[4][5] 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.
Bifenox was first synthesized by R.J. Theissen of the agricultural research section of Mobil Chemical's Central Research Laboratory in 1969 .The preparation of bifenox first described in the Mobil patent includes as its final step an Ullmann condensation between the potassium salt of 2,4-dichlorophenol and methyl 2-nitro-5-chlorobenzoic acid.
[7][10]: 43 The methyl 2-nitro-5-chlorobenzoic acid was made starting from Toluene/Chlorine/benzoic acid/Methanol/nitric acid/ in a 5 steps synthesis http://www.microchem.fr/patent_alas/process_info/bifenox/bifenox.html The detailed mechanism of action for nitrofen, acifluorfen and related diphenyl ether herbicides was unknown at the time they were invented.
[11] The now-accepted explanation for the damage is that these compounds inhibit the enzyme protoporphyrinogen oxidase, which leads to an accumulation of protoporphyrin IX in the plant cells.
[5][12] Bifenox is not currently used in the United States[13] although in 1981 it had been subject to a full regulatory review, under the then-new "Registration Standard" process.