松香是来自松树的非木质林产品,是我国的再生性天然优势生物质资源,主要成分为树脂酸.为拓展松香在生物活性方面的应用途径,以松香为原料,与丙烯酸Diels-Alder加成反应制备丙烯海松酸(1),再与氨基硫脲反应获得丙烯海松酸基双噻二唑(2),最后与系列取代苯甲酰氯进行N-酰化反应,合成得到7个新型丙烯海松酸基双酰胺-噻二唑化合物(3a~3g).采用FTIR、1 H NMR、13 C NMR、ESI-MS等技术手段对目标化合物进行结构表征;分别采用稗草小杯法和油菜平皿法测试目标化合物对稗草(Echinochloa crusgalli)株高生长和油菜(Brassica campestris)胚根生长的抑制活性.结果表明,在100μg/mL质量浓度下,目标化合物对油菜胚根生长的抑制活性较强,化合物3e(R=p-Br)的抑制率高达92.4%(活性级别为A级),化合物3b(R=p-CH3)和3d(R=p-Cl)的抑制率分别为77.4%和73.2%(活性级别均为B级).采用离体法(即琼脂稀释法)测试目标化合物对苹果轮纹病菌(Physalospora piricola)、黄瓜枯萎病菌(Fusarium oxysporum f.sp.cucumerinum)、番茄早疫病菌(Al-ternaria solani)、小麦赤霉病菌(Gibberella zeae)和花生褐斑病菌(Cercospora arachidicola)的抑菌活性.结果表明,目标化合物在50μg/mL质量浓度下对所测5种植物病原菌表现出一定抑制效果.目标化合物3e对油菜胚根生长具有较好的抑制活性,值得进一步研究.%As a non-wood forest product obtained from pines and some other plants, rosin with its dominant component as resin acids is a renewable, natural and preponderant biomass resource of China. In an attempt to expand its utiliza-tion in biological activities, acrylpimaric acid ( 1) was prepared by the Diels-Alder cycloaddition reaction between ros-in and acrylic acid. Then, acrylpimaric acid-based dithiadiazole ( 2) was prepared by the reaction of acrylpimaric acid with thiosemicarbazide. Seven novel acrylpimaric acid-based diamide-thiadiazole compounds ( 3a-3g ) were synthe-tized followed by N-acylation reaction with a series of substituted benzoyl chlorides. The target compounds were char-acterized by means of FTIR, 1 H NMR, 13 C NMR, and ESI-MS. The herbicidal activity of the target compounds 3a-3g was preliminarily evaluated by the barnyard grass beaker method and the rape petri dish method against the seed-ling-growth of barnyard grass ( Echinochloa crusgalli) and the root-growth of rape ( Brassica campestris) , respective-ly. The results showed that some target compounds had good growth inhibitory activity against the root-growth of rape at a concentration of 100 μg/mL, in which compound 3e ( R=p-Br) exhibited the highest inhibitory rate of 92.4%( A-class level) , and compounds 3b ( R=p-CH3 ) and 3b ( R=p-Cl) displayed inhibitory rate of 77.4% ( B-class lev-el) and 73.2% ( B-class level) , respectively. The antifungal activity of the target compounds 3a-3g was also evalua-ted by in vitro method ( also known as the agar dilution method) against Physalospora piricola, Fusarium oxysporum f. sp. cucumerinum, Alternaria solani, Gibberella zeae, and Cercospora arachidicola at a concentration of 50 μg/mL. It was found that the title compounds 3a-3g showed a certain antifungal activity against all the tested fungi. The target compound 3e with excellent herbicidal activity is a leading compound worthy of further research.
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