Flufenacet
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Basic Info
| Common Name | Flufenacet(F05072) |
| 2D Structure | |
| Description | Flufenacet is a thiadiazole herbicide which is applied to the soil surface or incorporated preemergence in field corn, corn grown for silage, or soybeans to control certain annual grasses and broadleaf weeds. |
| FRCD ID | F05072 |
| CAS Number | 142459-58-3 |
| PubChem CID | 86429 |
| Formula | C14H13F4N3O2S |
| IUPAC Name | N-(4-fluorophenyl)-N-propan-2-yl-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide |
| InChI Key | IANUJLZYFUDJIH-UHFFFAOYSA-N |
| InChI | InChI=1S/C14H13F4N3O2S/c1-8(2)21(10-5-3-9(15)4-6-10)11(22)7-23-13-20-19-12(24-13)14(16,17)18/h3-6,8H,7H2,1-2H3 |
| Canonical SMILES | CC(C)N(C1=CC=C(C=C1)F)C(=O)COC2=NN=C(S2)C(F)(F)F |
| Isomeric SMILES | CC(C)N(C1=CC=C(C=C1)F)C(=O)COC2=NN=C(S2)C(F)(F)F |
| Synonyms |
142459-58-3
BAY-FOE 5043
Flufenacet
Thiafluamide
Fluthiamide
Fluthiamid
Flufenacet [ISO]
Foe 5043
UNII-OL44PP5145
HSDB 7011
|
| 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 | Anilides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Anilide - Alkyl aryl ether - Fluorobenzene - Halobenzene - Aryl fluoride - Aryl halide - Azole - Heteroaromatic compound - Thiadiazole - Tertiary carboxylic acid amide - Carboxamide group - Azacycle - Organoheterocyclic compound - Carboxylic acid derivative - Ether - Organic nitrogen compound - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Alkyl halide - Alkyl fluoride - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 363.331 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 5 |
| Complexity | 431 |
| Monoisotopic Mass | 363.066 |
| Exact Mass | 363.066 |
| XLogP | 3.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| 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+ | 0.9641 |
| Human Intestinal Absorption | HIA+ | 0.9929 |
| Caco-2 Permeability | Caco2- | 0.5455 |
| P-glycoprotein Substrate | Non-substrate | 0.8285 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.7204 |
| Non-inhibitor | 0.8391 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8273 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7616 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8456 |
| CYP450 2D6 Substrate | Non-substrate | 0.8006 |
| CYP450 3A4 Substrate | Substrate | 0.6825 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5251 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5601 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8076 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7590 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9506 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7165 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9964 |
| Non-inhibitor | 0.7412 | |
| AMES Toxicity | Non AMES toxic | 0.6100 |
| Carcinogens | Non-carcinogens | 0.7142 |
| Fish Toxicity | High FHMT | 0.9859 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9751 |
| Honey Bee Toxicity | Low HBT | 0.7560 |
| Biodegradation | Not ready biodegradable | 1.0000 |
| Acute Oral Toxicity | III | 0.7810 |
| Carcinogenicity (Three-class) | Non-required | 0.5252 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.8088 | LogS |
| Caco-2 Permeability | 1.0184 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7588 | LD50, mol/kg |
| Fish Toxicity | 1.2010 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4914 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Rhubarbs | 0270070 | European Union | 0.05* | 13/05/2015 | |
| Palm hearts | 0270090 | European Union | 0.05* | 13/05/2015 | |
| Brussels sprouts (Flower sprouts,) | 0242010 | European Union | 0.05* | 13/05/2015 | |
| Others (2) | 0242990 | European Union | 0.05* | 13/05/2015 | |
| (c) leafy brassica | 0243000 | European Union | 0.05* | 13/05/2015 | |
| Chinese cabbages/pe-tsai (Chinese flat cabbages/tatsoi/tai goo choi, Indian mustards/mustard greens, Komatsuna/mustard spinaches, Mizuna (4), Pak-choi/paksoi, Turnip greens/turnip tops (5), Seakale,) | 0243010 | European Union | 0.05* | 13/05/2015 | |
| Others (2) | 0243990 | European Union | 0.05* | 13/05/2015 | |
| (d) kohlrabies | 0244000 | European Union | 0.05* | 13/05/2015 | |
| Leaf vegetables, herbs and edible flowers | 0250000 | European Union | 0.05* | 13/05/2015 | |
| (a) lettuces and salad plants | 0251000 | European Union | 0.05* | 13/05/2015 | |
| Lamb's lettuces/corn salads (Italian corn salads,) | 0251010 | European Union | 0.05* | 13/05/2015 | |
| Stem vegetables | 0270000 | European Union | 0.05* | 13/05/2015 | |
| Escaroles/broad-leaved endives (Curly endives/ frisée endives, Dandelions, Puntarelle, Radicchio/red-leaved chicories, Sugar loaf chicories, Wild chicories/common chicories,) | 0251030 | European Union | 0.05* | 13/05/2015 | |
| Land cresses | 0251050 | European Union | 0.05* | 13/05/2015 | |
| Roman rocket/rucola (Wall rocket,) | 0251060 | European Union | 0.05* | 13/05/2015 | |
| Red mustards | 0251070 | European Union | 0.05* | 13/05/2015 | |
| Baby leaf crops (including brassica species) (Chards/beet leaves, Escaroles/broad-leaved endives, Indian mustards/mustard greens, Lettuces, Spinaches, Other species harvested at baby leaf stage,) | 0251080 | European Union | 0.05* | 13/05/2015 | |
| Others (2) | 0251990 | European Union | 0.05* | 13/05/2015 | |
| (b) spinaches and similar leaves | 0252000 | European Union | 0.05* | 13/05/2015 | |
| Spinaches (Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-khom, Amaranths/Chinese spinaches/pak-kh... | 0252010 | European Union | 0.05* | 13/05/2015 |
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 ]
- 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 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 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:
- 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 ]