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合成了用于诱导植物系统获得抗性的化合物 6 羧基 1,2 ,3 苯并噻二唑 ,其合成步骤如下 :以对氨基苯甲酸 (I)为原料 ,用乙酰酐作为乙酰化试剂 ,在加热回流下反应 4h ,将化合物I的氨基进行保护 ,得对 乙酰氨基苯甲酸 (Ⅱ )。将化合物Ⅱ在 12～ 15℃下缓慢加入到氯磺酸中去进行氯磺化反应 .氯磺酸对化合物Ⅱ的量比为n(氯磺酸 )∶n(对 乙酰氨基苯甲酸 ) =4∶1,反应温度维持在 6 0℃ ,得化合物 2 乙酰氨基 5 羧基苯磺酰氯 (Ⅲ )。以锌粉加醋酸作为还原剂 ,在 70℃下搅拌回流 6h ,将化合物Ⅲ还原为 3 巯基 4 氨基 -苯甲酸 (Ⅳ )。将化合物Ⅳ在 0～ 5℃下用亚硝酸钠加冰醋酸去进行重氮化反应 ,然后用乙醚萃取 ,蒸去溶剂后得红棕色固体产物 6 羧基 1,2 ,3 苯并噻二唑 (V) ,产率 43 %
The synthesis of a carboxylated 1,2,6-benzothiadiazole compound 6 for inducing plant system resistance was as follows: The synthesis was carried out using p-aminobenzoic acid (I) as a starting material, acetic anhydride as an acetylating agent, and The reaction was heated under reflux for 4h, the amino compound I was protected to give acetamidobenzoic acid (II). Compound 2 is chlorosulfonated by slowly adding chlorosulfonic acid at 12-15 ° C. The ratio of chlorosulfonic acid to compound II is n (chlorosulfonic acid): n (para-acetamidobenzoic acid) = 4 : 1, maintaining the reaction temperature at 60 ° C to obtain the acetamido 5-carboxybenzenesulfonyl chloride (III) compound 2. Zinc powder and acetic acid as reducing agent were added, and the mixture was reduced to 3-mercapto-4-amino-benzoic acid (Ⅳ) by refluxing at 70 ℃ for 6h. Compound IV is diazotized with sodium nitrite and glacial acetic acid at 0-5 ° C and then extracted with ether. The solvent is distilled off to give the product as a red-brown solid 6 Carboxyl 1,2,3 benzothiadiazole ( V), yield 43%