Structure via PubChem · Public domain (PubChem)
acifluorfen
Sign in to saveAlso known as 5-(2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-2-nitrobenzoic acid, 2-nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acid, 5-[2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY]-2-NITROBENZOIC ACID
Acifluorfen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to acifluorfen and its salts, via metabolic disposal by glutathione S-transferase. It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.
Chemical data
- Formula
- C14H7ClF3NO5
- Molecular weight
- 361.65 g/mol
- IUPAC name
- 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid
- SMILES
- C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)O
- InChIKey
- NUFNQYOELLVIPL-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 92.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
146 papers- Exposure to acifluorfen induces developmental toxicity in the early life stage of zebrafish.Comparative biochemistry and physiology. Toxicology & pharmacology : CBP · 2024
- Nitroreductase DnrA, Utilizing Strategies Secreted in Bacillus sp. Za and SCK6, Enhances the Detoxification of Acifluorfen.Journal of agricultural and food chemistry · 2024
- Preparation of Acifluorfen-Based Ionic Liquids with Fluorescent Properties for Enhancing Biological Activities and Reducing the Risk to the Aquatic Environment.Journal of agricultural and food chemistry · 2020
- Acifluorfen Enhancement of Cryptochrome-Modulated Sporulation following an Inductive Light Pulse.Plant physiology · 1987
- Stable Fluorescent Nanoparticles Based on Co-assembly of Acifluorfen and Poly(salicylic acid) for Enhancing Herbicidal Activity and Reducing Environmental Risks.ACS applied materials & interfaces · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 360.996
- Has use
- herbicide
Show 4 more facts
- Commons category
- Acifluorfen
- chemical formula
- C₁₄H₇ClF₃NO₅
- canonical SMILES
- C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)O
- subject has role
- enzyme inhibitor
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
7 sectionsContents
- History
- Synthesis
- Mechanism of action
- Usage
- Safety
- See also
- References
Acifluorfen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to acifluorfen and its salts, via metabolic disposal by glutathione S-transferase. It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.
==History== The nitrophenyl ethers are a well-known class of herbicides, the oldest member of which was nitrofen, invented by Rohm & Haas and first registered for sale in 1964. This area of chemistry became very competitive, with the Mobil Oil Corporation's filing in 1969 and grant in 1974 of a patent to the structural analog with a COOCH3 group adjacent to the nitro group of nitrofen. This product, bifenox, was launched with the brand name Mowdown in 1981. Meanwhile, Rohm & Haas introduced acifluorfen (as its sodium salt with brand name Blazer) in 1980, having developed it under the code number RH-6201. It had much improved properties including a wider spectrum of herbicidal effect and good safety to soybean crops. The first patent for the material was published in December 1975, although an earlier Belgian patent published in September 1973 had described related chemistry.
Excerpted from Wikipedia’s “acifluorfen” article, available under the CC BY-SA 4.0 licence.
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