Boscalid
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Basic Info
| Common Name | Boscalid(F05034) |
| 2D Structure | |
| Description | Boscalid is a fungicide developed by BASF and launched in 2003 for use on food crops. It works as a succinate dehydrogenase inhibitor to kill fungal target organisms. It is practically nontoxic to terrestrial animals and is moderately toxic to aquatic animals on an acute exposure basis. In subchronic and chronic feeding studies in rats, mice and dogs, boscalid generally caused decreased body weights and body weight gains (primarily in mice) and effects on the liver (increase in weights, changes in enzyme levels and histopathological changes) as well as on the thyroid (increase in weights and histopathological changes). In a developmental toxicity study in rats, no developmental toxicity was observed in the fetuses at the highest dose tested. Boscalid is classified as, suggestive evidence of carcinogenicity, but not sufficient to assess human carcinogenic potential, according to the EPA. |
| FRCD ID | F05034 |
| CAS Number | 188425-85-6 |
| PubChem CID | 213013 |
| Formula | C18H12Cl2N2O |
| IUPAC Name | 2-chloro-N-[2-(4-chlorophenyl)phenyl]pyridine-3-carboxamide |
| InChI Key | WYEMLYFITZORAB-UHFFFAOYSA-N |
| InChI | InChI=1S/C18H12Cl2N2O/c19-13-9-7-12(8-10-13)14-4-1-2-6-16(14)22-18(23)15-5-3-11-21-17(15)20/h1-11H,(H,22,23) |
| Canonical SMILES | C1=CC=C(C(=C1)C2=CC=C(C=C2)Cl)NC(=O)C3=C(N=CC=C3)Cl |
| Isomeric SMILES | C1=CC=C(C(=C1)C2=CC=C(C=C2)Cl)NC(=O)C3=C(N=CC=C3)Cl |
| Synonyms |
2-Chloro-N-(4'-chloro-[1,1'-biphenyl]-2-yl)nicotinamide
Boscalid
188425-85-6
Nicobifen
Endura
Anilide
Emerald
Cantus
Boscalid [ISO]
UNII-32MS8ZRD1V
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Anilides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aromatic anilides |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aromatic anilide - Chlorinated biphenyl - Biphenyl - Nicotinamide - Pyridinecarboxamide - Pyridine carboxylic acid or derivatives - Chlorobenzene - Halobenzene - 2-halopyridine - Pyridine - Aryl halide - Aryl chloride - Vinylogous halide - Heteroaromatic compound - Secondary carboxylic acid amide - Carboxamide group - Organoheterocyclic compound - Azacycle - Carboxylic acid derivative - Hydrocarbon derivative - Organopnictogen compound - Organohalogen compound - Organic oxygen compound - Organochloride - Organonitrogen compound - Organic nitrogen compound - Organooxygen compound - Organic oxide - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 343.207 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Complexity | 399 |
| Monoisotopic Mass | 342.033 |
| Exact Mass | 342.033 |
| XLogP | 4.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 23 |
| 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+ | 0.9884 |
| Human Intestinal Absorption | HIA+ | 0.9896 |
| Caco-2 Permeability | Caco2+ | 0.6390 |
| P-glycoprotein Substrate | Non-substrate | 0.8738 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7763 |
| Non-inhibitor | 0.9093 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8541 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8538 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7772 |
| CYP450 2D6 Substrate | Non-substrate | 0.9021 |
| CYP450 3A4 Substrate | Non-substrate | 0.5101 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9658 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.9360 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.5296 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.9425 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5133 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.9192 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9906 |
| Non-inhibitor | 0.7395 | |
| AMES Toxicity | Non AMES toxic | 0.6654 |
| Carcinogens | Non-carcinogens | 0.7456 |
| Fish Toxicity | High FHMT | 0.8885 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8144 |
| Honey Bee Toxicity | Low HBT | 0.9386 |
| Biodegradation | Not ready biodegradable | 0.9962 |
| Acute Oral Toxicity | III | 0.6324 |
| Carcinogenicity (Three-class) | Non-required | 0.6302 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3054 | LogS |
| Caco-2 Permeability | 1.7571 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5721 | LD50, mol/kg |
| Fish Toxicity | 1.0073 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2188 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Walnut | Japan | 0.70ppm | |||
| Almond | Japan | 0.70ppm | |||
| Kale | Canada | 18mg/kg | |||
| Liver | 1016030 | European Union | 0.15 | 26/08/2016 | |
| Muscle | 1016010 | European Union | 0.01* | 26/08/2016 | |
| Fat | 1016020 | European Union | 0.08 | 26/08/2016 | |
| Citrus fruits | 0110000 | European Union | 2 | 26/08/2016 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 2 | 26/08/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 2 | 26/08/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 2 | 26/08/2016 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 2 | 26/08/2016 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 2 | 26/08/2016 | |
| Brazil nuts | 0120020 | European Union | 0.05* | 26/08/2016 | |
| Cashew nuts | 0120030 | European Union | 0.05* | 26/08/2016 | |
| Chestnuts | 0120040 | European Union | 0.05* | 26/08/2016 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.05* | 26/08/2016 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.05* | 26/08/2016 | |
| Macadamias | 0120070 | European Union | 0.05* | 26/08/2016 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.05* | 26/08/2016 | |
| Pistachios | 0120100 | European Union | 1 | 26/08/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Time-to-death approach to reveal chronic and cumulative toxicity of a fungicide for honeybees not revealed with the standard ten-day test. | Sci Rep | 2018 May 8 | 29739960 |
| Multiple nucleobase transporters contribute to boscalid sensitivity inAspergillus nidulans. | Fungal Genet Biol | 2018 Jun | 29501616 |
| Biological Control of Botrytis cinerea: Interactions with Native Vineyard Yeasts from Washington State. | Phytopathology | 2018 Jun | 29334476 |
| High-Efficiency Control of Gray Mold by the Novel SDHI Fungicide BenzovindiflupyrCombined with a Reasonable Application Approach of Dipping Flower. | J Agric Food Chem | 2018 Jul 5 | 29889512 |
| Transfer of the Active Ingredients of Some Plant Protection Products fromRaspberry Plants to Beehives. | Arch Environ Contam Toxicol | 2018 Jul | 29247388 |
| Target vs non-target analysis to determine pesticide residues in fruits fromSaudi Arabia and influence in potential risk associated with exposure. | Food Chem Toxicol | 2018 Jan | 29109044 |
| Pesticide Residues in Table Grapes and Exposure Assessment. | J Agric Food Chem | 2018 Feb 21 | 29364655 |
| Transfer of plant protection products from raspberry crops of Laszka and Seedlingvarieties to beehives. | Environ Monit Assess | 2018 Feb 12 | 29435675 |
| Halogenated 1-Hydroxynaphthalene-2-Carboxanilides Affecting PhotosyntheticElectron Transport in Photosystem II. | Molecules | 2017 Oct 12 | 29023407 |
| Behavioral responses of honey bees (Apis mellifera) to natural and syntheticxenobiotics in food. | Sci Rep | 2017 Nov 21 | 29162843 |
| Behavior of fluopyram and tebuconazole and some selected pesticides in ripeapples and consumer exposure assessment in the applied crop protection framework. | Environ Monit Assess | 2017 Jul | 28646436 |
| Study on Mobility, Distribution and Rapid Ion Mobility Spectrometry Detection of Seven Pesticide Residues in Cucumber, Apple, and Cherry Tomato. | J Agric Food Chem | 2017 Jan 11 | 27936707 |
| [Estimations of application dosage and greenhouse gas emission of chemicalpesticides in staple crops in China.] | Ying Yong Sheng Tai Xue Bao | 2016 Sep | 29732850 |
| Efficacy of SDHI fungicides, including benzovindiflupyr, against Colletotrichumspecies. | Pest Manag Sci | 2016 Oct | 26732510 |
| Influence of the presence of ethanol on in vitro bioavailability of fungicideresidues. | Food Chem Toxicol | 2016 Jul | 27112541 |
| Lipase-catalyzed synthesis of palmitanilide: Kinetic model and antimicrobialactivity study. | Enzyme Microb Technol | 2016 Jan | 26672452 |
| Dissipation of Fungicide Residues during Winemaking and Their Effects onFermentation and the Volatile Composition of Wines. | J Agric Food Chem | 2016 Feb 17 | 26808836 |
| Fungicide multiresidue monitoring in international wines by immunoassays. | Food Chem | 2016 Apr 1 | 26593617 |
| Occurrence of pesticide residues in fruiting vegetables from production farms in south-eastern region of Poland | Rocz Panstw Zakl Hig | 2016 | 27925705 |
| Analysis of the Fungicide Boscalid in Horticultural Crops Using an Enzyme-Linked Immunosorbent Assay and an Immunosensor Based on Surface Plasmon Resonance. | J Agric Food Chem | 2015 Sep 16 | 26340386 |
Targets
- General Function:
- Cholesterol binding
- Specific Function:
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
- Gene Name:
- TSPO
- Uniprot ID:
- P30536
- Molecular Weight:
- 18827.81 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 ]
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 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:
- 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:
- 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:
- 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:
- Xenobiotic-transporting atpase activity
- Specific Function:
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name:
- ABCB1
- Uniprot ID:
- P08183
- Molecular Weight:
- 141477.255 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:
- Vitamin d 24-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.
- Gene Name:
- CYP1A1
- Uniprot ID:
- P04798
- Molecular Weight:
- 58164.815 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:
- 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:
- 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 ]