【作者】 钟江春；

【导师】 王敏；

【作者基本信息】 中国农业大学 ， 农药学， 2004， 硕士

【摘要】 论文综述了植物诱导抗病剂的作用机理，以及在植物病害防治上的研究进展。苯并[1，2，3]噻二唑-7-羧酸硫甲酯(BTH)是一类新型的植物诱导剂，此类物质出现后受到了广泛的重视，在植物病害防治中取得了良好的效果。 本论文根据苯并噻二唑诱导剂的构效关系设计了新的苯并噻二唑的结构，并合成了9个未见文献报道的化合物，合成步骤如下： 采用2-氯-3，5-二硝基苯甲酸为起始原料，苯环上的氯原子被叔丁基硫醇置换，羧酸由溴乙烷酯化，硝基由铁粉还原，随后经重氮化关环生成苯并[1，2，3]噻二唑-7-羧酸乙酯(中间体Ⅰ)。中间体Ⅰ在低温-78℃下经二异丁基氢化铝(DIBAL-H)还原制备了苯并[1，2，3]噻二唑-7-甲醛，随后苯并[1，2，3]噻二唑-7-甲醛经Witting-Homer反应制备了目标产物(E)-苯并[1，2，3]噻二唑-7-丙烯酸酯。所合成化合物的结构已经通过~1HNMR、IR谱及元素分析的确认。 生测结果表明在活体上有一定生物诱导活性，而离体没有杀菌活性。更多还原

【Abstract】 This paper summarys plant inducer’s mechanism and application on plant disease protection. S-methyl benzo[d][l,2,3]thiadiazole-7-carbothioate ( BTH ) as one of a new plant inducer has been widely studied rencently, and has been already used as pesticide in agriculture.In this study, new benzo[d][l,2,3]thiadiazole derivatives were designed according to relationship of structure and efficacy. The 9 novel compounds were synsthesized with following reactions.The chlorine atom in 2-chloro-3,5-dinitro-benzoic acid as beginning raw material was substituted by 2-methylpropane-2-thiol, esterified then with bromoethane, reduced by iron powder and cyclized to obtain ethyl benzo[d][l,2,3]thiadiazole-7 (intermediate I) after diazonation reation. Intermediate I was reduced at -78℃ by DIBAL-H to obtain benzo[d][l,2,3]thiadiazole-7-carbaldehyde, and benzo[d][l,2,3]thiadiazole-7-carbaldehyde treated via Wittig-Horner reaction to (E)-3-(benzo[d][l,2,3]thiadiazol-7-yl)acrylic acid esters as target compounds. All compounds were confirmed by ’HNMR, IR and elemental analysis.(E)-methyl 3-(benzo[d][l,2,3]thiadiazol-7-yl)acrylate estersBioassy results showed all novel compounds exhibit certain fungicidal activity in vitro, but no fungicidal activity in vivo.更多还原