Carfentrazone-ethyl is a synthetic herbicide belonging to the triazolinone class. It acts as a potent inhibitor of protoporphyrinogen oxidase (PPO), an enzyme essential for chlorophyll biosynthesis in plants. This inhibition leads to the accumulation of protoporphyrin IX, a photosensitizing compound that disrupts the photosynthetic process. Carfentrazone-ethyl is widely used as a pre-emergent and post-emergent herbicide for controlling broadleaf weeds in various crops, including corn, soybeans, and wheat. Its effectiveness against a wide range of weed species has made it an important tool for weed management in agriculture. The synthesis of carfentrazone-ethyl involves a multi-step process starting from commercially available starting materials. The detailed synthesis involves several chemical reactions, including cyclization, alkylation, and oxidation. The mechanism of action of carfentrazone-ethyl is well-studied, and its selectivity for weeds over crops is attributed to differences in PPO enzyme sensitivity and plant metabolism. Research on carfentrazone-ethyl focuses on optimizing its efficacy, understanding its environmental fate and residues, and assessing its potential impacts on non-target organisms. The development of resistance to carfentrazone-ethyl is a concern, and research aims to understand the resistance mechanisms and develop strategies to manage it. '
carfentrazone-ethyl: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
carfentrazone-ethyl : A racemate comprising equimolar amounts of (R)- and (S)-carfentrazone-ethylcarfentrazone-ethyl. A proherbicide for the herbicide carfentrazone (by hydrolysis of the ester group to the corresponding acid), it is used to control broad-leafed weeds in potatoes and cereal 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]
ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate : An ethyl ester resulting from the formal condensation of the carboxy group of 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid with ethanol. [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 | 86222 |
| CHEMBL ID | 2145069 |
| CHEBI ID | 138244 |
| CHEBI ID | 3416 |
| SCHEMBL ID | 38936 |
| MeSH ID | M0389331 |
| Synonym |
|---|
| f 8426 |
| ethyl 2-chloro-3-(2-chloro-4-fluoro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl)phenyl)propanoate |
| f8426 |
| aurora |
| spotlight 24ec |
| carfentrazone-ethyl [iso:bsi] |
| einecs annex i index 607-309-00-5 |
| kuaimieling |
| benzenepropanoic acid, .alpha.,2-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl)-4-fluoro-, ethyl ester |
| aurora 50wg |
| hsdb 7253 |
| aurora (pesticide) |
| 128639-02-1 |
| carfentrazone-ethyl |
| AIM , |
| NCGC00163914-01 |
| ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate |
| NCGC00163914-02 |
| CHEBI:138244 |
| ethyl 2-chloro-3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluorophenyl]propanoate |
| NCGC00163914-03 |
| benzenepropanoic acid, alpha, 2-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl)-4-fluoro-, ethyl ester |
| 45y208ao5k , |
| ((14)c)carfentrazone-ethyl |
| unii-45y208ao5k |
| NCGC00254896-01 |
| dtxcid2012532 |
| dtxsid4032532 , |
| cas-128639-02-1 |
| tox21_300994 |
| affinity |
| ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl]-4-fluoro-phenyl}propionate |
| FT-0631126 |
| carfentrazone-ethyl [iso] |
| ethyl 2-chloro-3-(2-chloro-4-fluoro-5-(4-(difluoromethyl)- 4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1- yl)phenyl)propanoate |
| aurora [hsdb] |
| benzenepropanoic acid, .alpha.,2-dichloro-5-(4- (difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4- triazol-1-yl)-4-fluoro-, ethyl ester |
| ethyl (rs)-2-chloro-3-(2-chloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl)-4-fluorophenyl)propionate |
| carfentrazone-ethyl [mi] |
| SCHEMBL38936 |
| CHEMBL2145069 |
| chebi:3416 |
| ethyl 2-chloro-3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenyl]propanoate |
| carfentrazone ethyl |
| ethyl 2-chloro-3-(2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl]-4-fluorophenyl)propanoate # |
| J-005617 |
| carfentrazone-ethyl, pestanal(r), analytical standard |
| carfentrazone-ethyl 10 microg/ml in cyclohexane |
| ethyl 2-chloro-3-(2-chloro-5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl)-4-fluorophenyl)propanoate |
| 6(5h)-pteridinone,2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydro |
| Q22807209 |
| benzenepropanoic acid, alpha,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl]-4-fluoro-, ethyl ester |
| ethyl-alpha,2-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl]-4-fluorobenzenepropanoate |
| carfentrazone-ethyl 10 microg/ml in acetonitrile |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Its non-target toxic effects on soil microorganisms and soil enzymes are reported recently." | ( Ecotoxicity of herbicide carfentrazone-ethyl towards earthworm Eisenia fetida in soil. Li, M; Ma, X; Saleem, M; Wang, Y; Yang, Y; Zhang, Q, 2022) | 1.02 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Dose-response analysis determined 50% growth reduction rates in CE-resistant (SIR and ACR) and sensitive (SEN) waterhemp populations, which showed SIR was 30-fold resistant compared to SEN and two-fold more resistant than ACR." | ( Carfentrazone-ethyl resistance in an Amaranthus tuberculatus population is not mediated by amino acid alterations in the PPO2 protein. Lygin, AV; Ma, R; O'Brien, SR; Obenland, OA; Riechers, DE, 2019) | 1.96 |
| 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. |
| [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 |
|---|---|
| ethyl ester | Any carboxylic ester resulting from the formal condensation of the carboxy group of a carboxylic acid with ethanol. |
| [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 | 49.4175 | 0.0025 | 41.7960 | 15,848.9004 | AID1347395; AID1347398 |
| SMAD family member 2 | Homo sapiens (human) | Potency | 43.6412 | 0.1737 | 34.3047 | 61.8120 | AID1346924 |
| SMAD family member 3 | Homo sapiens (human) | Potency | 43.6412 | 0.1737 | 34.3047 | 61.8120 | AID1346924 |
| AR protein | Homo sapiens (human) | Potency | 35.4998 | 0.0002 | 21.2231 | 8,912.5098 | AID743035; AID743063 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 44.2183 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 74.1159 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 34.3762 | 0.0002 | 29.3054 | 16,493.5996 | AID743079 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 54.4827 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 54.4827 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 36.9069 | 0.0006 | 27.2152 | 1,122.0200 | AID651741; AID743219 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 34.3762 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [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 | 8 (50.00) | 29.6817 |
| 2010's | 6 (37.50) | 24.3611 |
| 2020's | 2 (12.50) | 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 (41.18) 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 | 16 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||