CN112209948A - 一种马兜铃酸衍生物及应用 - Google Patents
一种马兜铃酸衍生物及应用 Download PDFInfo
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- CN112209948A CN112209948A CN202010995316.4A CN202010995316A CN112209948A CN 112209948 A CN112209948 A CN 112209948A CN 202010995316 A CN202010995316 A CN 202010995316A CN 112209948 A CN112209948 A CN 112209948A
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Abstract
本发明公开了一种马兜铃酸衍生物及应用,其具体结构如式(Ⅰ)所示;
Description
技术领域
本发明属杀菌剂领域,具体涉及一种马兜铃酸衍生物及应用。
背景技术
植物细菌病害是一类重要的植物病害,每年给农业生产造成巨大的损失。为防治植物病害的发生,减少由其造成的损失,大量的抑菌及杀菌活性化合物被报道并应用。由于抗药性等方面的因素,新杀菌剂的研发一直是各农药企业和科研人员关注的热点。
近年来,由于抗生素的滥用和细菌的耐药性发展,临床上细菌感染耐药问题愈发严重,耐药性感染性疾病已成为我国临床感染性疾病死亡的主要因素。研制有效的耐药性菌株抑制剂具有广泛的应用价值。天然药物以其作用靶点广、低毒的优势,逐渐成为抗菌药物研究的焦点。目前,医药和农药应用的许多药物都直接或间接来源于天然产物,天然产物不仅可以作为药物半合成的先导化合物,而且可以作为药物合成的模板,为新药设计提供新颖的思路。天然药物的生物活性成分逐渐显示出了独特的优势和广阔的应用前景。
细辛〔学名:Asarum heterotropoides Fr.Schmidt var.mandshuricum(Maxim.)Kitag.〕马兜铃科细辛属(Asarum)的一个多年生草本植物。细辛是一味历史悠久的中药,古时便被《神农本草经》列为上等品,并被多版中国药典和历代本草书籍录入。细辛根细,味辛,性温,具有温肺化饮、祛风散寒、通窍止痛的作用。细辛提取物具有丰富的生物活性,包括抗肿瘤、抗炎、杀虫、抑菌等,其挥发油成分所占比例非常高、其次为木脂素类和黄酮类化合物等。
发明内容
本发明的目的在于提供一种马兜铃酸衍生物(aristoloxazine C)及应用,能够用于制备杀菌剂和/或保鲜剂的应用。
本发明的技术方案如下:
一种马兜铃酸衍生物,所述衍生物的化学结构式如式(Ⅰ)所示:
本发明所述的马兜铃酸衍生物用于制备杀菌剂的应用。
可选的,所述的杀菌剂不限于人、动物和植物能够使用的杀菌领域。
可选的,所述的人和动物的杀菌领域包括:金黄色葡萄球菌、蜡样芽孢杆菌、枯草芽孢杆菌、肺炎双球菌、炭疽杆菌、白喉杆菌、破伤风杆菌中的一种或任意组合的细菌感染;
所述的植物杀菌领域包括:
粮食作物细菌病害:水稻细菌性条斑病、水稻白叶枯病、水稻基腐病、水稻细菌性褐条病、水稻细菌性褐斑病、马铃薯青枯病、马铃薯软腐病、马铃薯黑胫病、马铃薯环腐病、甘薯瘟病、玉米茎腐病、小麦黑颖病和木薯细菌性枯萎病;
果树细菌病害:脐橙溃疡病、柑橘溃疡病、橙溃疡病、柚溃疡病、文旦溃疡病、柠檬溃疡病、巨橘溃疡病、枳壳溃疡病、枳橙溃疡病、沙田柚溃疡病、梨根癌病、苹果根癌病、板栗根癌病、梅根癌病、李根癌病、杏根癌病、葡萄根癌病、梨火疫病、桃细菌性穿孔病、李细菌性穿孔病、油桃细菌性穿孔病、樱桃细菌性穿孔病、菠萝心腐病、枇杷芽枯病、枇杷癌肿病、核桃黑斑病、猕猴桃溃疡病和芒果细菌性黑斑病;
瓜菜类细菌病害:西瓜细菌性青枯病、西瓜细菌性果腐病、番茄青枯病、茄子青枯病、辣椒青枯病、番茄软腐病、茄子软腐病、辣椒软腐病、番茄疮痂病、茄子疮痂病、辣椒疮痂病、黄瓜角斑病、甜瓜角斑病、丝瓜角斑病、大白菜软腐病、白菜黑腐病、白菜黑斑病、甘蓝软腐病、甘蓝黑腐病、甘蓝黑斑病、萝卜软腐病、萝卜黑斑病、萝卜黑腐病、花椰菜软腐病、花椰菜黑腐病、花椰菜黑斑病、菜豆细菌性角斑病、扁豆细菌性角斑病、豇豆细菌性角斑病、豌豆细菌性角斑病、绿豆细菌性角斑病、菜豆细菌性疫病、扁豆细菌性疫病、豇豆细菌性疫病、豌豆细菌性疫病、绿豆细菌性疫病、姜瘟病、姜腐败病、姜腐烂病、瓜类青枯病、辣椒细菌性斑点病、辣椒细菌性叶斑病、葱类细菌性软腐病、莴苣细菌性斑点病、芋艿细菌性斑点病、芋艿腐败病、芋软腐病、芹菜软腐病和魔芋软腐病;
经济作物类细菌病害:棉花角斑病、棉红叶根腐病、花生青枯病、油菜黑腐病、油菜软腐病、油菜细菌性黑斑病、大豆细菌性叶烧病、大豆细菌性斑点病、大豆细菌性斑疹病、甜菜软腐病、甜菜细菌性根癌病、甜菜细菌性尾腐病、甜菜细菌性斑枯病、芝麻细菌性角斑病、芝麻青枯病、烟草青枯病、烟草角斑病、烟草野火病、烟草空茎病、向日葵细菌性茎基腐、甘蔗白条病、咖啡细菌性叶斑病和胡椒细菌性叶斑病;
其它作物细菌性病害:桑青枯病、桑细菌性黑枯病、桑疫病、茶树细菌性根癌病、黄麻细菌性斑点病、萱麻青枯病、红麻青枯病、苜蓿细菌性叶斑病、苜蓿细菌性茎疫病、紫云英细菌性黑斑病、药材类细菌性病害和花卉类细菌性病害。
本发明所述的马兜铃酸衍生物用于制备保鲜剂的应用。
可选的,所述的保鲜剂不限于水果保鲜剂及肉类保鲜剂。
一种组合物,所述的组合物包含本发明所述的马兜铃酸衍生物与至少一种杀菌剂、杀虫剂、杀螨剂、杀藻剂、拒食剂、杀鸟剂、驱鸟剂、杀真菌剂、化学绝育剂、除草剂、灭草剂、昆虫引诱剂、驱昆虫剂、交配干扰剂、软体动物杀灭剂、植物激活剂、植物生长调节剂、灭鼠剂、增效剂、落叶剂、干燥剂、消毒剂、化学信息素和杀病毒剂的组合。
一种组合物,其包含本发明所述的马兜铃酸衍生物与至少一种选自如下的成员:氟吗啉、烯酰吗啉、叶枯酞、磺菌胺、甲磺菌胺、噻氟菌胺、环氟菌胺、硅噻菌胺、吡噻菌胺、环酰菌胺、苯酰菌胺、环丙酰菌胺、噻酰菌胺、氰菌胺、双氯氰菌胺、高效甲霜灵、高效苯霜灵、萎锈灵、呋吡酰胺、甲呋酰胺、氟酰胺、嘧菌酯、肟菌酯、啶氧菌酯、唑菌胺酯、氟嘧菌酯、烯肟菌酯、苯氧菌胺、烯肟菌胺、嘧菌胺、肟嘧菌胺、噻菌灵、氟菌唑、高效抑霉唑、咪唑菌酮、氰霜唑、抑霉唑、咪鲜胺、恶咪唑、麦穗宁、稻瘟酯、氧环唑、氟环唑、氟喹唑、苯醚甲环唑、四氟醚唑、戊唑醇、氟硅唑、硅氟唑、三唑醇、联苯三唑醇、环丙唑醇、高效烯唑醇、烯唑醇、粉唑醇、己唑醇、丙硫菌唑、灭菌唑、戊菌唑、腈菌唑、腈苯唑、亚胺唑、糖菌唑、种菌唑、叶菌唑;噻唑类:噻唑菌胺、苯噻硫氰、辛噻酮、土菌灵、十二环吗啉、丁苯吗啉、十三吗啉;吡咯类:拌种咯、咯菌腈、氟啶胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、环啶菌胺、啶斑肟、嘧啶环胺、氯苯嘧啶醇、氟苯嘧啶醇、嘧霉胺、嘧菌腙、嘧菌胺、氟嘧菌胺、灭螨猛、二氰蒽醌、乙氧喹啉、8-羟基喹啉、丙氧喹啉、苯氧喹啉、异丙菌胺、乙霉威、苯噻菌胺、霜霉威、硫菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯灵、梧宁霉素、灭瘟素、春雷霉素、多抗霉素、多氧霉素、活化酯、吲哚酯、溴硝醇、苯磺菌胺、甲苯磺菌胺、螺环菌胺、嗪胺灵、敌磺钠、戊菌隆、四氯苯酞、三环唑、烯丙苯噻唑、苯锈啶、氯硝胺、双胍辛胺、多果定、霜脲氰、咯喹酮、苯菌酮、喹菌酮、哒菌酮、链霉素、甲霜灵、丙森锌、苯霜灵、叶枯唑、有效霉素、井冈霉素、五氯硝基苯、代森锰锌、三乙膦酸铝、乙嘧酚磺酸酯、乙嘧酚、二甲嘧酚、三唑酮、甲基硫菌灵、多菌灵、苯菌灵、克菌丹、敌菌丹、灭锈胺、灭菌丹、呋酰胺、氟氯菌核利、乙烯菌核利、菌核净、福美双、稻瘟灵、稻瘟净、百菌清、硫磺、波尔多液、氢氧化铜、氧化亚铜、氧氯化铜、硫酸铜、苦参碱、蛇床子素、虎杖提取物、樟脑、腐殖酸铜、松脂酸铜(钠)、混合氨基酸铜、琥胶肥酸铜、柠檬酸铜、络氨铜、中生菌素、松脂酸铜、噻枯唑、丁子香酚、香芹酚、小檗碱、乙蒜素、几丁聚糖、低聚糖素、葡聚烯糖和大蒜素。
一种控制细菌的方法,通过将细菌暴露于本发明所述的的马兜铃酸衍生物或含马兜铃酸衍生物的组合物来抑制细菌的生长。
可选的,不限于使动物口服或对动物施用权利要求1所述马兜铃酸衍生物制剂以控制体内细菌和/或皮外细菌;
不限于给植物施用本发明所述的马兜铃酸衍生物制剂;
不限于对果、蔬、鱼、肉施用本发明所述的马兜铃酸衍生物制剂。
本发明提供的马兜铃酸衍生物,分离自细辛植物根部,通过结构鉴定为一种新的化合物,且通过实验证明,该化合物在杀菌领域,比如常见的金黄色葡萄球菌,特别是农业致病菌中的细菌病害具有良好的活性,同时还通过实验证明该化合物在水果保鲜、肉类保鲜中也具有良好的应用前景。
附图说明
附图是用来提供对本公开的进一步理解,并且构成说明书的一部分,与下面的具体实施方式一起用于解释本公开,但并不构成对本公开的限制。在附图中:
图1为aristoloxazine C的1H NMR谱图;
图2为aristoloxazine C的13C NMR谱图;
图3为aristoloxazine C的HSQC NMR谱图;
图4为aristoloxazine C的HMBC NMR谱图;
图5为aristoloxazine C的1H-1H COSY NMR谱图;
图6为aristoloxazine C的液质谱图;
图7为aristoloxazine C的红外谱图;
图8为aristoloxazine C的CD谱图。
具体实施方式
以下结合具体实验及附图对本发明的技术方案进行详细的描述,但本发明不受下列实施例的限制。如无特殊说明,以下实验中使用的试剂均为常见的常规产品,以下实验中使用的方法均为本领域的常用方法。
细辛〔学名:Asarum heterotropoides Fr.Schmidt var.mandshuricum(Maxim.)Kitag.〕马兜铃科细辛属(Asarum)的一个多年生草本植物。细辛是一味历史悠久的中药,古时便被《神农本草经》列为上等品,并被多版中国药典和历代本草书籍录入。细辛根细,味辛,性温,具有温肺化饮、祛风散寒、通窍止痛的作用。细辛提取物具有丰富的生物活性,包括抗肿瘤、抗炎、杀虫、抑菌等,其挥发油成分所占比例非常高、其次为木脂素类和黄酮类化合物等,本研究在系统研究细辛杀菌活性成分的基础上,对分离得到的化合物进行了系统的杀菌活性测定,从中发现一种新化合物aristoloxazine C,并发现其对多种细菌具有广谱高效的抑制生长作用。
本发明的马兜铃酸衍生物的结构式如(I)所示;
本发明的结构式如(I)所示的马兜铃酸衍生物,以下称为aristoloxazine C,从细辛根中分离得到,具体的分离方法如下:
细辛根10kg粉碎后10倍量(v/v)乙醇热回流提取3次,提取温度75℃,每次3小时。过滤并合并滤液,滤液减压浓缩得提取物浸膏1.1kg。将乙醇粗提物加水揉捏分散,依次用10倍量(m/v)的石油醚、乙酸乙酯和氯仿萃取三次,浓缩得到石油醚段提取物101g,乙酸乙酯段提取物35g,氯仿段提取物119g,氯仿段提取物浸膏硅胶以80~100目硅胶拌样,200~300目硅胶(10×150cm)划段分离,流动相选择石油醚/丙酮系统(石油醚:丙酮=99:1,98:2,97:3,95:5,90:10,80:20,50:50,0:100,v/v)梯度洗脱,按薄层显色分为7个馏分段,分别为:F1-F7(小极性到大极性)。其中F6段(64.0g)以80~100目硅胶拌样,200~300目硅胶(10×100cm)划段分离,流动相选择氯仿/甲醇系统(氯仿:甲醇=100:0,98:2,97:3,95:5,90:10,80:20,70:30,60:40,40:60,0:100,v/v)梯度洗脱,按薄层显色分为8个馏分段,分别为F6-1–F6-8(小极性到大极性)。其中F6-2(22.7g)以甲醇/水系统反相硅胶柱层析,依次用20%、40%、60%、80%和100%(体积浓度)的甲醇洗脱剂洗脱,得到5个段提取物(Fr.6-2-1–Fr.6-2-5)(流动相的流动方向)。Fr.6-2-3用制备性高效液相色谱,以55%(体积浓度)的甲醇为流动相,柱温25℃,保留时间为24.7分钟,得化合物aristoloxazine C(55.7mg)。
化合物结构鉴定采用核磁共振方法。各化合物结构解析如下:
Aristoloxazine C:黄色结晶,用洗脱液重结晶为黄色粉末,其分子式经高分辨电喷雾电离质谱光谱中421.0463[m+Na]+m/z处的正离子峰(图6)鉴定为C19H14N2O6SNa,表明其不饱和度为13度。红外光谱中3438、1672、1725和1591cm-1处的吸收(图7)表明化合物中存在氨基、两个羰基和苯基团。在275nm处的紫外吸收显示苯环的存在。化合物的1H和13C NMR、DEPT和HMQC数据(图1-5)支持五取代苯环的存在,因为在δH 7.64处H-3有一个单重信号,在δH7.88(d,J=8.0Hz,H-11)、7.52(dd,J=8.2,8.0Hz,H-10)和7.21处有一个1,2,3-三取代苯环(d,J=8.3Hz,H-9),一个修饰的半胱氨酸残基[δC 34.9(t,C-2′)、δH 3.34(d,J=15.2Hz)和3.21(d,J=15.2Hz);δC 170.0(s,C-1′);和δH 7.29(brs,NHa-1′)和7.14(brs,NHb-1′)],并从δC 152.1(C-6a)处的信号推导出有一个亚胺部分,该部分通过氧原子连接到羰基,以形成亚胺1,2-恶嗪环(D环)。最后,菲核的C环上有一个sp3c-7与硫原子相连,这与它在δC 38.7处的化学位移一致(表1)。
Aristoloxazine A是Rios et al.(2017)从马兜铃属植物中分离出的一种马兜铃酸衍生物,将aristoloxazine C的1H和13C核磁共振数据与aristoloxazine A的1H和13C核磁共振数据进行对比,它们具有相同的骨架(具体见aristoloxazine C和aristoloxazine A的化学式)。其主要区别在于,aristoloxazineA中C-1和C-2的甲氧基的信号被aristoloxazine C的HMBC光谱中H-二氧基亚甲基到C-1和C-2的的交叉峰亚甲基二氧基(δH6.46,6.55)所取代(图4-1)。aristoloxazine C的CD谱(图8)显示在284nm处呈正Cotton效应(Rios et al.,2017),化合物5的C-7位置呈S形。因此aristoloxazine C被表征为(S)-2-(1,2-[亚甲基双(氧基)]-8-三甲氧基-4-氧代-7H-菲罗[10,1-cd][1,2]恶嗪-7-基)-硫代乙酰胺,并命名为aristoloxazine C。
结合以上分析,最终确定aristoloxazine C的结构如下所示:
表1.Aristoloxazine C a的1H NMR光谱数据(500MHz for 1H,括号中的J值单位为Hz)和13C NMR数据(125MHz)
注:a CD3OD在3.31ppm和49.15ppm下的溶剂残留和溶剂信号分别被参考。
研究表明,aristoloxazine C对农业或其他领域的多种细菌显示出优异的活性。因此,本发明的技术方案为aristoloxazine C在农业领域或其他领域中用作制备杀菌剂的用途。
Aristoloxazine C可用于防治下列病害(包括但并非限于此):粮食作物细菌病害,如水稻细菌性条斑病、水稻白叶枯病、水稻基腐病、水稻细菌性褐条病、水稻细菌性褐斑病、马铃薯青枯病、马铃薯软腐病、马铃薯黑胫病、马铃薯环腐病、甘薯瘟病、玉米茎腐病、小麦黑颖病、木薯细菌性枯萎病;果树细菌病害,脐橙溃疡病、柑橘溃疡病、橙溃疡病、柚溃疡病、文旦溃疡病、柠檬溃疡病、巨橘溃疡病、枳壳溃疡病、枳橙溃疡病、沙田柚溃疡病、梨根癌病、苹果根癌病、板栗根癌病、梅根癌病、李根癌病、杏根癌病、葡萄根癌病、梨火疫病、桃细菌性穿孔病、李细菌性穿孔病、油桃细菌性穿孔病、樱桃细菌性穿孔病、菠萝心腐病、枇杷芽枯病、枇杷癌肿病、核桃黑斑病、猕猴桃溃疡病、芒果细菌性黑斑病;瓜菜类细菌病害:西瓜细菌性青枯病、西瓜细菌性果腐病、番茄青枯病、茄子青枯病、辣椒青枯病、番茄软腐病、茄子软腐病、辣椒软腐病、番茄疮痂病、茄子疮痂病、辣椒疮痂病、黄瓜角斑病、甜瓜角斑病、丝瓜角斑病、大白菜软腐病、白菜黑腐病、白菜黑斑病、甘蓝软腐病、甘蓝黑腐病、甘蓝黑斑病、萝卜软腐病、萝卜黑斑病、萝卜黑腐病、花椰菜软腐病、花椰菜黑腐病、花椰菜黑斑病、菜豆细菌性角斑病、扁豆细菌性角斑病、豇豆细菌性角斑病、豌豆细菌性角斑病、绿豆细菌性角斑病、菜豆细菌性疫病、扁豆细菌性疫病、豇豆细菌性疫病、豌豆细菌性疫病、绿豆细菌性疫病、姜瘟病、姜腐败病、姜腐烂病、瓜类青枯病、辣椒细菌性斑点病、辣椒细菌性叶斑病、葱类细菌性软腐病、莴苣细菌性斑点病、芋艿细菌性斑点病、芋艿腐败病、芋软腐病、芹菜软腐病、魔芋软腐病;经济作物类细菌病害,棉花角斑病、棉红叶根腐病、花生青枯病、油菜黑腐病、油菜软腐病、油菜细菌性黑斑病、大豆细菌性叶烧病、大豆细菌性斑点病、大豆细菌性斑疹病、甜菜软腐病、甜菜细菌性根癌病、甜菜细菌性尾腐病、甜菜细菌性斑枯病、芝麻细菌性角斑病、芝麻青枯病、烟草青枯病、烟草角斑病、烟草野火病、烟草空茎病、向日葵细菌性茎基腐、甘蔗白条病、咖啡细菌性叶斑病、胡椒细菌性叶斑病;其它作物细菌性病害,桑青枯病、桑细菌性黑枯病、桑疫病、茶树细菌性根癌病、黄麻细菌性斑点病、萱麻青枯病、红麻青枯病、苜蓿细菌性叶斑病、苜蓿细菌性茎疫病、紫云英细菌性黑斑病、药材类细菌性病害、花卉类细菌性病害等。特别对烟草青枯病、水稻白叶枯病、猕猴桃溃疡病在较低计量下仍有很好的防治效果。
由于其积极的特性,aristoloxazine C可以利用与保护农业及园艺业重要的作物、家畜和种畜,以及人类常去的环境免于病菌的伤害。可以用于生鲜肉、水果、蔬菜的保鲜。
为获得理想的效果,化合物的用量因各种因素而改变,例如所用化合物、预保护的作物、有害生物的类型、感染程度、气候条件、施药方法、采用的剂型。
由于经济与协同作用两个方面,aristoloxazine C也可以与各种杀菌剂一同使用。此类杀菌剂包括但不限于以下;酰胺类:氟吗啉、烯酰吗啉、叶枯酞、磺菌胺、甲磺菌胺、噻氟菌胺、环氟菌胺、硅噻菌胺、吡噻菌胺、环酰菌胺、苯酰菌胺、环丙酰菌胺、噻酰菌胺、氰菌胺、双氯氰菌胺、高效甲霜灵、高效苯霜灵、萎锈灵、呋吡酰胺、甲呋酰胺、氟酰胺;甲丙烯和咪唑类:嘧菌酯、肟菌酯、啶氧菌酯、唑菌胺酯、氟嘧菌酯、烯肟菌酯、苯氧菌胺、烯肟菌胺、嘧菌胺、肟嘧菌胺、噻菌灵、氟菌唑、高效抑霉唑、咪唑菌酮、氰霜唑、抑霉唑、咪鲜胺、恶咪唑、麦穗宁、稻瘟酯;三唑类:氧环唑、氟环唑、氟喹唑、苯醚甲环唑、四氟醚唑、戊唑醇、氟硅唑、硅氟唑、三唑醇、联苯三唑醇、环丙唑醇、高效烯唑醇、烯唑醇、粉唑醇、己唑醇、丙硫菌唑、灭菌唑、戊菌唑、腈菌唑、腈苯唑、亚胺唑、糖菌唑、种菌唑、叶菌唑;噻唑类:噻唑菌胺、苯噻硫氰、辛噻酮、土菌灵;吗啉类:十二环吗啉、丁苯吗啉、十三吗啉;吡咯类:拌种咯、咯菌腈;吡啶类:氟啶胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、环啶菌胺、啶斑肟;嘧啶类:嘧啶环胺、氯苯嘧啶醇、氟苯嘧啶醇、嘧霉胺、嘧菌腙、嘧菌胺、氟嘧菌胺;喹(唑)啉(酮)类:灭螨猛、二氰蒽醌、乙氧喹啉、8-羟基喹啉、丙氧喹啉、苯氧喹啉;氨基甲酸酯类:异丙菌胺、乙霉威、苯噻菌胺、霜霉威、硫菌威;有机磷类:敌瘟磷、异稻瘟净、吡菌磷、甲基立枯灵;抗生素类:梧宁霉素、灭瘟素、春雷霉素、多抗霉素、多氧霉素;其他类:活化酯、吲哚酯、溴硝醇、苯磺菌胺、甲苯磺菌胺、螺环菌胺、嗪胺灵、敌磺钠、戊菌隆、四氯苯酞、三环唑、烯丙苯噻唑、苯锈啶、氯硝胺、双胍辛胺、多果定、霜脲氰、咯喹酮、苯菌酮、喹菌酮、哒菌酮;常规杀菌剂品种:链霉素、甲霜灵、丙森锌、苯霜灵、叶枯唑、有效霉素、井冈霉素、五氯硝基苯、代森锰锌、三乙膦酸铝、乙嘧酚磺酸酯、乙嘧酚、二甲嘧酚、三唑酮、甲基硫菌灵、多菌灵、苯菌灵、克菌丹、敌菌丹、灭锈胺、灭菌丹、呋酰胺、氟氯菌核利、乙烯菌核利、菌核净、福美双、稻瘟灵、稻瘟净、百菌清、硫磺、波尔多液、氢氧化铜、氧化亚铜、氧氯化铜、硫酸铜;及植物源杀菌剂:苦参碱、蛇床子素、虎杖提取物、苦参碱、蛇床子素、虎杖提取物、樟脑、腐殖酸铜、松脂酸铜(钠)、混合氨基酸铜、琥胶肥酸铜、柠檬酸铜、丁子香酚、香芹酚、小檗碱、乙蒜素、几丁聚糖、低聚糖素、葡聚烯糖、大蒜素等。
另外,可使用以上杀菌剂的任意组合。
由于经济与协同作用两个方面,aristoloxazine C也可以与杀菌剂和除草剂或上述两种一同使用。
由于经济与协同作用两个方面,aristoloxazine C也可以与杀螨剂、杀藻剂、拒食剂、杀鸟剂、杀真菌剂、除草剂安全剂、灭草剂、昆虫诱引剂、植物生长调节剂、增效剂、落叶剂、干枯剂、消毒剂、化学信息素和杀病毒剂一同使用(这些类型不互相排斥)。
由于经济与协同作用两个方面,aristoloxazine C可以制备成药肥来施用。
纯净形式的杀菌剂很少适合于应用。通常必需加入其他物质以使杀菌剂可以所需浓度和适宜的形式使用,从而允许施用、处理、运输、储藏的简便和最大杀菌活性。
本发明的组合物可以制剂的形式施用。aristoloxazine C作为活性组分溶解或分散于载体中或配制成制剂以便作为杀菌使用时更易分散。例如:这些化合物可以被制成浓缩乳状液、粉剂、乳油、水乳剂、糊剂、崩解剂、熏剂、诱饵、凝胶、颗粒、微胶囊、拌种剂、悬浮体浓缩液、悬乳剂、片剂、水溶性液体、水分散粒、或干悬浮剂、可湿性粉剂和超低体积溶液。在这些组合物中,至少加入一种液体或固体载体,并且当需要时可以加入适当的表面活性剂。
应明确的是,在本发明的权利要求所限定的范围内,可进行各种变换和改动。
实施例1:aristoloxazine C离体抑菌活性测定
抑菌试验样品的准备:称取一定量的化合物,用5%(体积分数)甲醇将化合物配制成质量浓度为100ppm的供试药液做抑菌试验用。
菌的活化培养:供试细菌从4℃冰箱取出,接种于LB液体培养基离心管中,37℃活化培养12小时。
菌悬液的制备:取已活化的供试细菌少量加入到适量液体LB培养基中,37℃培养8~12小时,取2ml菌悬液于比色皿测试其吸光度,稀释菌液到0.5麦氏浊度(600nm波长条件下吸光度为0.08~0.13),再将其以液体培养基稀释200倍,混匀。此时菌液浓度约1×106cfu/ml。
采用计数法测定化合物aristoloxazine C抑菌活性,共选取37个病原菌种,菌液浓度稀释至1×106cfu/ml,吸取100μl按顺序加入至无菌的96孔板,将配制好的药液每个吸取100μl分别加入含等量菌液的96孔板中,同时设置加100μl溶剂和100μl药液的阳性对照,和100μl溶剂和100μl菌液的阴性对照,每个处理重复三个孔。将96孔板置于恒温培养箱中37℃条件下培养16-24小时,每孔加入10μl的INT溶液,染色30min后观察颜色变化:活细胞经INT染色后为紫色,无活细胞则不变色。供试菌种及100μg/ml浓度下化合物的抑制活性列于表2。结果表明,在100μg/ml浓度下,aristoloxazine C对多种病原细菌具有显著的抑制生长作用,aristoloxazine C的抑菌范围广谱。
表2 100μg/ml浓度下aristoloxazine C对37种病原菌抑菌活性
注:“-”表示无活细胞,下表同。
实施例2:Aristoloxazine C盆栽生物活性测定
对烟草青枯病的防治采用盆栽实验法进行,对猕猴桃溃病的防治采用活体组织法进行。
病原菌的接种:将活化后的烟草青枯病原菌设置108cfu/ml个悬液浓度,处理为108cfu/ml菌悬液浇灌的烟草;试验化合物aristoloxazine C 500mg/L处理,以灌根(每盆10mL)进行施药;同时设等量LB培养基对照,处理后的烟草置于温室中培养。
将新鲜采摘的猕猴桃枝条截成约15cm的小枝条,两端用蜡油封口,用75%乙醇进行表面消毒,晾干后用消过毒的高温镊子在枝条中部造成条状伤口,喷施活化后的108cfu/ml个悬液浓度的猕猴挑溃疡病原菌,试验化合物aristoloxazine C 500mg/L喷施接菌伤口;同时设等量LB培养基对照;处理后的猕猴桃枝条置于温室中培养。
保护作用试验,先对烟草苗和猕猴桃枝条进行喷药或灌根处理,24h后接种。治疗作用试验,先接种病菌于活体组织上,24h后再喷药或灌根处理。每个处理设6次重复,培养7d检查试验结果,并按如下公式计算防治效果,测定结果如表4。结果表明,室内条件下,aristoloxazine C对烟草青枯病和猕猴桃溃疡病具有显著的防效。
表3烟草青枯病病害分级
病情指数和防治效果计算公式为:
猕猴桃活体组织测定防治效果计算公式为:
表4 Aristoloxazine C对烟草青枯病、猕猴桃溃疡病的活体药效试验结果(防效)
实施例3:Aristoloxazine C与其他杀菌剂复配离体生物活性测定
该实施例采用计数法测定,方法同实施例1中所描述。试样中1为AristoloxazineC,浓度列为aristoloxazine C的浓度+复配药剂浓度。抑菌测定结果如表5。结果表明,aristoloxazine C与多种药剂复配对几种病原菌均具有显著的抑制效果。
表5 Aristoloxazine C与代表性杀菌剂对7种病原菌抑菌效果
实施例4:aristoloxazine C对猪肉保鲜效果评价
活猪宰杀后的胴体立即于-23℃以下急冻降温1.5~2h,再转入0~4℃的冷却间保持6~8h,待肉的中心温度降到10℃以下时,转入10~15℃分割间进行剔骨分割,取后腿肌肉(股二头肌)切割成150g左右的小块,每组30块,每组肉块在其对应的不同浓度的(I)中化合物1-11的(500、250、125ug/ml)无菌水溶液和无菌水中浸渍3~5s后,取出摆于干净的盘筛中,沥水3~5min,然后装入聚乙烯薄膜袋内,真空包装,贴上分组的标签,在0~4℃预冷间中冷藏保存。
表6 Aristoloxazine C对冷鲜肉的保鲜效果评价
研究结果见表6,表6中显示:冷却肉采用aristoloxazine C处理6天后,显示一定保鲜效果,肉有微弱异味,色泽评分高于对照组;pH值升高至6.2,低于对照组的6.54;挥发性盐基氮(TVB值)处理组的冷却肉保鲜效果明显优于对照组;细菌总数处理组明显优于对照组。以上说明化合物aristoloxazine C处理降低了鲜肉中的微生物数量,延缓了挥发性盐基氮的含量增加,可以应用于肉类保鲜。
以上结合附图详细描述了本公开的优选实施方式,但是,本公开并不限于上述实施方式中的具体细节,在本公开的技术构思范围内,可以对本公开的技术方案进行多种简单变型,这些简单变型均属于本公开的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合,为了避免不必要的重复,本公开对各种可能的组合方式不再另行说明。
此外,本公开的各种不同的实施方式之间也可以进行任意组合,只要其不违背本公开的思想,其同样应当视为本公开所公开的内容。
参考文献:
Rios,M.Y.,Navarro,V.,Ramírez-Cisneros,M.A.n.,Salazar-Rios,E.,2017.Sulfur-Containing Aristoloxazines and Other Constituents of the Roots ofAristolochia orbicularis.Journal of natural products.80,3112-3119.
Claims (10)
2.权利要求1所述的马兜铃酸衍生物用于制备杀菌剂的应用。
3.根据权利要求2所述的应用,其特征在于,所述的杀菌剂不限于人、动物和植物能够使用的杀菌领域。
4.根据权利要求3所述的应用,其特征在于,所述的人和动物的杀菌领域包括:金黄色葡萄球菌、蜡样芽孢杆菌、枯草芽孢杆菌、肺炎双球菌、炭疽杆菌、白喉杆菌、破伤风杆菌中的一种或任意组合的细菌感染;
所述的植物杀菌领域包括:
粮食作物细菌病害:水稻细菌性条斑病、水稻白叶枯病、水稻基腐病、水稻细菌性褐条病、水稻细菌性褐斑病、马铃薯青枯病、马铃薯软腐病、马铃薯黑胫病、马铃薯环腐病、甘薯瘟病、玉米茎腐病、小麦黑颖病和木薯细菌性枯萎病;
果树细菌病害:脐橙溃疡病、柑橘溃疡病、橙溃疡病、柚溃疡病、文旦溃疡病、柠檬溃疡病、巨橘溃疡病、枳壳溃疡病、枳橙溃疡病、沙田柚溃疡病、梨根癌病、苹果根癌病、板栗根癌病、梅根癌病、李根癌病、杏根癌病、葡萄根癌病、梨火疫病、桃细菌性穿孔病、李细菌性穿孔病、油桃细菌性穿孔病、樱桃细菌性穿孔病、菠萝心腐病、枇杷芽枯病、枇杷癌肿病、核桃黑斑病、猕猴桃溃疡病和芒果细菌性黑斑病;
瓜菜类细菌病害:西瓜细菌性青枯病、西瓜细菌性果腐病、番茄青枯病、茄子青枯病、辣椒青枯病、番茄软腐病、茄子软腐病、辣椒软腐病、番茄疮痂病、茄子疮痂病、辣椒疮痂病、黄瓜角斑病、甜瓜角斑病、丝瓜角斑病、大白菜软腐病、白菜黑腐病、白菜黑斑病、甘蓝软腐病、甘蓝黑腐病、甘蓝黑斑病、萝卜软腐病、萝卜黑斑病、萝卜黑腐病、花椰菜软腐病、花椰菜黑腐病、花椰菜黑斑病、菜豆细菌性角斑病、扁豆细菌性角斑病、豇豆细菌性角斑病、豌豆细菌性角斑病、绿豆细菌性角斑病、菜豆细菌性疫病、扁豆细菌性疫病、豇豆细菌性疫病、豌豆细菌性疫病、绿豆细菌性疫病、姜瘟病、姜腐败病、姜腐烂病、瓜类青枯病、辣椒细菌性斑点病、辣椒细菌性叶斑病、葱类细菌性软腐病、莴苣细菌性斑点病、芋艿细菌性斑点病、芋艿腐败病、芋软腐病、芹菜软腐病和魔芋软腐病;
经济作物类细菌病害:棉花角斑病、棉红叶根腐病、花生青枯病、油菜黑腐病、油菜软腐病、油菜细菌性黑斑病、大豆细菌性叶烧病、大豆细菌性斑点病、大豆细菌性斑疹病、甜菜软腐病、甜菜细菌性根癌病、甜菜细菌性尾腐病、甜菜细菌性斑枯病、芝麻细菌性角斑病、芝麻青枯病、烟草青枯病、烟草角斑病、烟草野火病、烟草空茎病、向日葵细菌性茎基腐、甘蔗白条病、咖啡细菌性叶斑病和胡椒细菌性叶斑病;
其它作物细菌性病害:桑青枯病、桑细菌性黑枯病、桑疫病、茶树细菌性根癌病、黄麻细菌性斑点病、萱麻青枯病、红麻青枯病、苜蓿细菌性叶斑病、苜蓿细菌性茎疫病、紫云英细菌性黑斑病、药材类细菌性病害和花卉类细菌性病害。
5.权利要求1所述的马兜铃酸衍生物用于制备保鲜剂的应用。
6.根据权利要求5所述的应用,其特征在于,所述的保鲜剂不限于水果保鲜剂及肉类保鲜剂。
7.一种组合物,其特征在于,所述的组合物包含权利要求1中的马兜铃酸衍生物与至少一种杀菌剂、杀虫剂、杀螨剂、杀藻剂、拒食剂、杀鸟剂、驱鸟剂、杀真菌剂、化学绝育剂、除草剂、灭草剂、昆虫引诱剂、驱昆虫剂、交配干扰剂、软体动物杀灭剂、植物激活剂、植物生长调节剂、灭鼠剂、增效剂、落叶剂、干燥剂、消毒剂、化学信息素和杀病毒剂的组合。
8.一种组合物,其特征在于,其包含根据权利要求1所述的马兜铃酸衍生物与至少一种选自如下的成员:氟吗啉、烯酰吗啉、叶枯酞、磺菌胺、甲磺菌胺、噻氟菌胺、环氟菌胺、硅噻菌胺、吡噻菌胺、环酰菌胺、苯酰菌胺、环丙酰菌胺、噻酰菌胺、氰菌胺、双氯氰菌胺、高效甲霜灵、高效苯霜灵、萎锈灵、呋吡酰胺、甲呋酰胺、氟酰胺、嘧菌酯、肟菌酯、啶氧菌酯、唑菌胺酯、氟嘧菌酯、烯肟菌酯、苯氧菌胺、烯肟菌胺、嘧菌胺、肟嘧菌胺、噻菌灵、氟菌唑、高效抑霉唑、咪唑菌酮、氰霜唑、抑霉唑、咪鲜胺、恶咪唑、麦穗宁、稻瘟酯、氧环唑、氟环唑、氟喹唑、苯醚甲环唑、四氟醚唑、戊唑醇、氟硅唑、硅氟唑、三唑醇、联苯三唑醇、环丙唑醇、高效烯唑醇、烯唑醇、粉唑醇、己唑醇、丙硫菌唑、灭菌唑、戊菌唑、腈菌唑、腈苯唑、亚胺唑、糖菌唑、种菌唑、叶菌唑;噻唑类:噻唑菌胺、苯噻硫氰、辛噻酮、土菌灵、十二环吗啉、丁苯吗啉、十三吗啉;吡咯类:拌种咯、咯菌腈、氟啶胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、环啶菌胺、啶斑肟、嘧啶环胺、氯苯嘧啶醇、氟苯嘧啶醇、嘧霉胺、嘧菌腙、嘧菌胺、氟嘧菌胺、灭螨猛、二氰蒽醌、乙氧喹啉、8-羟基喹啉、丙氧喹啉、苯氧喹啉、异丙菌胺、乙霉威、苯噻菌胺、霜霉威、硫菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯灵、梧宁霉素、灭瘟素、春雷霉素、多抗霉素、多氧霉素、活化酯、吲哚酯、溴硝醇、苯磺菌胺、甲苯磺菌胺、螺环菌胺、嗪胺灵、敌磺钠、戊菌隆、四氯苯酞、三环唑、烯丙苯噻唑、苯锈啶、氯硝胺、双胍辛胺、多果定、霜脲氰、咯喹酮、苯菌酮、喹菌酮、哒菌酮、链霉素、甲霜灵、丙森锌、苯霜灵、叶枯唑、有效霉素、井冈霉素、五氯硝基苯、代森锰锌、三乙膦酸铝、乙嘧酚磺酸酯、乙嘧酚、二甲嘧酚、三唑酮、甲基硫菌灵、多菌灵、苯菌灵、克菌丹、敌菌丹、灭锈胺、灭菌丹、呋酰胺、氟氯菌核利、乙烯菌核利、菌核净、福美双、稻瘟灵、稻瘟净、百菌清、硫磺、波尔多液、氢氧化铜、氧化亚铜、氧氯化铜、硫酸铜、苦参碱、蛇床子素、虎杖提取物、樟脑、腐殖酸铜、松脂酸铜(钠)、混合氨基酸铜、琥胶肥酸铜、柠檬酸铜、络氨铜、中生菌素、松脂酸铜、噻枯唑、丁子香酚、香芹酚、小檗碱、乙蒜素、几丁聚糖、低聚糖素、葡聚烯糖和大蒜素。
9.一种控制细菌的方法,其特征在于,通过将细菌暴露于权利要求1中的马兜铃酸衍生物或含马兜铃酸衍生物的组合物来抑制细菌的生长。
10.根据权利要求9所述的控制细菌的方法,其特征在于,不限于使动物口服或对动物施用权利要求1所述马兜铃酸衍生物制剂以控制体内细菌和/或皮外细菌;
不限于给植物施用权利要求1所述的马兜铃酸衍生物制剂;
不限于对果、蔬、鱼、肉施用权利要求1所述的马兜铃酸衍生物制剂。
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114469930A (zh) * | 2022-04-12 | 2022-05-13 | 中国中医科学院中药研究所 | 马兜铃酸IVa在制备抗组胺或治疗肺炎药物中的应用 |
WO2023121320A1 (ko) * | 2021-12-21 | 2023-06-29 | 한국한의학연구원 | 항암 활성을 갖는 아리스톨록사진 c의 용도 |
WO2023121321A1 (ko) * | 2021-12-21 | 2023-06-29 | 한국한의학연구원 | 항암 활성을 갖는 아사로이독사진 b의 용도 |
WO2023121311A1 (ko) * | 2021-12-21 | 2023-06-29 | 한국한의학연구원 | 신규 아사로이독사진 c 및 이의 항암 용도 |
US11839216B1 (en) | 2022-08-23 | 2023-12-12 | Qingdao Agricultural University | Quinoline-2,3-fused nine-membered ring scaffold compound, and preparation method and application thereof as effective component in plant fungicide |
WO2024040639A1 (zh) * | 2022-08-23 | 2024-02-29 | 青岛农业大学 | 喹啉-2,3-稠合九元环骨架化合物、其制备方法及作为植物杀菌剂中有效成分的用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES431812A1 (es) * | 1974-11-09 | 1976-10-16 | Roger Lab | Procedimiento de obtencion de un derivado de la ciprohepta-dina. |
CN107602575A (zh) * | 2017-09-19 | 2018-01-19 | 海南大学 | 一类潜在的绿色的有效防治南方根结线虫的马兜铃酸及其衍生物类化合物的分离筛选方法 |
-
2020
- 2020-09-21 CN CN202010995316.4A patent/CN112209948A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES431812A1 (es) * | 1974-11-09 | 1976-10-16 | Roger Lab | Procedimiento de obtencion de un derivado de la ciprohepta-dina. |
CN107602575A (zh) * | 2017-09-19 | 2018-01-19 | 海南大学 | 一类潜在的绿色的有效防治南方根结线虫的马兜铃酸及其衍生物类化合物的分离筛选方法 |
Non-Patent Citations (3)
Title |
---|
MARÍA YOLANDA RIOS ET AL.: "Sulfur-Containing Aristoloxazines and Other Constituents of the Roots of Aristolochia orbicularis", 《J.NAT.PROD.》 * |
XIAOJING FAN ET AL.: "Phenanthrene Derivatives from Asarum heterotropoides Showed Excellent Antibacterial Activity against Phytopathogenic Bacteria", 《J.AGRIC.FOOD CHEM.》 * |
朴红善等: "马兜铃酸-A衍生物合成及其生物活性研究", 《内蒙古大学学报(自然科学版)》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2023121320A1 (ko) * | 2021-12-21 | 2023-06-29 | 한국한의학연구원 | 항암 활성을 갖는 아리스톨록사진 c의 용도 |
WO2023121321A1 (ko) * | 2021-12-21 | 2023-06-29 | 한국한의학연구원 | 항암 활성을 갖는 아사로이독사진 b의 용도 |
WO2023121311A1 (ko) * | 2021-12-21 | 2023-06-29 | 한국한의학연구원 | 신규 아사로이독사진 c 및 이의 항암 용도 |
CN114469930A (zh) * | 2022-04-12 | 2022-05-13 | 中国中医科学院中药研究所 | 马兜铃酸IVa在制备抗组胺或治疗肺炎药物中的应用 |
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WO2023197484A1 (zh) * | 2022-04-12 | 2023-10-19 | 中国中医科学院中药研究所 | 马兜铃酸IVa在制备抗组胺或治疗肺炎药物中的应用 |
US11839216B1 (en) | 2022-08-23 | 2023-12-12 | Qingdao Agricultural University | Quinoline-2,3-fused nine-membered ring scaffold compound, and preparation method and application thereof as effective component in plant fungicide |
WO2024040639A1 (zh) * | 2022-08-23 | 2024-02-29 | 青岛农业大学 | 喹啉-2,3-稠合九元环骨架化合物、其制备方法及作为植物杀菌剂中有效成分的用途 |
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