Dicamba
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Dicamba(F06126) |
| 2D Structure | |
| FRCD ID | F06126 |
| CAS Number | 1918-00-9 |
| PubChem CID | 3030 |
| Formula | C8H6Cl2O3 |
| IUPAC Name | 3,6-dichloro-2-methoxybenzoic acid |
| InChI Key | IWEDIXLBFLAXBO-UHFFFAOYSA-N |
| InChI | InChI=1S/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12) |
| Canonical SMILES | COC1=C(C=CC(=C1C(=O)O)Cl)Cl |
| Isomeric SMILES | COC1=C(C=CC(=C1C(=O)O)Cl)Cl |
| Synonyms |
Dianat
dicamba
3,6-Dichloro-2-methoxybenzoic acid
1918-00-9
Mdba
Mediben
Banvel
3,6-Dichloro-o-anisic acid
Banlen
Brush buster
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Methoxybenzoic acids and derivatives |
| Direct Parent | O-methoxybenzoic acids and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | 2,5-dichlorobenzoic acid - O-methoxybenzoic acid or derivatives - 2-halobenzoic acid or derivatives - 3-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Halobenzoic acid - 3-halobenzoic acid - 2-halobenzoic acid - Benzoic acid - Phenoxy compound - 1,4-dichlorobenzene - Benzoyl - Anisole - Phenol ether - 1-carboxy-2-haloaromatic compound - Methoxybenzene - Alkyl aryl ether - Halobenzene - Chlorobenzene - Aryl halide - Aryl chloride - Vinylogous halide - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Ether - Organohalogen compound - Organochloride - Organooxygen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as o-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 2 of the benzene ring is replaced by a methoxy group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 221.033 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 198 |
| Monoisotopic Mass | 219.969 |
| Exact Mass | 219.969 |
| XLogP | 2.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| 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+ | 0.9137 |
| Human Intestinal Absorption | HIA+ | 0.9908 |
| Caco-2 Permeability | Caco2+ | 0.7945 |
| P-glycoprotein Substrate | Non-substrate | 0.7180 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9623 |
| Non-inhibitor | 0.9833 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8861 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9237 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7573 |
| CYP450 2D6 Substrate | Non-substrate | 0.9055 |
| CYP450 3A4 Substrate | Non-substrate | 0.6428 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5957 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8827 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9511 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7470 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9608 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8707 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9340 |
| Non-inhibitor | 0.9776 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8039 |
| Fish Toxicity | High FHMT | 0.9356 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9827 |
| Honey Bee Toxicity | High HBT | 0.7827 |
| Biodegradation | Not ready biodegradable | 0.7402 |
| Acute Oral Toxicity | III | 0.8287 |
| Carcinogenicity (Three-class) | Non-required | 0.5018 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4342 | LogS |
| Caco-2 Permeability | 1.2516 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3592 | LD50, mol/kg |
| Fish Toxicity | 0.5800 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8430 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.05* | 24/06/2015 | |
| Others (2) | 0212990 | European Union | 0.05* | 24/06/2015 | |
| Celeries | 0270030 | European Union | 0.05* | 24/06/2015 | |
| Citrus fruits | 0110000 | European Union | 0.05* | 24/06/2015 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.05* | 24/06/2015 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.05* | 24/06/2015 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.05* | 24/06/2015 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.05* | 24/06/2015 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.05* | 24/06/2015 | |
| Others (2) | 0110990 | European Union | 0.05* | 24/06/2015 | |
| Tree nuts | 0120000 | European Union | 0.05* | 24/06/2015 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.05* | 24/06/2015 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 24/06/2015 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 24/06/2015 | |
| Chestnuts | 0120040 | European Union | 0.05* | 24/06/2015 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 24/06/2015 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 24/06/2015 | |
| Macadamias | 0120070 | European Union | 0.05* | 24/06/2015 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 24/06/2015 | |
| Pistachios | 0120100 | European Union | 0.05* | 24/06/2015 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Dicamba-Tolerant Soybeans (Glycine max L.) MON 87708 and MON 87708 × MON 89788Are Compositionally Equivalent to Conventional Soybean. | J Agric Food Chem | 2017 Sep 13 | 28825823 |
| Plant reproduction is altered by simulated herbicide drift to constructed plantcommunities. | Environ Toxicol Chem | 2017 Oct | 28444907 |
| Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids. | J Agric Food Chem | 2017 Jan 18 | 27997185 |
| Magnetic polyethyleneimine functionalized reduced graphene oxide as a novelmagnetic solid-phase extraction adsorbent for the determination of polar acidicherbicides in rice. | Anal Chim Acta | 2017 Jan 1 | 27876142 |
| Screening Auxin Response, In Vitro Culture Aptitude and Susceptibility toAgrobacterium-Mediated Transformation of Italian Commercial Durum WheatVarieties. | Molecules | 2016 Oct 28 | 27801844 |
| Unravelling the resistance mechanisms to 2,4-D (2,4-dichlorophenoxyacetic acid)in corn poppy (Papaver rhoeas). | Pestic Biochem Physiol | 2016 Oct | 27742363 |
| Sex Steroid Hormone Single-Nucleotide Polymorphisms, Pesticide Use, and the Risk of Prostate Cancer: A Nested Case-Control Study within the Agricultural HealthStudy. | Front Oncol | 2016 Nov 21 | 27917368 |
| Safety assessment of dicamba mono-oxygenases that confer dicamba tolerance tovarious crops. | Regul Toxicol Pharmacol | 2016 Nov | 27575686 |
| A subchronic feeding study of dicamba-tolerant soybean with the dmo gene inSprague-Dawley rats. | Regul Toxicol Pharmacol | 2016 Jun | 26850684 |
| The discovery of Arylex™ active and Rinskor™ active: Two novel auxin herbicides. | Bioorg Med Chem | 2016 Feb 1 | 26321602 |
| Differences in Germination, Growth, and Fecundity Characteristics ofDicamba-Fluroxypyr-Resistant and Susceptible Kochia scoparia. | PLoS One | 2016 Aug 18 | 27537419 |
| Quantitative analysis of dicamba residues in raw agricultural commodities withthe use of ion-pairing reagents in LC-ESI-MS/MS. | Talanta | 2016 | 26717820 |
| Sublethal exposure to commercial formulations of the herbicides dicamba,2,4-dichlorophenoxyacetic acid, and glyphosate cause changes in antibioticsusceptibility in Escherichia coli and Salmonella enterica serovar Typhimurium. | MBio | 2015 Mar 24 | 25805724 |
| Glyphosate and dicamba herbicide tank mixture effects on native plant andnon-genetically engineered soybean seedlings. | Ecotoxicology | 2015 Jul | 25821135 |
| Complete genome sequence of the phenanthrene-degrading soil bacterium Delftiaacidovorans Cs1-4. | Stand Genomic Sci | 2015 Aug 15 | 26380642 |
| Evaluation of polyethersulfone performance for the microextraction of polarchlorinated herbicides from environmental water samples. | Talanta | 2014 May | 24720994 |
| Influence of soil organic matter on the sensitivity of selected wild and cropspecies to common herbicides. | Ecotoxicology | 2013 Oct | 23996626 |
| Effects of glyphosate and two herbicide mixtures on microbial communities inprairie wetland ecosystems: a mesocosm approach. | J Environ Qual | 2012 May-Jun | 22565255 |
| Evidence for behavioral preference toward environmental concentrations ofurban-use herbicides in a model adult fish. | Environ Toxicol Chem | 2011 Sep | 21647945 |
| Genetic engineering of maize (Zea mays) for high-level tolerance to treatmentwith the herbicide dicamba. | J Agric Food Chem | 2011 Jun 8 | 21133415 |
Targets
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
- Gene Name:
- SLCO1B1
- Uniprot ID:
- Q9Y6L6
- Molecular Weight:
- 76447.99 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 hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 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:
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
- Gene Name:
- NR3C1
- Uniprot ID:
- P04150
- Molecular Weight:
- 85658.57 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:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]