Butralin is a pre-emergence herbicide used to control broadleaf weeds in crops such as cotton, soybeans, peanuts, and rice. It is synthesized through a multi-step process involving the reaction of 2,6-dichlorobenzoyl chloride with 2,6-dimethylaniline followed by a series of reactions with a methylated derivative of 3,5-dimethylpyrazole. Butralin is a selective herbicide that disrupts the growth of weeds by inhibiting the synthesis of carotenoids, which are essential pigments involved in photosynthesis. It is absorbed by the roots of germinating weed seedlings and translocated to the shoots, where it exerts its herbicidal effect. Butralin has been studied extensively for its environmental fate, efficacy, and potential impact on non-target organisms. Studies have shown that butralin can persist in the soil for several months, depending on soil type and environmental conditions. However, it is generally considered to have a low potential for leaching into groundwater. Butralin is considered to be relatively safe for mammals and birds, but it can be toxic to aquatic organisms, particularly fish. Research on butralin continues to focus on developing safer and more effective formulations, as well as understanding its environmental fate and potential risks to non-target organisms.'
butralin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 36565 |
| CHEMBL ID | 1256669 |
| CHEBI ID | 81847 |
| SCHEMBL ID | 55786 |
| MeSH ID | M0049654 |
| Synonym |
|---|
| zitsaosol |
| 4-(1,1-dimethylethyl)-n-(1-methylpropyl)-2,6-dinitrobenzenamine |
| amex 820 |
| technical amex-820 |
| dibutalin |
| hsdb 7355 |
| amex |
| 70-314b |
| n-sec-butyl-4-tert-butyl-2,6-dinitrobenzamine |
| brn 2947948 |
| 72-a34 |
| 4-(1,1-dimethylethyl)-n-(1-methylpropyl)-2,6-dinitrobenzeneamine |
| 4-(tert-butyl)-n-sec-butyl-2,6-dinitroaniline |
| tamex |
| butraline |
| caswell no. 125e |
| ai3-62691 |
| einecs 251-607-4 |
| aniline, n-sec-butyl-4-tert-butyl-2,6-dinitro- |
| rutralin |
| amchem 70-25 |
| epa pesticide chemical code 106501 |
| butraline [iso-french] |
| a 820 |
| butralin [ansi:bsi:iso] |
| amchem a-280 |
| benzenamine, 4-(1,1-dimethylethyl)-n-(1-methylpropyl)-2,6-dinitro- |
| butralin |
| 33629-47-9 |
| n-sec-butyl-4-tert-butyl-2,6-dinitroaniline |
| NCGC00168294-01 |
| 4-tert-butyl-2,6-dinitro-n-sec-butyl-aniline |
| n-butan-2-yl-4-tert-butyl-2,6-dinitroaniline |
| NCGC00168294-02 |
| C18582 |
| dtxsid3032337 , |
| cas-33629-47-9 |
| dtxcid1012337 |
| NCGC00255019-01 |
| tox21_301120 |
| CHEMBL1256669 |
| chebi:81847 , |
| n-butan-2-yl-4-tert-butyl-2,6-dinitro-aniline |
| A821882 |
| unii-5czk3k1ypb |
| 5czk3k1ypb , |
| FT-0630572 |
| AKOS015888337 |
| 4-(1,1-dimethylethyl)-n-(1-methylpropyl)-2,6- dinitrobenzenamine |
| 4-tert-butyl-n-mono-sec-butyl-2,6-dinitroaniline |
| butalin |
| 4-tert-butyl-n-sec-butyl-2,6-dinitroaniline |
| rutralin [hsdb] |
| butralin [iso] |
| butralin [mi] |
| SCHEMBL55786 |
| butralin;dibutaline;amexine;tamex |
| 4-tert-butyl-n-sec-butyl-2,6 -dinitroaniline |
| n-sec-butyl-2,6-dinitro-4-t-butylaniline |
| n-(sec-butyl)-4-(tert-butyl)-2,6-dinitroaniline |
| butralin, pestanal(r), analytical standard |
| butralin 100 microg/ml in acetonitrile |
| J-019280 |
| ams_cnc_id-458061711 |
| smssf-0625534 |
| Q2570341 |
| a820 |
| a-820 |
| n-(butan-2-yl)-4-tert-butyl-2,6-dinitroaniline |
| AKOS040744428 |
Butralin is a good herbicide for Gramineae.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Butralin is a good herbicide for Gramineae." | ( [Chemical weed control of medicinal plant Bupleurum falcatum L]. Wang, KC; Wang, ZY; Yang, WQ, 2000) | 1.03 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Butralin-treated rats showed a rise in serum creatinine (41%), BUN (47.3%), and MDA (140.9%) as well as decrease in activity of the antioxidant markers (CAT (-21%); GPx (-70.7%); and TAC (43.2%)) in comparison with the control group." | ( DNA Damage and Expression Profile of Genes Associated with Nephrotoxicity Induced by Butralin and Ameliorating Effect of Arabic Gum in Female Rats. Kassem, SM; Khalil, WKB; Refaie, AA; Shalby, AB, 2021) | 1.57 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Risk assessment demonstrated that, at recommended dosage and frequency, butralin would not induce significant harm on humans." | ( Dissipation behavior and risk assessment of butralin in soybean and soil under field conditions. He, Y; Li, C; Li, L; Li, W; Liu, R; Yuan, L, 2017) | 0.95 |
| Class | Description |
|---|---|
| C-nitro compound | A nitro compound having the nitro group (-NO2) attached to a carbon atom. |
| [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) |
|---|---|---|---|---|---|---|---|
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 70.9799 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 35.4813 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 24.3365 | 0.0060 | 38.0041 | 19,952.5996 | AID1159523 |
| AR protein | Homo sapiens (human) | Potency | 22.9752 | 0.0002 | 21.2231 | 8,912.5098 | AID743054 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 33.4001 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 48.5577 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 12.5209 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 43.6412 | 0.0008 | 17.5051 | 59.3239 | AID1159527 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 12.2780 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1259401 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 4.4668 | 0.3758 | 27.4851 | 61.6524 | AID588526 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 32.0736 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 38.4897 | 0.0002 | 29.3054 | 16,493.5996 | AID588513; AID743079 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 58.1965 | 0.0010 | 19.4141 | 70.9645 | AID743140 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 23.4515 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 64.8601 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 25.7006 | 0.0006 | 27.2152 | 1,122.0200 | AID720636 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID522807 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin S6I mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522816 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243S mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522814 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin T239I mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522810 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin L136F mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522805 | Antimicrobial activity against Toxoplasma gondii RH infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522808 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin F24H mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522806 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin V4L mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522812 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235T mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522813 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235V mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522809 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin H28Q mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522811 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235L mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| AID522815 | Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243C mutation infected in HFF cells by plaque assay | 2010 | Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4 | Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 1 (7.14) | 18.7374 |
| 1990's | 1 (7.14) | 18.2507 |
| 2000's | 2 (14.29) | 29.6817 |
| 2010's | 3 (21.43) | 24.3611 |
| 2020's | 7 (50.00) | 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 (31.49) 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] | ||