CN113135863A - 一种新型三唑类化合物及其在农业中的应用 - Google Patents
一种新型三唑类化合物及其在农业中的应用 Download PDFInfo
- Publication number
- CN113135863A CN113135863A CN202010056209.5A CN202010056209A CN113135863A CN 113135863 A CN113135863 A CN 113135863A CN 202010056209 A CN202010056209 A CN 202010056209A CN 113135863 A CN113135863 A CN 113135863A
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- compound
- alkyl
- cinerea
- hydrogen
- alkoxy
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- 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
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
技术领域
本发明涉及农业领域,具体地,本发明涉及农业杀菌剂领域;本发明涉及新型三唑类化合物及其制备方法、包含该三唑类化合物的组合物及该三唑类化合物及其包含该三唑类化合物的组合物在农业中作为植物病害,特别是由植物病原性真菌引起的植物病害防治剂的应用。
背景技术
植物病害是作物栽培过程中最普遍、危害性最大的病害之一,根据联合国粮农组织估计,全世界的粮食和棉花生产因病害常年损失在10%以上。我国是一个农业大国,耕地少,人口多,使得粮食问题是我们亟待解决的重要问题之一。而植物真菌性病害一直是粮食作物生产和产品储藏过程中的制约因素之一,对于产品的发育阶段、营养价值、有限保质期等问题方面都造成了严重损失。长期以来,化学农药的使用仍是防治上述病害最重要也是最有效的方式。但是,由于不加节制地长期使用化学药剂,造成了防治效果差、药物残留、耐药性等一系列问题。这些不仅引起作物产量的减少,造成巨大的经济损失,并且在一定程度上严重威胁到农产品的质量安全。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。
本发明提供一种新型的三唑类化合物,其对植物病害,特别是小麦白粉病、玉米锈病、水稻纹枯病等具有优异的防效。
发明内容
本发明的目的在于提供一种对植物病害防治效果显著的新的杀菌化合物、含有该杀菌化合物的杀菌剂组合物和/或制剂及其作为杀真菌剂的应用。
一方面,本发明提供一种化合物,其为具有式(I)所示的化合物,或式(I)所示化合物的立体异构体、氮氧化物或其盐:
其中,
M为三唑基;
Ra为氢或C1-4烷基;
Rb、Rc和Rd各自独立地为氢;其中,Rb、Rc和Rd均不被取代;
B为-O-或-S-;
L为-CR1R2-、-CR3R4-CR5R6-或-CR7R8-CR9R10-CR11R12-;
其中,R1和R2各自独立地为氢、C1-4烷基或任选被1、2、3、4或5个选自氟、氯、溴或碘取代的苯基;
R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢或C1-4烷基;
或R3、R5和与之相连接的碳原子形成-C=C-;
或R7、R9和与之相连接的碳原子形成-C=C-;
或R9、R11和与之相连接的碳原子形成-C=C-;
A为C3-6环烷基、C6-10芳基或5-6元杂芳基;其中,A任选地被1、2、3、4或5个选自氟、氯、溴、碘、羟基、硝基、氰基、C1-4烷基、C1-4烷氧基、卤代C1-4烷基或卤代C1-4烷氧基的取代基取代。
一些实施方案中,Ra为氢、甲基、乙基、丙基或异丙基。
一些实施方案中,L为-CR1R2-、-CR3R4-CR5R6-或-CR7R8-CR9R10-CR11R12-;
其中,R1和R2各自独立地为氢、甲基、乙基、苯基或被1、2、3、4或5个选自氟、氯、溴或碘取代的苯基;
R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢或甲基;
或R3、R5和与之相连接的碳原子形成-C=C-;
或R7、R9和与之相连接的碳原子形成-C=C-;
或R9、R11和与之相连接的碳原子形成-C=C-。
又一些实施方案中,L为-CR1R2-、-CH2CH2-、-CH2CH2CH2-、-CH=CH-或-CH=CH-CH2-;
其中,R1和R2各自独立地为氢、甲基、乙基、苯基或被1、2、3、4或5个选自氟、氯、溴或碘取代的苯基。
又一些实施方案中,L为-CH2-、-CH(CH3)-、-CH2CH2-、-CH2CH2CH2-、-CH=CH-或-CH=CH-CH2-。
一些实施方案中,A为环丙基、环丁基、环戊基、环己基、苯基、噻吩基、呋喃基或吡啶基;其中,A任选地被1、2、3、4或5个选自氟、氯、溴、碘、羟基、硝基、氰基、C1-4烷基、C1-4烷氧基、卤代C1-4烷基或卤代C1-4烷氧基的取代基取代。
其中,A任选地被1、2、3、4或5个选自氟、氯、溴、碘、羟基、硝基、氰基、C1-4烷基、C1-4烷氧基、卤代C1-4烷基或卤代C1-4烷氧基的取代基取代。
其中,A任选地被1、2、3、4或5个选自氟、氯、溴、碘、羟基、硝基、氰基-CH3、-OCH3、-CF3或-OCF3的取代基取代。
又一些实施方案中,A为以下子结构式:
一些实施方案中,本发明提供一种化合物,其为具有式(I-1)所示的化合物,或式(I-1)所示化合物的立体异构体、氮氧化物或其盐:
其中,A、L、B、Ra和M具有本发明式(I)中相应取代基所述的含义。
又一些实施方案中,本发明提供一种化合物,其为具有式(I-2)所示的化合物,或式(I-2)所示化合物的立体异构体、氮氧化物或其盐:
其中,A、L、B、Ra和M具有本发明式(I)中相应取代基所述的含义。
一些实施方案中,本发明提供一种化合物,其为具有式(I-3)所示的化合物,或式(I-3)所示化合物的立体异构体、氮氧化物或其盐:
其中,A、L、Ra和M具有本发明式(I)中相应取代基所述的含义。
又一些实施方案中,本发明提供一种化合物,其为具有式(I-4)所示的化合物,或式(I-4)所示化合物的立体异构体、氮氧化物或其盐:
其中,A、L、Ra和M具有本发明式(I)中相应取代基所述的含义。
又一些实施方案中,本发明提供一种化合物,其为具有式(I-5)所示的化合物,或式(I-5)所示化合物的立体异构体、氮氧化物或其盐:
其中,A、L和Ra具有本发明式(I)中相应取代基所述的含义。
一些实施方案中,本发明提供一种化合物,其为具有式(I-5)所示的化合物,或式(I-5)所示化合物的立体异构体、氮氧化物或其盐:
其中,Ra为甲基、乙基、丙基或异丙基;
其中,A为苯基或被1、2、3、4或5个任选自氟、氯、溴或碘取代的苯基;
R11、R12、R13、R14、R15、R16、R17、R18、R19、R20、R21、R22、R23、R24和R25各自独立地为氢、氟、氯、溴或碘。
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立体异构体、氮氧化物或其盐:
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。
具体地,农药学上可接受的辅料为表面活性剂和/或载体。
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杀菌剂的应用。
又另一方面,本发明提供一种防治植物病害的方法,其方法包括在病害萌发前或萌发后,将本发明所述的化合物和/或本发明所述的组合物施用于植物和/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“卤素”是指氟(F)、氯(Cl)、溴(Br)或碘(I)。
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“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“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。
术语“杂芳基”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“杂芳基”可以与术语“杂芳环”或“杂芳族化合物”交换使用。所述杂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。
在一实施方案中,5-10个原子组成的杂芳基包含1,2,3或4个独立选自O,S和N的杂原子。
在另一实施方案中,杂芳基的环原子包含1-9个碳原子和1-4个选自N、O或S的杂原子;在另一实施方案中,杂芳基的环原子包含1-5个碳原子和1-4个选自N、O或S的杂原子。
在又一实施方案中,杂芳基表示含1-4个N杂原子的5元或6元杂芳基;在又一实施方案中,杂芳基表示含1-3个选自N、O或S的杂原子的5元杂芳基;在又一实施方案中,杂芳基表示含1-3个选自N或O的杂原子的5元杂芳基;在又一实施方案中,杂芳基表示含1-3个选自N或S的杂原子的5元杂芳基。
杂芳基基团的实例包括,但并不限于,2-噻吩基,3-噻吩基,2-呋喃基,3-呋喃基,N-咪唑基,2-咪唑基,4-咪唑基,5-咪唑基,3-异噁唑基,4-异噁唑基,5-异噁唑基,2-噁唑基,4-噁唑基,5-噁唑基,N-吡咯基,2-吡咯基,3-吡咯基,2-吡啶基,3-吡啶基,4-吡啶基,2-嘧啶基,4-嘧啶基,5-嘧啶基,哒嗪基(如3-哒嗪基),2-噻唑基,4-噻唑基,5-噻唑基,四唑基(如5-四唑基),三唑基(如2-三唑基和5-三唑基),2-噻吩基,3-噻吩基,吡唑基,异噻唑基,1,2,3-噁二唑基,1,2,5-噁二唑基,1,2,4-噁二唑基,1,2,3-三唑基,1,2,3-硫代二唑基,1,3,4-硫代二唑基,1,2,5-硫代二唑基,吡嗪基,1,3,5-三嗪基,嘧啶酮基,吡啶酮基;也包括以下的双环,但绝不限于这些双环:苯并咪唑基,苯并呋喃基,苯并四氢呋喃基,苯并噻吩基,吲哚基(如2-吲哚基),等等。
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。本发明所述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)对本发明所述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和/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。
本发明化合物及组合物的应用
本发明的化合物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本发明所述化合物的杀真菌组合物。本发明的化合物和/或组合物可对由担子菌纲、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(Guignardiabidwell),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(Septoria nodorum)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(Erysiphegraminis)和萝白粉病菌(Erysiphe polygoni))、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(Pseudocercosporella herpotrichoides),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。
术语“室温”是指事物所处位置周围的自然温度,所述环境温度可以依据所处地区、所处季节、所处时间有所不同,一般在-20℃~45℃之间或在大约18℃~30℃,或大约20℃~25℃或大约22℃。
合成方案
合成方案一
式(I)所示的目标化合物可以通过合成方案一制备得到。式a所示化合物与式b所示化合物在碱性条件下(如叔丁醇钾、碳酸钾、氢氧化钠、氢氧化钾、磷酸钾等)发生亲核取代反应,得到式c所示化合物;式c所示化合物与三甲基碘化锍(或三甲基碘化亚砜)发生科里-柴可夫斯基反应,得到式d所示化合物;式d所示化合物在碱性条件(如氢氧化钠、氢化钠、氢氧化钾等)与式e所示化合物发生开环反应,得到式(I)所示的目标化合物;
其中,M、Ra、Rb、Rc、Rd、B、L和A具有本发明所述的含义。
实施例
实施例1:2-(4-((4-氯苄基)氧)-2-(三氟甲基)苯基)-1-(1H-1,2,4-三唑-1-基)丙-2-醇的合成
步骤1:1-(4-((4-氯苄基)氧)-2-(三氟甲基)苯基)乙-1-酮的合成
将4-氟-2(三氟甲基)苯乙酮(4.00g,19.40mmol),对氯苄醇(2.85g,20.00mmol)溶于N,N-二甲基甲酰胺(30mL)中,加入叔丁醇钾(2.80g,25.00mmol),室温搅拌5h。将反应液倒入水中,用乙酸乙酯萃取,粗产物经柱层析(石油醚:乙酸乙酯(v:v)=90:10),得4.55g黄色油状液体,产率:71.3%。
LC-MS:(M+1)m/z=329.0.
步骤2:2-(4-((4-氯苄基)氧)-2-(三氟甲基)苯基)-2-甲基环氧乙烷的合成
将氢化钠(1.66g,69.20mmol)加入到四氢呋喃(20ml)中,0℃搅拌下逐滴加入三甲基碘化锍(4.08g,20.00mmol)的二甲基亚砜溶液20mL,0℃反应1h,滴加1-(4-((4-氯苄基)氧)-2-(三氟甲基)苯基)乙-1-酮(4.55g,13.84mmol)的二甲基亚砜溶液20mL,0℃反应1h后室温反应5h。加水淬灭反应,用乙酸乙酯萃取,粗产物经柱层析(石油醚:乙酸乙酯(v:v)=90:10),得3.88g无色油状液体,产率:81.8%。
LC-MS:(M+1)m/z=343.1.
步骤3:2-(4-((4-氯苄基)氧)-2-(三氟甲基)苯基)-1-(1H-1,2,4-三唑-1-基)丙-2-醇的合成
将1,2,4-三氮唑(3.45g,50.00mmol)溶于二甲基亚砜(20mL)中,加入氢氧化钠(1.60g,40.00mmol),90℃搅拌1h,加入2-(4-((4-氯苄基)氧)-2-(三氟甲基)苯基)-2-甲基环氧乙烷(3.43g,10.00mmol),130℃搅拌8h。将反应液倒入水中,用乙酸乙酯萃取,粗产物经柱层析纯化(石油醚:乙酸乙酯(v:v)=70:30),得2.87g无色油状液体,产率:69.7%。
1H NMR(400MHz,CDCl3)δ7.99(s,1H),7.79(s,1H),7.51(d,J=8.9Hz,1H),7.34(s,5H),6.99(dd,J=8.9,2.6Hz,1H),5.01(s,2H),4.69(s,1H),4.55(d,J=14.2Hz,1H),4.40(d,J=14.2Hz,1H),1.59(s,3H).
LC-MS:(M+1)m/z=412.1.
使用相应的物料为原料,参照实施例1的制备方法或参照现有技术中的制备方法,制备得到表1中的目标化合物。
表1
活性测试例
测试例1:小麦白粉病(wheat powdery mildew)
选择1叶1心期长势一致盆栽小麦苗,用油性记号笔写上标签编号,供试验用。原药用溶剂DMSO溶解后加入含0.1%吐温-80水稀释至200mg/L。茎叶喷雾,处理后将试材在通风处阴干。处理后24h左右进行接种。将成熟的小麦白粉病菌孢子轻轻抖落,接种于麦苗上。接种后麦苗温室低湿度培养(15~26℃),8d后根据空白对照发病情况分级调查,按照病指计算防效。
结果显示:在200mg/L剂量下本发明化合物实施例1、实施例2、实施例3、实施例4、实施例5、实施例6、实施例7、实施例9、实施例10、实施例11、实施例12、实施例13、实施例14、实施例15、实施例16、实施例17、实施例18、实施例19、实施例25、实施例31、实施例44、实施例46、实施例47和实施例48对小麦白粉病的防效均为100%。
测试例2:玉米锈病(soybean rust(Puccinia sorghi Schw.))
选择两叶期长势一致的盆栽玉米苗,用油性记号笔在杯身写上编号,按序排放,供试验用。原药用溶剂DMSO溶解后加入含0.1%吐温-80水稀释至200mg/L。茎叶喷雾,处理后将试材在通风处阴干。处理后24h左右进行接种。取锈病孢子成熟的玉米叶片,加入含有表面活性剂的水中,用毛笔洗下孢子,经双层纱布过滤后,制成孢子悬浮液(2×106~5×106个/mL),用接种喷雾器(压力0.1MPa)在玉米苗上均匀喷雾接种。将接种后的盆栽玉米置于保湿箱(室)或人工气候室(温度为25℃,相对湿度100%)培养,24h后置于光照强度大于2000lx的培养箱(室)或温室高湿培养,7d天左右根据空白对照发病情况进行分级调查,按照病指计算防效。
结果显示:在200mg/L剂量下本发明化合物实施例1、实施例4、实施例7、实施例17、实施例18、实施例21、实施例22和实施例44对玉米锈病的防效在90-95%。
测试例3:水稻纹枯病(Rhizoctonia solani)
选择两叶一心、长势一致的盆栽玉米苗,喷雾处理后自然晾干,24h左右进行接种,待药剂喷雾晾干后,接菌饼于叶片上。25-26℃暗光保湿24h后,恢复自然光照保湿培养约3d。待对照充分发病后用卡尺计量每个接种点病斑长度,计算防效。
结果显示:在200mg/L剂量下本发明化合物实施例27和实施例29对水稻纹枯病的的防效均为100%。
另外,本发明化合物实施例3、化合物实施例12在0.78125mg/L剂量下对小麦白粉病的防效在95%以上,而化合物Mefentrifluconazole在相同剂量下,对小麦白粉病的防效为70%。
由上述测试结果可知,本发明化合物对植物病害,特别是对小麦白粉病、玉米锈病、水稻纹枯病具有显著的防效,可进一步开发作为农药杀菌剂使用。
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 (10)
1.一种化合物,其为具有式(I)所示的化合物,或式(I)所示化合物的立体异构体、氮氧化物或其盐:
其中,
M为三唑基;
Ra为氢或C1-4烷基;
Rb、Rc和Rd各自独立地为氢;其中,Rb、Rc和Rd均不被取代;
B为-O-或-S-;
L为-CR1R2-、-CR3R4-CR5R6-或-CR7R8-CR9R10-CR11R12-;
其中,R1和R2各自独立地为氢、C1-4烷基或任选被1、2、3、4或5个选自氟、氯、溴或碘取代的苯基;
R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立地为氢或C1-4烷基;
或R3、R5和与之相连接的碳原子形成-C=C-;
或R7、R9和与之相连接的碳原子形成-C=C-;
或R9、R11和与之相连接的碳原子形成-C=C-;
A为C3-6环烷基、C6-10芳基或5-6元杂芳基;其中,A任选地被1、2、3、4或5个选自氟、氯、溴、碘、羟基、硝基、氰基、C1-4烷基、C1-4烷氧基、卤代C1-4烷基或卤代C1-4烷氧基的取代基取代。
2.根据权利要求1所述的化合物,其中,
L为-CR1R2-、-CH2CH2-、-CH2CH2CH2-、-CH=CH-或-CH=CH-CH2-;
其中,R1和R2各自独立地为氢、甲基、乙基、苯基或被1、2、3、4或5个任选自氟、氯、溴或碘取代的苯基。
4.根据权利要求1所述的化合物,其中,
A为环丙基、环丁基、环戊基、环己基、苯基、噻吩基、呋喃基或吡啶基;其中,A任选地被1、2、3、4或5个选自氟、氯、溴、碘、羟基、硝基、氰基、C1-4烷基、C1-4烷氧基、卤代C1-4烷基或卤代C1-4烷氧基的取代基取代。
9.一种组合物,包含至少一种权利要求1-8任意一项所述的化合物和农药学上可接受的辅料。
10.权利要求1-8任意一项所述的化合物或权利要求9所述的组合物在农业中作为植物病害防治剂应用。
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WO2019093522A1 (ja) * | 2017-11-13 | 2019-05-16 | 株式会社クレハ | アゾール誘導体、中間体化合物、及びアゾール誘導体の製造方法、ならびに農園芸用薬剤及び工業用材料保護剤 |
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