Trifluoromethylpyridines as building blocks for new agrochemicals: discovery of a new turf herbicides.
1991
Haga T. | Tsujii Y. | Hayashi K. | Kimura F. | Sakashita N. | Fujikawa K.
The introduction of fluorine substituents in structures of known activity is an important strategy for optimizing the properties of agrochemicals and pharmaceuticals. Research in our laboratories has focused on a novel application of this strategy, the use of 3-trifluoromethyl(tfm)pyridines as building blocks for new agrochemicals. The following paper discusses two aspects of this research. First, the usefulness of the approach was demonstrated by incorporating a 3-tfm-pyridinyloxy moiety in phenoxylactate herbicides and benzoylurea insect growth regulators. Studies were also done to understand the role of this moiety in improving activity, and we propose that it can act as a carrier, enhancing transport of agrochemicals to their target sites. Second, the strategy was extended to sulfonylurea herbicides, using 2-chloro-3-tfm-pyridine as the key intermediate. As a result, a new herbicide for turf, SL-160, was discovered. This compound shows high herbicidal activity, low mammalian toxicity, and rapid soil degradation through a novel chemical mechanism.
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