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acifluorfen

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EntityQ2103461· pop 12· linked from 164 articles

acifluorfen

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Also 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

Wikidata facts

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)

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Encyclopedic overview

7 sections
Contents
  • 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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