Synthesis of new compounds related to the commercial fungicide tricyclazole |
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| Authors: | Balcer Jesse L DeAmicis Carl V Johnson Peter L Klosin Jerzy Whiteker Gregory T Rao C Srinivas Dai Donghua |
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| Institution: | Dow AgroSciences, Indianapolis, IN 46268, USA. |
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| Abstract: | BACKGROUND: Tricyclazole is a commercial fungicide used to control rice blast. As part of re‐registration activities, samples of metabolites and process impurities are required. In addition, isotopically labeled tricyclazole samples are also required. RESULTS: Four new compounds related to tricyclazole are reported. An isotopically labeled sample of tricyclazole was prepared that contained two 15N atoms and one 13C atom. Radiolabeled tricyclazole with 14C at the triazole C3 position was also synthesized. A new process impurity in technical tricyclazole was identified and synthesized. A new metabolite of tricyclazole was identified, independently synthesized and characterized by X‐ray crystallography. CONCLUSION: A previously unreported metabolite of tricyclazole has been identified and structurally characterized. In addition, a new process impurity has been identified by independent synthesis. Identification of these new compounds has facilitated the continued registration of this important fungicide. Copyright © 2011 Society of Chemical Industry |
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| Keywords: | Tricyclazole metabolite fungicide |
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