Discovered at Kumiai, pyroxasulfone is a substituted pyrazolyl methanesulfonylisoxazoline herbicide in development for preemergent weed control in corn, soybeans, and cereals. The compound is representative of a new class of potent very long chain fatty acid (VLCFA) biosynthesis inhibitors that have a much lower use rate and broader activity spectrum than older acetanilide-based products with this mode of action. In our search for a novel chemotype from this area of chemistry, we recently reported that pyrimidinone substituted methylsulfonylisoxazolines such as 1  also expressed very high levels of herbicidal activity with crop safety. Potent inhibition of VLCFA biosynthesis was also observed for 1  . This work demonstrated that a �carbonyl-containing� heterocycle could serve as an effective surrogate to a traditional heteroaryl ring and, in the case of 1  , the pyrimidinone carbonyl group also served as a critical ortho substituent to the methanesulfonyl bridge. In the substantial optimization effort that followed, a number of carbonyl-containing heterocyclic variations were explored. Here, we report on the synthesis and herbicidal activity of a series of pyridazin-3(2H)-one methylsulfonylisoxazolines as represented by 2  .

Synthesis and herbicidal activity of novel substituted pyridazin-3(<i>2H</i>)-one methanesulfonylisoxazolines

244th National Meeting (2012)

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Synthesis and herbicidal activity of novel substituted pyridazin-3(2H)-one methanesulfonylisoxazolines