4-[3-(吡啶-4-基)-3-取代苯基丙烯酰]吗啉类化合物的合成及杀菌活性

Synthesis and Fungicidal Activities of a Novel Series of 4-[3-(Pyrid-4-yl)-3-substituted phenyl acryloyl]morpholine

为了寻找具有高活性的含吡啶杂环杀菌剂,以烯酰吗啉为模板化合物,以异烟酸为起始原料,通过卤代反应、Friedel-Crafts酰基化反应、Wittig-Horner反应等,将吡啶-4-基或2-氯吡啶-4-基引入到模板结构中,设计合成了27个4-[3-(吡啶-4-基)-3-取代苯基丙烯酰]吗啉类化合物,其结构通过1H NMR和元素分析确证.对目标化合物的初步杀菌活性测定结果表明,所有目标化合物对立枯丝核菌(Rhizoctonia solani Kuhn.)和掘氏疫霉菌(Phytophthora drechsler Tucker)均有较强的抑制作用,其中4-20,4-21,4-22化合物对立枯丝核菌的EC50值分别为28.94,5.27和0.87μg/mL(对照药剂多菌灵为1.54μg/mL,烯酰吗啉为60.95μg/mL);对掘氏疫霉菌的EC50值分别为0.33,0.27和0.09μg/mL(对照药剂百菌清为20.39μg/mL,烯酰吗啉为0.24μg/mL),表明该类化合物具有重大的研究开发价值.

In searching for novel and high active fungicides with pyridyl moiety, with Dimethomorph as a model compound and isonicotinic acid as the main starting material, twenty-seven title compounds were designed and synthesized through chlorination, Friedel-Crafts acylation, Wittig-Horner reaction and other steps. All the target structures were confirmed via ^1H NMR and elementary analysis. In the preliminary fungicidal evaluation, all the compounds exhibit a significant inhibiting activity against Rhizoctonia solani Kuhn and Phytophthora drechsler Tucker. Among them, the EC50 values of compounds 4-20, 4-21 and 4-22 to Rhizoctonia solani Kuhn were 28.94, 5.27 and 0.87 μg/mL, respectively, compared to 1.54 μg/mL of Carbendazim and 60.95 μg/mL of Dimethomorph; and to Phytophthora drechsler Tucker were 0.33, 0.27 and 0.09 μg/mL, respectively, compared to 20.39 μg/mL of Chlorothalonil and 0.24 μg/mL of Dimethomorph. The results suggest that they might be valuable in the control of plant diseases.