Chloridazon
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Basic Info
| Common Name | Chloridazon(F05039) |
| 2D Structure | |
| Description | Chloridazon is a selective herbicide belonging to the group of pyridazone - derivatives , which was put on the market by BASF in the 1960s and used mainly in beet cultivation to control annual broad-leafed weeds. It acts by inhibiting photosynthesis and the Hill reaction and is rapidly absorbed through the roots of plants with tranlocation acropetally to all plant parts. |
| FRCD ID | F05039 |
| CAS Number | 1698-60-8 |
| PubChem CID | 15546 |
| Formula | C10H8ClN3O |
| IUPAC Name | 5-amino-4-chloro-2-phenylpyridazin-3-one |
| InChI Key | WYKYKTKDBLFHCY-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H8ClN3O/c11-9-8(12)6-13-14(10(9)15)7-4-2-1-3-5-7/h1-6H,12H2 |
| Canonical SMILES | C1=CC=C(C=C1)N2C(=O)C(=C(C=N2)N)Cl |
| Isomeric SMILES | C1=CC=C(C=C1)N2C(=O)C(=C(C=N2)N)Cl |
| Synonyms |
Chloridazon
1698-60-8
5-Amino-4-chloro-2-phenylpyridazin-3(2H)-one
PYRAZON
Chloridazone
Curbetan
Clorizol
Phenosane
Pyrazonl
Suzon
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Diazines |
| Subclass | Pyridazines and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyridazinones |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aminopyridazine - Pyridazinone - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Vinylogous amide - Lactam - Azacycle - Amine - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Organochloride - 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 pyridazinones. These are compounds containing a pyridazine ring which bears a ketone. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 221.644 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 332 |
| Monoisotopic Mass | 221.036 |
| Exact Mass | 221.036 |
| XLogP | 0.8 |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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+ | 0.9823 |
| Human Intestinal Absorption | HIA+ | 0.9974 |
| Caco-2 Permeability | Caco2+ | 0.5652 |
| P-glycoprotein Substrate | Non-substrate | 0.8233 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8428 |
| Non-inhibitor | 0.9561 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8528 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7668 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8131 |
| CYP450 2D6 Substrate | Non-substrate | 0.8325 |
| CYP450 3A4 Substrate | Substrate | 0.5849 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8497 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5526 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9256 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7167 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8819 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7152 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9757 |
| Non-inhibitor | 0.7895 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.8588 |
| Fish Toxicity | High FHMT | 0.9910 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8307 |
| Honey Bee Toxicity | Low HBT | 0.9345 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.8446 |
| Carcinogenicity (Three-class) | Non-required | 0.5287 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.9325 | LogS |
| Caco-2 Permeability | 1.2828 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.1572 | LD50, mol/kg |
| Fish Toxicity | 1.6289 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7711 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| (d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark... | 0639000 | European Union | 0.1* | 19/01/2017 | |
| Edible offals (other than liver and kidney) | 1014050 | European Union | 0.4 | 19/01/2017 | |
| Citrus fruits | 0110000 | European Union | 0.1* | 19/01/2017 | |
| Liver | 1014030 | European Union | 0.3 | 19/01/2017 | |
| Kidney | 1014040 | European Union | 0.4 | 19/01/2017 | |
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.1* | 19/01/2017 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.1* | 19/01/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.1* | 19/01/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.1* | 19/01/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.1* | 19/01/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.1* | 19/01/2017 | |
| Others (2) | 0110990 | European Union | 0.1* | 19/01/2017 | |
| Tree nuts | 0120000 | European Union | 0.1* | 19/01/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 19/01/2017 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 19/01/2017 | |
| Cashew nuts | 0120030 | European Union | 0.1* | 19/01/2017 | |
| Chestnuts | 0120040 | European Union | 0.1* | 19/01/2017 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 19/01/2017 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 19/01/2017 | |
| Macadamias | 0120070 | European Union | 0.1* | 19/01/2017 |
Targets
- 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:
- 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:
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
- Gene Name:
- CYP1A2
- Uniprot ID:
- P05177
- Molecular Weight:
- 58293.76 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TGFA/TGF-alpha, amphiregulin, epigen/EPGN, BTC/betacellulin, epiregulin/EREG and HBEGF/heparin-binding EGF. Ligand binding triggers receptor homo- and/or heterodimerization and autophosphorylation on key cytoplasmic residues. The phosphorylated receptor recruits adapter proteins like GRB2 which in turn activates complex downstream signaling cascades. Activates at least 4 major downstream signaling cascades including the RAS-RAF-MEK-ERK, PI3 kinase-AKT, PLCgamma-PKC and STATs modules. May also activate the NF-kappa-B signaling cascade. Also directly phosphorylates other proteins like RGS16, activating its GTPase activity and probably coupling the EGF receptor signaling to the G protein-coupled receptor signaling. Also phosphorylates MUC1 and increases its interaction with SRC and CTNNB1/beta-catenin.Isoform 2 may act as an antagonist of EGF action.
- Gene Name:
- EGFR
- Uniprot ID:
- P00533
- Molecular Weight:
- 134276.185 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 ]