| It is well known that obtaining bioactive compounds from natural product is one of the most important ways to find lead compound. In recent years, it has been become a trend that develop and research new pesticide on the basis of Natural-product model. It is demonstrated that kakuol and it’s analogues especially those bearing a C=C bond conjugated to the C=O group have a remarkable antifungal activities. In a study aiming to determine the structural elements essential to antifungal activity of kakuol, we take kakuol analogue ( compound 1 ):1-(6-Hydroxy-1,3-benzodioxol-5-yl)-2-methylprop-2-en-1-one which showing a excellent antifungal activity against some important plant pathogens as lead compound, synthesized 30 kakuol analogues from etherification, esterification and oximation. Of which 27 compounds were firstly reported. Their structures were characterized by 1H-NMR, IR. and MS.We assayed their in vitro antifungal activity against 5 fungi: Fusarium graminearum, Botrytis cirerea, Gloeosporium orbiculare Ars, Fusarium solani and Magnaporthe grisea. Taking Tiabendazole as positive control.Giving the concentration of 100 mg/L, most of the analogs showed a remarkable in vitro activity, and some of them appeared significantly more effective than the natural product. In particular, compound 3a, 3b,3c and 3f showed a similar bioactivity to compound 1, the most sensitive organisms to the action of these four compounds were Fusarium graminearum, Botrytis cirerea, Fusarium solani and Magnaporthe grisea; compaired with Tiabendazole, the four compounds showed a higher inhibition ratio to the Gloeosporium orbiculare Ars. While among the 15 ester derivatives, only 5b and 5d displayed a outstanding antifungal activity against Fusarium graminearum and Botrytis cirerea; As for the oxime 6, it revealed a similar bioactivity to Tiabendazole, but it’s inhibition ratio to Botrytis cirerea (90.2%) was higher than which of the positive control’s(66.7%). |
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