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CN118307440A - 一种苯甲酰腙类化合物及其合成方法、以及含有该化合物的药物及应用 - Google Patents

一种苯甲酰腙类化合物及其合成方法、以及含有该化合物的药物及应用 Download PDF

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CN118307440A
CN118307440A CN202410339877.7A CN202410339877A CN118307440A CN 118307440 A CN118307440 A CN 118307440A CN 202410339877 A CN202410339877 A CN 202410339877A CN 118307440 A CN118307440 A CN 118307440A
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pathogenic bacteria
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apple
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wilt
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沙赟颖
杨珊珊
刘竺云
燕韦婷
单阳
郑怡宁
周恩哲
叶雯倩
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Taizhou Polytechnic College
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Abstract

本发明涉及一种苯甲酰腙类化合物及其合成方法、以及含有该化合物的药物及应用，属于植物抗菌药物技术领域，该苯甲酰腙类化合物对十多种植物病原真菌具有显著的抑制活性，同时具有结构简单、易于规模化制备和对动植物安全性高的特点，可作为有效成分用于高效低毒的新型植物抗菌剂的开发。

Description

一种苯甲酰腙类化合物及其合成方法、以及含有该化合物的 药物及应用
技术领域
本发明涉及一种苯甲酰腙类化合物及其合成方法、以及含有该化合物的药物及应用，属于植物抗菌药物技术领域。
背景技术
据联合国粮农组织的数据表明，全球每年约有25％的农产品收到真菌毒素的污染，2％的农产品因受到的污染严重而失去营养、经济价值。此外，真菌毒素不仅对植物有害，还能通过饲料和食物进入动物和人类体内，从而损害人的中枢神经系统，严重时造成中毒和死亡。如黄曲霉、副曲霉和其他真菌产生各种黄曲霉毒素，具有致癌性和诱变性，对人类健康构成巨大威胁。随着新的人类疾病不断被发现，农业害虫和杂草逐渐演变进化，抗药性不断增强，这些都对药效提出了更高的要求，低效高毒的药品和农药逐渐被高效低毒的药物所取代。由此，有必要开发出具有新的分子框架或作用机制的新型杀虫剂，从而解决长久使用一种杀虫剂所带来的植物真菌耐药性问题。
含酰腙结构的化合物由于分子结构中存在Schiff碱基 (-CH=N-) 和酰胺键 (-CONH-) 等活性基团，大多具有抑菌、杀虫、除草活性，该类化合物是当今农药界的研究热点之一。岳敏等合成了含酰腙结构的新型吡唑酰胺衍生物并试验了其对小菜蛾的杀虫活性；马敬中等合成了1, 4-二氧喹喔啉-2-甲醛酰腙，活性试验结果表明，该类化合物对稗草和油菜具有除草活性；麻宝成等研究结果表明，含羧基的酰腙化合物对金黄色葡萄球菌（Staphyloccocus aureus）、大肠杆菌（Scherichia coli）、枯草杆菌（Acillus subtilis）具有抑菌作用；许雪裳等报道了马来松香酸酰腙类化合物的合成，该类化合物对小麦赤霉病菌（Ibberella zeae）有较强的抑菌活性；叶英等合成的吲哚-6-酰腙类化合物对金黄色葡萄球菌、大肠杆菌及沙门氏菌（Almonella lignieres）具不同程度的抑菌活性。目前，关于苯甲醛苯甲酰腙类化合物的抗真菌活性鲜有报道。
发明内容
为解决现有技术存在的技术问题，本发明提供了一种苯甲酰腙类化合物及其合成方法、以及含有该化合物的药物及应用，此类化合物能够对多种植物病原菌具有显著的抑制活性。
为实现上述目的，本发明所采用的技术方案为一种苯甲酰腙类化合物，具有如下分子结构，其中：B环是苯、呋喃、噻吩、吡咯、噻唑、咪唑、吡啶、吡嗪、嘧啶、哒嗪、吲哚、喹啉、蝶啶、吖啶中的一种；R1、R2是相同或不同的氢、烷基、烷氧基、苯氧基、卤素原子或硝基。
一种苯甲酰腙类化合物的合成方法，具有以下合成路线：其中：B环可以是苯、呋喃、噻吩、吡咯、噻唑、咪唑、吡啶、吡嗪、嘧啶、哒嗪、吲哚、喹啉、蝶啶、吖啶中的一种；R1、R2是相同或不同的氢、烷基、烷氧基、苯氧基、卤素原子或硝基。
一种苯甲酰腙类化合物的应用，该类化合物作为有效成分或增效成分在制备植物抗菌药物中的应用。
优选的，该类化合物对以下植物病原菌均具有显著的抑制活性：棉花枯萎病原菌；西瓜枯萎病原菌；马铃薯干腐病原菌；小麦赤霉病原菌；番茄早疫病原菌；白菜黑斑病原菌；烟草赤星病原菌；玉米弯孢病原菌；苹果炭疽病原菌；南瓜枯萎病原菌；苹果腐烂病原菌；水稻稻瘟病原菌；苹果轮纹病原菌。
一种含有苯甲酰腙类化合物的药物，该药物以苯甲酰腙类化合物为有效成分或增效成分。
优选的，该药物作为植物抗菌药物的应用。
优选的，该药物对以下病原菌引起的植物病具有预防和治疗效果：棉花枯萎病原菌；西瓜枯萎病原菌；马铃薯干腐病原菌；小麦赤霉病原菌；番茄早疫病原菌；白菜黑斑病原菌；烟草赤星病原菌；玉米弯孢病原菌；苹果炭疽病原菌；南瓜枯萎病原菌；苹果腐烂病原菌；水稻稻瘟病原菌；苹果轮纹病原菌。
与现有技术相比，本发明具有以下技术效果：本发明所涉及的苯甲酰腙类化合物具有如下优点：分子量小，结构简单；合成方法简单，工艺条件简单、环保，适宜于规模化生产；收率高，纯化方法简单易行；抗菌活性强，抗菌谱广且不易产生抗药性，对十多种常见植物病原菌均具有良好的防治效果；对动植物的安全性高。因此，本发明所涉及的苯甲酰腙类化合物具有作为植物抗菌剂的巨大开发潜力。
附图说明
图1为本发明中化合物A11对小麦幼苗生长的影响示意图。
具体实施方式
为了使本发明所要解决的技术问题、技术方案及有益效果更加清楚明白，以下结合附图及实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
本发明基于含酰腙结构的化合物分子结构中存在Schiff碱基 (-CH=N-) 和酰胺键 (-CONH-) 等结构，通过活性结构单元的组合，设计并合成出一系列苯甲酰腙类化合物，并发现该类化合物对多种植物病均具有高效的抑制活性，及对动植物的毒性较低，具有作为有效成分或增效成分用于新型高效低毒植物抗菌剂的开发。
上述苯甲酰腙类化合物，具有如下分子结构特征：其中：
B环可以是苯、呋喃、噻吩、吡咯、噻唑、咪唑、吡啶、吡嗪、嘧啶、哒嗪、吲哚、喹啉、蝶啶、吖啶等；R1、R2是相同或不同的氢、烷基、烷氧基、苯氧基、卤素原子、硝基等；
上述苯甲酰腙类化合物的合成方法，具有以下合成路线：其中：
B环可以是苯、呋喃、噻吩、吡咯、噻唑、咪唑、吡啶、吡嗪、嘧啶、哒嗪、吲哚、喹啉、蝶啶、吖啶等；R1、R2是相同或不同的氢、烷基、烷氧基、苯氧基、卤素原子、硝基等；
化合物的抗菌活性采用菌丝生长速率法进行测定。采用商业抗菌剂醚菌酯的标准品为阳性对照。通过与阳性药物的活性进行比较，证明本发明所涉及的苯甲酰腙类化合物对棉花枯萎病原菌；西瓜枯萎病原菌；马铃薯干腐病原菌；小麦赤霉病原菌；番茄早疫病原菌；白菜黑斑病原菌；烟草赤星病原菌；玉米弯孢病原菌；苹果炭疽病原菌；南瓜枯萎病原菌；苹果腐烂病原菌；水稻稻瘟病原菌；苹果轮纹病原菌等多种植物病原菌普遍具有强的抑制活性，具有作为抗菌活性成分或增效成分用于制备植物抗菌剂的巨大潜力
以下结合附表和合成方法及其活性测定对本发明作进一步详细说明：
一、苯甲酰腙类化合物的制备
通用方法：向反应瓶（100 mL）中加入苯甲酰肼或取代苯甲酰肼（5 mmol）和乙醇（50 mL），搅拌至固体全溶。在搅拌下，向其中依次加入苯甲醛或取代苯甲醛的乙醇溶液（5mmol），安装回流装置，控制温度80-90℃，继续搅拌。当TLC检测到反应完成后，将反应液转移至玻璃茄形烧瓶（100ml），减压蒸去溶剂，得粗产物。使用石油醚和乙酸乙酯的混合液进行重结晶，得到纯的苯甲酰腙类化合物。
以下是采用上述方法合成的苯甲酰腙类化合物的名称、理化性质和核磁共振谱数据。
苯甲醛苯甲酰腙（A1）：白色针状结晶；产率90.4%；mp 207.8-208.4 °C；1H NMR(400 MHz, DMSO-d 6) δ 11.90 (s, 1H), 8.50 (s, 1H), 7.95 (d, J = 7.1 Hz, 2H),7.79 – 7.71 (m, 2H), 7.61 – 7.44 (m, 6H). 13C NMR (101 MHz, DMSO-d 6) δ 163.64,148.27, 134.82, 133.91, 132.23, 130.56, 129.32, 128.95, 128.11, 127.57.
苯甲醛-4-氟苯甲酰腙（A2）：白色针状结晶；产率95.1%；mp 187.4-188.5 °C; 1HNMR (400 MHz, DMSO-d 6) δ 11.92 (s, 1H), 8.48 (s, 1H), 8.02 (dd, J = 8.6, 5.5Hz, 2H), 7.79 – 7.71 (m, 2H), 7.49 – 7.35 (m, 5H). 13C NMR (101 MHz, DMSO-d 6)δ 164.63 (J = 250.5 Hz), 162.55, 148.36, 134.76, 130.84 (J = 9.09 Hz),130.58, 129.32, 127.58, 115.94 (J = 22.2 Hz).
苯甲醛-4-氯苯甲酰腙（A3）：白色针状结晶；产率88.4%；mp 197.5-198.0℃; 1HNMR (400 MHz, DMSO-d 6) δ 11.95 (s, 1H), 8.47 (s, 1H), 7.97 (d, J = 8.5 Hz,2H), 7.78 – 7.70 (m, 2H), 7.62 (d, J = 8.5 Hz, 2H), 7.47 (d, J = 6.5 Hz, 3H).13C NMR (101 MHz, DMSO-d 6) δ 162.54, 148.59, 137.08, 134.70, 132.58, 130.64,130.04, 129.32, 129.05, 127.61.
苯甲醛-4-溴苯甲酰腙（A4）：棕色固体；产率94.8%；mp 206.9-207.9 ℃; 1H NMR(400 MHz, DMSO-d 6) δ 11.94 (s, 1H), 8.47 (s, 1H), 7.89 (d, J = 8.3 Hz, 2H),7.76 (dd, J = 8.0, 4.6 Hz, 4H), 7.47 (d, J = 6.3 Hz, 3H). 13C NMR (101 MHz,DMSO-d 6) δ 162.65, 148.61, 134.70, 132.93, 132.00, 130.65, 130.21, 129.33,127.62, 126.03.
4-氰基苯甲醛苯甲酰腙（A5）：白色粉末；产率93.8%；mp 196.1-196.6 ℃; 1H NMR(400 MHz, DMSO-d 6) δ 12.12 (s, 1H), 8.52 (s, 1H), 7.92 (d, J = 6.4 Hz, 6H),7.58 (dt, J = 28.9, 7.4 Hz, 3H). 13C NMR (101 MHz, DMSO-d 6) δ 163.83, 146.23,139.28, 133.58, 133.22, 132.46, 129.00, 128.20, 128.10, 119.13, 112.36.
4-氟苯甲醛苯甲酰腙（A6）：白色粉末；产率78.6%；mp 186.8-187.4 ℃; 1H NMR(400 MHz, DMSO-d 6) δ 11.90 (s, 1H), 8.48 (s, 1H), 7.97 – 7.90 (m, 2H), 7.81(dd, J = 8.6, 5.8 Hz, 2H), 7.60 – 7.51 (m, 3H), 7.31 (t, J = 8.9 Hz, 2H). 13CNMR (101 MHz, DMSO-d 6) δ 164.82, 163.59 (J = 120.2 Hz), 162.36, 147.12,133.87, 132.23, 131.43 (J = 3.03 Hz), 129.73 (J = 86.9 Hz), 128.94, 128.09,116.38 (J = 22.2 Hz).
4-硝基苯甲醛苯甲酰腙（A7）：黄色针状结晶；产率74.2%；mp 247.2-247.7 ℃; 1HNMR (400 MHz, DMSO-d 6) δ 12.17 (s, 1H), 8.56 (s, 1H), 8.30 (d, J = 8.4 Hz,2H), 7.97 (dd, J = 20.0, 8.0 Hz, 4H), 7.64 – 7.53 (m, 3H). 13C NMR (101 MHz,DMSO-d 6) δ 163.89, 148.29, 145.71, 141.11, 133.53, 132.51, 129.01, 128.45,128.21, 124.53.
4-甲氧基苯甲醛苯甲酰腙（A8）：白色颗粒；产率89.6%；mp 158.3-159.0℃; 1HNMR (400 MHz, DMSO-d 6) δ 11.76 (s, 1H), 8.42 (s, 1H), 7.95 – 7.90 (m, 2H),7.72 – 7.67 (m, 2H), 7.60 – 7.50 (m, 3H), 7.03 (d, J = 8.8 Hz, 2H), 3.81 (s,3H). 13C NMR (101 MHz, DMSO-d 6) δ 163.46, 161.32, 148.17, 134.05, 132.10,129.18, 128.92, 128.04, 127.36, 114.81, 55.76.
2-甲基苯甲醛苯甲酰腙（A9）：白色针状结晶；产率76.0%；mp 192.7-193.8℃; 1HNMR (400 MHz, DMSO-d 6) δ 11.86 (s, 1H), 8.78 (s, 1H), 7.98 – 7.93 (m, 2H),7.87 (dd, J = 7.5, 1.7 Hz, 1H), 7.63 – 7.53 (m, 3H), 7.34 – 7.24 (m, 3H),2.46 (s, 3H). 13C NMR (101 MHz, DMSO-d 6) δ 163.46, 146.87, 137.34, 133.91,132.79, 132.23, 131.34, 130.24, 128.96, 128.05, 126.66, 126.28, 19.48.
3-甲基苯甲醛苯甲酰腙（A10）：白色针状结晶；产率94.0%；mp 196.6-197.6℃; 1HNMR (400 MHz, DMSO-d 6) δ 11.87 (s, 1H), 8.45 (s, 1H), 7.97 – 7.91 (m, 2H),7.62 – 7.51 (m, 5H), 7.35 (t, J = 7.6 Hz, 1H), 7.26 (d, J = 7.6 Hz, 1H), 2.36(s, 3H). 13C NMR (101 MHz, DMSO-d 6) δ 163.61, 148.31, 138.55, 134.77, 133.92,132.22, 131.27, 129.21, 128.94, 128.10, 127.82, 125.01, 21.36.
4-甲基苯甲醛苯甲酰腙（A11）：浅黄色固体；产率91.3%；mp 122.5-123.2 ℃; 1HNMR (400 MHz, DMSO-d 6) δ 11.82 (s, 1H), 8.45 (s, 1H), 7.96 – 7.91 (m, 2H),7.65 – 7.52 (m, 5H), 7.28 (d, J = 7.8 Hz, 2H), 2.35 (s, 3H). 13C NMR (101 MHz,DMSO-d 6) δ 163.54, 148.31, 140.38, 133.98, 132.17, 132.11, 129.93, 128.94,128.08, 127.55, 21.50.
肉桂醛苯甲酰腙（A12）：白色絮状结晶；产率72.2%；mp 195.3-195.9℃；1H NMR(400 MHz, DMSO-d 6) δ 11.78 (s, 1H), 8.29 – 8.24 (m, 1H), 7.95 – 7.89 (m, 2H),7.65 – 7.57 (m, 3H), 7.53 (t, J = 7.3 Hz, 2H), 7.40 (t, J = 7.3 Hz, 2H), 7.36– 7.32 (m, 1H), 7.09 (d, J = 7.4 Hz, 2H). 13C NMR (101 MHz, DMSO-d 6) δ 163.51,150.25, 139.52, 136.38, 133.88, 132.21, 129.30, 128.94, 128.10, 127.57,126.15.
2-喹啉甲醛苯甲酰腙（A13）：白色固体；产率81.9%；mp 199.1-199.6℃； 1H NMR(400 MHz, DMSO-d 6) δ 12.24 (s, 1H), 8.64 (s, 1H), 8.43 (d, J = 8.6 Hz, 1H),8.15 (d, J = 8.6 Hz, 1H), 8.08 – 7.95 (m, 4H), 7.80 (ddd, J = 8.4, 6.8, 1.5Hz, 1H), 7.61 (dt, J = 26.9, 7.4 Hz, 4H). 13C NMR (101 MHz, DMSO-d 6) δ 164.03,154.29, 148.44, 147.84, 137.23, 133.67, 132.53, 130.57, 129.39, 129.07,128.50, 128.39, 128.27, 127.81, 117.99.
2-吡咯甲醛苯甲酰腙（A14）：淡黄色颗粒；产率50.1%；mp 194.8-195.7 ℃； 1HNMR (400 MHz, DMSO-d 6) δ 11.53 (s, 2H), 8.30 (s, 1H), 7.93 – 7.87 (m, 2H),7.60 – 7.48 (m, 3H), 6.92 (d, J = 2.1 Hz, 1H), 6.49 (t, J = 2.1 Hz, 1H), 6.15(q, J = 2.6 Hz, 1H); 13C NMR (101 MHz, DMSO-d 6) δ 163.12, 141.36, 134.26,131.91, 128.87, 127.97, 127.52, 122.99, 113.80, 109.72.
2-吡啶甲醛苯甲酰腙（A15）：白色颗粒；产率79.7%；mp 79.7-81.4℃；1H NMR (400MHz, DMSO-d 6) δ 12.07 (s, 1H), 8.70 – 8.43 (m, 2H), 7.94 (tt, J = 15.7, 8.0Hz, 4H), 7.64 – 7.52 (m, 3H), 7.46 – 7.39 (m, 1H); 13C NMR (101 MHz, DMSO-d 6)δ 163.85, 153.75, 150.00, 148.50, 137.35, 133.66, 132.44, 129.02, 128.19,124.88, 120.38.
3-吡啶甲醛苯甲酰腙（A16）：白色颗粒；产率88.4%；mp 189.4-190.7℃；1H NMR(400 MHz, DMSO-d 6) δ 12.05 (s, 1H), 8.88 (d, J = 2.2 Hz, 1H), 8.63 (dd, J =4.8, 1.7 Hz, 1H), 8.53 (s, 1H), 8.20 – 8.12 (m, 1H), 7.99 – 7.92 (m, 2H),7.56 (td, J = 18.7, 17.5, 8.6 Hz, 4H). 13C NMR (101 MHz, DMSO-d 6) δ 163.73,151.19, 149.23, 145.51, 133.92, 133.70, 132.36, 130.72, 128.98, 128.15,124.48.
4-吡啶甲醛苯甲酰腙（A17）：白色固体；产率92.9%；mp 206.7-207.5 ℃; 1H NMR(400 MHz, DMSO-d 6) δ 12.16 (s, 1H), 8.67 (d, J = 5.2 Hz, 2H), 8.47 (s, 1H),7.95 (d, J = 7.6 Hz, 2H), 7.71 – 7.52 (m, 5H). 13C NMR (101 MHz, DMSO-d 6) δ163.90, 150.76, 145.79, 141.96, 133.54, 132.51, 129.02, 128.22, 121.47.
二、苯甲酰腙类化合物的抗菌活性
1、供试菌：
棉花枯萎病原菌（MK）；西瓜枯萎病原菌（XK）；马铃薯干腐病原菌（MG）；小麦赤霉病原菌（XC）；番茄早疫病原菌（FZ）；白菜黑斑病原菌（BH）；烟草赤星病原菌（YC）；玉米弯孢病原菌（YW）；苹果炭疽病原菌（PT）；南瓜枯萎病原菌（NK）；苹果腐烂病原菌（PF）；水稻稻瘟病原菌（SD）；苹果轮纹病原菌（PL）。
2、样品配制：
准确称取供试化合物27mg于小玻璃瓶中，加入 1mL DMSO，超声溶解，加入9 mL的无菌水，配成药液。以含10%的DMSO水溶液（v/v）作为空白对照，以含醚菌酯（纯度≥99%）的药液作为阳性对照。
3、PDA培养基的制备：
将去皮土豆200.0 g切碎，加入1000 mL水，煮沸30 min，纱布过滤，滤液用水定容到1000 mL，加入20.0 g葡萄糖，15.0 g琼脂粉，加热使其全部溶解后，分装在三角瓶内。
4、抗菌活性的测定：
抗菌活性采用菌丝线性生长速率法进行测定。按药液:培养基=1:26（v/v）的比例，取事先配制好的供试品药液10 mL，加入到260 mL热熔的PDA培养基。充分摇匀后，分倒于各培养皿中，每皿20mL。培养基中的药物浓度为100μg/mL。当培养基凝固后，用直径为0.5 cm的打孔器从供试菌菌落边缘菌丝生长旺盛的地方制取菌饼，用接种针小心地将菌饼置于含药培养基上面。菌饼的菌丝面朝下，放于培养皿的中央，然后加盖并标记后，置于25 ℃恒温恒湿培养箱中培养。每个试验设每次设三个平行，并重复三次。培养72 h后，采取十字交叉法测量菌落直径，取其平均值，按下面公式计算各供试化合物的抑菌率。
菌落扩展直径/cm = 菌落直径平均值 ‒ 0.5（菌饼直径）
测定结果以平均抑制率来表示。
表1. 苯甲酰腙类化合物对植物病原菌的抑制活性（50 μg/mL）
5、安全性评价：
以小麦为试验植物，采用幼苗浸渍法测定高活性化合物A11在不同浓度下（400、200、100、50 μg/mL）对幼苗生长的影响，通过比较处理组和对照组幼苗发生萎蔫的时间与萎蔫的程度来测定供试化合物从根部吸收后对幼苗叶片生长的影响，结果如图1所示。
注：每组中，从左到右测试浓度依次为0、50、100、200、400 μg/mL
从图1可以明显看出，小麦幼苗通过根部吸收不同浓度的化合物A11后，与对照组相比，幼苗叶片没有发生萎蔫，且幼苗生长情况与对照组也没有明显差异。除此之外，随着时间的延长，各处理组的幼苗生长均没有受到明显影响，说明化合物A11在400 μg/mL时经过根部吸收后对小麦幼苗叶片生长没有影响，表现出了较高的安全性。
结果表明，在100 μg/mL浓度时，几乎所有的苯甲酰腙类化合物对13种供试植物病原菌都表现出了较高的的抑制率。其中大多数化合物对大多数菌的活性强于阳性药物——醚菌酯。由此可见，本发明涉及的苯甲酰腙类化合物对植物病原菌具有高效广谱的抑制活性，具有制备植物抗菌药物的潜在用途，可作为植物抗菌药物的有效成分或增效成分。
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等，均应包在本发明范围内。

Claims (7)

1.一种苯甲酰腙类化合物，其特征在于：具有如下分子结构，其中：B环是苯、呋喃、噻吩、吡咯、噻唑、咪唑、吡啶、吡嗪、嘧啶、哒嗪、吲哚、喹啉、蝶啶、吖啶中的一种；R1、R2是相同或不同的氢、烷基、烷氧基、苯氧基、卤素原子或硝基。
2.如权利要求1所述的一种苯甲酰腙类化合物的合成方法，其特征在于：具有以下合成路线：其中：B环可以是苯、呋喃、噻吩、吡咯、噻唑、咪唑、吡啶、吡嗪、嘧啶、哒嗪、吲哚、喹啉、蝶啶、吖啶中的一种；R1、R2是相同或不同的氢、烷基、烷氧基、苯氧基、卤素原子或硝基。
3.如权利要求1所述的一种苯甲酰腙类化合物的应用，其特征在于：该类化合物作为有效成分或增效成分在制备植物抗菌药物中的应用。
4.根据权利要求3所述的一种苯甲酰腙类化合物的应用，其特征在于：该类化合物对以下植物病原菌均具有显著的抑制活性：棉花枯萎病原菌；西瓜枯萎病原菌；马铃薯干腐病原菌；小麦赤霉病原菌；番茄早疫病原菌；白菜黑斑病原菌；烟草赤星病原菌；玉米弯孢病原菌；苹果炭疽病原菌；南瓜枯萎病原菌；苹果腐烂病原菌；水稻稻瘟病原菌；苹果轮纹病原菌。
5.含有如权利要求1所述的一种苯甲酰腙类化合物的药物，其特征在于：该药物以权利要求1所述的苯甲酰腙类化合物为有效成分或增效成分。
6.权利要求5所述的一种苯甲酰腙类化合物的药物的应用，其特征在于：该药物作为植物抗菌药物的应用。
7.根据权利要求6所述的一种含有苯甲酰腙类化合物的药物的应用，其特征在于：该药物对以下病原菌引起的植物病具有预防和治疗效果：棉花枯萎病原菌；西瓜枯萎病原菌；马铃薯干腐病原菌；小麦赤霉病原菌；番茄早疫病原菌；白菜黑斑病原菌；烟草赤星病原菌；玉米弯孢病原菌；苹果炭疽病原菌；南瓜枯萎病原菌；苹果腐烂病原菌；水稻稻瘟病原菌；苹果轮纹病原菌。
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