CN112624965B - 一种新型肟类衍生物及其在农业中应用 - Google Patents
一种新型肟类衍生物及其在农业中应用 Download PDFInfo
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- CN112624965B CN112624965B CN201910903954.6A CN201910903954A CN112624965B CN 112624965 B CN112624965 B CN 112624965B CN 201910903954 A CN201910903954 A CN 201910903954A CN 112624965 B CN112624965 B CN 112624965B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
本发明涉及一种新型肟类衍生物及其在农业中应用,其中,新型肟类衍生物具有如式(I)所示的结构,R1、R2、R3、R4和R5各自独立地为氢、氟、氯等,A为其中R11和R12各自独立地为氢、C1‑4烷基、苯基等,Ra为C1‑4烷氧基等,Rb为氢或C1‑4烷基。本发明的新型肟类衍生物结构新颖、合成工艺简单,且对植物病害,特别是黄瓜霜霉病具有优异的防效。
Description
技术领域
本发明涉及农药杀菌剂领域,具体的本发明涉及一种新型肟类衍生物及其制备方法与其在农业中作为杀菌剂的应用。
背景技术
植物真菌性病害一直是粮食作物生长和储藏过程中的制约因素之一,影响产品的发育、营养价值、保质期等。目前,植物病害的防治主要还是依赖于化学农药的使用,因其用量少,见效快故而备受人们青睐,但是由于农民用药技术把握不准,为追求效果盲目加大剂量,导致“抗药性、再猖獗,农药残留”等问题日趋严重,因此研究与开发能有效控制有害生物的高效、低毒、低残留的新型农药,已成为目前农药创制的首要目标。
现有技术未报道本发明涉及的肟类衍生物,且本发明的肟类衍生物在低浓度下对黄瓜霜霉病具有优异的防效,可作为新型杀真菌剂进行开发。
发明内容
本发明公开了一种新的肟类衍生物、其制备方法及其在农业中作为杀菌剂的应用,另外本发明还公开了一种包含新的肟类衍生物的组合物和/或制剂以及这种组合物和/或制剂在农业中的应用。
一方面,本发明公开了一种化合物,其为式(I)所示的化合物,或式(I)所示化合物的氮氧化物、盐、(Z)型异构体、(E)型异构体或(Z)型异构体和(E)型异构体的混合物:
其中:
R1、R2、R3、R4和R5各自独立地为氢、氟、氯、溴、碘、氰基、硝基、氨基、C1-6烷基、C1-6烷氧基、C1-6烷硫基、卤代C1-6烷基、卤代C1-6烷氧基或卤代C1-6烷硫基;
A为
其中,R11和R12各自独立地为氢、C1-6烷基、C3-8环烷基、C6-10芳基、C3-8环烷基C1-3烷基-或C6-10芳基C1-3烷基-;
或者,R11、R12和与之相连接的N原子形成5-6元杂环或5-10元杂芳环;所述的5-6元杂环和5-10元杂芳环任选地被1或2个选自氟、氯、溴、碘、C1-6烷基、卤代C1-6烷基、5-6元杂环、5-6元杂芳环或任选地被氟、氯、溴或碘取代的苯基取代;
Ra为C1-4烷基或C1-6烷氧基;
Rb为氢或C1-6烷基;
条件为:不为/>
一些实施例中,R1、R2、R3、R4和R5各自独立地为氢、氟、氯、溴、碘、氰基、硝基、氨基、C1-4烷基、C1-4烷氧基、C1-4烷硫基、卤代C1-4烷基、卤代C1-4烷氧基或卤代C1-4烷硫基。
另一些实施例中,R1、R2、R3、R4和R5各自独立地为氢、氟、氯、溴、碘、氰基、硝基、氨基、CH3-、CH3CH2-、CH3CH2CH2-、-CH(CH3)2、-OCH3、CF3-或-OCF3。
又另一些实施例中,R1、R2、R3、R4和R5各自独立地为氢。
一些实施例中,Ra为C1-4烷基或C1-4烷氧基。
另一些实施例中,Ra为C1-4烷氧基。
又另一些实施例中,Ra为CH3-、CH3CH2-、CH3CH2CH2-、-CH(CH3)2、CH3CH2CH2CH2-、-C(CH3)3、CH3O-、CH3CH2O-、CH3CH2CH2O-、(CH3)2CHO-、CH3CH2CH2CH2O-或-OC(CH3)3。
又另一些实施例中,Ra为-OC(CH3)3。
一些实施例中,Rb为氢或C1-4烷基。
另一些实施例中,Rb为氢。
又另一些实施例中,Rb为氢或CH3-。
一些实施例中,R11和R12各自独立地为氢、C1-4烷基、C3-6环烷基、苯基、C3-6环烷基C1-3烷基-或苯基C1-3烷基-。
另一些实施例中,R11和R12各自独立地为氢、C1-4烷基或苯基;优选地,R11和R12各自独立地为氢、C1-3烷基或苯基;更优选地,R11和R12各自独立地为C1-3烷基或苯基。
又另一些实施例中,R11和R12各自独立地为氢、甲基、乙基或苯基;优选地,R11和R12各自独立地为甲基、乙基或苯基。
一些实施例中,R11、R12和与之相连接的N原子形成5-6元杂环或5-10元杂芳环;所述的5-6元杂环和5-10元杂芳环任选地被1或2个选自氟、氯、溴、碘、C1-4烷基、卤代C1-4烷基、5-6元杂环、5-6元杂芳环或任选地被氟、氯、溴或碘取代的苯基取代。
另一些实施例中,R11、R12和与之相连接的N原子形成5-6元杂环;所述的5-6元杂环任选地被1或2个选自氟、氯、溴、碘、C1-4烷基、吗啉环、吡啶环、嘧啶环或任选地被氟、氯、溴或碘取代的苯基取代。
又另一些实施例中,R11、R12和与之相连接的N原子形成四氢吡咯环、哌啶环、吗啉环、硫代吗啉环、硫代吗啉-1,1-二氧化物或哌嗪环;所述的四氢吡咯环、哌啶环、吗啉环、硫代吗啉环、硫代吗啉-1,1-二氧化物和哌嗪环任选地被1或2个选自氟、氯、溴、碘、C1-4烷基、吗啉环、吡啶环、嘧啶环或任选地被氟、氯、溴或碘取代的苯基取代。
又另一些实施例中,R11、R12和与之相连接的N原子形成哌嗪环;所述的哌嗪环任选地被C1-4烷基取代。
又另一些实施例中,R11、R12和与之相连接的N原子形成四氢吡咯环、哌啶环、吗啉环、硫代吗啉环、硫代吗啉-1,1-二氧化物或哌嗪环;所述的四氢吡咯环、哌啶环、吗啉环、硫代吗啉环、硫代吗啉-1,1-二氧化物和哌嗪环任选地被1或2个选自氟、氯、溴、碘、CH3-、CH3CH2-、CH3CH2CH2-、-CH(CH3)2、吗啉环、吡啶环、嘧啶环或任选地被氟、氯、溴或碘取代的苯基取代。
又另一些实施例中,R11、R12和与之相连接的N原子形成哌嗪环;所述的哌嗪环任选地被CH3-、CH3CH2-、CH3CH2CH2-或-CH(CH3)2取代。
一些实施例中,R11、R12和与之相连接的N原子形成四氢异喹啉环、吲哚啉环、咪唑环或吡唑环;所述的四氢异喹啉环、吲哚啉环、咪唑环和吡唑环任选地被1或2个选自氟、氯、溴、碘、C1-4烷基、吗啉环、吡啶环、嘧啶环或任选地被氟、氯、溴或碘取代的苯基取代。
另一些实施例中,R11、R12和与之相连接的N原子形成四氢异喹啉环或咪唑环;所述的咪唑环任选地被1或2个选自吡啶环或苯基取代。
又另一些实施例中,R11、R12和与之相连接的N原子形成四氢异喹啉环、吲哚啉环、咪唑环或吡唑环;所述的四氢异喹啉环、吲哚啉环、咪唑环和吡唑环任选地被1或2个选自氟、氯、溴、碘、CH3-、CH3CH2-、CH3CH2CH2-、-CH(CH3)2、吗啉环、吡啶环、嘧啶环或任选地被氟、氯、溴或碘取代的苯基取代。
一些实施例中,本发明提供一种化合物,其为具有式(II)所示的化合物或式(II)所示化合物的氮氧化物、盐、(Z)型异构体、(E)型异构体或(Z)型异构体和(E)型异构体的混合物:
其中,R11、R12具有式(I)中所对应的取代基所述的含义。
另一些实施例中,本发明提供一种化合物,其为具有式(III)所示的化合物或式(III)所示化合物的立体异构体、氮氧化物或其盐:
其中,R11、R12具有式(I)或式(II)中所对应的取代基所述的含义。
一些实施例中,为以下子结构式:
另一方面,本发明提供一种化合物,其为具有下列之一结构的化合物或具有下列之一结构化合物的氮氧化物、盐、(Z)型异构体、(E)型异构体或(Z)型异构体和(E)型异构体的混合物:
又另一方面,本发明提供一种组合物,其包含至少一种本发明所述的化合物。
进一步地,本发明所述的组合物包含农药学上可接受的辅料。
又另一方面,本发明提供本发明所述的化合物或本发明所述的组合物在农业中作为植物病害防治剂的应用。
进一步地,本发明所述的植物病害为黄瓜霜霉病。
又另一方面,本发明提供一种防治植物病害的方法,其包含将本发明所述的化合物或本发明所述的组合物施用于植物或植物生长环境。
本发明的详细说明
定义和一般术语
现在详细描述本发明的某些实施方案,其实例由随附的结构式和化学式说明。本发明意图涵盖所有的替代、修改和等同技术方案,它们均包括在如权利要求定义的本发明范围内。本领域技术人员应认识到,许多与本发明所述类似或等同的方法和材料能够用于实践本发明。本发明绝不限于本发明所述的方法和材料。在所结合的文献、专利和类似材料的一篇或多篇与本申请不同或相矛盾的情况下(包括但不限于所定义的术语、术语应用、所描述的技术,等等),以本申请为准。
应进一步认识到,本发明的某些特征,为清楚可见,在多个独立的实施方案中进行了描述,但也可以在单个实施例中以组合形式提供。反之,本发明的各种特征,为简洁起见,在单个实施方案中进行了描述,但也可以单独或以任意适合的子组合提供。
除非另外说明,本发明所使用的所有科技术语具有与本发明所属领域技术人员的通常理解相同的含义。本发明涉及的所有专利和公开出版物通过引用方式整体并入本发明。
除非另外说明,应当应用本发明所使用的下列定义。出于本发明的目的,化学元素与元素周期表CAS版,和《化学和物理手册》,第75版,1994一致。此外,有机化学一般原理可参考"Organic Chemistry",Thomas Sorrell,University Science Books,Sausalito:1999,和"March's Advanced Organic Chemistry"by Michael B.Smith and JerryMarch,John Wiley&Sons,New York:2007中的描述,其全部内容通过引用并入本发明。
除非另有说明或者上下文中有明显的冲突,本发明所使用的冠词“一”、“一个(种)”和“所述”旨在包括“至少一个”或“一个或多个”。因此,本发明所使用的这些冠词是指一个或多于一个(即至少一个)宾语的冠词。例如,“一组分”指一个或多个组分,即可能有多于一个的组分被考虑在所述实施方案的实施方式中采用或使用。
术语“包含”为开放式表达,即包括本发明所指明的内容,但并不排除其他方面的内容。
“立体异构体”是指具有相同化学构造,但原子或基团在空间上排列方式不同的化合物。立体异构体包括对映异构体、非对映异构体、构象异构体(旋转异构体)、几何异构体(顺/反)异构体、阻转异构体,等等。
“对映异构体”是指一个化合物的两个不能重叠但互成镜像关系的异构体。
“非对映异构体”是指有两个或多个手性中性并且其分子不互为镜像的立体异构体。非对映异构体具有不同的物理性质,如熔点、沸点、光谱性质和反应性。非对映异构体混合物可通过高分辨分析操作如电泳和色谱,例如HPLC来分离。
本发明所使用的立体化学定义和规则一般遵循S.P.Parker,Ed.,McGraw-HillDictionary of Chemical Terms(1984)McGraw-Hill Book Company,New York;andEliel,E.and Wilen,S.,“Stereochemistry of Organic Compounds”,John Wiley&Sons,Inc.,New York,1994中的描述。
许多有机化合物以光学活性形式存在,即它们具有使平面偏振光的平面发生旋转的能力。在描述光学活性化合物时,使用前缀D和L或R和S来表示分子关于其一个或多个手性中心的绝对构型。前缀d和l或(+)和(-)是用于指定化合物所致平面偏振光旋转的符号,其中(-)或l表示化合物是左旋的。前缀为(+)或d的化合物是右旋的。一种具体的立体异构体是对映异构体,这种异构体的混合物称作对映异构体混合物。对映异构体的50:50混合物称为外消旋混合物或外消旋体,当在化学反应或过程中没有立体选择性或立体特异性时,可出现这种情况。
本发明公开化合物的任何不对称原子(例如,碳等)都可以以外消旋或对映体富集的形式存在,例如(R)-、(S)-或(R,S)-构型形式存在。在某些实施方案中,各不对称原子在(R)-或(S)-构型方面具有至少50%对映体过量,至少60%对映体过量,至少70%对映体过量,至少80%对映体过量,至少90%对映体过量,至少95%对映体过量,或至少99%对映体过量。
依据起始物料和方法的选择,本发明化合物可以以可能的异构体中的一个或它们的混合物,例如外消旋体和非对应异构体混合物(这取决于不对称碳原子的数量)的形式存在。光学活性的(R)-或(S)-异构体可使用手性合成子或手性试剂制备,或使用常规技术拆分。如果化合物含有一个双键,取代基可能为E或Z构型;如果化合物中含有二取代的环烷基,环烷基的取代基可能有顺式或反式构型。
所得的任何立体异构体的混合物可以依据组分物理化学性质上的差异被分离成纯的或基本纯的几何异构体,对映异构体,非对映异构体,例如,通过色谱法和/或分步结晶法。
可以用已知的方法将任何所得终产物或中间体的外消旋体通过本领域技术人员熟悉的方法拆分成光学对映体,如,通过对获得的其非对映异构的盐进行分离。外消旋的产物也可以通过手性色谱来分离,如,使用手性吸附剂的高效液相色谱(HPLC)。特别地,对映异构体可以通过不对称合成制备。
像本发明所描述的,本发明的化合物可以任选地被一个或多个取代基所取代,如上面的通式化合物,或者像实施例里面特殊的例子,子类,和本发明所包含的一类化合物。应了解“任选取代的”这个术语与“取代或非取代的”这个术语可以交换使用。一般而言,术语“取代的”表示所给结构中的一个或多个氢原子被具体取代基所取代。除非其他方面表明,一个任选的取代基团可以在基团各个可取代的位置进行取代。当所给出的结构式中不只一个位置能被选自具体基团的一个或多个取代基所取代,那么取代基可以相同或不同地在各个位置取代。具体地,“一个或多个”的实例是指1、2、3、4、5、6、7、8、9或10个。其中所述的取代基可以是,但并不限于,氘,氟,氯,溴,碘,氰基,羟基,硝基,氨基,羧基,烷基,烷氧基,烷氧基烷基,烷氧基烷氧基,烷氧基烷氨基,芳氧基,杂芳基氧基,杂环基氧基,芳基烷氧基,杂芳基烷氧基,杂环基烷氧基,环烷基烷氧基,烷氨基,烷氨基烷基,烷氨基烷氨基,环烷基氨基,环烷基烷氨基,烷硫基,卤代烷基,卤代烷氧基,羟基取代的烷基,羟基取代的烷氨基,氰基取代的烷基,氰基取代的烷氧基,氰基取代的烷氨基,氨基取代的烷基,烷基酰基,杂烷基,环烷基,环烯基,环烷基烷基,杂环基,杂环基烷基,杂环基酰基,芳基,芳基烷基,芳氨基,杂芳基,杂芳基烷基,杂芳基氨基,酰胺基,磺酰基,氨基磺酰基等等。
另外,需要说明的是,除非以其他方式明确指出,在本发明中所采用的描述方式“各…独立地为”与“…各自独立地为”和“…独立地为”可以互换,均应做广义理解,其既可以是指在不同基团中,相同符号之间所表达的具体选项之间互相不影响,也可以表示在相同的基团中,相同符号之间所表达的具体选项之间互相不影响。
在本说明书的各部分,本发明公开化合物的取代基按照基团种类或范围公开。特别指出,本发明包括这些基团种类和范围的各个成员的每一个独立的次级组合。例如,术语“C1-C6烷基”或“C1-6烷基”特别指独立公开的甲基、乙基、C3烷基、C4烷基、C5烷基和C6烷基。
本发明使用的术语“烷基”或“烷基基团”,表示含有1至20个碳原子,饱和的直链或支链一价烃基基团;其中所述烷基基团任选地被一个或多个本发明描述的取代基所取代。除非另外详细说明,烷基基团含有1-20个碳原子。在一实施方案中,烷基基团含有1-12个碳原子;在一实施方案中,烷基基团含有1-8个碳原子;在另一实施方案中,烷基基团含有1-6个碳原子;在又一实施方案中,烷基基团含有1-4个碳原子;还在一实施方案中,烷基基团含有1-3个碳原子。
烷基基团的实例包含,但并不限于,甲基(Me、-CH3),乙基(Et、-CH2CH3),正丙基(n-Pr、-CH2CH2CH3),异丙基(i-Pr、-CH(CH3)2),正丁基(n-Bu、-CH2CH2CH2CH3),异丁基(i-Bu、-CH2CH(CH3)2),仲丁基(s-Bu、-CH(CH3)CH2CH3),叔丁基(t-Bu、-C(CH3)3),正戊基(-CH2CH2CH2CH2CH3),2-戊基(-CH(CH3)CH2CH2CH3),3-戊基(-CH(CH2CH3)2),2-甲基-2-丁基(-C(CH3)2CH2CH3),3-甲基-2-丁基(-CH(CH3)CH(CH3)2),3-甲基-1-丁基(-CH2CH2CH(CH3)2),2-甲基-1-丁基(-CH2CH(CH3)CH2CH3),等等。
术语“烷氧基”表示烷基基团通过氧原子与分子其余部分相连,其中烷基基团具有如本发明所述的含义。烷氧基基团的实例包括,但并不限于,甲氧基(MeO、-OCH3),乙氧基(EtO、-OCH2CH3),1-丙氧基(n-PrO、n-丙氧基、-OCH2CH2CH3),2-丙氧基(i-PrO、i-丙氧基、-OCH(CH3)2)等等。
术语“烷硫基”表示烷基基团通过硫原子与分子其余部分相连,其中烷基基团具有如本发明所述的含义。烷硫基基团的实例包括,但并不限于,甲硫基(MeS、-SCH3),乙硫基(EtS、-SCH2CH3)等等。
术语“卤代烷基”表示烷基基团被一个或多个卤素原子所取代,这样的实例包含,但并不限于,-CF3,-CHF2,-CH2Cl,-CH2CF3,-CH2CHF2,-CH2CH2CF3等等。
术语“卤代烷氧基”表示烷氧基基团被一个或多个卤素原子所取代,这样的实例包含,但并不限于,-OCF3,-OCHF2,-OCHCl2,-OCH2CHF2,-OCH2CHCl2,-OCH(CH3)CHF2等等。术语“卤代烷硫基”表示烷硫基基团被一个或多个卤素原子所取代,这样的实例包含,但并不限于,-SCF3,-SCH2CHF2等等。
术语“环烷基”表示含有3-12个碳原子的,单价或多价的饱和单环、双环或三环体系。在一实施方案中,环烷基包含3-10个碳原子;在另一实施方案中,环烷基包含3-8个碳原子;在又一实施方案中,环烷基包含3-6个碳原子。所述环烷基基团任选地被一个或多个本发明所描述的取代基所取代。这样的实例包括,但并不限于,环丙基,环丁基,环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基,环十二烷基,等等。
术语“环烷基烷基”表示烷基基团被一个或多个环烷基基团所取代,其中烷基基团和环烷基基团具有如本发明所述的含义。
在本发明书的各部分,描述了连接取代基。当该结构清楚地需要连接基团时,针对该基团所列举的马库什变量应理解为连接基团。例如,如果该结构需要连接基团并且针对该变量的马库什基团定义列举了“烷基”或“芳基”,则应当理解,该“烷基”或“芳基”分别代表连接的亚烷基基团或亚芳基基团。
术语“亚烷基”表示从饱和的直链或支链烃中去掉两个氢原子所得到的饱和的二价烃基基团。除非另外详细说明,亚烷基基团含有1-12个碳原子。在一实施方案中,亚烷基基团含有1-8个碳原子;在一实施方案中,亚烷基基团含有1-6个碳原子;在另一实施方案中,亚烷基基团含有1-4个碳原子;在又一实施方案中,亚烷基基团含有1-3个碳原子;还在一实施方案中,亚烷基基团含有1-2个碳原子。这样的实例包括亚甲基(-CH2-),亚乙基(-CH2CH2-),亚丙基(-CH2CH2CH2-),-CH(CH3)CH2-,-C(CH3)2-,-CH2CH2CH(CH3)-,-CH2CH2C(CH3)2-,等等。
术语“杂环基”和“杂环”在此处可交换使用,都是指包含3-15个环原子的饱和或部分不饱和的单环、双环或三环,其中单环、双环或三环中不包含芳香环,且至少一个环原子选自氮、硫和氧原子。除非另外说明,杂环基可以是碳基或氮基,且-CH2-基团可以任选地被-C(=O)-替代。环的硫原子可以任选地被氧化成S-氧化物。环的氮原子可以任选地被氧化成N-氧化合物。
术语“5-10元杂环”或“5-6元杂环”,其中“5-10元”或“5-6元”典型地描述分子中成环原子的数目。例如,哌啶基是6元杂环基。
其中,本发明中R11、R12和与之相连接的N形成的5-6元杂环的实例包括:四氢吡咯环哌啶环/>吗啉环/>硫代吗啉环/>硫代吗啉-1,1-二氧化物/>哌嗪环/>等等。
本发明中,R11、R12和与之相连接的N原子形成任选地被C1-4烷基取代的哌嗪环时,式(III)所示的化合物在低剂量下(如实施例7或实施例25在12.5m/L下)对黄瓜霜霉病的防效仍可以达到90%以上;而当R11、R12和与之相连接的N原子形成任选取代的四氢吡咯环、哌啶环、吗啉环、硫代吗啉环或硫代吗啉-1,1-二氧化物时,式(III)所示的化合物在200m/L或50m/L下对黄瓜霜霉病的防效均在50%以下。
在本发明中所使用的术语“不饱和的”表示基团中含有一个或多个不饱和度。
术语“杂原子”是指O、S、N、P和Si,包括N、S和P任何氧化态的形式;伯、仲、叔胺和季铵盐的形式;或者杂环中氮原子上的氢被取代的形式,例如,N(像3,4-二氢-2H-吡咯基中的N),NH(像吡咯烷基中的NH)或NR(像N-取代的吡咯烷基中的NR)。
术语“芳基”表示含有6-14个环原子,或6-12个环原子,或6-10个环原子的单环、双环和三环的碳环体系,其中,至少一个环体系是芳香族的,其中每一个环体系包含3-7个原子组成的环,且有一个或多个附着点与分子的其余部分相连。术语“芳基”可以和术语“芳香环”交换使用。芳基基团的实例可以包括苯基,茚基,萘基和蒽基。所述芳基基团任选地被一个或多个本发明所描述的取代基所取代。
术语“芳基烷基”或“芳烷基”表示烷基基团被一个或多个芳基基团所取代,其中烷基基团和芳基基团具有如本发明所述的含义。
术语“杂芳环”表示含有5-12个环原子,或5-10个环原子,或5-6个环原子的单环、双环和三环体系,其中至少一个环体系是芳香族的,且至少一个环体系包含一个或多个杂原子,其中每一个环体系包含5-7个原子组成的环,且有一个或多个附着点与分子其余部分相连。术语“杂芳环”可以与术语“杂芳基”或“杂芳族化合物”交换使用。所述杂芳环基团任选地被一个或多个本发明所描述的取代基所取代。
在一实施方案中,5-10个原子组成的杂芳环包含1,2,3或4个独立选自O,S和N的杂原子。
其中,本发明中R11、R12和与之相连接的N形成的5-10元杂芳环的实例包括:四氢异喹啉环吲哚啉环/>咪唑环/>吡唑环/>等等。
本发明中,表示Z型异构体/>E型异构体或Z型异构体和E型异构体的混合物;/>表示Z型异构体E型异构体/>或Z型异构体和E型异构体的混合物;其中,Z型异构体、E型异构体或Z型异构体和E型异构体的混合物可以通过常规方法进行分离、确认,如高效液相色谱法、核磁共振氢谱法和/或单晶衍射法。
本发明所述化合物的盐,包括衍生自碱金属或碱土金属的那些以及衍生自氨和胺的那些。优选的阳离子包括钠、钾、镁以及具有化学式N+(RARBRCRD)的铵阳离子,其中RA、RB、RC和RD独立地选自氢、C1-C6烷基和C1-C6羟基烷基。具有式(I)、式(II)或式(III)的化合物的盐可以通过用金属氢氧化物(例如氢氧化钠)或胺(例如氨、三甲胺、二乙醇胺、2-甲硫基丙胺、双烯丙基胺、2-丁氧基乙胺、吗啉、环十二胺或苄胺)对具有式(I)、式(II)或式(III)的化合物进行处理来制备。
当本发明的化合物包含一个碱部分时,可接受的盐可以由有机酸和无机酸形成,例如乙酸、丙酸、乳酸、柠檬酸、酒石酸、琥珀酸、富马酸、马来酸、丙二酸、扁桃酸、苹果酸、邻苯二甲酸、盐酸、氢溴酸、磷酸、硝酸、硫酸、甲磺酸、萘磺酸、苯磺酸、甲苯磺酸、樟脑磺酸以及类似地已知可接受的酸。
本发明化合物的组合物和制剂
本发明的化合物一般可用作组合物或制剂中的杀菌剂活性成分,通常还包括农药学上可接受的辅料;所述的辅料包括表面活性剂和/或载体。
上述表面活性剂可以为农药剂型领域所公知的各种表面活性剂,本发明优选为乳化剂、分散剂和润湿剂中的一种或多种。
除上述表面活性剂外的其它载体可以为农药剂型领域所公知的各种载体,包括各种硅酸盐类、碳酸盐类、硫酸盐类、氧化物类、磷酸盐类、植物载体类、合成载体类。具体地,例如:白炭黑、高岭土、硅藻土、粘土、滑石、有机膨润土、浮石、二氧化钛、糊精、纤维素粉、轻质碳酸钙、可溶性淀粉、玉米淀粉、锯末粉、尿素、胺肥、尿素和胺肥的混合物、葡萄糖、麦芽糖、蔗糖、无水碳酸钾、无水碳酸钠、无水碳酸氢钾、无水碳酸氢钠、凹凸棒土、无水碳酸钾与无水碳酸氢钾的混合物和无水碳酸钠与无水碳酸氢钠的混合物中的一种或多种。
上述乳化剂可以为农药剂型领域所公知的各种乳化剂,具体地,该乳化剂可以为十二烷基苯磺酸钙、三苯乙基酚聚氧乙烯醚磷酸酯、脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、烷基酚聚氧乙烯聚氧丙烯醚、脂肪胺、脂肪酰胺的环氧乙烷加成物、脂肪酸聚氧乙烯酯、松香酸环氧乙烷加成物、多元醇脂肪酸酯及其环氧乙烷加成物、苯乙烯基苯基聚氧乙烯醚、烷基酚甲醛树脂聚氧乙烯醚、端羟基聚氧乙烯聚氧丙烯醚、苯乙烯基苯酚甲醛树脂聚氧乙烯聚氧丙烯醚和蓖麻油聚氧乙烯醚中的一种或多种。
上述分散剂可以为农药剂型领域所公知的各种分散剂,具体地,该分散剂为丙烯酸均聚物钠盐、马来酸二钠盐、萘磺酸甲醛缩合物钠盐、松香嵌段聚氧乙烯醚聚氧丙烯醚磺酸盐、端羟基聚氧乙烯聚氧丙烯醚嵌段共聚物、三苯乙基酚聚氧乙烯醚磷酸酯、脂肪醇聚氧乙烯醚磷酸酯和对羟苯基木质素磺酸钠盐中的一种或多种。
上述润湿剂可以为农药剂型领域所公知的各种润湿剂,具体地,该润湿剂可以为十二烷基硫酸钠、仲烷基硫酸钠、十二烷基苯磺酸钠、脂肪醇聚氧乙烯醚、烷基萘磺酸盐、烷基酚树脂聚氧乙烯醚硫酸盐中的一种或多种。
根据本发明的杀菌剂组合物,该杀菌剂组合物还可以含有农药剂型领域所常用的各种制剂用助剂,具体地,该制剂用助剂可以为溶剂、助溶剂、增稠剂、防冻剂、囊材、保护剂、消泡剂、崩解剂、稳定剂、防腐剂和粘结剂中的一种或多种。
上述溶剂可以为农药剂型领域所公知的各种溶剂,具体地,该溶剂可以为有机溶剂、植物油、矿物油、溶剂油和水中的一种或多种。
其中,所述有机溶剂包括N-甲基吡咯烷酮、四氢呋喃、二甲基亚砜、N,N-二甲基癸酰胺、N,N-二甲基甲酰胺、三甲苯、四甲苯、二甲苯、甲苯、辛烷、庚烷、甲醇,异丙醇、正丁醇、四氢糠醇、磷酸三丁酯、1,4-二氧六环和环己酮中的一种或多种。
所述植物油包括甲基化植物油,松脂基植物油,松节油,环氧大豆油、大豆油、花生油、菜籽油、蓖麻油、玉米油和松籽油中的一种或多种。
所述矿物油包括液蜡、机油、煤油和润滑油中的一种或多种。
同时,上述溶剂也可以作为助溶剂使用。
上述防冻剂可以为农药剂型领域所公知的各种防冻剂,本发明优选为乙二醇、丙二醇、甘油和尿素中的一种或多种。
上述增稠剂可以为农药剂型领域所公知的各种增稠剂,具体地,该增稠剂可以为黄原胶、聚乙烯醇、聚丙烯醇、聚乙二醇、白炭黑、硅藻土、高岭土、粘土、海藻酸钠、硅酸铝镁、硅酸铝钠、羧甲基纤维素、羟丙基纤维素钠和有机膨润土中的一种或多种。
上述囊材可以为农药剂型领域所公知的各种囊材,本发明优选为聚氨酯、聚脲和脲醛树脂中的一种或多种。
上述保护剂可以为农药剂型领域所公知的各种保护剂,本发明优选为聚乙烯醇和/或聚乙二醇。
上述消泡剂可以为农药剂型领域所公知的各种消泡剂,本发明优选为有机硅氧烷、磷酸三丁酯和硅酮中的一种或多种。
上述稳定剂选自亚磷酸三苯酯、环氧氯丙烷和醋酐中的一种或多种。
上述防腐剂选自苯甲酸、苯甲酸钠、1,2-苯并异噻唑啉-3-酮(简称BIT)、卡松和山梨酸钾中的一种或多种。
本发明还提供一种由上述杀菌剂组合物所制备的制剂,所述制剂的剂型为乳油、水乳剂、微乳剂、可溶性液剂、水悬浮剂、悬乳剂、超低容量喷雾剂、油悬浮剂、微囊悬浮剂、水面展膜油剂、可湿性粉剂、水分散性颗粒剂、干悬浮剂、可溶性粉剂、可溶性粒剂、可乳化粉剂、可乳化颗粒剂、颗粒剂、固体微胶囊制剂、泡腾片剂、泡腾颗粒剂、水漂浮分散颗粒剂或种衣剂。上述剂型均可由本领域的常规方法来制备。
上述乳油制剂的制备方法例如可以包括将各活性组分、溶剂、助溶剂及乳化剂混合搅拌使其形成均匀透明油相,即可得到乳油制剂。
上述水乳剂制备方法例如可以包括将活性成分、乳化剂、助溶剂和溶剂混合,使其成为均匀油相;将水、增稠剂、防冻剂等混合,使其成均一水相。在高速剪切下,将水相加入到油相或将油相加入到水相,形成分散性良好的水乳剂。
上述微乳剂的制备方法例如可以是将活性成分,乳化剂,溶剂混合搅拌成均一透明的油相。在搅拌的条件下,逐渐的加入水,使其形成均一透明的微乳液。
上述水/油悬浮剂的制备方法:例如可以是以水或油为介质,将活性组分、表面活性剂等助剂加入砂磨釜中,进行研磨至一定粒径后,过滤。再将计量好的增稠剂加入到研磨好的母液中,剪切分散均匀。制成油悬浮剂或水悬浮剂。
上述水分散性粒剂及可溶性粒剂的制备方法:例如可以是将各活性组分、分散剂、润湿剂、载体等混合均匀,然后通过气流粉碎至一定粒径,再加入水进行捏合,最后加入造粒机中进行造粒,干燥后即可得到水分散性粒剂或可溶性粒剂。
上述可溶性粉剂及可湿性粉剂的制备方法:例如可以是将各活性组分、各种助剂及其他载体等填料充分混合,用超细粉碎机粉碎。
本发明的杀菌剂组合物可以以成品制剂形式提供,即组合物中各物质已经混合;也可以以单独制剂形式提供,使用前在桶或罐中自行混合,并根据所需活性物质的浓度选择性地与水混合进行稀释即可。
本发明化合物、包含本发明化合物的组合物和/或制剂的应用
本发明的化合物、包含本发明化合物的组合物和/或制剂可用作植物病害防治剂。因此,本发明还可包括用于控制由植物病原真菌引起的植物病害的方法,所述方法包括向待保护植物或其部分或向待保护植物种子施用有效量的本发明的化合物或包含所述化合物的杀菌组合物和/或制剂。本发明的化合物、包含本发明化合物的组合物和/或制剂可对由担子菌纲、子囊菌纲、卵菌纲和半知菌纲广谱植物病原真菌引起的病害提供控制。它们可有效地控制广谱植物病害,尤其是观赏作物、草坪作物、蔬菜作物、大田作物、谷类作物和果树作物的叶片病原体。这些病原体包括:卵菌纲,包括疫霉属(Phytophthora)病害诸如致病疫霉菌(Phytophthora infestans)、大豆疫霉病菌(Phytophthora megasperma)、柑桔脚腐病菌(Phytophthora parasitica)、樟疫霉菌(Phytophthora cinnamomi)和南瓜疫病菌(Phytophthora capsici)的病害,草腐霉枯萎属(Pythium)物种病害诸如坪草腐霉枯萎病菌(Pythium aphanidermatum)的病害,以及霜霉科(Peronosporaceae)物种病害诸如葡萄霜霉病菌(Plasmopara viticola),霜霉属病害(Peronospora spp.)(包括烟草霜霉菌(Peronospora tabacina)和寄生霜霉菌(Peronospora parasitica)),假霜霉属(Pseudoperonospora spp.)病害(包括黄瓜霜霉病菌(Pseudoperonospora cubensis)和盘梗霉菌病菌(Bremia lactucae));子囊菌(包括链格孢属(Alternaria)病菌如番茄早疫病菌(Alternaria solani)和甘蓝黑斑病菌(Alternaria brassicae),球座菌属(Guignardia)病害如葡萄黑腐病菌(Guignardia bidwell),黑星菌属(Venturia)病害如苹果黑星病菌(Venturia inaequalis),壳针孢属(Septoria)病害如颖枯病菌(Septorianodorum)和叶枯病菌(Septoria tritici),白粉(powdery mildew)病害如白粉菌属病菌(Erysiphe spp.)(包括小麦白粉病菌(Erysiphe graminis)和萝白粉病菌(Erysiphepolygoni))、葡萄白粉病菌(Uncinula necatur)、黄瓜白粉病菌(Sphaerotheca fuligena)和苹果白粉病菌(Podosphaera leucotricha)、小麦基腐病菌(Pseudocercosporellaherpotrichoides),灰霉菌属(Botrytis)病害如草莓灰霉病菌(Botrytis cinerea)、桃褐腐病菌(Monilinia fructicola),菌核菌属(Sclerotinia)病害如油菜菌核病菌(Sclerotinia sclerotiorum)、稻瘟病菌(Magnaporthe grisea)、葡萄枝枯病菌(Phomopsis viticola),蠕形菌属(Helminthosporium)病害如玉米大斑病菌(Helminthosporium tritici repentis)、网纹病菌(Pyrenophora teres),炭疽病菌如黑果病菌(Glomerella)或炭疽菌属(Colletotrichum spp.)病害(如粱炭疽病菌(Colletotrichum graminicola)和西瓜炭疽病菌(Colletotrichum orbiculare)),和小麦全蚀病菌(Gaeumannomyces graminis);担子菌,包括由锈菌属(Puccinia spp.)造成的锈菌病害(如隐匿柄锈菌(Puccinia recondita)、条锈菌(Puccinia striiformis)、叶锈菌(Puccinia hordei)、杆锈菌(Puccinia graminis)和柄锈菌(Puccinia arachidis)),咖啡锈菌(Hemileia vastatrix)和大豆锈菌(Phakopsora pachyrhizi);其它病原体包括丝核菌属物种(Rhizoctonia spp.)(如立枯丝核菌(Rhizoctonia solani));镰刀菌属(Fusarium)物种病害诸如粉红镰刀菌(Fusarium roseum)、禾谷镰刀菌(Fusariumgraminearum)和尖孢镰刀菌(Fusarium oxysporum);大丽轮枝菌(Verticilliumdahliae);白绢菌(Sclerotium rolfsii);云纹菌(Rynchosporium secalis);黑涩病菌(Cercosporidium personatum)、黑斑病菌(Cercospora arachidicola)和褐斑病菌(Cercospora beticola);以及其它与这些病原体密切相关的类别和菌种。除了它们的杀真菌活性之外,所述组合物或组合还对细菌诸如梨火疫病菌(Erwinia amylovora)、野油菜黄单胞菌(Xanthomonas campestris)、丁香假单胞菌(Pseudomonas syringae)以及其它菌种具有抵抗活性。
本发明的杀菌剂组合物和/或制剂的使用方法简单,在植物病害萌发之前或萌发之后,向作物及作物生长的场所按常规方法施用,如拌土、喷雾、喷射、浇注等,其施用量根据气候条件或作物状态而定,一般情况下每亩施用的有效量为10-5000g,稀释成10-400mg/L(优选为100-300mg/L)施用。稀释剂优选为水。
本发明的杀菌剂组合物,其杀菌效果通常与外界因素如气候有关,但通过使用适当的剂型可以减缓气候的影响。
本发明的组合物还可与其它具有杀菌、杀虫或除草性能的化合物混合使用,也可与杀线虫剂、杀螨剂、防护剂、除草安全剂、生长调节剂、植物营养素或土壤调节剂等混合使用。
一般合成过程
下述方案描述本发明化合物的制备,除非有进一步的说明,本发明的化合物可以通过本发明所描述的方法制备得到。制备本发明的化合物所使用的原料、试剂等等均是可以商购的;或者原料、试剂等可以通过本领域常规的方法制备得到。在本说明书中,如果在化学名称和化学结构间存在任何差异,结构是占优的。本发明所述的室温为0℃~35℃。
本发明核磁共振氢谱的测试条件是:室温条件下,布鲁克(Bruker)400MHz或600MHz的核磁仪,以CDC13,d6-DMSO,CD3OD或d6-丙酮为溶剂(报导以ppm为单位),用TMS(0ppm)或氯仿(7.26ppm)作为参照标准。当出现多重峰的时候,将使用下面的缩写:s(singlet,单峰),d(doublet,双峰),t(triplet,三重峰),q(quartet,四重峰),m(multiplet,多重峰),br(broadened,宽峰),dd(doublet of doublets,双二重峰),dt(doublet of triplets,双三重峰)。偶合常数,用赫兹(Hz)表示。
本发明低分辨率质谱(MS)数据测定的条件是:Agilent 6120Quadrupole HPLC-MS(柱子型号:Zorbax SB-C18,2.1x 30mm,3.5μm,6min,流速为0.6mL/min,流动相:5%-95%(含0.1%甲酸的CH3CN)在(含0.1%甲酸的H2O)中的比例)),在210/254nm用UV检测,用电喷雾电离模式(ESI)。
合成方案
合成方案一
式(III)所示的目标化合物可以通过合成方案一制备得到。式(a)化合物与化合物b在碱性条件下(如氢氧化钾、氢氧化钠、氢化钠等)发生亲核取代反应,得到式(III)所示的目标化合物;
其中,化合物b对应的名称为:(6-(溴甲基)吡啶-2-基)氨基甲酸叔丁基酯;R11、R12具有本发明所述的含义。
实施例
中间体:(Z)-苯基(吡咯烷-1-基)甲酮肟
步骤A:(E)-苯甲醛肟的合成
将苯甲醛(4.0g,40.7mmol),盐酸羟胺(3.0g,46.9mmol)和碳酸钾(5.8g,46.9mmol)加入到反应瓶中,加入甲醇(60mL)后,室温下搅拌反应2小时。加水(100mL)淬灭反应,再用乙酸乙酯(50mL x 3)萃取,饱和食盐水(100mL)洗,合并有机相后,用无水硫酸钠干燥,减压浓缩得4.5g无色透明油状液体,产率:92%。
步骤B:(Z)-(苯基)(吡咯烷-1-基)甲酮肟的合成
在-5℃条件下,将(E)-苯甲醛肟(0.41g,3.3mmol)溶于二氯甲烷(18mL)和N,N-二甲基甲酰胺(2mL)的混合溶液中,分批加入N-氯代丁二酰亚胺(1.3g,9.9mmol),室温下反应2小时后,滴加四氢吡咯(0.26g,3.6mmol),室温继续搅拌反应2小时。浓缩除去二氯甲烷,加水(100mL)稀释,乙酸乙酯(50mL x 3)萃取,合并有机相,经饱和食盐水(100mL)洗,无水硫酸钠干燥后,减压浓缩,得到0.5g白色固体,产率:80%。
LC-MS:m/z 191.1[M+H]+。
使用相应的化合物作为原料,经过中间体(Z)-苯基(吡咯烷-1-基)甲酮肟的类似制备方法,即可得到表1中的中间体化合物。
表1
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实施例1:(Z)-(6-((((苯基(吡咯烷-1-基)亚甲基)氨基)氧)甲基)吡啶-2-基)氨基甲酸叔丁基酯的合成
室温下,将(Z)-(苯基)(吡咯烷-1-基)甲酮肟(0.31g,1.6mmol)溶于二甲基亚砜(10mL)和水(3mL)的混合溶液中,加入氢氧化钾(0.80g,14.2mmol),室温下反应30分钟后,滴加(6-(溴甲基)吡啶-2-基)氨基甲酸叔丁基酯(0.42g,1.73mmol),室温下继续搅拌反应5小时。加水(20mL)稀释,用乙酸乙酯(20mL x 3)萃取,合并有机相后,饱和食盐水(100mL)洗,浓缩后柱层析[石油醚/乙酸乙酯(v/v)=8/1],得到0.17g白色固体,产率:27%。
1H NMR(400MHz,DMSO-d6)δ9.66(s,1H),7.69-7.61(m,1H),7.43(dq,J=14.3,7.1Hz,3H),7.34-7.30(m,3H),6.84(d,J=7.0Hz,1H),4.72(s,2H),3.09-2.88(m,4H),1.77-1.68(m,4H),1.45(s,9H);
LC-MS:m/z 397.2[M+H]+。
参照实施例1的类似制备方法,将中间体(6-(溴甲基)吡啶-2-基)氨基甲酸叔丁基酯与相应的表1中的中间体化合物进行反应,即可得到表2中的目标化合物。
表2
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活性测试
测试例
本测试例用于测定实施例中制得的化合物的杀菌活性。本测试例中的试验靶标为黄瓜霜霉病菌。用N,N-二甲基甲酰胺溶解成1%EC备用。采用活体盆栽法,评价这些化合物在不同剂量下,如200mg/L、100mg/L、50mg/L、25mg/L、12.5mg/L、3.125mg/L剂量下对试验靶标的杀菌活性。试验方法采用创制农药生物活性评价SOP(杀菌剂卷)。
黄瓜霜霉病菌(Pseudoperonospora cubensis):
选择1张真叶期(摘去生长点)长势一致的盆栽黄瓜苗,喷雾处理后自然晾干,处理后24h后进行接种,取新鲜黄瓜霜霉病病叶,用毛笔蘸取蒸馏水洗下病叶背面孢子囊,配成孢子囊悬浮液(2-3×105个/mL)。用接种喷雾器(压力0.1MPa)在黄瓜苗上均匀喷雾接种,接种后的试材移至人工气候室,保持相对湿度100%,温度为21℃左右,24h后保持温度21℃左右,相对湿度95%左右保湿诱发,5d后视空白对照发病情况进行分级调查,按病指计算防效。
测试结果显示:200mg/L剂量下,实施例7、实施例8、实施例15、实施例23对黄瓜霜霉病的防效在95%以上;200mg/L剂量下,实施例12、实施例19对黄瓜霜霉病的防效为80%;
50mg/L剂量下,实施例7、实施例8、实施例25对黄瓜霜霉病的防效为100%;50mg/L剂量下,实施例23对黄瓜霜霉病的防效为80%;
12.5mg/L剂量下,实施例7、实施例8、实施例25对黄瓜霜霉病的防效在90%以上;
3.125mg/L剂量下,实施例7对黄瓜霜霉病的防效为80%。
由上述试验结果可知本发明化合物对植物病原性真菌,尤其是对黄瓜霜霉病菌具有良好的防治效果,具备进一步研发的价值。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。
Claims (4)
1.一种化合物,其为具有下列之一结构的化合物或具有下列之一结构化合物的盐、(Z)型异构体、(E)型异构体或(Z)型异构体和(E)型异构体的混合物:
2.一种组合物,包含权利要求1所述的化合物和农药学上可接受的辅料。
3.权利要求1所述的化合物或权利要求2所述的组合物在农业中作为植物病害防治剂的应用,所述植物病害为黄瓜霜霉病。
4.一种防治植物病害的方法,包含将权利要求1所述的化合物或权利要求2所述的组合物施用于植物或植物生长环境。
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