Diclosulam
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Basic Info
| Common Name | Diclosulam(F05056) |
| 2D Structure | |
| Description | Diclosulam is a herbicide. It is primarily used for control of annual and certain perennial broadleaf weeds when applied as soil, foliar, or burndown treatments in crops such as sugar cane, peanuts and soybeans, as well as forestry applications. Diclosulam technical is very highly toxic to aquatic organisms on an acute basis. It is practically nontoxic to birds, mammals, insects, earthworms, fish and aquatic invertebrates. |
| FRCD ID | F05056 |
| CAS Number | 145701-21-9 |
| PubChem CID | 3081304 |
| Formula | C13H10Cl2FN5O3S |
| IUPAC Name | N-(2,6-dichlorophenyl)-5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide |
| InChI Key | QNXAVFXEJCPCJO-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H10Cl2FN5O3S/c1-2-24-13-17-9(16)6-10-18-12(19-21(10)13)25(22,23)20-11-7(14)4-3-5-8(11)15/h3-6,20H,2H2,1H3 |
| Canonical SMILES | CCOC1=NC(=CC2=NC(=NN21)S(=O)(=O)NC3=C(C=CC=C3Cl)Cl)F |
| Isomeric SMILES | CCOC1=NC(=CC2=NC(=NN21)S(=O)(=O)NC3=C(C=CC=C3Cl)Cl)F |
| Synonyms |
N-(2,6-dichlorophenyl)-5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide
Diclosulam
145701-21-9
Diclosulam [ISO]
UNII-6X5DO0I08Z
6X5DO0I08Z
CHEBI:81984
N-(2,6-Dichlorophenyl)-5-ethoxy-7-fluoro-(1,2,4)triazolo(1,5-c)pyrimidine-2-sulfonamide
N-(2,6-Dichlorophenyl)-5-ethoxy-7-fluoro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide
(1,2,4)Triazolo(1,5-c)pyrimidine-2-sulfonamide, N-(2,6-dichlorophenyl)-5-ethoxy-7-fluoro-
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Sulfanilides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Sulfanilides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Sulfanilide - Triazolopyrimidine - 1,3-dichlorobenzene - Alkyl aryl ether - Chlorobenzene - Halobenzene - Halopyrimidine - Aryl chloride - Aryl fluoride - Aryl halide - Pyrimidine - Organosulfonic acid amide - Sulfonyl - Organosulfonic acid or derivatives - Organic sulfonic acid or derivatives - Heteroaromatic compound - Aminosulfonyl compound - 1,2,4-triazole - Triazole - Azole - Organoheterocyclic compound - Azacycle - Ether - Organic nitrogen compound - Organohalogen compound - Hydrocarbon derivative - Organic oxide - Organochloride - Organopnictogen compound - Organic oxygen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 406.213 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 5 |
| Complexity | 558 |
| Monoisotopic Mass | 404.987 |
| Exact Mass | 404.987 |
| XLogP | 3.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 25 |
| 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+ | 0.5514 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2- | 0.5514 |
| P-glycoprotein Substrate | Non-substrate | 0.7907 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6950 |
| Non-inhibitor | 0.8564 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8465 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4331 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.5243 |
| CYP450 2D6 Substrate | Non-substrate | 0.8072 |
| CYP450 3A4 Substrate | Non-substrate | 0.5190 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.5541 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6770 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8200 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.6260 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.7286 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7139 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8227 |
| Non-inhibitor | 0.7650 | |
| AMES Toxicity | Non AMES toxic | 0.6449 |
| Carcinogens | Non-carcinogens | 0.6516 |
| Fish Toxicity | High FHMT | 0.9929 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9068 |
| Honey Bee Toxicity | Low HBT | 0.8161 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.6346 |
| Carcinogenicity (Three-class) | Non-required | 0.6036 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.0939 | LogS |
| Caco-2 Permeability | 1.1118 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.4541 | LD50, mol/kg |
| Fish Toxicity | 1.5213 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5699 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Peanuts,Dry | Japan | 0.02ppm | |||
| Soybeans,Dry | Japan | 0.02ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Penoxsulam--structure-activity relationships of triazolopyrimidine sulfonamides. | Bioorg Med Chem | 2009 Jun 15 | 19464188 |
| Analysis of triazolopyrimidine herbicides in soils using field-enhanced sampleinjection-coelectroosmotic capillary electrophoresis combined with solid-phaseextraction. | J Chromatogr A | 2005 Dec 30 | 16212970 |
| Determination of herbicides in mineral and stagnant waters at ng/L levels usingcapillary electrophoresis and UV detection combined with solid-phase extractionand sample stacking. | J Chromatogr A | 2005 Apr 8 | 15861801 |
| Terrestrial field dissipation of diclosulam at four sites in the United States. | J Agric Food Chem | 2001 Jul | 11453764 |
| Aerobic metabolism of diclosulam on U.S. and South American soils. | J Agric Food Chem | 2000 Sep | 10995360 |
Targets
- 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:
- Ubiquitin protein ligase binding
- Specific Function:
- Receptor for TNFSF5/CD40LG. Transduces TRAF6- and MAP3K8-mediated signals that activate ERK in macrophages and B cells, leading to induction of immunoglobulin secretion.
- Gene Name:
- CD40
- Uniprot ID:
- P25942
- Molecular Weight:
- 30618.76 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:
- 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:
- 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 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:
- 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 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 peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
- Gene Name:
- PPARG
- Uniprot ID:
- P37231
- Molecular Weight:
- 57619.58 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 ]