(S)-famoxadone
Basic information
- CAS
132584-12-4- Standard SMILES
C[C@@]1(c2ccc(Oc3ccccc3)cc2)OC(=O)N(Nc2ccccc2)C1=O- InChIKey
PCCSBWNGDMYFCW-QFIPXVFZSA-N- Molecular formula
- C22H18N2O4
- Average molar mass
- 374.4 g/mol
- Monoisotopic mass
- 374.12665706
Overview
(S)-famoxadone is a 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione that is the (active) (S)-enantiomer of famoxadone. It prevents spore germination and mycelial growth of sensitive fungi and is used in agriculture for the control of various fungal diseases. It has a role as a quinone outside inhibitor, a fungicide, an agrochemical and a mitochondrial cytochrome-bc1 complex inhibitor. It is an enantiomer of a (R)-famoxadone.
Names & identifiers
- Preferred name
- (S)-famoxadone
- IUPAC
- (5S)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione
- English name
- (S)-famoxadone
- Molecular formula
- C22H18N2O4
- Molecular weight
- 374.38932
Names & synonyms
(S)-famoxadone(-)-famoxadone(S)-(-)-famoxadone(5S)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dioneCHEBI:106738(S)-5-Methyl-5-(4-phenoxy-phenyl)-3-phenylamino-oxazolidine-2,4-dione(5S)-5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dioneRefChem:408124132584-12-4FMXCHEMBL10118SCHEMBL673443
Show more names
Fensulfothion Impurity 10
PCCSBWNGDMYFCW-QFIPXVFZSA-NDTXSID901153295DB07778Q63390517(5S)-5-Methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione(S)-5-Methyl-5-(4-phenoxyphenyl)-3-(phenylamino)oxazolidine-2,4-dione(s)-5-methyl-5-(4-phenoxy-phenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione
Database identifiers
- CAS
132584-12-4- PubChem CID
- 446845
- DTXSID
DTXSID901153295- ChEMBL
CHEMBL10118- ChEBI
Properties
Computed structural properties
- XLogP
- 5
- Topological polar surface area
- 67.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 563
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Chemistry & industry
Applications
Uses(S)-Famoxadone is a commercially available chiral fungicide used on tomato, apple, and grape, and sold as a rac-Famoxadone (F102300).
Additional notes
DefinitionChEBI: (S)-famoxadone is a 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione that is the (active) (S)-enantiomer of famoxadone. It prevents spore germination and mycelial growth of sensitive fungi and is used in agriculture for the control of various fungal diseases. It has a role as a fungicide, an agrochemical, a mitochondrial cytochrome-bc1 complex inhibitor and a quinone outside inhibitor. It is an enantiomer of a (R)-famoxadone.
Related reactions
0 records
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Compound notes
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