Bromacil
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Basic Info
| Common Name | Bromacil(F05035) |
| 2D Structure | |
| Description | Bromacil is an organic compound with the chemical formula C9H13BrN2O2, commercially available as an herbicide. Bromacil was first registered as a pesticide in the U.S. in 1961. It is used for brush control and non-cropland areas. It works by interfering with photosynthesis by entering the plant through the root zone and moving throughout the plant. Bromacil is one of a group of compounds called substituted uracils. These materials are broad spectrum herbicides used for nonselective weed and brush control on non-croplands, as well as for selective weed control on a limited number of crops, such as citrus fruit and pineapple. Bromacil is also found to be excellent at controlling perennial grasses. |
| FRCD ID | F05035 |
| CAS Number | 314-40-9 |
| PubChem CID | 9411 |
| Formula | C9H13BrN2O2 |
| IUPAC Name | 5-bromo-3-butan-2-yl-6-methyl-1H-pyrimidine-2,4-dione |
| InChI Key | CTSLUCNDVMMDHG-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H13BrN2O2/c1-4-5(2)12-8(13)7(10)6(3)11-9(12)14/h5H,4H2,1-3H3,(H,11,14) |
| Canonical SMILES | CCC(C)N1C(=O)C(=C(NC1=O)C)Br |
| Isomeric SMILES | CCC(C)N1C(=O)C(=C(NC1=O)C)Br |
| Synonyms |
5-Bromo-3-sec-butyl-6-methyluracil
Bromazil
Uragan
Hyvar X
Borea
BROMACIL
314-40-9
Borocil
Bromax
Cynogan
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Diazines |
| Subclass | Pyrimidines and pyrimidine derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Halopyrimidines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Halopyrimidine - Pyrimidone - Aryl bromide - Aryl halide - Hydropyrimidine - Heteroaromatic compound - Vinylogous amide - Lactam - Urea - Azacycle - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organobromide - Organohalogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 261.119 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 312 |
| Monoisotopic Mass | 260.016 |
| Exact Mass | 260.016 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9814 |
| Human Intestinal Absorption | HIA+ | 0.9886 |
| Caco-2 Permeability | Caco2+ | 0.5000 |
| P-glycoprotein Substrate | Non-substrate | 0.7185 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7075 |
| Non-inhibitor | 0.9452 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8514 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6024 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7758 |
| CYP450 2D6 Substrate | Non-substrate | 0.8461 |
| CYP450 3A4 Substrate | Non-substrate | 0.5596 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5832 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8220 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9173 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7917 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9653 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8498 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8970 |
| Non-inhibitor | 0.8753 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8098 |
| Fish Toxicity | High FHMT | 0.5281 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9789 |
| Honey Bee Toxicity | Low HBT | 0.8837 |
| Biodegradation | Not ready biodegradable | 0.9406 |
| Acute Oral Toxicity | III | 0.7818 |
| Carcinogenicity (Three-class) | Non-required | 0.6185 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5822 | LogS |
| Caco-2 Permeability | 1.3168 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5788 | LD50, mol/kg |
| Fish Toxicity | 2.1448 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.6962 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Fruit | Austria | 0.05mg/kg | |||
| Avocado | Japan | 0.05ppm | |||
| Milk | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Edible Offal | Japan | 0.04ppm | |||
| Pig,Edible Offal | Japan | 0.04ppm | |||
| Cattle,Edible Offal | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.04ppm | |||
| Pig,Kidney | Japan | 0.04ppm | |||
| Cattle,Kidney | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.04ppm | |||
| Pig,Liver | Japan | 0.04ppm | |||
| Cattle,Liver | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 0.04ppm | |||
| Pig,Fat | Japan | 0.04ppm | |||
| Cattle,Fat | Japan | 0.04ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.04ppm | |||
| Pig,Muscle | Japan | 0.04ppm | |||
| Cattle,Muscle | Japan | 0.04ppm | |||
| Other Spices | Japan | 0.05ppm | |||
| Other Nuts | Japan | 0.05ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Influence of Three Citrus Herbicides on Potential Production of Sorghum bicolor 'Topper 76-6' as a Bioenergy Crop. | Bull Environ Contam Toxicol | 2016 Nov | 27686087 |
| UV-MALDI mass spectrometric quantitation of uracil based pesticides in fruit softdrinks along with matrix effects evaluation. | Ecotoxicol Environ Saf | 2014 Feb | 24018142 |
| Toxicity of the herbicides bromacil and simazine to the aquatic macrophyte,Vallisneria americana Michx. | Environ Toxicol Chem | 2010 Jan | 20821436 |
| Low molecular weight polylactic acid as a matrix for the delayed release ofpesticides. | J Agric Food Chem | 2005 May 18 | 15884842 |
| Water purification from organic pollutants by optimized micelle-clay systems. | Environ Sci Technol | 2005 Apr 1 | 15871274 |
| A comparison of crop and non-crop plants as sensitive indicator species forregulatory testing. | Pest Manag Sci | 2002 Dec | 12476989 |
| Controlled release of a herbicide from matrix granules based onsolvent-fractionated organosolv lignins. | J Agric Food Chem | 2000 Aug | 10956165 |
| A novel and simple model of the uptake of organic chemicals by vegetation fromair and soil. | Chemosphere | 1997 Sep | 9297787 |
| Excised Barley root uptake of several (14)C labeled organic compounds. | Environ Monit Assess | 1985 Dec | 24258104 |
Targets
- General Function:
- Receptor binding
- Specific Function:
- Chemotactic for monocytes and T-lymphocytes. Binds to CXCR3.
- Gene Name:
- CXCL10
- Uniprot ID:
- P02778
- Molecular Weight:
- 10880.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transferase activity
- Specific Function:
- Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger for glucose-induced insulin secretion. Also has cADPr hydrolase activity. Also moonlights as a receptor in cells of the immune system.
- Gene Name:
- CD38
- Uniprot ID:
- P28907
- Molecular Weight:
- 34328.145 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Cytokine activity
- Specific Function:
- Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
- Gene Name:
- IL1A
- Uniprot ID:
- P01583
- Molecular Weight:
- 30606.29 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid binding
- Specific Function:
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
- Gene Name:
- UGT1A1
- Uniprot ID:
- P22309
- Molecular Weight:
- 59590.91 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Sulfotransferase activity
- Specific Function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular Weight:
- 33779.57 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide (PubMed:11159812). Catalyzes 4-beta-hydroxylation of cholesterol. May catalyze 25-hydroxylation of cholesterol in vitro (PubMed:21576599).
- Gene Name:
- CYP3A4
- Uniprot ID:
- P08684
- Molecular Weight:
- 57342.67 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
- Gene Name:
- CYP2B6
- Uniprot ID:
- P20813
- Molecular Weight:
- 56277.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]