Prometryne is a triazine herbicide used to control broadleaf weeds in various crops, including soybeans, corn, and cotton. It is a selective herbicide, meaning it primarily targets broadleaf weeds while minimally affecting the crops themselves. Prometryne works by inhibiting photosynthesis in plants, leading to their death. It is synthesized through a multi-step process that involves reacting cyanuric chloride with an amine and an alcohol. Prometryne's persistence in the environment and its potential to contaminate water bodies have raised concerns, leading to research focusing on its degradation pathways, environmental fate, and the development of safer alternatives. The study of prometryne is crucial to understand its effects on ecosystems, human health, and agricultural practices. Despite its potential environmental impacts, prometryne remains an important tool in weed management for various crops, and ongoing research aims to mitigate its risks and improve its application.'
Prometryne: A triazine used as a selective pre- and post-emergence herbicide. (From Merck Index, 11th ed) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
prometryn : A diamino-1,3,5-triazine that is N,N'-di(propan-2-yl)-1,3,5-triazine-2,4-diamine substituted by a methylsulfanediyl group at position 6. [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 | 4929 |
| CHEMBL ID | 1880257 |
| CHEBI ID | 26276 |
| SCHEMBL ID | 7622 |
| MeSH ID | M0017722 |
| Synonym |
|---|
| BRD-K32582260-001-02-5 |
| s-triazine, 2,4-bis(isopropylamino)-6-(methylthio)- |
| 1,3,5-triazine-2,4-diamine, n,n'-bis(1-methylethyl)-6-(methylthio)- |
| DIVK1C_006534 |
| KBIO1_001478 |
| caparol 4l |
| 2,4-diamine-n,n'-bis(1-methylethyl)-6-(methylthio)triazine |
| 2,4-bis(isopropylamino)-6-methylthio-1,3,5-triazine |
| 2,4-bis(isopropylamino)-6-(methylthio)triazine |
| cotton-pro |
| caparol 80w |
| g-34161 |
| bis(isopropylamino)-6-(methylthio)-s-triazine |
| SPECTRUM_001837 |
| 6-(methylsulfanyl)-n,n'-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| n,n'-diisopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine |
| n,n'-bis(1-methylethyl)-6-methylthio-1,3,5-triazine-2,4-diamine |
| CHEBI:26276 , |
| SPECTRUM5_001970 |
| BSPBIO_002357 |
| 2,4-bis(isopropylamino)-6-(methylthio)-s-triazine |
| polisin |
| g 34161 |
| 2-(methylmercapto)-4,6-bis(isopropylamino)-s-triazine |
| s-triazine,4-bis(isopropylamino)-6-(methylthio)- |
| mercasin |
| mercazin |
| 1,5-triazine-2,4-diamine, n,n'-bis(1-methylethyl)-6-(methylthio)- |
| gesagard |
| primatol q |
| prometrex |
| a 1114 |
| nsc163049 |
| prometryn |
| wln: t6n cn enj bs1 dmy1&1 fmy1&1 |
| prometrin |
| selectin |
| 2,4-bis(isopropylamino)-6-methylmercapto-s-triazine |
| nsc-163049 |
| merkazin |
| selectin 50 |
| caparol |
| selektin |
| 7287-19-6 |
| 2,4-bis(isopropylamino)-6-(methylmercapto)-s-triazine |
| prometryne |
| gesagard 50 |
| uvon |
| sesagard |
| gesagarde 50 wp |
| 2-(methylthio)-4,6-bis(isopropylamino)-s-triazine |
| s-triazine,6-bis(isopropylamino)-2-(methylmercapto)- |
| prometryn, analytical standard |
| NCGC00094530-02 |
| NCGC00094530-01 |
| brn 0613575 |
| prometrene |
| promepin |
| n2,n4-di-isopropyl-6-methylthio-1,3,5-triazine-2,4-diamine |
| 2,4-bis(propylamino)-6-methylthio-1,3,5-triazin [german] |
| prometryn [ansi:bsi:iso] |
| caswell no. 097 |
| epa pesticide chemical code 080805 |
| einecs 230-711-3 |
| n,n'-diisopropyl-6-methylthio-1,3,5-triazine-2,4-diyldiamine |
| hsdb 4060 |
| nsc 163049 |
| ai3-60366 |
| n,n'-bis(1-methylethyl)-6-methyl-thio-1,3,5-triazine-2,4-diamine |
| promethryn |
| n,n-di-isopropyl-6-methylthio-1,3,5-triazine-2,4-diamine |
| prometryne [iso-french:jmaf] |
| 2-methylmercapto-4,6-bis(isopropylamino)-s-triazine |
| 2,4-bis(isopropylamino)-6-methylthio-s-triazine |
| s-triazine, 4,6-bis(isopropylamino)-2-methylmercapto- |
| 2-methylthio-4,6-bis(isopropylamino)-s-triazine |
| KBIO2_007475 |
| KBIOSS_002342 |
| KBIO2_004907 |
| KBIO3_001857 |
| KBIOGR_001077 |
| KBIO2_002339 |
| SPECPLUS_000438 |
| SPECTRUM3_000829 |
| SPBIO_001794 |
| SPECTRUM2_001887 |
| SPECTRUM4_000669 |
| SPECTRUM330037 |
| NCGC00094530-03 |
| NCGC00094530-04 |
| MLS002695921 |
| smr000778056 |
| aaevyovxgofmjo-uhfffaoysa- |
| inchi=1/c10h19n5s/c1-6(2)11-8-13-9(12-7(3)4)15-10(14-8)16-5/h6-7h,1-5h3,(h2,11,12,13,14,15) |
| 6-methylsulfanyl-n,n'-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| 6-methylsulfanyl-2-n,4-n-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| STK687533 |
| 6-methylsulfanyl-n2,n4-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| 6-(methylthio)-n2,n4-di(propan-2-yl)-1,3,5-triazine-2,4-diamine |
| A837648 |
| NCGC00094530-06 |
| NCGC00094530-05 |
| C18542 |
| HMS3089A14 |
| NCGC00259887-01 |
| NCGC00254711-01 |
| dtxsid4024272 , |
| dtxcid704272 |
| tox21_202338 |
| tox21_300807 |
| cas-7287-19-6 |
| CHEMBL1880257 |
| AKOS005206531 |
| CCG-39425 |
| 1k20tb75il , |
| unii-1k20tb75il |
| 2,4-bis(propylamino)-6-methylthio-1,3,5-triazin |
| FT-0630367 |
| prometryn [mi] |
| prometryn [iso] |
| prometryn [hsdb] |
| SCHEMBL7622 |
| 2-methylthio-4,6-bis(isopropylamino)-1,3,5triazine |
| n2,n4-diisopropyl-6-(methylthio)-1,3,5-triazine-2,4-diamine |
| W-104476 |
| n,n'-diisopropyl-6-(methylsulfanyl)-1,3,5-triazine-2,4-diamine |
| caparol 4l (salt/mix) |
| cotton-pro (salt/mix) |
| s-triazine, 4,6-bis(isopropylamino)-2-(methylmercapto)- |
| s-triazine, 2,4-bis(isopropylamino)-6-methylmercapto- |
| promethryne |
| 2,4-bis(isopropylamino)-6-(methylthio)-1,3,5-triazine |
| B6186 |
| prometryn, pestanal(r), analytical standard |
| 2-methylthio-4,6-bis(isopropyl amino)-1,3,5-triazine |
| 1705649-52-0 |
| prometryn 100 microg/ml in acetonitrile |
| prometryn 10 microg/ml in acetonitrile |
| Q1257341 |
| AMY22226 |
| 2,4-bis-(isopropylamino)-6-methylthio-1,3,5-triazine (prometryn) |
| mfcd00055396 |
| prometryn 1000 microg/ml in acetone |
| HY-121324 |
| CS-0081435 |
| prometryn 10 microg/ml in cyclohexane |
| AS-83740 |
| n,n'-diisopropyl-6-methylsulfanyl-[1,3,5]triazine-2,4-diamine |
| prometryn-d6 100 amicrog/ml in acetone |
| n-isopropyl-n-[4-(isopropylamino)-6-(methylsulfanyl)-1,3,5-triazin-2-yl]amine |
Prometryne is a methylthio-s-triazine herbicide. Used to control annual broadleaf and grass weeds in many cultivated plants.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Prometryne is a methylthio-s-triazine herbicide used to control annual broadleaf and grass weeds in many cultivated plants. " | ( The effects of prometryne on subchronically treated mice evaluated by SCGE assay. Benković, V; Dikić, D; Horvat-Knezević, A; Lisicić, D; Remenar, A; Sajli, L; Springer, O; Zidovec-Lepej, S, 2009) | 2.15 |
| "Prometryne is a methylthio-s-triazine herbicide. " | ( Brain toxicokinetics of prometryne in mice. Benković, V; Brozović, G; Dikić, D; Knezević, AH; Lisicić, D; Mojsović, A; Orsolić, N; Sajli, L, 2010) | 2.11 |
| "Prometryne is a selective herbicide of the s-triazine chemical family. " | ( Mobilization and plant accumulation of prometryne in soil by two different sources of organic matter. Han, SQ; Jiang, L; Ma, L; Sui, Y; Yang, H, 2011) | 2.08 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " In conclusion, multiwavelength-excitation PAM fluorometry has considerable potentials in multispecies and multiparameter assessment of toxic effects on community level in terms of (1) a combined and rapid evaluation of structural and functional parameters in parallel, (2) screening of trends over time, (3) observing effects in replication and (4) being non-destructive." | ( Community-level microalgal toxicity assessment by multiwavelength-excitation PAM fluorometry. Altenburger, R; Schmitt-Jansen, M, 2008) | 0.35 |
| "A series of calorimetric experiments were performed to investigate the toxic effects of beta-cypermethrin (BCP), bensulfuron-methyl (BSM) and prometryne (PM) on Pseudomonas putida (P." | ( Acute toxic effects of three pesticides on Pseudomonas putida monitored by microcalorimeter. Bramanti, E; Chen, HL; Maskow, T; Wang, F; Yao, J; Zaray, G, 2009) | 0.55 |
| " Collectively, our findings suggest that prometryn is a potential contaminate for non-target sites and organisms, especially aquatic, and emphasize the need to consider the toxic effects of prometryn." | ( Developmental toxicity of prometryn induces mitochondrial dysfunction, oxidative stress, and failure of organogenesis in zebrafish (Danio rerio). An, G; Hong, T; Lim, W; Min, N; Park, H; Song, G, 2023) | 0.91 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Soil amendment with manure compost may influence environmental behaviors and bioavailability of toxic organic chemicals (e." | ( Effect of manure compost on the herbicide prometryne bioavailability to wheat plants. Feng, YX; Han, SQ; Jiang, L; Ma, L; Sui, Y; Wu, ZY; Yang, H, 2010) | 0.62 |
| " In this study, we demonstrated the effect of pig manure compost (PMC) and lake-bed sludge (SL) on the sorption/desorption, mobility and bioavailability of prometryne in soil using comprehensive analysis approaches." | ( Mobilization and plant accumulation of prometryne in soil by two different sources of organic matter. Han, SQ; Jiang, L; Ma, L; Sui, Y; Yang, H, 2011) | 0.84 |
| Role | Description |
|---|---|
| herbicide | A substance used to destroy plant pests. |
| xenobiotic | A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. |
| environmental contaminant | Any minor or unwanted substance introduced into the environment that can have undesired effects. |
| [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 |
|---|---|
| diamino-1,3,5-triazine | Any member of the class of 1,3,5-triazines that consists of a 1,3,5-triazine skeleton substituted by two amino groups. |
| methylthio-1,3,5-triazine | |
| [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 | 0.6310 | 0.0032 | 45.4673 | 12,589.2998 | AID2517 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 39.8107 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 68.5896 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 1.5950 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 54.9410 | 0.0002 | 21.2231 | 8,912.5098 | AID743035 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 38.5914 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 68.5896 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 61.1306 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 20.5554 | 0.0008 | 17.5051 | 59.3239 | AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 68.5896 | 0.0015 | 30.6073 | 15,848.9004 | AID1224849 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 22.0991 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 43.5522 | 0.0002 | 29.3054 | 16,493.5996 | AID588513; AID743069; AID743078; AID743079 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 6.9167 | 0.0010 | 19.4141 | 70.9645 | AID743191 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 54.6924 | 0.0578 | 21.1097 | 61.2679 | AID1159526 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 27.1672 | 0.0003 | 23.4451 | 159.6830 | AID743065 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 72.5999 | 0.0006 | 27.2152 | 1,122.0200 | AID743202 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 89.1251 | 0.0501 | 27.0736 | 89.1251 | AID588590 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 27.3060 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID977602 | Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| AID977599 | Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM | 2013 | Molecular pharmacology, Jun, Volume: 83, Issue:6 | Structure-based identification of OATP1B1/3 inhibitors. |
| 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. |
| 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. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| 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 | |||
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
| AID1159550 | Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening | 2015 | Nature cell biology, Nov, Volume: 17, Issue:11 | 6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 23 (17.83) | 18.7374 |
| 1990's | 10 (7.75) | 18.2507 |
| 2000's | 22 (17.05) | 29.6817 |
| 2010's | 47 (36.43) | 24.3611 |
| 2020's | 27 (20.93) | 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 (23.26) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (1.39%) | 6.00% |
| Case Studies | 1 (0.69%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 141 (97.92%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||