CN115594641B - 一类含苄基1,2,3-***结构的化合物及其作为杀菌剂的应用 - Google Patents
一类含苄基1,2,3-***结构的化合物及其作为杀菌剂的应用 Download PDFInfo
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- CN115594641B CN115594641B CN202211587729.4A CN202211587729A CN115594641B CN 115594641 B CN115594641 B CN 115594641B CN 202211587729 A CN202211587729 A CN 202211587729A CN 115594641 B CN115594641 B CN 115594641B
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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Abstract
Description
技术领域
本发明涉及含苄基1,2,3-***结构的化合物及其制备方法、包含它们的农药组合物和它们在防治植物病害中的用途;具体而言,本发明涉及可抑制真菌和卵菌附着胞形成的含苄基1,2,3-***结构的化合物及其制备方法和在防治真菌和卵菌引起的植物病害中的用途。
背景技术
植物病害的70~80%是由真菌和卵菌引起的,一种植物上可出现几种甚至几十种不同的真菌和卵菌引起的病害。例如,水稻的纹枯病、稻瘟病、稻曲病、胡麻斑和恶苗病等,小麦的赤霉病、白粉病、条锈病、杆锈病、叶锈病、根腐病和纹枯病等,玉米的大斑病、小斑病、茎基腐、锈病、纹枯病、弯孢霉叶斑病、丝黑穗病、黑粉病等,均是真菌引起的。这些真菌病害危害面积和引起的损失占作物病害的90%以上。除真菌病害外,卵菌引起的病害在许多作物上危害严重,如马铃薯晚疫病、大豆疫霉病、辣椒疫霉病、葡萄霜霉病和黄瓜霜霉病等。
对由真菌和卵菌引起的植物病害,一般多以施用化学药剂作为主要防治手段。目前在化学防治中常用的杀菌剂包括波尔多液、百菌通、百菌清、甲基托布津、多菌灵、嘧菌酯、吡唑醚菌酯、咪鲜胺和三环唑等。其中作为保护剂使用的有波尔多液、百菌清、嘧菌酯、咪鲜胺和三环唑等,兼有保护剂和治疗剂效果的包括百菌通、甲基托布津、多菌灵和吡唑醚菌酯等。保护剂与治疗剂的分子结构多种多样,但大多数包括含氮杂环结构,其中较为常见的是嘧啶、咪唑、吡唑和1,2,4-***。
三氮唑类农用化合物常用的结构为1,2,4-***。包含该类结构的化合物包括以苯醚甲环唑和戊唑醇等为代表的内吸性杀菌剂,该类杀菌剂通过抑制病原真菌甾醇的脱甲基化来完成病害防控。目前,有关1,2,4-***类化合物的研究报道非常广泛,而缺乏针对1,2,3-***类化合物的杀菌的研究。1,2,3-***类化合物作为新型的具有杀菌潜力的化合物,逐渐成为杀菌剂研发的新方向。同时,1,2,3-***类化合物作为1,2,4-***类化合物的电子等排体,在农用杀菌剂领域表现出了潜在的研究价值。
由真菌和卵菌引起的病害大多数在田间主要通过无性孢子传播。其中不少真菌或卵菌的无性孢子,如稻梨孢菌和炭疽病菌分生孢子,在着陆植物体表后发芽,在发芽管顶端形成附着胞,并通过附着胞膨压进入植物组织、引起病害。附着胞是许多植物和动物病原真菌形成的一种特异侵染结构,因此,有不少研究在揭示真菌附着胞形成的分子机理,以期为绿色杀菌剂开发提供靶标。目前,生产上广泛用于稻瘟病防治的三环唑就是通过抑制稻梨孢菌附着胞的黑色素形成,从而达到控制病害的目的。但是目前抑制附着胞形成的杀菌剂种类很少,因此,创制附着胞形成的抑制剂对于研发植物真菌和卵菌病害的杀菌剂具有重大意义。
目前关于评价候选化合物杀菌活性的通用方法包括测定候选化合物对病原真菌营养菌丝生长的抑制率,进而推断其对病原真菌的防治效果。但是,该方法在很大程度上不能客观地反映候选化合物的功能,尤其是对于形成附着胞类的病原真菌和卵菌。以能形成附着胞的模式病原真菌—稻瘟菌为例,据已有文献报道,稻瘟菌营养菌丝的生长速率与其致病能力没有明显的相关性,而分生孢子萌发、芽管生长和附着胞形成和成熟直接决定稻瘟菌的致病能力。
由于自然界中的致病菌针对某种特定的杀菌剂会不断产生耐药性或者在使用过程中也会发现某些杀菌剂存在环境问题,因此,开发具有更好的应用性质的杀菌剂是本领域所面对的问题。
发明内容
针对现有技术中存在的不利之处,本发明的目的在于提供一种具有防治真菌和卵菌引起的植物病害的含苄基1,2,3-***结构的化合物。
因此,本发明的第一方面提供了式(I)所示的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物:
,
其中,
R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷基。
根据本发明的实施方案,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C3烷基、C1-C3烷氧基或卤代C1-C3烷基。
根据本发明优选的实施方案,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、Br、Cl、F、CF3或OCH3。
在一个优选的实施方案中,R1、R2、R4和R5为H;R3为Br、Cl、F、CF3或OCH3。
在一个优选的实施方案中,R1、R4和R5为H;R2、R3相同或不同,彼此独立地选自Br、Cl、F、CF3或OCH3。
在一个优选的实施方案中,R1、R4和R5为H;R2、R3为Cl。
本发明的第二方面提供了一种农药组合物,例如杀菌剂、除草剂、植物保护剂组合物,其包含作为活性成分的式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物中的一种、两种或更多种。
根据本发明的一些实施方案,所述农药组合物是杀菌剂,所述杀菌剂中含有选自式(I)的化合物和任选的农业上可接受的辅料。优选地,农药组合物作为植物保护剂,用于预防植物病害或使植物免受植物病害的侵害,所述植物病害包括稻瘟病、炭疽病、霜霉病、疫霉病和白粉病。更优选地,所述病害选自水稻稻瘟病、辣椒炭疽病、瓜类霜霉病如黄瓜霜霉病、草莓炭疽病、玉米炭疽病、马铃薯晚疫病、辣椒疫霉病和小麦白粉病。
根据本发明的一些实施方案,所述组合物中活性成分式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物的重量百分含量为0.1-99.9%,例如为0.5-99%。
根据本发明的一些实施方案,所述组合物中还包括农业,和/或林业,和/或畜牧业,和/或园艺学上可接受的载体中的一种、两种或者更多种。
根据本发明的一些实施方案,所述组合物可以以制剂的形式施用。
例如,式(I)的化合物作为活性成分溶解或分散于载体中或配制成制剂以便作为除草使用时更易于分散。
根据本发明的一些实施方案,所述制剂包括但不限于如下形式:颗粒剂、可湿性粉剂、油悬剂、水悬剂、水乳剂、水剂、乳油或微胶囊等。
根据本发明的一些实施方案,所述组合物中还可以加入一种液体或固体载体,及任选的表面活性剂。
本发明的第三方面提供了式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物中的一种、两种或更多种的用途,其用于防治水稻稻瘟病、辣椒炭疽病、瓜类霜霉病如黄瓜霜霉病、草莓炭疽病、玉米炭疽病、马铃薯晚疫病、辣椒疫霉病和小麦白粉病。
根据本发明的一些实施方案,本发明的式(I)的化合物、其立体异构体、消旋体、互变异构体、同位素标记物、氮氧化物、农业上可接受的盐或酯、溶剂合物或者农业上可接受的盐的溶剂合物的有效量为每公顷10克到1000克,优选有效量为每公顷20克到500克。
本发明的有益效果
本发明公开了1,2,3-***衍生物,其具有抑制真菌和卵菌附着胞形成的活性。且式(I)的化合物可有效地抑制真菌和卵菌的分生孢子萌发,芽管生长或附着胞的形成。
本发明人发现,1,2,3-***类化合物可以通过抑制分生孢子萌发,芽管生长或附着胞形成,有效阻止病菌侵染植物,进而用于防治危害巨大的植物病害,包括:稻瘟病、炭疽病、霜霉病、疫霉病和白粉病,提供了植物保护用药的新选择。
本发明人发现,本发明具有特定结构的1,2,3-***类化合物在10-1000ppm的浓度内即可有效抑制病原真菌和卵菌附着胞的形成。
本发明人发现,本发明具有特定结构的1,2,3-***类化合物在10-1000ppm的浓度内可在稻瘟病和马铃薯晚疫病的田间施用中产生相应防效。
术语和解释
除非另外指明,否则本文所有科技术语具有的含义与所属技术领域的技术人员通常理解的含义相同。除非另外指明,否则本文中以全文或部分引用的所有专利和非专利文献或以其他方式公开的材料均通过引用方式并入本文。
在本文中,在描述一个/种、两个/种或更多个/种时,“更多个/种”应当是指大于2的情形,例如代表大于等于3的整数情形,例如3、4、5、6、7、8、9或10。
在本文中,术语“任选(的/地)”表示所述特征存在或不存在这两种情形。
术语“卤素”表示氟、氯、溴和碘。
术语“C1-C12烷基”表示具有1、2、3、4、5、6、7、8、9、10、11或12个碳原子的直链和支链饱和烃基,包括甲基、乙基、正丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、2-甲基丁基、1-甲基丁基、1-乙基丙基、1,2-二甲基丙基、新戊基、1,1-二甲基丙基、正己基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、2-乙基丁基、1-乙基丁基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、2,3-二甲基丁基、1,3-二甲基丁基或1,2-二甲基丁基或它们的异构体。
术语“C1-C12烷氧基”指-O-C1-C12烷基,其中C1-C12烷基的定义如上段所述。烷氧基的非限制性实例包括:甲氧基、乙氧基、丙氧基、丁氧基、环丙氧基、环丁氧基、环戊氧基、环己氧基。
术语“卤代C1-C12烷基”指上述C1-C12烷基上至少一个H原子被卤素取代的情况。卤代C1-C12烷基的非限制性实例包括:三氟甲基。
应当理解,可在参考文献(包括Carey and Sundberg,"ADVANCED ORGANICCHEMISTRY 4TH ED." Vols. A (2000) and B (2001), Plenum Press, New York)中找到对标准化学术语的定义。除非另有说明,否则采用本领域技术范围内的常规方法,如质谱、NMR、IR和UV/Vis光谱法和药理学方法。除非另有具体定义,否则本文在分析化学、有机合成化学以及药物和药物化学的有关描述中采用的术语是本领域已知的。可在化学合成、化学分析、药物制备、制剂和递送,以及对患者的治疗中使用标准技术。例如,可利用厂商对试剂盒的使用说明,或者按照本领域公知的方式或本申请的说明来实施反应和进行纯化。通常可根据本说明书中引用和讨论的多个概要性和较具体的文献中的描述,按照本领域熟知的常规方法实施上述技术和方法。在本说明书中,可由本领域技术人员选择基团及其取代基以提供稳定的结构部分和化合物。
本文所用术语“农业上可接受的盐”是指保留了指定化合物的游离酸和游离碱的生物效力,并且在生物学或其它方面上没有不良作用的盐。本申请中的农业上可以接受的盐包括一般在农业、林业、畜牧业和/或园艺领域能够使用的盐,例如钠盐、钾盐、钙盐、锌盐等。农业上可接受的盐尤其是指将母体化合物中的酸性基团和/或碱性基团转换成盐的形式。
农业上可接受的盐包括,但不仅限于,衍生自酸性基团如羧基、磺基、酚羟基等的无机或有机碱盐类。根据本发明的农业上可接受的盐可以由母体化合物合成,即母体化合物中的酸性基团与适量的碱,例如1-4当量的碱在一个溶剂***中反应;或类似地在母体化合物中存在碱性基团如氨基的情况下,与合适的无机或有机酸所成的盐类;在母体化合物既包含酸性中心(例如羧基)又包含碱性中心(例如氨基)的情况下,则其还可以形成内盐。合适的盐列举在Remingtong’s Pharmaceutical Scicences, 17thed., Mack PublishingCompany, Easton, Pa., 1985, p. 1418和Journal of Pharmaceutical Science, 66, 2(1977)中,例如钠盐。
本发明的化合物可以溶剂合物(如水合物)的形式存在,其中本发明的化合物包含作为所述化合物晶格的结构要素的极性溶剂,特别是例如水、甲醇或乙醇。极性溶剂特别是水的量可以化学计量比或非化学计量比存在。
根据其分子结构,本发明的化合物可以是手性的,因此可能存在各种对映异构体形式。因而这些化合物可以以消旋体形式或光学活性形式存在。本发明的化合物或其中间体可以通过本领域技术人员公知的化学或物理方法分离为对映异构体化合物,或者以此形式用于合成。在外消旋的胺的情况中,通过与光学活性的拆分试剂反应,从混合物制得非对映异构体。适当的拆分试剂的示例是光学活性的酸,例如R和S形式的酒石酸、二乙酰酒石酸、二苯甲酰酒石酸、扁桃酸、苹果酸、乳酸、适当的N-保护的氨基酸(例如N-苯甲酰脯氨酸或N-苯磺酰基脯氨酸)或各种光学活性的樟脑磺酸。借助光学活性的拆分试剂(例如固定在硅胶上的二硝基苯甲酰基苯基甘氨酸、三乙酸纤维素或其它碳水化合物的衍生物或手性衍生化的异丁烯酸酯聚合物),也可有利地进行色谱对映体拆分。用于此目的的适当的洗脱剂是含水或含醇的溶剂混合物,例如,己烷/异丙醇/乙腈。
术语“互变异构体”是指因分子中某一原子在两个位置迅速移动而产生的官能团异构体。本发明化合物可表现出互变异构现象。互变异构的化合物可以存在两种或多种可相互转化的种类。质子移变互变异构体来自两个原子之间共价键合的氢原子的迁移。互变异构体一般以平衡形式存在,尝试分离单一互变异构体时通常产生一种混合物,其理化性质与化合物的混合物是一致的。平衡的位置取决于分子内的化学特性。例如,在很多脂族醛和酮如乙醛中,酮型占优势;而在酚中,烯醇型占优势。本发明包含化合物的所有互变异构形式。
可以根据已知的方法,例如通过萃取、过滤或柱层析来分离相应的稳定异构体。
术语“杀菌剂”在本文中包括能够有效控制和/或杀灭对植物有害的病原微生物如细菌、真菌、卵菌、立克次氏体、支原体、病毒和/或藻类等的化学品和/或制剂。
术语“农药组合物”表示含有一种、两种或更多种本文所述化合物或其农业上可接受的盐或前体药物与其他活性或非活性组分如辅料的混合物,特别地例如含有载体和赋形剂。
由于其积极的特性,式(I)化合物可有利地用于保护耕地和非耕地中重要的作物,以及人类常去的环境免于有害病原体的侵害。
为获得理想效果,式(I)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、有害病原体的类型、感染程度、气候条件、施药方法和采用的剂型。
本文中所述剂型或组合物成分的选择应与有效成分的物理性质,应用方式和环境因素例如土壤类型,湿度与温度相一致。
有用的剂型包括液剂如溶液(包括乳油),悬浮剂,乳液(包括微乳剂和/或悬浮剂)等等,它们可任选被粘稠成胶状物。有用的剂型也包括固体的如粉剂,粉末,颗粒剂,片剂,丸剂,薄膜等,它们可以是水分散性的(“可湿的”) 或水溶性的。有效成分可被微囊化再制成悬浮剂或固体剂型;另外有效成分的整个剂型也可以成胶囊化。成胶囊可以控制或延缓释放有效成分。可喷雾剂型可在适当的介质中冲稀,使用的喷雾体积为每公顷大约一百至几百升。高浓度的组合物主要用作进一步加工的中间体。
典型的固体稀释剂在Watkins等人,Handbook of Insecticide Dust Diluentsand Carriers,2nd Ed.,Dorland Books,Caldwell,New Jersey 中作了介绍。典型的液体稀释剂在Marsden,SolventsGuide,2nd Ed.,Interscience,New York,1950 中作了介绍。McCutcheon′s Detergents and Emulsifiers Annual,Allured Publ.Corp.,Ridgewood,New Jersey,以及Sisely and Wood,Encyclopedia of Surface Active Agents,ChemicalPubl.Co.,Inc.,New York,1964,列出了表面活性剂和推荐应用。所有剂型都可含有少量的添加剂,以减少泡沫,结并,腐蚀,微生物的生长等,或加增稠剂以增加粘度。
表面活性剂包括,例如,聚乙氧基化醇,聚乙氧基化烷基酚,聚乙氧基化脱水山梨醇脂肪酸酯,磺化丁二酸二烷基酯,硫酸烷基酯,烷基苯磺酸盐,有机硅烷,N,N-二烷基牛磺酸酯,木质素磺酸盐,萘磺酸盐用醛缩合物,聚羧酸酯和聚氧乙烯/聚氧丙烯嵌段共聚物。
固体稀释剂例如包括粘土,如膨润土、蒙脱石、硅镁土、高岭土、淀粉、糖、二氧化硅、滑石、硅藻土、尿素、碳酸钙、碳酸钠、碳酸氢钠、和硫酸钠;液体稀释剂例如包括、水、N,N-二甲基甲酰胺、二甲砜、N-烷基吡咯啉酮、乙二醇、聚丙二醇、石腊、烷基苯、烷基萘、橄榄油、蓖麻油、亚麻籽油、桐油、芝麻油、玉米油、花生油、棉籽油、大豆油、菜籽油和可可油、脂肪酸酯;酮类如环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮;和醇类如甲醇、环己醇、十二烷醇和四氢呋喃醇。
溶液、悬浮液、乳油等可以通过简单地混合各组分来制备。粉剂和细粉可通过混合和通常在锤磨或液能磨中通过研磨来制备悬浮剂一般通过湿磨来制备。
本文中,对于所述组合物的某些应用,例如在农业上可在本发明的组合物中加入一种、两种或多种其它的杀菌剂、杀虫杀螨剂、除草剂、植物生长调节剂、植物保护剂或肥料等,由此可产生附加的优点和效果。
式(I)化合物可以以未经改变的形式使用或优选与制剂领域中常用的载体和助剂一起使用。
因此,本发明还涉及防治或保护对抗致植物病微生物的组合物,其包含式(I)的化合物和惰性载体,以及防治或预防有用植物被致植物病微生物侵染的方法,其中将包含作为活性成分的式(I)的化合物和惰性载体的组合物施用至植物、至其部分或其处所。
为此,式(I)化合物和惰性载体以已知方式方便地配制为乳油、可包衣糊剂、可直接喷雾或可直接稀释的溶液剂、稀释乳剂、可湿性粉剂、可溶性粉剂、粉剂、颗粒剂以及例如在聚合物质中胶囊化。与组合物的类型相似地,同样根据目标对象和主要环境来选择施用方法,比如喷雾、雾化、喷粉、撒播、被覆或浇注。该组合物还可以包含其它助剂比如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂以及肥料、微量营养素供体或其它用来获得特殊效果的配制剂。
适宜的载体和助剂可以是固体或液体并且是制剂技术中有用的物质,例如天然的或经再生的矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或肥料。
制剂,也即包含式(I)化合物和根据需要的固体或液体助剂的组合物,是以已知方式制备的:通常通过将该化合物与增量剂紧密混合和/ 或磨粉,所述增量剂例如是溶剂、固体载体并任选是表面活性化合物(表面活性剂)。
农业化学制剂通常包括0.1到99%重量、优选0.1到95%重量的式(I)的化合物,99.9到1%重量、优选99.8到5%重量的固体或液体助剂,以及0到25%重量、优选0.1到25%重量的表面活性剂。
本发明所述1,2,3-***类衍生物可以与本领域常用的任意一种或两种或更多种农药活性成分组合,以用于防治农业和林业以及园艺植物病害。
所述农药活性成分可以选自:苯并噻二唑、噻酰菌胺、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺、3,4-二氯异噻唑-5-甲酸、3,4-二氯异噻唑-5-甲酸钠、3,4-二氯异噻唑-5-甲酸乙酯、病毒唑、安托芬、宁南霉素、水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、萎锈灵、氧化萎锈灵、麦锈灵、甲呋酰胺、灭锈胺、氟酰胺、呋吡菌胺、噻呋酰胺、啶酰菌胺、吡噻菌胺、吡唑萘菌胺、联苯吡菌胺、氟吡菌酰胺、氟唑环菌胺、氟唑菌酰胺、氟唑菌苯胺、苯丙烯氟菌唑、异丙噻菌胺、氟唑菌酰羟胺、氟苯醚酰胺、氟醚菌酰胺、双炔酰菌胺、苯酰菌胺、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、***醇、灭菌唑、联苯***醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、多菌灵、苯菌灵、甲基硫菌灵、***酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、丰索磷、虫线磷、除线磷、丁硫环磷、杀线威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑等。
附图说明
图1为生物学实施例G2中化合物A-007对湘晚籼11的预防喷雾接种和治疗喷雾接种测试结果,图中从左到右分别为:在不喷雾小分子药剂下接种7天后的测试结果;A-007在接种7天后的预防喷雾接种测试结果;A-007在接种7天后的治疗喷雾接种测试结果。
图2为化合物A-003的核磁共振氢谱图。
图3为化合物A-007的核磁共振氢谱图。
具体实施方式
下文将结合具体实施例对本发明的制备方法做更进一步的详细说明。应当理解,下列实施例仅为示例性地说明和解释本发明,而不应被解释为对本发明保护范围的限制。凡基于本发明的内容所实现的技术方案均涵盖在本发明旨在保护的范围内。
除非另外指明,否则下述实施例中所使用的实验方法均为本领域常规方法;下述实施例中所使用的试剂、原料、仪器、设备等,均可从商业途径获得。
使用的试剂
除乙酸乙酯、石油醚及二氯甲烷以外,其余试剂均经过无水,无氧处理后使用。所使用的合成前体从毕得医药集团、安耐吉化学集团、阿拉丁集团购买,所使用的金属催化剂均从萨恩化学集团公司购买。
仪器和设备
用Bruker DPX500和Varian Mercury 400两种核磁共振仪测定1H、13C、19F NMR图谱,其中1H NMR和13C NMR分析中,以四甲基硅烷(TMS)作为内标,化学位移的单位均为ppm。高分辨质谱法由Bruker Apex IV FTMS spectrometer, Thermo Q-Exactive HRMS仪器进行测定。红外光谱法由Nicolet AVATAR 330 FT-IR进行测定。
通过制备实施例和生物学实施例示例性说明本发明的代表性式(I)的1,2,3-***类化合物的合成与生物活性及相关应用。
根据以下通用合成路线IA,本领域技术人员可以分别采用对应的本领域常规和已知的起始原料合成下表1中的各种化合物并对其进行表征。
通用合成路线IA(适用于制备下表1中的A系列编号的化合物):
将4-(4-甲基哌嗪)苯甲醛置于反应瓶中,向其中加入30.0毫升乙醇,开始搅拌,室温下缓慢加入硼氢化钠(40.0 mmol)。40摄氏度下搅拌1小时。TLC检测反应完毕,加入水和二氯甲烷萃取,饱和食盐水洗,合并有机层,无水硫酸钠干燥。有机层进行浓缩,使用柱层析进行分离,获得化合物B-A-1。
将化合物B-A-1 (20.0 mmol)置于反应瓶中,向其中加入30.0毫升二氯甲烷,搅拌下加入三乙胺(40.0 mmol)和甲基磺酰氯(30.0 mmol),室温下搅拌。TLC检测反应完毕,体系浓缩后加入30毫升N,N-二甲基甲酰胺,冰水浴下分批次加入叠氮化钠(21.0 mmol),50摄氏度下反应。TLC检测反应完毕,加入水和二氯甲烷萃取,饱和食盐水洗,合并有机层,无水硫酸钠干燥。有机层进行浓缩,使用柱层析进行分离,获得化合物B-A-2。
将取代的苯酚(20.0 mmol)置于反应瓶中,向其中加入30.0毫升丙酮,搅拌下加入碳酸钾(40.0 mmol),3-溴丙炔(21.0 mmol),TLC检测反应完毕。过滤,将滤液减压浓缩,柱层析分离残余物,获得化合物B-A-3。
将化合物B-A-3(10.0 mmol)置于反应瓶中,向其中加入8.0毫升N,N-二甲基甲酰胺,搅拌下加入五水硫酸铜(2.0 mmol),叠氮化合物B-A-2 (11.0 mmol),抗坏血酸钠(20.0mmol)和2.0毫升水。TLC检测反应完毕,过滤,将滤液浓缩后加入水和二氯甲烷萃取,饱和食盐水洗,合并有机层,无水硫酸钠干燥,浓缩,柱层析分离残余物,获得下表1中的A系列编号的化合物。
化合物实施例
实施例1
第一步:
取1.0克化合物a-1于反应瓶中,加入10毫升无水乙醇,开始搅拌,室温下缓慢加入373毫克硼氢化钠,40摄氏度下搅拌1小时。TLC检测反应完毕,加入20毫升水,再使用20毫升二氯甲烷萃取三次,合并有机层,使用30毫升饱和氯化钠溶液洗涤有机层,使用无水硫酸钠进行干燥。有机层进行浓缩,使用柱层析进行分离,得到0.81克化合物a-2。
第二步:
取1.0克化合物a-2于反应瓶中,加入10毫升二氯甲烷,搅拌下滴加1.35毫升三乙胺和0.57毫升甲基磺酰氯,室温反应1.5小时。TLC检测反应完毕,体系浓缩后加入10毫升N,N-二甲基甲酰胺,冰水浴下缓慢加入331毫克叠氮化钠,50摄氏度下反应。反应12小时后TLC检测反应完毕,加入30毫升水淬灭反应,使用30毫升二氯甲烷萃取三次,有机层合并加入30毫升饱和氯化钠溶液洗涤,随后加入无水硫酸钠干燥。柱层析分离得到570毫克化合物a-3。
第三步:
取0.50克化合物a-4于反应瓶中,加入10毫升丙酮,搅拌下加入1.47克碳酸钾,665毫克3-溴丙炔,回流反应,TLC检测反应完毕。过滤,减压浓缩,柱层析分离得594毫克化合物a-5。
第四步:
取250毫克化合物a-5于反应瓶中,加入4.0毫升N,N-二甲基甲酰胺,搅拌下加入95毫克五水硫酸铜,481毫克化合物a-3,750毫克抗坏血酸钠和1.0毫升水,50摄氏度反应,TLC检测反应完毕。过滤,浓缩后加入水和二氯甲烷萃取,饱和食盐水洗合并有机层,无水硫酸钠干燥,柱层析分离得509毫克化合物A-001。
以类似于实施例1的方法,参考通用合成路线IA,通过对原料进行替换,获得下表1中以A编号的化合物。
表1
化合物 | <![CDATA[R<sub>1</sub>]]> | <![CDATA[R<sub>2</sub>]]> | <![CDATA[R<sub>3</sub>]]> | <![CDATA[R<sub>4</sub>]]> | <![CDATA[R<sub>5</sub>]]> |
A-002 | H | H | Br | H | H |
A-003 | H | H | Cl | H | H |
A-004 | H | H | F | H | H |
A-005 | H | H | <![CDATA[CF<sub>3</sub>]]> | H | H |
A-006 | H | H | <![CDATA[OCH<sub>3</sub>]]> | H | H |
A-007 | H | Cl | Cl | H | H |
表2:化合物结构表征数据
表2显示化合物A-001及表1中所列出的化合物的质谱数据和1H-NMR数据。除非另有说明,否则将氘代氯仿(CDCl3)或氘代二甲亚砜(DMSO
-d 6)用作测试溶剂。
在表2以及下文的全部描述中,“NMR”意指核磁共振谱,MS代表质谱。并使用下述缩写:
s = 单峰,br = 宽峰,d = 双峰,dd = 双二重峰,t = 三重峰,td = 三二重峰,q= 四重峰,m = 多重峰。
表2
化合物 | <![CDATA[<sup>1</sup>H-NMR数据]]> | <![CDATA[MS[M+H]<sup>+</sup><!-- 10 -->]]> |
A-001 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.51 (s,1H), 7.31 – 7.25 (m,2H), 7.21 (d, <i>J</i> = 8.2Hz, 2H), 7.00 – 6.92(m, 3H), 6.89 (d, <i>J</i>= 8.2 Hz, 2H), 5.44(s, 2H), 5.16 (s, 2H),3.52 – 3.38 (m, 4H),3.03 – 2.87 (m, 4H),2.61 (s, 3H).]]> | 364.23 |
A-002 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.38 – 7.34 (m,2H), 7.22 – 7.18 (m,2H), 6.92 – 6.88 (m,2H), 6.87 – 6.82 (m,2H), 5.44 (s, 2H),5.14 (s, 2H), 3.45 –3.39 (m, 4H), 2.98 –2.81 (m, 4H), 2.58(s, 3H).]]> | 442.11 |
A-003 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.24 – 7.18 (m,4H), 6.92 – 6.87 (m,4H), 5.44 (s, 2H),5.13 (s, 2H), 3.42 –3.35 (m, 4H), 2.90 –2.76 (m, 4H), 2.53 (s,3H).]]> | 398.18 |
A-004 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.48 (s,1H), 7.23 – 7.18 (m,2H), 6.99 – 6.93 (m,2H), 6.92 – 6.87 (m,4H), 5.44 (s, 2H),5.13 (s, 2H), 3.47 –3.39 (m, 4H), 2.98 –2.83 (m, 4H), 2.59 (s,3H).]]> | 382.21 |
A-005 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.53 (d, <i>J</i> =8.7 Hz, 2H), 7.50 (s,1H), 7.22 – 7.19 (m,2H), 7.03 (d, <i>J</i> = 8.7Hz, 2H), 6.92 – 6.88(m, 2H), 5.45 (s, 2H),5.21 (s, 2H), 3.43 –3.37 (m, 4H), 2.98 –2.77 (m, 4H), 2.56 (s,3H).]]> | 432.22 |
A-006 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.23 – 7.18 (m,2H), 6.92 – 6.88 (m,4H), 6.84 – 6.80 (m,2H), 5.44 (s, 2H),5.12 (s, 2H), 3.76 (s,3H), 3.48 – 3.33 (m,4H), 3.01 – 2.74 (m,4H), 2.56 (s, 3H).]]> | 394.24 |
A-007 | <![CDATA[<sup>1</sup>H NMR (500 MHz, 氘代氯仿) δ 7.47 (s,1H), 7.31 (d, <i>J</i> = 8.8Hz, 1H), 7.20 (d, <i>J</i> =8.3 Hz, 2H), 7.06(d, <i>J</i> = 3.0 Hz, 1H),6.90 (d, <i>J</i> = 8.3 Hz,2H), 6.83 (dd, <i>J</i> =8.8, 3.0 Hz, 1H), 5.44(s, 2H), 5.13 (s, 2H),3.41 – 3.32 (m, 4H),2.85 – 2.72 (m, 4H),2.51 (s, 3H).]]> | 432.14 |
生物学实施例
鉴于稻瘟菌通常经由附着胞介导侵染植物的模式及能在室内人工培养,因此可以以稻瘟菌为模型病原真菌进行本发明化合物对稻瘟菌分生孢子萌发、芽管生长或附着胞形成抑制测试。通过以下实施例示例性说明本发明化合物的相关活性。
生物学实施例G1:含苄基结构的1,2,3-***类化合物对稻瘟菌分生孢子萌发和附着胞形成的抑制作用
a.待测病菌:稻瘟菌(
Magnaporthe oryzae)菌株P131
b.试验方法:
1)稻瘟菌分生孢子的产生:将待测的稻瘟菌菌株P131点接到西红柿燕麦平板(OTA)上,置于28℃恒温光照培养箱培养。3-5天后将OTA上的稻瘟菌菌落充分打断,然后均匀地涂布到新的OTA上,于28℃恒温光照培养箱培养。当肉眼可见新生菌丝长出培养基表面时(一般为1-2天),用棉签轻轻将菌丝打断,并用灭菌水冲洗干净,晾干。用单层纱布盖上培养皿,于28℃光照培养48小时,在OTA表面产生大量的分生孢子。
2)配制稻瘟菌分生孢子悬浮液:用无菌水将OTA上的培养物洗脱下来,用三层擦镜纸过滤,滤液为分生孢子液。用血球计数板将分生孢子液中的分生孢子浓度调整为2小105个/mL。
3)将待测化合物按不同浓度梯度加入到分生孢子悬浮液中,分别配制成工作浓度为200ppm,50ppm和25ppm的溶液,并依次点在疏水玻片上。每个玻片上点接四个点,黑暗保湿处理。接种12小时后在显微镜下观察并计数分生孢子萌发率和附着胞形成率。
4)统计与分析:每个疏水玻片计数三个接种点,每个接种点计数其中心的100个分生孢子的萌发个数和附着胞形成个数。计算三组数据平均值,得出分生孢子萌发率和附着胞形成率。
表3显示本发明化合物的生物学实施例G1的数据,其中“-”代表在200ppm无抑制效果,“+”代表200ppm抑制效果低于40%,“++”代表在50ppm抑制效果高于40%,“+++”代表25ppm抑制效果大于70%。
表3
化合物 | 分生孢子萌发 | 附着胞形成 |
A-001 | + | + |
A-002 | + | + |
A-003 | ++ | +++ |
A-004 | + | + |
A-005 | - | + |
A-006 | + | ++ |
A-007 | +++ | +++ |
生物学实施例G2:含苄基1,2,3-***结构的化合物对稻瘟病的预防和治疗作用—水稻盆栽实验
水稻的准备:准备感病品种CO39和湘晚籼11,取四叶一心的水稻幼苗置于接种箱中待用。
稻瘟菌分生孢子的产生:将稻瘟菌菌株P131点接到西红柿燕麦平板(OTA)上,置于28℃恒温光照培养箱培养。3-5天后将OTA上的稻瘟菌菌落充分打断,然后均匀地涂布到新的OTA上,于28℃恒温光照培养箱培养。当肉眼可见新生菌丝长出培养基表面时(一般为1-2天),用棉签轻轻将菌丝打断,并用灭菌水冲洗干净,晾干。用单层纱布盖上培养皿,于28℃光照培养48小时,即在OTA表面产生大量的分生孢子。
配制稻瘟菌分生孢子悬浮液:用无菌水将OTA上的培养物洗脱下来,用三层擦镜纸过滤,滤液为分生孢子液。5000rpm室温离心5分钟。将沉淀的分生孢子悬浮于明胶中,用血球计数板将分生孢子浓度调整为5×104个/mL。
待测化合物溶液的制备:将待测化合物母液加入到制备好的稻瘟菌分生孢子液中,稀释至其为200ppm的工作浓度;将待测化合物母液稀释至其为200ppm的工作浓度。
预防喷雾接种:将稻瘟菌分生孢子与小分子药剂的混合物喷雾接种水稻感病品种湘晚籼11和CO39,每个处理喷雾15mL混合物。黑暗保湿培养36小时,然后进行正常培养。接种7天后,评价待测化合物对稻瘟病的预防效果(表4)。
治疗喷雾接种:将稻瘟菌分生孢子喷雾接种水稻感病品种湘晚籼11,每个处理喷雾15mL小分子药剂。黑暗保湿培养36小时,然后进行正常培养。接种7天后,评价待测化合物对稻瘟病的治疗效果(表5)。
参照农业行业标准“水稻稻瘟病抗性田间监测技术规程”(NYT3685-2020)进行稻瘟病叶瘟病害调查,具体标准如下:0级:全叶片无病;1级:叶片上有针尖大小的褐色坏死斑;2级:叶片上有较大(直径1mm~2mm)的褐色坏死斑,但无典型的病斑;3级:有典型的稻瘟病病斑,病斑面积<2%;4级:有典型的稻瘟病病斑,2%≤病斑面积<5%;5级:有典型的稻瘟病病斑,5%≤病斑面积<10%;6级:有典型的稻瘟病病斑,10%≤病斑面积<25%;7级:有典型的稻瘟病病斑,25%≤病斑面积<50%;8级:有典型的稻瘟病病斑,50%≤病斑面积<75%;9级:有典型的稻瘟病病斑,病斑面积≥75%。
表4显示本发明化合物的生物学实施例G2的数据。
表4
化合物 | 病害等级 |
A-001 | 4 |
A-002 | 3 |
A-003 | 1 |
A-004 | 5 |
A-005 | 7 |
A-006 | 2 |
A-007 | 0 |
表5显示本发明化合物的生物学实施例G2的数据。
表5
化合物 | 病害等级 |
A-001 | 6 |
A-002 | 7 |
A-003 | 6 |
A-004 | 7 |
A-005 | 7 |
A-006 | 6 |
A-007 | 5 |
生物学实施例G3:含苄基1,2,3-***结构的化合物对小麦白粉病的防治作用—小麦盆栽实验
小麦的准备:“小偃6号”感白粉病品种小麦幼苗正常培养至2叶期后置于接种箱中待用。同时准备已感染白粉菌系63号的“小偃6号”小麦幼苗,继续进行培养。
喷雾工作液的制备:将待测化合物母液加入水中,稀释至其为200ppm的工作浓度。
喷雾接种:将喷雾工作液喷施于小麦幼苗,喷雾后放置阴凉处自然晾干。将发病小麦叶片上24小时内产生的白粉病菌新鲜孢子均匀抖落接种于处理的盆栽小麦苗,每处理3盆,每盆10株。之后置于适宜条件继续培养。接种6天后评价待测化合物的防治效果。
表6显示本发明化合物的生物学实施例G3的数据,参照分级标准对小麦白粉病病情进行病害调查,具体标准如下:0级:无病;1级:病斑面积占整片叶面积的5%以下;3级:病斑面积占整片叶面积的6%~15%;5级:病斑面积占整片叶面积的16%~25%;7级:病斑面积占整片叶面积的26%~50%;9级:病斑面积占整片叶面积的50%以上。
表6
化合物 | 病害等级 |
A-001 | 5 |
A-002 | 3 |
A-003 | 3 |
A-004 | 3 |
A-005 | 7 |
A-006 | 3 |
A-007 | 1 |
由上述结果可知,本发明化合物对稻瘟菌分生孢子萌发和附着胞的形成具有抑制作用,且化合物A-007抑制效果明显最优。在对水稻叶片稻瘟病的喷雾接种试验中,本发明化合物具有明显的治疗效果。本发明化合物对稻瘟病不仅具有好的预防效果,还具有一定的治疗效果。
Claims (10)
1.式(I)所示的化合物:
,
其中,
R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷基。
2.根据权利要求1所述的化合物,其特征在于,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、卤素、C1-C3烷基、C1-C3烷氧基或卤代C1-C3烷基。
3.根据权利要求1或2所述的化合物,其特征在于,R1、R2、R3、R4和R5相同或不同,彼此独立地选自H、Br、Cl、F、CF3或OCH3。
4.根据权利要求3所述的化合物,其特征在于,R1、R2、R4和R5为H;R3为Br、Cl、F、CF3或OCH3。
5.根据权利要求3所述的化合物,其特征在于,R1、R4和R5为H;R2、R3相同或不同,彼此独立地选自Br、Cl、F、CF3或OCH3。
6.根据权利要求3所述的化合物,其特征在于,R1、R4和R5为H;R2、R3为Cl。
7.一种农药组合物,其特征在于,包含作为活性成分的权利要求1-6任一项所述的化合物。
8.根据权利要求7所述的农药组合物,其特征在于,所述农药组合物作为植物保护剂用于预防植物病害或使植物免受植物病害的侵害,所述植物病害包括:稻瘟病、炭疽病、霜霉病、疫霉病和白粉病。
9.根据权利要求8所述的农药组合物,其特征在于,所述植物病害选自:水稻稻瘟病、辣椒炭疽病、瓜类霜霉病、草莓炭疽病、玉米炭疽病、马铃薯晚疫病、辣椒疫霉病和小麦白粉病。
10.根据权利要求7-9任一项所述的农药组合物,其特征在于,所述组合物中活性成分式(I)所示的化合物的重量百分含量为0.1-99.9%。
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