CN108471747A - 活性物质用于防治植物病毒感染的用途 - Google Patents
活性物质用于防治植物病毒感染的用途 Download PDFInfo
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Abstract
本发明公开了特定的活性物质单独或组合用于防治植物病毒感染的用途,以及在植物保护和材料保护领域,使用所述特定的活性物质防治所述病毒感染的方法。
Description
技术领域
本发明涉及活性物质用于刺激植物抗病毒的天然防御机制以防治植物病毒感染的用途,以及防治植物病毒感染的方法。本发明还涉及活性物质用于激活植物抗病毒的基于RNA干扰的天然防御机制(本文中也命名为基于RNA沉默的天然防御机制)的用途。
背景技术
植物病毒是世界各地主要作物损害的原因。的确,有些病毒家族,如马铃薯Y病毒科,在发达国家和新兴国家都导致严重的产量损失,这与不断增长的粮食需求相冲突。为了限制病毒感染和传播,主要通过预防进行病害治理,因为治疗性方法无效或低效。
已经确定了几种尝试用于防治植物病毒的化合物。WO2011/030816教导了某些抗坏血酸衍生物用于防治某些植物病毒的用途。WO2012/016048提供了叠氮化物改性的生物分子作为抗病毒剂,包括抗植物病毒的用途。WO2014/050894教导了其他抗坏血酸的相关化合物用于防治植物病毒的用途。
植物已经进化得可以用它们可利用的资源来持续应对威胁,并在生长或防御生物和非生物威胁之间平衡可利用的资源。RNA沉默在这一平衡中起重要作用,其通过转录基因沉默(TGS)和转录后基因沉默(PTGS)将发育程序和环境应激反应与基因表达变化进行动态连接而起作用。植物的抗病性依赖于预先形成的屏障、有毒次生代谢产物和诱导型防御机制。一经病原体识别,植物通常引发过敏反应,导致感染部位的细胞死亡并防止病原体扩散。此外,病原体检测在远离原发感染部位的植物部位中触发各种诱导型系统防御。这一过程被称为系统获得性抗性(SAR),在许多植物物种中都是有效的。所获得的抗性对于抵抗广泛范围的病原体例如真菌、细菌和病毒的后续感染是持久并且有效的。
甲氧基丙烯酸酯(Strobilurin)类的杀菌剂包含各种各样具有广谱性的合成植物保护化合物。在2002年,通过烟草花叶病毒(TMV)或野火病病原体烟草野火病菌(Pseudomonas syringae pv tabaci)已证实甲氧基丙烯酸酯唑菌胺酯(Pyraclostrobin)增强烟草抗感染的抗性(Herms等人,Plant Physiology 2002,130:120-127)。唑菌胺酯也能够增强无法积累大量的内源性水杨酸的NahG转基因烟草植物的TMV抗性。唑菌胺酯通过在水杨酸(SA)信号机制中作用于SA的下游或通过独立作用于SA而增强烟草的TMV抗性。后一假设更有可能,因为在浸润的叶片中,唑菌胺酯未引起SA诱导的发病机制相关(PR)-1蛋白的积累,所述蛋白通常用作对SA诱导的抗病性的常规分子标记。甲氧基丙烯酸酯类杀菌剂的应用被记载为单独使用(WO 01/82701)或以与代森联的混合物的形式使用(WO 2007/104669)。
在对植物病毒的植物防御反应中,抗病毒RNA沉默途径是影响一系列病毒的局部及系统累积的最广泛的防御体系。RNA沉默是直接使植物宿主细胞防御外源核酸,包括病毒和转座因子的机制。这种防御通过衍生自侵入性核酸的增殖的双链RNA(dsRNA)触发,所述侵入性核酸被宿主处理成尺寸为20-24个核苷酸(nt)的小干扰RNA(siRNAs)。然后,所述siRNAs通过PTGS或TGS分别用于引导病毒或转座因子RNA或DNA的沉默。
然后,RNA沉默是一种有效的抗病毒机制,其中将由病毒双链RNA复制中间体通过Dicer酶处理得到的小干扰siRNAs载入ARGONAUTE效应蛋白,并转回侵入者的RNA基因组,以诱导其退化。这种先天性免疫应答是非常通用的,因为其完全由结构和核苷酸序列基因组特征进行编程,其可以对几乎任何植物病毒作出应答(Shimura等人,2011,Biochimica etBiophysicaActa 1809:601-612)。证实了RNA沉默在植物防御中的重要性,siRNA产生或活性受损的植物对植物病毒是高度敏感的,并且反过来,许多病毒已经进化出RNAi抑制子,以保持毒性(Voinnet O.等人,Nature Review Microbiology 2013Nov;11(11):745-60)。
尽管在过去已经确定了某些化合物作为某些抗病毒植物防御机制的潜在诱导剂,但仍然需要提供适于刺激植物抗病毒的天然防御机制、特别是刺激植物抗病毒的广泛的非特异性的基于RNA沉默的防御机制,以防治植物的病毒性疾病的活性物质。
附图说明
图1说明了仅使用DMSO或DFPM处理7天后,SUC-SUL植物的SUL mRNA相对水平的qPCR分析,已标准化为EXP10。误差线表示3次独立实验的标准偏差。
图2表示接种的叶片感染5天后感染灶的平均数目。误差线表示12株植物的标准偏差。
图3说明了感染6天后在全身组织中积累的HcPro mRNA的RT-qPCR分析。误差线表示3次独立PCR结果的标准偏差。
定义
本文中使用的术语“(C1-C6)烷基”指的是含有1至6个碳原子的支-或直链烷基基团。(C1-C6)烷基的代表性实例包括甲基、乙基、正丙基、异丙基和不同的丁基、戊基或己基同分异构体。
本文中使用的术语“卤素”指的是氟、氯、碘或溴原子。
本文中使用的术语“(C1-C6)卤代烷基”指的是如上定义的(C1-C6)烷基基团,其中至少一个氢原子被卤素原子取代。(C1-C6)卤代烷基的代表性实例包括-CF3、-CH2Cl和-CH2-CF3。
本文中使用的术语“(C1-C6)氰烷基”指的是如上定义的(C1-C6)烷基基团,其中至少一个氢原子被氰基基团取代。
本文中使用的术语“(C3-C6)环烷基”指的是饱和单环烷基基团,其中环骨架具有3至6个碳原子。“(C3-C6)环烷基”的代表性实例包括环丙烷、环丁烷和环戊烷。
本文中使用的术语“氮杂双环烷基”指的是在双环上含有5至最高10个碳原子和1个氮原子的完全饱和的单价基团。“氮杂双环烷基”的代表性实例包括杂氮双环[3.1.0]己基、杂氮双环[2.2.1]庚基和杂氮双环[2.2.2]辛基。
本文中使用的表述“可被取代”(例如可被取代的苯基)意指所述取代是任选的,且因此包括未取代的和取代的原子或基团(例如未取代的和取代的苯基)。当原子或基团被取代时,指定的原子或基团上的任意氢可以被取代基取代(最多且包括每个氢均被取代基取代),条件是不超过指定的原子或基团的正常化合价且所述取代得到稳定的化合物。
本文中使用的术语“活性物质”指定为如本文所述的式(I)的化合物或其任意混合物。
详细说明
现在已发现,如本文所公开的式(I)的化合物适用于刺激植物抗病毒的天然防御机制,特别是用于刺激植物抗病毒的基于RNA沉默的防御机制。因此,如本文所公开的式(I)的化合物对防治植物的病毒性疾病可以是有用的。本文中使用的术语“防治”(control)或“防治”(controlling)指定为预防性或治疗性防治。
因此,本发明涉及一种用于防治植物的病毒性疾病的方法,更具体地涉及一种用于刺激植物抗病毒的天然防御机制、特别是用于刺激植物抗病毒的基于RNA沉默的防御机制的方法。所述方法包括将一种或多种式(I)的化合物施用至植物:
其中
-R1为苯基,其可被一个或两个卤素、优选氯和溴取代;
-R2为-NR’R”基团,其中:
-R’和R”独立选自(C1-C6)烷基(优选甲基、乙基和正丙基)和(C3-C6)环烷基(优选环戊基),或
-R’和R”与它们连接的氮原子一起形成选自吡咯烷、哌啶、吗啡或哌嗪的5-或6-元杂环,其中所述杂环可被一个或多个选自卤素、(C1-C6)烷基和(C1-C6)氰烷基的取代基取代,或
-R’和R”与它们连接的氮原子一起形成可被(C1-C6)卤代烷基取代的氮杂双环烷基、优选可被(C1-C6)卤代烷基取代的杂氮双环[3.1.0]己基。
在一些实施方案中,所述活性物质为式(I)的化合物,其中:
-R1为苯基,其被一个或两个独立选自氯和溴的卤素取代;和/或
-R2为-NR’R”基团,其中:
-R’和R”独立地选自甲基、乙基、正丙基和环戊基,或
-R’和R”与它们连接的氮原子一起形成选自吡咯烷、哌啶、吗啡或哌嗪的5-或6-元杂环,其中所述杂环可被一个或多个选自甲基、氟和氰乙基的取代基取代,或
-R’和R”与它们连接的氮原子一起形成被(C1-C6)卤代烷基取代的杂氮双环[3.1.0]己基,例如三氟甲基。
在一些优选的实施方案中,所述活性物质为式(I)的化合物,其中:
-R1选自3-氯苯基、4-氯苯基、4-溴苯基、2,3-二氯苯基和3,4-二氯苯基;和/或
-R2选自-NEt2、-N(正丙基)2、-N(环戊基)甲基、哌啶-1-基、吡咯烷-1-基、N-吗啉代、4,4-二氟哌啶-1-基、4-(2-氰乙基)-哌嗪-1-基、2,6-二甲基吗啉-4-基和6-(三氟甲基)-3-杂氮双环[3.1.0]己-3-基。
在一些实施方案中,所述活性物质为式(I)的化合物,其中选择R1和R2,以便提供下文表1中公开的特定化合物。
在一些优选的实施方案中,所述活性物质为式(I)的化合物,其中:
-R1为3,4-二氯苯基且R2为4,4-二氟哌啶基-1-基;或
-R1为3,4-二氯苯基且R2为哌啶-1-基;或
-R1为4-溴苯基且R2为哌啶-1-基。
其中R1为3,4-二氯苯基且R2为哌啶-1-基的式(I)的化合物称为DFPM[5-(3,4-二氯苯基)呋喃-2-基]-哌啶-1-基甲硫酮。
DFPM迅速下调植物的ABA依赖性基因表达,并抑制ABA诱导的气孔关闭。DFPM还刺激植物防御相关基因的表达,包括植物抗毒素缺陷4(PHYTOALEXIN DEFICIENT4,PAD4)-和增强的疾病易感性1(ENHANCED DISEASE SUSCEPTIBILITY1,EDS1)(Kim等人,CurrentBiology 2011,21,11:990-997)。
式(I)的5-芳基呋喃-2-硫代酰胺可以适当地制备:
-由5-芳基呋喃-2-羧醛和胺通过Wilgerodt-Kindler反应,如Fedorovich,Ganushchak,Karpyak,Obushchak,Lesyuk,Russian Journal of Organic Chemistry2007,43(8),1190-1195[10.1134/S1070428007080180]中所公开
-或通过相应的5-芳基呋喃-2-羰酰胺的硫代反应(使用经典方法,如用五硫化二磷或路易斯试剂处理,参见例如“Thionation reactions of Lawesson′s reagents”:Cava,Levinson,Tetrahedron 1985,41(22),5061-5087[10.1016/S0040-4020(01)96753- 5]),相应地,其中5-芳基呋喃-2-羰酰胺很容易通过文献已知的方法(参见例如Drizin,Gregg等人,Bioorganic&Medicinal Chemistry 2008,16(12),6379-6386[10.1016/ j.bmc.2008.05.003];Gargano,Perspicace等人,European Journal of MedicinalChemistry 2014,87,203-219[10.1016/j.ejmech.2014.09.061])而获得。
通常将有效量的活性物质施用至植物。施用至植物的有效量的活性物质将取决于不同的因素,如活性物质的性质、制剂、所针对的植物(植物性质和植物部分)、施用方法、处理的目的(预防或治疗)和所针对的病毒。施用至植物的量的范围可以适当地为0.01至5kg/ha,或0.1至3kg/ha,或0.5至2kg/ha。
如上所述,将所述活性物质施用至植物。本文中使用的术语“植物”包括植物及其部分,如植物的地上和/或地下部分以及收获物。地下植物部分包括根、根茎、块茎、吸根、插条(slips)、籽(seeds)和种子(seed)。地上植物部分包括茎(stem)、树皮、芽、叶、花、果、子实体、杆(stalk)、针和枝。因此,所述活性物质可以有效地施用到植物的根、根茎、块茎、吸根、插条、籽、种子、茎、树皮、芽、叶、花、果、子实体、杆、针、枝、收获物上。在可选择的实施方案中,用于防治植物病毒性疾病的方法包括将所公开的活性物质施用到植物的生境和/或储存地。
可以将所述活性物质有效地施用到大范围的各种各样的植物上。可以将它施用到市售可得的或使用中的植物品种上。但是,植物品种也理解为意指具有通过传统育种、诱变或借助重组DNA技术培育的新性状的植物,和/或可通过传统育种和优化方法或通过生物技术和基因工程方法或通过这些方法的组合而获得的植物;这包括转基因植物和能够受或不受植物育种者权利(Plant Breeders’Rights)保护的植物。
还可以将所述活性物质有效地施用到转基因生物(GMOs)上。转基因植物为异源基因已被稳定地整合到基因组中的植物。表述“异源基因”本质上意指在植物外提供或组装的基因,并且当将叶绿体或线粒体基因组引入核时,其通过使感兴趣的蛋白质或多肽表达、或使植物中存在的另一基因或植物中存在的其他基因下调或沉默,赋予被转化植物新的或改良的农艺或其他特性(例如,使用反义技术、共抑制技术或RNAi技术[RNA干扰])。位于基因组中的异源基因也称为转基因。转基因因其在植物基因组中的特定位置而被定义,被称为转化事件或转基因事件。
具有赋予这些植物尤其有利的、有用的性状(不论通过育种和/或生物技术获得)的遗传物质的所有植物可以用所公开的方法进行处理。
同样可以根据本发明进行处理的植物和植物品种为能够抵抗一种或多种非生物胁迫因素的那些植物。非生物胁迫条件可以包括,例如,干旱、寒冷和高温条件、渗透胁迫、积涝、土壤含盐量升高、暴露于矿物增加、臭氧条件、高光条件、氮营养物的有限利用率、磷营养物的有限利用率或避荫。
同样可以根据本发明进行处理的植物和植物品种为具有高产量特征的那些植物。这些棕榈植物的高产量的原因可以为,例如,改良的植物生理,改良的植物生长和改良的植物发育,如水利用效率、保水效率、提高的氮利用率、改善的碳同化、改善的光合作用、提高的发芽率和改良的成熟。产量还受改良的株型(plant architecture)影响(在胁迫条件下和非胁迫条件下),其中提早开花、生产杂交种子的开花控制、幼苗活力、植物大小、节间数和距离、根生长、种子大小、果实大小、英果大小、荚果数或穗数、每英或穗的种子数量、种子质量、改善的种子填充、减少的种子散播、减少的英开裂和抗倒伏性。其他产量性状包括种子成分,如碳水化合物含量、蛋白质含量、油含量和油成分,营养价值,抗营养化合物的减少,改善的可加工性和改善的可储存性。
同样可以根据本发明进行处理的植物为已经表达出杂种优势或杂交优势特征的杂交植物,其通常导致更高的产量、更高的生命力、更好的健康以及对生物和非生物胁迫因素更好的抗性。这类植物通常通过将雄性不育近交系亲本(母本)与另一雄性可育近交系亲本(父本)进行杂交而产生。通常从雄性不育植物中收获杂交种子并出售给种植者。雄性不育植物有时可以(例如在玉米中)通过去雄获得(即机械地去除雄性繁殖器官或雄花);但是,更典型地,雄性不育是植物基因组中的遗传决定子决定的。在这种情况下,特别是当种子为从杂交植物收获的所需产物时,确保含有负责雄性不育的遗传决定子的杂交植物的雄性能育性完全恢复通常是有用的。这点可以通过确保父本具有合适的育性恢复基因而实现,所述育性恢复基因能够恢复含有负责雄性不育的遗传决定子的杂交植物的雄性能育性。雄性不育的遗传决定子可以位于细胞质中。细胞质雄性不育性(CMS)的实例已记载于例如芸苔属(Brassica)物种(WO 1992/005251、WO 1995/009910、WO 1998/27806、WO 2005/002324、WO 2006/021972和US 6,229,072)。但是,雄性不育的遗传决定子也可以位于核基因组中。雄性不育植物也可以通过植物生物技术方法如基因工程而获得。在WO 89/10396中记载了产生雄性不育植物的特别有利的手段,其中,例如核糖核酸酶如芽孢杆菌RNA酶在雄蕊的绒毡层细胞中选择性表达。随后通过在绒毡层细胞中表达核糖核酸酶抑制因子如芽孢杆菌RNA酶来恢复能育性(例如WO 1991/002069)。
所述活性物质特别适于防治以下植物的病毒性疾病:棉花,亚麻,葡萄藤,水果,蔬菜,如蔷薇科(Rosaceae sp.)(例如仁果类如苹果和梨子,还有核果类如杏子、樱桃、扁桃和桃子,和软果类如草莓)、茶藨子亚科(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、桦木科(Betulaceae sp.)、漆树科(Anacardiaceae sp.)、山毛榉科(Fagaceae sp.)、桑科(Moraceae sp.)、木犀科(Oleaceae sp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceaesp.)、芭蕉科(Musaceae sp.)(例如香蕉树和种植园)、茜草科(Rubiaceae sp.)(例如咖啡)、山茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、芸香科(Rutaceae sp.)(例如柠檬、橙子和葡萄柚);茄科(Solanaceae sp.)(例如番茄)、百合科(Liliaceae sp.)、菊科(Asteraceae sp.)(例如生菜)、伞形科(Umbelliferae sp.)、十字花科(Cruciferae sp.)、藜科(Chenopodiaceae sp.)、葫芦科(Cucurbitaceae sp.)(例如黄瓜)、葱科(Alliaceaesp.)(例如韭菜、洋葱)、蝶形花科(Papilionaceae sp.)(例如豌豆);主要农作物,如禾本科(Gramineae sp.)(例如玉米、草皮、谷物如小麦、黑麦、大米、大麦、燕麦、小米和黑小麦)、菊科(例如向日葵)、芸苔科(Brassicaceae sp.)(例如白菜、紫甘蓝、绿花椰菜、菜花、抱子甘蓝、小白菜、球茎甘蓝、萝卜和油菜、芥菜、山葵和水芹)、豆科(Fabacae sp.)(例如豆、花生)、蝶形花科(例如大豆)、茄科(例如马铃薯)、藜科(例如糖用甜菜、饲料甜菜、瑞士甜菜、甜菜根);园林和林地的有用植物和观赏植物;以及这些植物各自的基因改良品种。
更具体地,所述活性物质适于防治蔬菜的病毒性疾病。
所述活性物质特别适于防治以下科或属的病毒:花椰菜病毒科(Caulimoviridae)、双生病毒科(Geminiviridae)、雀麦花叶病毒科(Bromoviridae)、长线形病毒科(Closteroviridae)、豇豆花叶病毒科(Comoviridae)、马铃薯Y病毒科(Potyviridae)、随伴病毒科(Sequiviridae)、番茄丛矮病毒科(Tombusviridae)、弹状病毒科(Rhabdoviridae)、布尼亚病毒科(Bunyaviridae)、分体病毒科(Partitiviridae)、呼肠孤病毒科(Rheoviridae)、毛发状病毒属(Capillovirus)、香石竹潜病毒属(Carlavirus)、豌豆耳突花叶病毒属(Enamovirus)、真菌传杆状病毒属(Furovirus)、大麦病毒属(Hordeivirus)、悬钩子病毒属(Idaeovirus)、黄矮病毒属(Luteovirus)、玉米雷亚朵非纳病毒属(Marafivirus)、马铃薯X病毒属(Potexvirus)、南方菜豆花叶病毒属(Sobemovirus)、纤细病毒属(Tenuivirus)、烟草花叶病毒属(Tobamovirus)、烟草脆裂病毒属(Tobravirus)、发状病毒属(Trichovirus)、芜菁黄花叶病毒属(Tymovirus)和伞形植物病毒属(Umbravirus)。
优选地,所述活性物质用于防治以下种的病毒:芜菁花叶病毒(turnip mosaicvirus)、芜菁皱缩病毒(turnip crinkle virus)、豆英斑驳病毒(bean pod mottlevirus)、花椰菜花叶病毒(cauliflower mosaic virus)、烟草花叶病毒(tobacco mosaicvirus)、番茄丛矮病毒(tomato bushy stunt virus)、水稻齿叶矮缩病毒(rice raggedstunt virus)、黄瓜花叶病毒(cucumber mosaic virus)、大麦黄矮病毒(barley yellowdwarf virus)、甜菜黄化病毒(beet yellows virus)、生菜黄化病毒(lettuce yellowsvirus)、玉米花叶病毒(maise mosaic virus)、花生矮化病毒(peanut stunt virus)和马铃薯Y病毒(potato virus Y)。
可以将所述活性物质以任何合适的形式施用至植物。例如,可以将所述活性物质以以下形式施用:悬浮液例如水基或油基悬浮液、乳液、溶液,粉末如可湿性粉末,泡沫,浆,颗粒,微粒,气雾剂或微型胶囊。可以以常规方式制备合适的制剂。包含所述活性物质的制剂可以为即用型组合物,即可以通过适当的装置直接施用至植物的组合物,或它们可以为使用前必须稀释的商品化浓缩物的形式。
所述制剂可以仅包含所述活性物质或包含所述活性物质与其他活性物质的组合,所述其他活性物质如杀虫剂、引诱剂、消毒剂(sterilants)、杀菌剂(bactericides)、杀螨剂、杀线虫剂、其他杀真菌剂、生长调节物质、除草剂、安全剂和/或肥料。
可以将所述活性物质或包含它的制剂以任何常规方式,例如浇水、喷洒、喷粉、喷雾,施用至植物。可以将所述活性物质直接或间接施用到植物、环境、生境和/或储存地。例如,可以将所述活性物质注射到树皮中或树皮下、倾倒或喷洒到植物周围的地上(土壤、沙土、砂砾土、岩土、壤质土或混合土)。另一种类型的施用为喷洒到植物或其植物部分上。可以将所述活性物质组合物以干燥的形式混入地面物质(土壤、沙土、砂砾土、岩土、壤质土或混合土)和/或种子。可以将所述活性物质以干燥的形式或者液体的形式施用到灌溉系统。优选地,将所述活性物质通过喷洒施用至植物。
本发明还涉及如本文所公开的式(I)的化合物用于防治植物病毒性疾病、更具体地用于刺激植物抗病毒的天然防御机制、特别是用于刺激植物抗病毒的基于RNA沉默的防御机制的用途。所述植物和/或病毒如上所公开。
所述式(I)的化合物通过增加小RNA的产生而刺激基于RNA沉默的植物防御机制。有利地,式(I)的化合物增加小RNA产生的能力也可以用在用RNAi构建体转化的转基因植物中,所述转基因植物被设计用于改善农艺性状和/或提供对病原体(例如细菌、真菌)的抗性、对昆虫/害虫和/或胁迫耐受性的抗性。因此,本发明还涉及一种或多种式(I)的化合物在用RNAi构建体转化的转基因植物中通过增加小RNA的产生,而改善农艺性状和/或提供对病原体的抗性、对昆虫/害虫和/或胁迫耐受性的抗性的用途。
本发明还涉及一种式(I)的化合物和/或包含它的组合物,其中式(I)的化合物如下所示:
其中
-R1为苯基,其被一个或两个卤素、优选氯和溴取代;
-R2为-NR’R”基团,其中:
-R’和R”独立地选自(C1-C6)烷基(优选甲基、乙基和正丙基)和(C3-C6)环烷基(优选环戊基),或
-R’和R”与它们连接的氮原子一起形成取代的哌啶或吗啉,其中所述取代的哌啶或吗啉被一个或多个选自卤素和(C1-C6)烷基的取代基取代,或
-R’和R”与它们连接的氮原子一起形成可被(C1-C6)卤代烷基取代的氮杂双环烷基、优选可被(C1-C6)卤代烷基取代的杂氮双环[3.1.0]己基。
在一些实施方案中,所述化合物为式(I)的化合物,其中:
-R1为苯基,其被一个或两个独立选自氯和溴的卤素取代;和/或
-R2为-NR’R”基团,其中:
-R’和R”独立地选自甲基、乙基、正丙基和环戊基,或
-R’和R”与它们连接的氮原子一起形成取代的哌啶或吗啡,其中所述取代的哌啶或吗啉被一个或多个选自甲基和氟的取代基取代,
-R’和R”与它们连接的氮原子一起形成被(C1-C6)卤代烷基取代的杂氮双环[3.1.0]己基,如三氟甲基。
在一些优选实施方案中,所述化合物为式(I)的化合物,其中:
-R1为3,4-二氯苯基;和/或
-R2选自-NEt2、-N(正丙基)2、-N(环戊基)甲基、4,4-二氟哌啶-1-基、2,6-二甲基吗啉-4-基和6-(三氟甲基)-3-杂氮双环[3.1.0]己-3-基。
本发明的组合物通常包含,除式(I)的化合物之外,一种或多种可接受的载体,特别是一种或多种农业上可接受的载体。
载体为天然的或合成的、有机或无机物质,与所述活性物质成分混合或组合,以获得更好的适用性,特别是对植物、植物部分或种子有更好的适用性。所述载体,可以为固体或液体,通常呈惰性。
合适的固体载体的实例包括但不限于,铵盐,天然岩石粉如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱土或硅藻土,以及合成岩石粉如二氧化硅粉、氧化铝粉和硅酸盐粉。用于制备颗粒的典型的有用的固体载体的实例包括但不限于,粉碎和分割的天然岩石如方解石、大理石、浮石、海泡石和白云石,无机和有机粉的合成颗粒以及有机材料如纸、锯末、椰子壳、玉米芯和烟草茎的颗粒。
合适的液体载体的实例包括但不限于,水,极性和非极性有机化学液体,例如芳香族和非芳香族烃(如环己烷,石蜡,烷基苯,二甲苯,甲苯烷基萘,氯化芳香或氯化脂肪烃如氯苯、氯乙烯或二氯甲烷),醇和多元醇(其也可以任选地被取代、醚化和/或酯化,如丁醇或乙二醇),酮(如丙酮,甲乙酮,甲基异丁基甲酮,环己酮),酯(包括脂肪和油)和(聚)醚,未取代和取代的胺,酰胺(如二甲基甲酰胺),内酰胺(如N-烷基吡咯烷酮)和内酯,砜和亚砜(如二甲基亚砜)。所述载体还可以是液化气体增量剂,即在标准温度和标准压力下为气体的液体,例如气雾喷射剂如卤代烃、丁烷、丙烷、氮气和二氧化碳。
所述组合物还可以包含一种或多种通常用于配制组合物的可接受的助剂(例如农业化学组合物),如一种或多种表面活性剂。
合适的表面活性剂的实例包括乳化剂和/或发泡剂、分散剂或具有离子或非离子性质的润湿剂,或其混合物。其实例为聚丙烯酸盐,木质素磺酸盐,苯酚磺酸盐或萘磺酸盐,环氧乙烷和/或环氧丙烷与脂肪醇的缩聚物,脂肪酸或脂肪胺(聚氧化乙烯脂肪酸酯,聚氧化乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚),取代的酚(优选烷基酚或芳基酚),磺基琥珀酸酯的盐,牛磺酸衍生物(优选烷基牛磺酸盐),聚乙氧基化醇或酚的磷酸酯,多元醇的脂肪酯,和含有硫酸盐、磺酸盐和磷酸盐的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐,蛋白质水解产物,木质素亚硫酸盐废液和甲基纤维素。当活性成分和/或载体不溶于水并且用水施用时,通常使用表面活性剂。然后,表面活性剂的量通常为组合物的5至40重量%。
常用于配制农用化学组合物的助剂的其他实例包括防水剂,干燥剂,粘合剂(胶粘剂,增粘剂,固定剂如羧甲基纤维素,粉末、颗粒或胶乳形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚醋酸乙烯酯,天然磷脂如脑磷脂和卵磷脂,以及合成磷脂,聚乙烯吡咯烷酮,聚醋酸乙烯酯,聚乙烯醇和甲基纤维素),增稠剂,稳定剂(例如冷稳定剂、防腐剂、抗氧化剂、光稳定剂或改进化学和/或物理稳定性的其他试剂),染料或颜料(如无机颜料,例如氧化铁、氧化钛和普鲁士蓝;有机染料,例如茜素、偶氮和金属酞菁染料),消泡剂(例如硅酮消泡剂和硬脂酸镁),防腐剂(例如二氯酚和苄醇半缩甲醛),二次增稠剂(纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土和二氧化硅粉),粘着剂,赤霉素和加工助剂,矿物油和植物油,香料,蜡和营养素(包括微量营养素,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐),保护胶体,触变物质,渗透剂,螯合剂和络合物形成剂(complex formers)。所述载体和/或助剂的选择将取决于组合物预定的施用方式和/或活性成分的物理性质。
如前所述,已知植物利用RNA沉默途径来抵御入侵病毒。在哺乳动物中,直到Y.Li等人和P.V.Maillard等人(Y.Li等人,Science,342:231-234,2013;P.V.Maillard等人,Science,342:235-238,2013)的最近发现,科学家们只能证明RNAi的基因调控作用。现在,Y.Li等人和P.V.Maillard等人已经证明了RNAi在哺乳动物中也可以起抗病毒应答的作用。因此,式(I)的化合物可以用于刺激哺乳动物抗病毒的天然防御机制,特别是用于刺激哺乳动物抗病毒的基于RNA沉默的防御机制。
因此,本发明还涉及如本文所公开的式(I)的化合物用作药物,特别是用于治疗或预防病毒感染。
如本文所公开的式(I)的化合物可以用于治疗或预防哺乳动物病毒感染的方法中,所述方法包括给予有此需要的哺乳动物有效量的如本文所公开的式(I)的化合物。本文中使用的术语“哺乳动物”包括人类。
借助于下面的实施例对本发明进行更详细的解释。
实施例
实施例1:植物沉默机制的调节剂-使用SUC-SUL报告基因植物的鉴定
用称为“SUC-SUL拟南芥(Arabidopsis)报告基因植物”的某些人造报告基因植物可以容易地监测植物的RNA沉默途径(Dunoyer等人,Nat.Genet,37,1356-1360,2005)。
SUC-SUL拟南芥报告基因植物为表达反向重复(IR)双链RNA的转基因植物,所述反向重复(IR)双链RNA设计成在SUC2启动子的控制下,在脉管系统中靶向SULFUR(SUL)转录物(Truernit等人,Planta196(3),564-570,1995)。一经表达,dsRNA被处理成指导SULPH转录物的非细胞自主转录后基因沉默的小干扰RNAs,继而导致以叶脉为中心的萎黄病。由于观察到的萎黄病是由SULPHUR转录物的沉默引起的,所以植物上直接可观察到的萎黄扩张与分子水平上RNA沉默途径的强化相关。
发芽5天后,用含有300ppm本发明活性分子的不同溶液、二甲基亚砜(DMSO)5%和标准乳油(EC)预混制剂喷洒拟南芥(A.thaliana)幼苗(n=6)(每次实验6株幼苗)。对每种分子重复四次。对照植物仅用DMSO处理(模拟处理的植物)。在透射照射下处理14天后,评估所述处理对SUC-SUL报告基因植物的影响,并使用立体显微镜通过测量萎黄区的表面和强度(萎黄百分比)进行数字化的记录。为了评估每种分子的萎黄平均百分比,进行了两个独立的实验。
结果示于下表1。用300ppm的DFPM([5-(3,4-二氯苯基)呋喃-2-基]-哌啶-1-基甲烷硫酮)及其类似物处理导致了萎黄百分比的显著增加,证实了作为RNA沉默的推定强壮增强子的活性物质的活性。
为了丢弃直接作用于启动子而非RNA沉默机制的分子,然后在第二步,在一些AtSUC2-GFP报告基因植物上,测试了经鉴定具有增加萎黄区表面和强度的能力的活性物质,所述AtSUC2-GFP报告基因植物特别报告SUC2启动子的活性(Wright等人,PlantPhysiol.131,1555-1565,2003)。
表1:在SUC-SUL报告基因植物上评估DFPM(化合物ID No.3)及其类似物。模拟处理植物的萎黄程度达到10%。
实施例2:沉默调节剂的分子效应的确认
已经在表现型和分子水平上验证了DFPM对RNAi机制的增强作用。用200ppm的DFPM对处于莲座期的四周大的SUC-SUL拟南芥植物进行喷洒。处理7天后,显示出DFMP诱导了RNAi依赖的以叶脉为中心的萎黄表现型的明显扩张,这在仅DMSO处理(模拟对照)中未观察到。
收集植物地上组织并使用现有技术的方法进行分子分析。萎黄病的可视化扩张与实时qRT-PCR(图1)分析中SUL转录物水平的降低、以及蛋白免疫印迹分析中可定量的SUL蛋白水平的降低相关。此外,这些作用与源自转基因SUL的SUL 21-nt和24-nt长siRNA的过度积累有关。总之,这些数据支持DFPM诱导植物的RNAi途径。
实施例3:沉默调节剂对拟南芥的抗病毒功效
芜菁花叶病毒(TuMV)属于已知植物病毒的最大科的马铃薯Y病毒科。该病毒感染种类繁多的植物,特别是芸苔科的植物。TuMV基因组由正义单链RNA分子(+ssRNA)组成。使用荧光标记的马铃薯Y病毒(TuMV-GFP)测试DFMP的抗病毒功效,以具体查明病毒初次感染及其局部或全身传播期间,分子的作用在何时何地被诱导。
在用TuMV-GFP病毒感染植物3天之前,用100或200ppm的DFMP对拟南芥植物进行喷洒。通过qPCR和/或在蛋白免疫印迹分析中的病毒蛋白质积累以及在TuMV-GFP的情况下通过在UV光下计数原发感染灶的数目来测量病毒滴度。
在拟南芥植物感染5天之后,DFPM导致病毒滴度积累的明显减少。如通过减少TuMV-衍生的HcPro mRNA水平的积累(图3)所测量的,经DFPM处理,在接种叶片上(图2)和全身组织上的TuMV-GFP均一致地观察到病毒积累的极大减少。
用DFPM与无关病毒芜菁皱缩病毒(TCV)和花椰菜花叶病毒(CaMV)获得类似的结果。TCV属于番茄丛矮病毒科,并且感染各种类型的植物物种,包括常见植物模型拟南芥和本氏烟(N.benthamiana)。它的基因组是正链RNA病毒的另一实例。CaMV属于花椰菜病毒科。它感染大多数芸苔科如芜菁和卷心菜,但也能够感染拟南芥。CaMV由双链DNA分子组成。
如通过减少TCV-衍生的P38mRNA和CaMV-衍生的P6mRNA的积累所测量的,100ppm的DFPM处理导致接种叶片上和全身组织上的病毒积累的极大减少。
实施例4:沉默调节剂对大豆植物的抗病毒功效
豆英斑驳病毒(BPMV)是豇豆花叶病毒科的植物病原性病毒。该病毒感染豆科植物,更特别是大豆。BPMV基因组由双向正义单链RNA分子(+ssRNA)组成。使用荧光标记的豇豆花叶病毒(BPMV-GFP)测试沉默增强子的抗病毒功效,以具体查明病毒初次感染、局部或全身传播期间,分子的作用在何时何地被诱导。
在用BPMV-GFP病毒感染植物1天之前,用100或200ppm的DFPM和乳油(EC)预混合物对大豆植物进行喷洒。每种条件使用12个重复样。在大豆感染7天之后,DFPM导致显示出BPMV症状的植物数量明显减少,并且大豆上的BPMV荧光明显减少(表2)。
表2:经100和200ppm的DFPM处理,BPMV症状和荧光的减少。
Claims (17)
1.一种防治植物病毒性疾病的方法,其包含将至少一种式(I)的化合物施用至植物:
其中
-R1为苯基,其可被一个或多个卤素取代;
-R2为-NR’R”基团,其中:
-R’和R”独立地选自(C1-C6)烷基和(C3-C6)环烷基,或
-R’和R”与它们连接的氮原子一起形成选自吡咯烷、哌啶、吗啡或哌嗪的5-或6-元杂环,其中所述杂环可被一个或多个选自卤素、(C1-C6)烷基和(C1-C6)氰烷基的取代基取代,或
-R’和R”与它们连接的氮原子一起形成可被(C1-C6)卤代烷基取代的氮杂双环烷基。
2.根据权利要求1的方法,其中R1选自3-氯苯基、4-氯苯基、4-溴苯基、2,3-二氯苯基和3,4-二氯苯基。
3.根据权利要求1或2的方法,其中R2选自-NEt2、-N(正丙基)2、-N(环戊基)甲基、哌啶-1-基、吡咯烷-1-基、N-吗啉代、4,4-二氟哌啶-1-基、4-(2-氰乙基)-哌嗪-1-基、2,6-二甲基吗啉-4-基和6-(三氟甲基)-3-杂氮双环[3.1.0]己-3-基。
4.根据权利要求1至3任一项的方法,其中所述防治基于刺激植物抗病毒的天然防御机制。
5.根据权利要求4的方法,其中所述植物抗病毒的天然防御机制为基于RNA沉默的植物防御机制。
6.根据前述权利要求任一项的方法,其中所述方法为预防性方法。
7.根据前述权利要求任一项的方法,其中所述植物选自棉花、亚麻、葡萄藤、水果、蔬菜、农作物、花园和林地的观赏植物以及这些植物各自的基因改良品种。
8.根据前述权利要求任一项的方法,其中所述植物选自茶藨子亚科、胡桃科、桦木科、漆树科、山毛榉科、桑科、木犀科、猕猴桃科、樟科、芭蕉科、茜草科、山茶科、梧桐科、芸香科、茄科、百合科、菊科、伞形科、十字花科、藜科、葫芦科、葱科、蝶形花科、菊科、芸苔科、豆科、蝶形花科、茄科和藜科。
9.根据前述权利要求任一项的方法,其中所述病毒选自以下科或属:花椰菜病毒科、双生病毒科、雀麦花叶病毒科、长线形病毒科、豇豆花叶病毒科、马铃薯Y病毒科、随伴病毒科、番茄丛矮病毒科、弹状病毒科、布尼亚病毒科、分体病毒科、呼肠孤病毒科、毛发状病毒属、香石竹潜病毒属、豌豆耳突花叶病毒属、真菌传杆状病毒属、大麦病毒属、悬钩子病毒属、黄矮病毒属、玉米雷亚朵非纳病毒属、马铃薯X病毒属、南方菜豆花叶病毒属、纤细病毒属、烟草花叶病毒属、烟草脆裂病毒属、发状病毒属、芜菁黄花叶病毒属和伞形植物病毒属。
10.根据前述权利要求任一项的方法,其中所述病毒选自:芜菁花叶病毒、芜菁皱缩病毒、豆英斑驳病毒、花椰菜花叶病毒、烟草花叶病毒、番茄丛矮病毒、水稻齿叶矮缩病毒、黄瓜花叶病毒、大麦黄矮病毒、甜菜黄化病毒、生菜黄化病毒、玉米花叶病毒、花生矮化病毒和马铃薯Y病毒。
11.根据前述权利要求任一项的方法,其中将所述式(I)的化合物通过喷洒施用至植物。
12.根据前述权利要求任一项的方法,其中将所述式(I)的化合物以0.01至5kg/ha的量施用至植物。
13.如权利要求1、2或3所述的式(I)的化合物的用途,用于刺激植物抗病毒的天然防御机制。
14.根据权利要求13的用途,其用于刺激基于RNA沉默的植物防御机制。
15.如权利要求1、2或3所述的式(I)的化合物的用途,其用于在用RNAi构建体转化的基因修饰植物中改善农艺性状和/或提供对病原体、昆虫、害虫的抗性和/或提供胁迫耐受性。
16.式(I)的化合物:
其中
-R1为苯基,其被一个或多个卤素取代;
-R2为-NR’R”基团,其中:
-R’和R”独立地选自(C1-C6)烷基和(C3-C6)环烷基,或
-R’和R”与它们连接的氮原子一起形成取代的哌啶或吗啉,其中所述取代的哌啶或吗啉被一个或多个选自卤素和(C1-C6)烷基的取代基取代,或
-R’和R”与它们连接的氮原子一起形成可被(C1-C6)卤代烷基取代的氮杂双环烷基。
17.式(I)的化合物用作药物:
其中
-R1为苯基,其可被一个或多个卤素取代;
-R2为-NR’R”基团,其中:
-R’和R”独立地选自(C1-C6)烷基和(C3-C6)环烷基,或
-R’和R”与它们连接的氮原子一起形成选自吡咯烷、哌啶、吗啡或哌嗪的5-或6-元杂环,其中所述杂环可被一个或多个选自卤素、(C1-C6)烷基和(C1-C6)氰烷基的取代基取代,或
-R’和R”与它们连接的氮原子一起形成可被(C1-C6)卤代烷基取代的氮杂双环烷基。
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PCT/EP2017/050583 WO2017121809A1 (en) | 2016-01-13 | 2017-01-12 | Use of active substances for controlling virus infection in plants |
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US20190053490A1 (en) | 2019-02-21 |
EA201891591A1 (ru) | 2019-01-31 |
ES2764800T3 (es) | 2020-06-04 |
UA122707C2 (uk) | 2020-12-28 |
WO2017121809A1 (en) | 2017-07-20 |
JP6960927B2 (ja) | 2021-11-05 |
JP2019508381A (ja) | 2019-03-28 |
EP3402333A1 (en) | 2018-11-21 |
AU2017206952B2 (en) | 2021-04-15 |
CN108471747B (zh) | 2021-02-09 |
CA3011340A1 (en) | 2017-07-20 |
BR112018014308A2 (pt) | 2018-12-11 |
MX2018008721A (es) | 2018-09-21 |
KR20180100680A (ko) | 2018-09-11 |
CL2018001888A1 (es) | 2018-11-05 |
PT3402333T (pt) | 2020-01-15 |
EP3402333B1 (en) | 2019-10-30 |
PL3402333T3 (pl) | 2020-09-07 |
ECSP18059520A (es) | 2018-08-31 |
AU2017206952A1 (en) | 2018-08-23 |
EA034906B1 (ru) | 2020-04-06 |
AR110456A1 (es) | 2019-04-03 |
CO2018008451A2 (es) | 2018-09-20 |
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