CAA fungicides were officially announced by the Fungicide Resistance Action Committee (FRAC) in 2005. In 2010, Blum et al. reported that both of the known mutations in the PiCesA3 gene of P. infestans, which is known to be involved in the synthesis of cellulose. CAA fungicides posses very similar structural fragments, including amide, halobenzene (or methylbenzene) and/or dialkoxy benzene moieties. Compounds belonging to the cinnamic acid amide and mandelic acid amide sub-classes possess all three of these active structural fragments, whereas compounds belonging to the valinamide carbamate sub-class only contain two of these three active structural fragments. With this in mind, we became interested in synthesizing and evaluating the fungicidal activities of valinamide carbamate analogues that contained all three of these active structural fragments. Bioassays showed that some title compounds exhibited very good in vitro fungicidal activityagainst Phytophthora capsici and in vivo fungicidal activities against Pseudoperonospora cubensis. Comparative molecular ?eld analysis was performed to explore the structure�activity relationship on the basis of in vitro data. The dimethoxy substituted aromatic analogue was found to display higher in vitro fungicidal activities against Phytophthora capsici than iprovalicarb and higher in vivo fungicidal activity against Pseudoperonospora cubensis than dimethomorph at a dosage of 6.25 �g mL-1.

Design, synthesis, and fungicide activities of novel carboxylic acid amides represented by N-benzhydryl valinamide carbamates

248th National Meeting (2014)

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