马来松香基双磺酰胺化合物的合成及杀菌活性初探

Synthesis and Fungicidal Activity of Maleated Rosin-based Disulfamide Compounds

以马来松香为原料,经酰氯化、与N-芳磺酰基乙二胺类化合物的N-酰化反应,合成得到14个新型马来松香基双磺酰胺类化合物(4a^4n),其结构经FT-IR、1H NMR、13C NMR、ESI-MS、UV-Vis和元素分析进行表征。经鉴定,14个化合物分别为马来松香基双苯基磺酰胺(4a)、马来松香基双对甲苯基磺酰胺(4b)、马来松香基双间甲苯基磺酰胺(4c)、马来松香基双对甲氧基苯基磺酰胺(4d)、马来松香基双间甲氧基苯基磺酰胺(4e)、马来松香基双对溴苯基磺酰胺(4f)、马来松香基双间溴苯基磺酰胺(4g)、马来松香基双对氯苯基磺酰胺(4h)、马来松香基双间氯苯基磺酰胺(4i)、马来松香基双对氟苯基磺酰胺(4j)、马来松香基双邻氟苯基磺酰胺(4k)、马来松香基双对硝基苯基磺酰胺(4l)、马来松香基双间硝基苯基磺酰胺(4m)、马来松香基双邻硝基苯基磺酰胺(4n)。初步的生物活性测试表明,化合物4a^4n对5种供试植物病菌均有一定的杀菌活性,其中在50 mg/L质量浓度下,化合物4k对苹果轮纹病菌的抑制效果较好,抑制率最好为66.8%。

Maleated rosin acyl chloride was prepared via acyl chlorination using maleated rosin as starting material. It was followed by the N-acylation reaction of maleated rosin aeyl chloride with N-aryl sulfonyl ethylenediamines to obtain fourteen novel maleated rosin-based disulfonamide compounds （4a-4n）. The target compounds were characterized by means of FT-IR, ^1H NMR,13C NMR, ESI-MS, UV-Vis, and elemental analysis. Compounds 4a-4n were identified to be maleated rosin-based diphenylsulfamide, maleated rosin-based di （p-methyl）phenylsulfamide, maleated rosin-based di （m-methyl）phenylsulfamide, maleated rosin-based di （p-methoxy） phenylsulfamide, maleated rosin-based di （m-methoxy） phenylsulfamide, maleated rosin- based di （ p-bromo ） phenylsulfamide, maleated rosin-based di （m-bromo） phenylsulfamide, maleated rosin-based di （ p-chloro ） phenylsulfamide, malated rosin-based di （m-chloro）phenylsulfamide, maleated rosin-based di （p-fluoro）phenylsulfamide, maleated rosin-bas-fluoro） phenylsulfamide, maleated rosin-based di （p-nitro） phenylsulfamide, maleated rosin-based di （m-nitro）phenylsulthmide, maleated rosin-based di （o-nitro）phenylsulfamide, respectively. The preliminary bioassay showed that compounds 4a-4n exhibited a certain fungicidal activity against five tested fungi. Among them compound 4k, maleated rosin-based di （ o-fluoro ） phenylsulfamide, had inhibition rate of 66. 8 % against Physalospora piricola at the concentration of 50 mg/L.