase | Homo sapiens (human) |
| heparin binding | Neutrophil elastase | Homo sapiens (human) |
| peptidase activity | Neutrophil elastase | Homo sapiens (human) |
| cytokine binding | Neutrophil elastase | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1664161 | Displacement of [3H]DPCPX from Sprague-Dawley rat whole brain membrane A1AR in presence of GTP by radioligand binding assay | |||
| AID23981 | Component acylation rate constant for interaction with human leukocyte elastase | 1990 | Journal of medicinal chemistry, Feb, Volume: 33, Issue:2 | Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase. |
| AID66497 | In vitro inhibitory activity against human leukocyte elastase (HLE) | 1999 | Bioorganic & medicinal chemistry letters, May-03, Volume: 9, Issue:9 | Synthesis and in vitro and in vivo evaluation of the 2-(6'methoxy-3',4'-dihydro-1'-naphtyl)-4H-3,1-benzoxazin-4- one as a new potent substrate inhibitor of human leukocyte elastase. |
| AID1664159 | Displacement of [3H]NECA from Sprague-Dawley rat striatal membrane A2A adenosine receptor by scintillation counting analysis | |||
| AID67501 | pKi against human leukocyte elastase (HLE) | 1999 | Bioorganic & medicinal chemistry letters, May-03, Volume: 9, Issue:9 | Synthesis and in vitro and in vivo evaluation of the 2-(6'methoxy-3',4'-dihydro-1'-naphtyl)-4H-3,1-benzoxazin-4- one as a new potent substrate inhibitor of human leukocyte elastase. |
| AID1664157 | Displacement of [3H]DPCPX from Sprague-Dawley rat whole brain membrane A1AR by scintillation counting analysis | |||
| AID1374783 | Inhibition of recombinant Escherichia coli N-terminal His-tagged rhomboid protease GlpG expressed in Escherichia coli C43(DE3) cells at 250 uM using gurken as substrate preincubated for 30 mins followed by substrate addition measured after 90 mins by SDS- | 2018 | Bioorganic & medicinal chemistry letters, 05-01, Volume: 28, Issue:8 | Discovery and validation of 2-styryl substituted benzoxazin-4-ones as a novel scaffold for rhomboid protease inhibitors. |
| AID233342 | Alkaline hydrolysis rate of the compound | 1990 | Journal of medicinal chemistry, Feb, Volume: 33, Issue:2 | Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase. |
| AID1664160 | Displacement of [3H]NECA from Sprague-Dawley rat striatal membrane A2A adenosine receptor at 100 uM by scintillation counting analysis relative to control | |||
| AID66662 | In vitro inhibitory activity against human leukocyte elastase (HLE), at a concentration of 75 uM | 1999 | Bioorganic & medicinal chemistry letters, May-03, Volume: 9, Issue:9 | Synthesis and in vitro and in vivo evaluation of the 2-(6'methoxy-3',4'-dihydro-1'-naphtyl)-4H-3,1-benzoxazin-4- one as a new potent substrate inhibitor of human leukocyte elastase. |
| AID67499 | Inhibition of human leukocyte elastase | 1990 | Journal of medicinal chemistry, Feb, Volume: 33, Issue:2 | Design and synthesis of 4H-3,1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase. |
| AID66660 | In vitro inhibitory activity against human leukocyte elastase (HLE), at a concentration of 1.5 uM | 1999 | Bioorganic & medicinal chemistry letters, May-03, Volume: 9, Issue:9 | Synthesis and in vitro and in vivo evaluation of the 2-(6'methoxy-3',4'-dihydro-1'-naphtyl)-4H-3,1-benzoxazin-4- one as a new potent substrate inhibitor of human leukocyte elastase. |
| AID66661 | In vitro inhibitory activity against human leukocyte elastase (HLE), at a concentration of 15 uM | 1999 | Bioorganic & medicinal chemistry letters, May-03, Volume: 9, Issue:9 | Synthesis and in vitro and in vivo evaluation of the 2-(6'methoxy-3',4'-dihydro-1'-naphtyl)-4H-3,1-benzoxazin-4- one as a new potent substrate inhibitor of human leukocyte elastase. |
| AID1664162 | Ratio of Ki for displacement of [3H]DPCPX from Sprague-Dawley rat whole brain membrane A1AR in presence of GTP to Ki for displacement of [3H]DPCPX from Sprague-Dawley rat whole brain A1AR | |||
| AID1802582 | α-Chymotrypsin Inhibition Kinetic Assay from Article 10.1016/j.bioorg.2017.01.001: \\Synthesis, structure-activity relationships studies of benzoxazinone derivatives as a-chymotrypsin inhibitors.\\ | 2017 | Bioorganic chemistry, 02, Volume: 70 | Synthesis, structure-activity relationships studies of benzoxazinone derivatives as α-chymotrypsin inhibitors. |
| AID1802581 | α-Chymotrypsin Inhibition Assay from Article 10.1016/j.bioorg.2017.01.001: \\Synthesis, structure-activity relationships studies of benzoxazinone derivatives as a-chymotrypsin inhibitors.\\ | 2017 | Bioorganic chemistry, 02, Volume: 70 | Synthesis, structure-activity relationships studies of benzoxazinone derivatives as α-chymotrypsin inhibitors. |
| [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 | 2 (40.00) | 18.2507 |
| 2000's | 0 (0.00) | 29.6817 |
| 2010's | 2 (40.00) | 24.3611 |
| 2020's | 1 (20.00) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (20.16) 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 | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||