Triflusulfuron-methyl is a sulfonylurea herbicide that is widely used to control annual and perennial broadleaf weeds in various crops, including cereals, soybeans, and rice. It is a highly effective herbicide, known for its selective action, meaning it targets weeds while minimizing damage to the desired crops. The synthesis of triflusulfuron-methyl involves multiple steps, starting with the reaction of a substituted aniline with a sulfonyl chloride. The resulting sulfonamide is then reacted with a substituted pyrimidine to form the final product. Triflusulfuron-methyl is a potent inhibitor of acetolactate synthase (ALS), an enzyme essential for amino acid biosynthesis in plants. By inhibiting ALS, triflusulfuron-methyl disrupts the growth and development of susceptible weeds. The herbicidal activity of triflusulfuron-methyl is influenced by several factors, including soil type, application rate, and environmental conditions. Its effectiveness is enhanced by its ability to penetrate plant leaves and roots, allowing it to reach the target sites within the plant. Due to its high efficacy and selectivity, triflusulfuron-methyl is extensively studied for its potential application in various agricultural settings. Researchers investigate its environmental fate and persistence, potential for resistance development, and its impact on non-target organisms. Understanding these aspects is crucial for optimizing its use and ensuring its sustainable application in agricultural practices.'
triflusulfuron-methyl: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
triflusulfuron-methyl : A methyl ester resulting from the formal condensation of the carboxy group of triflusulfuron with methanol. A proherbicide for triflusulfuron. [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 | 92434 |
| CHEMBL ID | 2143050 |
| CHEBI ID | 82047 |
| SCHEMBL ID | 55457 |
| MeSH ID | M0369928 |
| Synonym |
|---|
| AC-18026 |
| triflusulfuron-methyl [iso] |
| benzoic acid, 2-(((((4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)-3-methyl-, methyl ester |
| upbeet |
| dpx 66037 |
| NCGC00164313-01 |
| 126535-15-7 |
| methyl 2-[({[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}amino)sulfonyl]-3-methylbenzoate |
| triflusulfuron-methyl |
| NCGC00164313-02 |
| triflusulfuron methyl ester |
| methyl 2-[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoylsulfamoyl]-3-methylbenzoate |
| methyl 2-[[4-(dimethylamino)-6-[2,2,2-tris(fluoranyl)ethoxy]-1,3,5-triazin-2-yl]carbamoylsulfamoyl]-3-methyl-benzoate |
| 2-[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]-oxomethyl]sulfamoyl]-3-methylbenzoic acid methyl ester |
| A805565 |
| NCGC00164313-03 |
| C18901 |
| methyl-2-(4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2-ylcarbamoysulfamoyl)-m-toluate |
| y8ar13fyc0 , |
| unii-y8ar13fyc0 |
| methyl 2-[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylaminocarbonylaminosulfonyl]-3-methylbenzoate |
| FT-0631122 |
| AKOS015895276 |
| methyl 2-((((4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)-3-methylbenzoate |
| triflusulfuron-methyl [mi] |
| methyl 2-(4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl)-m-toluate |
| SCHEMBL55457 |
| methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate |
| CHEBI:82047 , |
| methyl 2-({[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}sulfamoyl)-3-methylbenzoate |
| methyl 2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-m-toluate |
| CHEMBL2143050 |
| triflusulfuron methyl |
| DTXSID2032502 |
| triflusulfuron-methyl, pestanal(r), analytical standard |
| IMEVJVISCHQJRM-UHFFFAOYSA-N , |
| methyl 2-[[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoylsulfamoyl]-3-methylbenzoate |
| methyl 2-(n-(4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoyl)sulfamoyl)-3-methylbenzoate |
| methyl 2-({[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2- yl]carbamoyl}sulfamoyl)-3-methylbenzoate |
| trifluorsulfuron-methyl |
| triflusulfuron-methyl 100 microg/ml in acetonitrile |
| methyl 2-(n-((4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)carbamoyl)sulfamoyl)-3-methylbenzoate |
| upbeet; dpx 66037 |
| Q18631953 |
| AMY22354 |
| mfcd03095701 |
| methyl 2-[n-[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl]sulfamoyl]-3-methylbenzoate |
| benzoic acid, 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methyl-, methyl ester |
| dpx-66037 |
| dpx66037 |
| 3h-1,2,4-triazolo[4,3-d][1,4]diazepin-3-one,2,5,6,7,8,9-hexahydro- |
| BS-42108 |
| SY295206 |
| EN300-19653444 |
| Z3234882788 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " A dose-response pot experiment was conducted in the greenhouse to evaluate the effectiveness of triflusulfuron-methyl, applied at the one leaf pair stage, for controlling Belgian Galinsoga populations." | ( Seed germination, seedling emergence, seed persistence and triflusulfuron-methyl sensitivity in Galinsoga parviflora and G. quadriradiata. Bulcke, R; Claerhout, S; De Cauwer, B; Devos, R; Reheul, D, 2013) | 0.85 |
| Role | Description |
|---|---|
| proherbicide | A compound that, on administration, must undergo chemical conversion by biochemical (enzymatic), chemical (possibly following an enzymatic step), or physical (e.g. photochemical) activation processes before becoming the pharmacologically active herbicide for which it is a proherbicide. |
| agrochemical | An agrochemical is a substance that is used in agriculture or horticulture. |
| EC 2.2.1.6 (acetolactate synthase) inhibitor | An EC 2.2.1.* (transketolase/transaldolase) inhibitor that interferes with the action of acetolactate synthase (EC 2.2.1.6). |
| [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 |
|---|---|
| benzoate ester | Esters of benzoic acid or substituted benzoic acids. |
| methyl ester | Any carboxylic ester resulting from the formal condensation of a carboxy group with methanol. |
| N-sulfonylurea | A urea in which one of the hydrogens attached to a nitrogen of the urea group is replaced by a sulfonyl group. The N-sulfonylurea moiety is a key group in various herbicides, as well as in a number of antidiabetic drugs used in the management of type 2 diabetis mellitus. |
| 1,3,5-triazines | Any compound with a 1,3,5-triazine skeleton, in which nitrogen atoms replace carbon at positions 1, 3 and 5 of the core benzene ring structure. |
| tertiary amino compound | A compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
| [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) |
|---|---|---|---|---|---|---|---|
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 25.1189 | 0.0023 | 19.5956 | 74.0614 | AID651743 |
| [prepared from compound, protein, and bioassay information 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 | 4 (66.67) | 29.6817 |
| 2010's | 2 (33.33) | 24.3611 |
| 2020's | 0 (0.00) | 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 (33.83) 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 | 6 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||