Pyroxasulfone is a substituted pyrazolyl methanesulfonylisoxazoline herbicide from Kumiai that represents a new class of very long chain fatty acid (VLCFA) biosynthesis inhibitors. With a lower use rate and broader weed spectrum than older acetanilide-based products, pyroxasulfone is used for preemergent weed control in row crops and cereals. In our search for a novel chemotype from this area, we reported at the 242nd ACS National Meeting in 2011 that pyrimidinone substituted methylsulfonylisoxazolines, i.e. 1,  were also active herbicides that inhibited VLCFA biosynthesis. This work demonstrated that a �carbonyl-containing� heterocycle can be an effective surrogate to a traditional heteroaryl ring where the pyrimidinone carbonyl group also served as a critical ortho substituent to the methanesulfonyl bridge. In our optimization effort, a number of other �carbonyl-containing� heterocyclic variations were explored. Here, we report on the synthesis and herbicidal activity of a series of pyridazin-3(2H)-one methylsulfonylisoxazolines such as 2 .

Substituted [(dihydroisoxazolyl)sulfonylmethyl]pyridazin-3(2H)-ones: Herbicidal inhibitors of VLCFA biosynthesis

248th National Meeting (2014)

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