Dichlorprop
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Basic Info
| Common Name | Dichlorprop(F03893) |
| 2D Structure | |
| Description | Dichlorprop is a chlorophenoxy herbicide similar in structure to 2,4-D that is used to kill annual and perennial broadleaf weeds. It is a component of many common weedkillers. About 4 million pounds of dichlorprop are used annually in the United States. (L369) |
| FRCD ID | F03893 |
| CAS Number | 120-36-5 |
| PubChem CID | 8427 |
| Formula | C9H8Cl2O3 |
| IUPAC Name | 2-(2,4-dichlorophenoxy)propanoic acid |
| InChI Key | MZHCENGPTKEIGP-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H8Cl2O3/c1-5(9(12)13)14-8-3-2-6(10)4-7(8)11/h2-5H,1H3,(H,12,13) |
| Canonical SMILES | CC(C(=O)O)OC1=C(C=C(C=C1)Cl)Cl |
| Isomeric SMILES | CC(C(=O)O)OC1=C(C=C(C=C1)Cl)Cl |
| Synonyms |
2-(2,4-Dichlorophenoxy)propanoic acid
Dichlorprop
120-36-5
2-(2,4-Dichlorophenoxy)propionic acid
DICHLOROPROP
Hormatox
Polymone
Polytox
Kildip
Celatox-dp
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | 2-phenoxypropionic acids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 2-phenoxypropionic acids |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | 2-phenoxypropionic acid - Phenoxyacetate - Phenoxy compound - Phenol ether - 1,3-dichlorobenzene - Alkyl aryl ether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid derivative - Carboxylic acid - Ether - Monocarboxylic acid or derivatives - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organochloride - Organic oxide - Organohalogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as 2-phenoxypropionic acids. These are aromatic compounds hat contain a phenol ether attached to the C2-atom of a phenylpropionic acid. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 235.06 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 210 |
| Monoisotopic Mass | 233.985 |
| Exact Mass | 233.985 |
| XLogP | 3.4 |
| 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+ | 0.8966 |
| Human Intestinal Absorption | HIA+ | 0.9929 |
| Caco-2 Permeability | Caco2+ | 0.7753 |
| P-glycoprotein Substrate | Non-substrate | 0.7069 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9440 |
| Non-inhibitor | 0.9736 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9098 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9380 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7431 |
| CYP450 2D6 Substrate | Non-substrate | 0.9091 |
| CYP450 3A4 Substrate | Non-substrate | 0.6241 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.7903 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8533 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9427 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8849 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9504 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8787 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9671 |
| Non-inhibitor | 0.9507 | |
| AMES Toxicity | Non AMES toxic | 0.9484 |
| Carcinogens | Non-carcinogens | 0.8058 |
| Fish Toxicity | High FHMT | 0.9485 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9674 |
| Honey Bee Toxicity | High HBT | 0.7350 |
| Biodegradation | Not ready biodegradable | 0.8085 |
| Acute Oral Toxicity | III | 0.8573 |
| Carcinogenicity (Three-class) | Non-required | 0.4716 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.3374 | LogS |
| Caco-2 Permeability | 1.0579 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.6172 | LD50, mol/kg |
| Fish Toxicity | 0.5871 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1358 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Barley | Britain | 0.05mg/kg | |||
| Hop | Britain | 0.1mg/kg | |||
| Tea | Britain | 0.1mg/kg | |||
| Figs | Britain | 0.05mg/kg | |||
| Dates | Britain | 0.05mg/kg | |||
| Melons | Japan | 3ppm | |||
| Water Melon | Japan | 3ppm | |||
| Blackberries | 0153010 | European Union | 0.02* | 20/10/2017 | |
| Parsley (Root parsley leaves,) | 0256040 | European Union | 0.05* | 20/10/2017 | |
| Citrus fruits | 0110000 | European Union | 0.3 | 20/10/2017 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.3 | 20/10/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.3 | 20/10/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.3 | 20/10/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.3 | 20/10/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.3 | 20/10/2017 | |
| Others (2) | 0110990 | European Union | 0.3 | 20/10/2017 | |
| Tree nuts | 0120000 | European Union | 0.02* | 20/10/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.02* | 20/10/2017 | |
| Brazil nuts | 0120020 | European Union | 0.02* | 20/10/2017 | |
| Cashew nuts | 0120030 | European Union | 0.02* | 20/10/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of a QuEChERS-Based Method for the Simultaneous Determination ofAcidic Pesticides, Their Esters, and Conjugates Following Alkaline Hydrolysis. | J Agric Food Chem | 2017 Feb 15 | 28099798 |
| Effects of a herbicide mixture on primary and bacterial productivity in fourprairie wetlands with varying salinities: an enclosure approach. | Sci Total Environ | 2015 Apr 15 | 25644848 |
| Application of capillary electrophoresis to study the enantioselectivetransformation of five chiral pesticides in aerobic soil slurries. | J Agric Food Chem | 2005 Aug 10 | 16076090 |
| Determination of bentazone, dichlorprop, and MCPA in different soils by sodiumhydroxide extraction in combination with solid-phase preconcentration. | J Agric Food Chem | 2001 Sep | 11559110 |
| Development of a solid-phase extraction method for phenoxy acids and bentazone inwater and comparison to a liquid-liquid extraction method. | J Agric Food Chem | 2000 Dec | 11141255 |
| Enzyme-linked immunosorbent assay by image analysis using a charge-coupled devicearray detector. | Anal Biochem | 1996 Jul 15 | 8660618 |
Targets
- 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:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X. In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity.
- Gene Name:
- MMP1
- Uniprot ID:
- P03956
- Molecular Weight:
- 54006.61 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 ]
- 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 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- Chlorinated dibenzo-p-dioxins cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. This includes 2,3,7,8-tetrachlorodibenzo-p-dioxin's carcinogenicity is thought to be the result of its ability to alter the capacity of both exogenous and endogenous substances to damage the DNA by inducing CYP1A1- and CYP1A2-dependent drug-metabolizing enzymes.
References
- ATSDR - Agency for Toxic Substances and Disease Registry (1998). Toxicological profile for chlorinated dibenzo-p-dioxins (CDDs). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). : http://www.atsdr.cdc.gov/toxprofiles/tp104.html