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Fomesafen

CAT: 0804-HY-B2010-01Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B2010-01Size:25 mg
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Description
Fomesafen is an orally active herbicide. Fomesafen inhibits protoporphyrinogen oxidase (PPO) . Fomesafen induces Apoptosis and increases ROS. Fomesafen exhibits developmental toxicity, immunotoxicity, and neurotoxicity. It induces precancerous lesions in the liver and hepaturoporphyria in mice. Fomesafen is used to control broadleaf weeds in soybean fields, rubber plantations, and orchards[1][2][3][4][5][6].
CAS Number
72178-02-0
UNSPSC
12352005
Hazard Statement
H302
Target
Apoptosis; Herbicide; Protoporphyrinogen IX oxidase; Reactive Oxygen Species (ROS)
Type
Reference compound
Related Pathways
Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Field of Research
Cancer; Metabolic Disease; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/fomesafen.html
Concentration
10mM
Purity
99.81
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(NS(=O)(C)=O)C1=CC(OC2=CC=C(C(F)(F)F)C=C2Cl)=CC=C1[N+]([O-])=O
Molecular Formula
C15H10ClF3N2O6S
Molecular Weight
438.76
Precautions
H302
References & Citations
[1]Li-Xia Zhao, et al. Novel Thiazole Phenoxypyridine Derivatives Protect Maize From Residual Pesticide Injury Caused by PPO-Inhibitor Fomesafen. Biomolecules. 2019 Sep 20;9 (10) :514.|[2]MACAR O, et al. FOMESAFEN-INDUCED MERISTEMATIC CELL DAMAGES IN ALLIUM CEPA L. (ONION) [J]. |[3]Xu Z, et al. Effect of fomesafen on the embryonic development of zebrafish. Chemosphere. 2020 Nov;259:127380.|[4]Krijt J, et al. Experimental hepatic uroporphyria induced by the diphenyl-ether herbicide fomesafen in male DBA/2 mice. Toxicol Appl Pharmacol. 2003 May 15;189 (1) :28-38. |[5]Krijt J, et al. Liver preneoplastic changes in mice treated with the herbicide fomesafen. Hum Exp Toxicol. 1999 May;18 (5) :338-44. |[6]Zhang Q, et al. Oxidative stress and lipid peroxidation in the earthworm Eisenia fetida induced by low doses of fomesafen. Environ Sci Pollut Res Int. 2013 Jan;20 (1) :201-8.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Fomesafen

Fomesafen is an N-sulfonylcarboxamide that is N-(methylsulfonyl)benzamide in which the phenyl ring is substituted by a nitro group at position 2 and a 2-chloro-4-(trifluoromethyl)phenoxy group at position 5. A protoporphyrinogen oxidase inhibitor, it was specially developed for use (generally as the corresponding sodium salt, fomesafen-sodium) for post-emergence control of broad-leaf weeds in soya. It has a role as a herbicide, an agrochemical and an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor. It is a member of phenols, an aromatic ether, a C-nitro compound, an organofluorine compound, a member of monochlorobenzenes and a N-sulfonylcarboxamide. It is a conjugate acid of a fomesafen(1-).

CAS Number72178-02-0
PubChem CID51556
IUPAC Name5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-methylsulfonyl-2-nitrobenzamide
Molecular FormulaC15H10ClF3N2O6S
Molecular Weight438.8
XLogP2.4
Topological Polar Surface Area127
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Heavy Atom Count28
Formal Charge0
Complexity693
SMILES
CS(=O)(=O)NC(=O)C1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-]
InChI
InChI=1S/C15H10ClF3N2O6S/c1-28(25,26)20-14(22)10-7-9(3-4-12(10)21(23)24)27-13-5-2-8(6-11(13)16)15(17,18)19/h2-7H,1H3,(H,20,22)
InChIKey
BGZZWXTVIYUUEY-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Fomesafen
CAS: 72178-02-0
CID: 51556
Formula: C15H10ClF3N2O6S
MW: 438.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight438.8
XLogP32.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass437.9900194
Monoisotopic Mass437.9900194
Topological Polar Surface Area127 Ų
Heavy Atom Count28
Formal Charge0
Complexity693
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
450884-01Fomesafen
CS-O-47488Fomesafen D3
TMIH-0244-01Fomesafen-d3
AR-F01972-01Fomesafen Impurity 2
AR-F01971-01Fomesafen Impurity 1

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