陈小员, 李兴海, 吴德财, 纪明山. 2-酰氧基环己烷基磺酰胺的组合合成与杀菌活性[J]. 农药学学报, 2014, 16(6): 651-658. DOI: 10.3969/j.issn.1008-7303.2014.06.04
    引用本文: 陈小员, 李兴海, 吴德财, 纪明山. 2-酰氧基环己烷基磺酰胺的组合合成与杀菌活性[J]. 农药学学报, 2014, 16(6): 651-658. DOI: 10.3969/j.issn.1008-7303.2014.06.04
    CHEN Xiaoyuan, LI Xinghai, WU Decai, JI Mingshan. Combinatorial synthesis and fungicidal activity of 2-acyloxycyclohexylsulfonamides[J]. Chinese Journal of Pesticide Science, 2014, 16(6): 651-658. DOI: 10.3969/j.issn.1008-7303.2014.06.04
    Citation: CHEN Xiaoyuan, LI Xinghai, WU Decai, JI Mingshan. Combinatorial synthesis and fungicidal activity of 2-acyloxycyclohexylsulfonamides[J]. Chinese Journal of Pesticide Science, 2014, 16(6): 651-658. DOI: 10.3969/j.issn.1008-7303.2014.06.04

    2-酰氧基环己烷基磺酰胺的组合合成与杀菌活性

    Combinatorial synthesis and fungicidal activity of 2-acyloxycyclohexylsulfonamides

    • 摘要: 为了快速获得具有杀菌活性的先导化合物,按照苯环上取代基的性质,将18个N-取代苯基-2-羟基环己烷基磺酰胺分成8个大小不等的原料库(A),分别与过量的2-乙氧基乙酰氯(B1)和4-氟苯甲酰氯(B2)反应,获得16个2-酰氧基环己烷基磺酰胺类组合库。通过气相色谱-质谱联用仪(GC-MS)和红外光谱分析了组合库中36个化合物的结构和含量。以番茄灰霉病菌Botrytis cinerea Pers.为供试靶标,菌丝生长速率法测试结果表明:当 A 的苯环上含有多个Cl或CF3等吸电子基团时,与 B1 反应生成的组合库的活性普遍较高,其中活性组合库 A5 B1、A6 B1 和 A7 B1 的杀菌活性均高于对照药剂腐霉利;黄瓜离体叶片试验表明,活性组合库 A6 B1 和 A7 B1 的防效也与腐霉利相当。在组合库生物活性筛选中化合物的结构、含量和数量是影响筛选结果的3个因素,其中结构为主要因素。

       

      Abstract: In order to rapidly prepare novel lead compounds of fungicides, 18 N-substituted phenyl-2-hydroxycyclohexylsulfonamides were divided into 8 material libraries (A) basing on the type of substituents on the phenyl ring. In total, 36 compounds in 16 liquid phase combinatorial libraries were obtained by the reaction of A with 2-ethoxyacetyl chloride (B1) or 4-fluorobenzoylchloride (B2). Structure and content of each compound were determined by GC-MS and IR. Activities of combinatorial libraries formed by the reaction of A bearing electron withdrawing group, such as Cl or CF3, on the phenyl ring and B1 were generally higher basing on the mycelial growth rate method of Botrytis cinerea Pers. In particular, A5B1, A6B1 and A7B1 are more active than procymidone. The A6B1 and A7B1 showed similar effect as procymidone in detached leaves of cucumber. Activities of combinatorial libraries were influenced by compound structure, content and quantity and structure was the major parameters.

       

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