124844-97-9Relevant academic research and scientific papers
Design, synthesis and herbicidal activity of 5-cyclopropyl-N-phenylisoxazole-4-carboxamides
Sun, Xinlin,Ji, Zhenmeng,Wei, Shaopeng,Ji, Zhiqin
, (2020)
4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a type of important herbicides, and they cause bleaching symptoms by indirectly inhibiting the biosynthesis of carotenoids. In this study, thirty isoxazolamide compounds were designed based on the structure of Isoxaflutole, a commercial HPPD herbicide. Starting from 1,1-dimethoxy-N,N-dimethyl-methanamine and methyl 3-cyclopropyl-3-oxo-propanoate, the title compounds were readily prepared and their structures were determined by MS and NMR analysis. In Petri dish tests, most of the title compounds showed strong inhibitory effect on the root and stem growth of both monocotyledon and dicotyledon weeds, and it was clearly different from the symptoms caused by HPPD inhibitors. However, several of them, especially I-17, showed characteristic bleaching symptoms of HPPD herbicides and good post-emergence herbicidal activity on tested weeds in glasshouse assay. These compounds are prodrugs, and compounds undergo conversion to the active entity diketonitrile (DKN) in plant and soil. The result of molecular docking analysis revealed that the DKN moiety of I-17 excellently binds to the active sites of HPPD. The 1,3-diketone can form bidentate interaction with FeII, and the benzene ring can form π-π interaction with Phe 360 and Phe 403. These results indicated that the title compounds bears other herbicidal mechanism except for HPPD inhibitor. Therefore, a lead compound for the discovery of novel multi-target herbicides is provided.
Antiarthritic isoxazole-4-carboxamides
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, (2008/06/13)
Disclosed herein are isoxazole-4-carboxamides having the formula STR1 wherein R1 is C3-6 cycloalkyl and R2 is selected from the group consisting of C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, C3-6 cycloalkyl, phenyl, and phenyl substituted with at least one group selected from C1-5 alkyl, C1-5 alkoxy, C1-5 alkylthio, and halo-substituted C1-5 alkyl; with the proviso that when R1 is cyclopropyl, R2 is not methyl, ethyl, or cyclobutyl; or R1 is C1-5 alkyl and R2 is phenylmethyl wherein the ring portion is opt. substituted with a halo-substituted C1-5 alkyl group. These compounds have antiinflammatory and antiarthritic activities and are also useful as intermediates in the preparation of β-ketonitriles.
