College of Plant Protection , Hebei Agricultural University , Baoding 071001 , P. R. China.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry , Nankai University , Tianjin 300071 , P. R. China.
J Agric Food Chem. 2019 Nov 13;67(45):12357-12365. doi: 10.1021/acs.jafc.9b03891. Epub 2019 Oct 29.
A series of isothiazole, 1,2,3-thiadiazole, and thiazole-based cinnamamide morpholine derivatives were rationally designed, synthesized, characterized, and evaluated for their fungicidal activities. Bioassay indicated that a combination of 3,4-dichloroisothiazole active substructures with cinnamamide morpholine lead to significant improvement of in vivo antifungal activities of the target compounds; among them, compound exhibited good fungicidal activity against in vivo with an inhibition rate of 100% at 100 μg/mL. A field experiment indicated that the difference of efficacy between (75.9%) and dimethomorph (77.1%) at 37.5 g ai/667 m was not significant; and also exhibited good activity against by triggering accumulation of and defense-related gene expression and the defense associated enzyme phenylalanine ammonia-lyase (PAL) expression on cucumber, rather than direct inhibition. These findings strongly supported that 3,4-dichloroisothiazole containing cinnamamide morpholine not only showed good fungicidal activity against but also exhibited plant innate immunity stimulation activity as a promising fungicide candidate with both fungicidal activity and systemic acquired resistance.
一系列基于异噻唑、1,2,3-噻二唑和噻唑的肉桂酰胺吗啉衍生物被合理设计、合成、表征，并评估其杀菌活性。生物测定表明，将 3,4-二氯异噻唑的活性结构与肉桂酰胺吗啉结合，可显著提高目标化合物的体内抗真菌活性；其中，化合物 表现出良好的杀菌活性，在 100μg/mL 时对 体内抑制率为 100%。田间试验表明，化合物 在 37.5g ai/667m 时的防治效果（75.9%）与烯酰吗啉（77.1%）差异不显著；同时，通过触发 和防御相关基因表达以及防御相关酶苯丙氨酸解氨酶（PAL）在黄瓜上的表达，化合物 对 也表现出良好的活性，而不是直接抑制。这些发现有力地支持了含有 3,4-二氯异噻唑的肉桂酰胺吗啉不仅对 表现出良好的杀菌活性，而且还表现出植物先天免疫刺激活性，作为一种有前途的杀菌剂候选物，具有杀菌活性和系统获得性抗性。
