tembotrione : An aromatic ketone that is 2-benzoylcyclohexane-1,3-dione in which the phenyl group is substituted at positions 2, 3, and 4 by chlorine, (2,2,2-trifluoroethoxy)methyl, and methylsulfonyl groups, respectively. It is a post-emergence herbicide used (particularly in conjunction with the herbicide safener cyprosulfamide) for the control of a wide range of broad-leaved and grassy weeds in corn and other crops. [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 | 11556911 |
| CHEMBL ID | 2272077 |
| CHEBI ID | 132273 |
| SCHEMBL ID | 116424 |
| MeSH ID | M0590324 |
| Synonym |
|---|
| tembotrione |
| 2-{2-chloro-4-mesyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione |
| 2-{2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione |
| 335104-84-2 |
| 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione |
| CHEBI:132273 |
| 2-{2-chloro-4-(methanesulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione |
| 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]cyclohexane-1,3-dione |
| unii-wa5uz202ks |
| tembotrione [iso] |
| wa5uz202ks , |
| hsdb 7881 |
| cas-335104-84-2 |
| dtxcid3027037 |
| tox21_302382 |
| dtxsid5047037 , |
| NCGC00256145-01 |
| 263401-02-1 |
| tembotrione [mi] |
| ae-0172747 |
| 2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-1,3-cyclohexanedione |
| 2-(2-chloro-4-mesyl-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)cyclohexane-1,3-dione |
| 2-cyclohexen-1-one, 2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-3-hydroxy- |
| 2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)-3-hydroxy-2-cyclohexen-1-one |
| SCHEMBL116424 |
| CHEMBL2272077 |
| 2-{2-chloro-4-methanesulfonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}cyclohexane-1,3-dione |
| AKOS027269927 |
| tembotrione, pestanal(r), analytical standard |
| 2-(2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoroethoxy)methyl)benzoyl)cyclohexane-1,3-dione |
| tembotrione 100 microg/ml in acetonitrile |
| mfcd11840613 |
| Q2372037 |
| AMY11225 |
| bdbm50264336 |
| W15593 |
| A935465 |
| AS-56908 |
| CS-0142853 |
| HY-137910 |
Tembotrione is a triketone group herbicide having worldwide applications for weed management in maize. It targets the 4-Hydroxyphenylpyruvate dioxygenase enzyme of weeds.
| Excerpt | Relevance | Reference |
|---|---|---|
| " Dose-response experiments indicated that the level of resistance to the HPPD inhibitor mesotrione is at least tenfold relative to sensitive biotypes." | ( Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. Hager, AG; Hausman, NE; Kaundun, SS; Polge, ND; Riechers, DE; Singh, S; Thomas, DA; Tranel, PJ, 2011) | 0.37 |
| Role | Description |
|---|---|
| herbicide | A substance used to destroy plant pests. |
| agrochemical | An agrochemical is a substance that is used in agriculture or horticulture. |
| EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor | An EC 1.13.11.* (oxidoreductase acting on single donors and incorporating 2 atoms of oxygen) inhibitor that interferes with the activity of 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27). |
| carotenoid biosynthesis inhibitor | Any pathway inhibitor that acts on the carotenoid biosynthesis pathway. |
| [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 |
|---|---|
| sulfone | An organosulfur compound having the structure RS(=O)2R (R =/= H). |
| cyclic ketone | |
| aromatic ketone | A ketone in which the carbonyl group is attached to an aromatic ring. |
| monochlorobenzenes | Any member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine. |
| organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
| ether | An organooxygen compound with formula ROR, where R is not hydrogen. |
| beta-triketone | A triketone in which the each ketone functionality is located beta- to the other two. |
| [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) |
|---|---|---|---|---|---|---|---|
| acetylcholinesterase | Homo sapiens (human) | Potency | 29.9816 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347398 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 27.5223 | 0.0002 | 29.3054 | 16,493.5996 | AID743069 |
| [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) |
|---|---|---|---|---|---|---|---|
| 4-hydroxyphenylpyruvate dioxygenase | Arabidopsis thaliana (thale cress) | Ki | 0.0130 | 0.0130 | 0.0130 | 0.0130 | AID1480422 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| tyrosine catabolic process | 4-hydroxyphenylpyruvate dioxygenase | Arabidopsis thaliana (thale cress) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| 4-hydroxyphenylpyruvate dioxygenase activity | 4-hydroxyphenylpyruvate dioxygenase | Arabidopsis thaliana (thale cress) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1104960 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 12 assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104987 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 15 assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104990 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 12 assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104976 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 12 assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1480422 | Inhibition of Arabidopsis thaliana HPPD expressed in Escherichia coli JM109 using HPPA as substrate after 10 mins | 2017 | Journal of medicinal chemistry, 05-25, Volume: 60, Issue:10 | 4-Hydroxyphenylpyruvate Dioxygenase and Its Inhibition in Plants and Animals: Small Molecules as Herbicides and Agents for the Treatment of Human Inherited Diseases. |
| AID1104969 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 16 assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104978 | Herbicidal activity against Amaranthus tuberculatus biotype ACR assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104996 | Herbicidal activity against Amaranthus tuberculatus biotype WCS assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104963 | Herbicidal activity against Amaranthus tuberculatus biotype ACR assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104972 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 15 assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104954 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 16 assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104993 | Herbicidal activity against Amaranthus tuberculatus biotype ACR assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104981 | Herbicidal activity against Amaranthus tuberculatus biotype WCS assessed as visual injury at 92 g/ha applied as spray after 14 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104957 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 15 assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104984 | Herbicidal activity against Amaranthus tuberculatus biotype MCR 16 assessed as visual injury at 92 g/ha applied as spray after 7 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| AID1104966 | Herbicidal activity against Amaranthus tuberculatus biotype WCS assessed as visual injury at 92 g/ha applied as spray after 21 days under green house conditions relative to untreated control | 2011 | Pest management science, Mar, Volume: 67, Issue:3 | Resistance to HPPD-inhibiting herbicides in a population of waterhemp (Amaranthus tuberculatus) from Illinois, United States. |
| [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 | 0 (0.00) | 29.6817 |
| 2010's | 10 (45.45) | 24.3611 |
| 2020's | 12 (54.55) | 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 strong demand-to-supply ratio for research on this compound.
| This Compound (40.95) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (13.64%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 19 (86.36%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||