Synthesis and herbicidal activity of a pentafluorosulfanyl analog of trifluralin

The synthesis of 2,6-dinitro-4-pentafluorosulfanyl-N,N-dipropylaniline, 2, was achieved in a straightforward manner from commercially available 1-nitro-4-pentafluorosulfanylbenzene. In post-emergence screening 2 was found to be approximately twice as potent as trifluralin with the same general spectrum of activity. In contrast, in pre-emergence tests, 2 was nearly 5 fold more potent against quackgrass and crabgrass. Given the existing structure–activity-relationship for adverse properties of the dinitroaniline herbicides, 2 is proposed to have properties quite comparable to the commercial agent trifluralin.