CN1553907A - 四唑基肟衍生物以及把其作为有效成分的农药 - Google Patents
四唑基肟衍生物以及把其作为有效成分的农药 Download PDFInfo
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Abstract
本发明提供了对有用植物体的药害小,而且比以往的杂环取代肟衍生物对于植物病害更具有优异药效的四唑基肟衍生物。用通式(1)表示的四唑基肟衍生物以及把其作为有效成分含有的植物病害防除剂,(X:氢原子、卤原子、烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基;A:1-烷基四唑基-5-基、5-烷基四唑基-1-基;Het:具有取代基的吡啶基、具有取代基的噻唑基)。
Description
技术领域
本发明涉及新的四唑基肟(tetrazoyl oxime)衍生物以及把其作为有效成分含有的农药,特别涉及植物病害防除剂。
背景技术
本发明人等在与发明有关的特开平11-269176号公报(WO99/29689号公报、欧洲专利公开第1038874号公报)以及特开2001-55387号公报(WO00/75138号公报、欧洲专利公开第1184382号公报)中,报告了杂环取代肟衍生物可用作植物病害防除剂。
具体地说,在特开平11-269176号公报(WO99/29689号公报、欧洲专利公开第1038874号公报)中,公开了用通式(A)表示的肟衍生物:
【式中,R1表示氢原子或者低级烷基;X表示卤原子、硝基、羟基、氰基、羧基、烷氧基羰基、低级烷基、低级烷氧基、低级烷硫基、低级烷基磺酰基、芳基、芳氧基或者氨基;N表示0~3的整数;HetA表示也可以用选自卤原子、低级烷基、低级烷硫基、低级烷基磺酰基、低级烷氧基、三氟甲基或者氰基的一个或者两个取代基取代的含有一个或者两个氮原子的六元环含氮芳香环或者其苯缩合环型含氮芳香环;HetB表示以下通式中的任一个表示的环结构
式中,Y表示氢原子、卤原子或者低级烷基。
另一方面,在特开2001-55387号公报(WO00/75138号公报、欧洲专利公开第1184382号公报)中,公开了用通式(B)表示的肟衍生物:
【式中,HetA表示用下述3个式子的任一个表示的基团
(式中,Q表示氢原子、卤原子或者低级烷基,R1表示氢原子、低级烷基、环烷基、低级链烯基、低级炔基、芳烷基或者芳基,R2表示氢原子或者低级烷基);HetB表示用下述9个式子的任一个表示的基团
(式中,Y表示氢原子或者低级烷基,R3表示氢原子或者低级烷基);HetC表示用下述9个式子的任一个表示的基团
(式中,R4表示氢原子或者低级烷基,X表示氢原子、卤原子、低级烷基、低级烷氧基或者氰基,Z表示氢原子、卤原子或者低级烷基,N表示0~3的整数)。
这些特开平11-269176号公报(WO99/29689号公报、欧洲专利公开第1038874号公报)以及特开2001-55387号公报(WO00/75138号公报、欧洲专利公开第1184382号公报)中记载的各个化合物虽然对于植物病害显示出了相当好的防除效果,但是要求开发防除效果更加杰出的药剂。
还有,另一方面,在文献(Bull.Soc.Chim.Belg.,96卷,675页,1987年)中,是与用作为本发明的权利要求1记载的四唑基肟衍生物的合成中间体使用的本发明的权利要求9中记载的通式(7)表示的四唑基氧肟衍生物类似的化合物,在上述通式(7)中,仅仅记载了X2是氢原子且Y2是甲基的化合物、X2是氢原子且Y2是异丙基的化合物以及X2是氯原子且Y2是甲基的化合物。这三个化合物是为了了解反应机理而进行的研究并合成的,在该文献中,完全没有包括使用这些化合物可以合成用本发明的权利要求1记载的通式(1)表示的四唑基肟衍生物和可用作农药中间体等的记载,也没有关于该化合物的有用性的记载。
发明内容
本发明所要解决的课题在于提供对于有用植物体的药害少,而且对于植物病害也具有比以往的杂环取代肟衍生物杰出的药效的四唑基肟衍生物。
本发明所要解决的另一个课题在于提供把上述四唑基肟衍生物作为有效成分含有的对植物病害的防除效果杰出的农药。
本发明所要解决的另一个课题在于提供为了制造上述四唑基肟衍生物而用作中间体的四唑基氧肟衍生物。
本发明人等为了解决该课题而合成了许多四唑基肟衍生物,同时专心研究了这些的生理活性,结果发现,不用担心用下述通式(1)表示的四唑基肟衍生物对有用植物的药害,而且以极低用量就可以显示出非常优异的植物病害的防除效果,至此完成了本发明。
即,本发明为了解决上述课题,提供了用通式(1)表示的四唑基肟衍生物:
式中,X表示氢原子、卤原子、烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基;A表示用通式(2)表示的四唑基
(式中,Y表示烷基)
或者用通式(3)表示的四唑基
(式中,Y表示烷基);
Het表示用通式(4)表示的吡啶基
【式中,R表示氢原子或者卤原子,Z表示氢原子、氨基、用通式QC(=O)NH-表示的基团:
(式中,Q表示氢原子、碳原子数1~8的烷基、用卤原子取代的碳原子数1~6的烷基、碳原子数3~6的环烷基、碳原子数1-8烷氧基、碳原子数3~6的环烷氧基、苄氧基、2-苯基乙氧基、用碳原子数1~4的烷基取代的硫代烷基、用碳原子数1~4的烷氧基取代的碳原子数1~2的烷基、用碳原子数1~4的酰胺基取代的碳原子数1~6的烷基、用碳原子数1~4的酰胺基取代的碳原子数1~6的烷氧基、碳原子数1~8的烷基氨基、碳原子数2~6的链烯基、芳烷基或者苯基)】
或者用通式(5)表示的噻唑基
(式中,R以及Z表示与上述通式(4)中定义的意思相同的意思)。
另外,本发明为了解决上述课题,提供了用作上述通式(1)表示的四唑基肟衍生物的合成中间体的用通式(6)表示的四唑基肟基衍生物
(式中,X1表示氢原子、卤原子、烷基或者烷氧基,Y1表示烷基)以及用通式(7)表示的四唑基肟基衍生物
(X2表示烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基,Y2表示烷基)。
另外,本发明为了解决上述课题,提供了把用上述通式(1)表示的四唑基肟衍生物作为有效成分含有的农药,特别提供了植物病害防除剂。
发明的最佳实施方式
在用上述通式(1)表示的四唑基肟衍生物中,对X的取代位置没有特别地限制,其表示氢原子、卤原子、烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基。
作为X表示的卤原子,可以举例为氯原子、溴原子、碘原子、氟原子。即使在这些当中,由于X为氯原子或者氟原子的化合物药害性低而且防除效果优异,所以特别优选。
作为X表示的烷基,优选碳原子数1~4的烷基,具体地可以举例为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基。即使在这些当中,由于X为甲基或者叔丁基的化合物药害性低而且防除效果优异,所以特别优选。
另外,作为X表示的烷氧基,优选碳原子数1~3的烷氧基,具体地可以举例为甲氧基、乙氧基、丙氧基、异丙氧基。即使在这些当中,由于X为甲氧基或者乙氧基的化合物药害性低而且防除效果优异,所以特别优选。
另外,作为X表示的芳基,可以举例为苯基、4-甲基苯基、4-氯苯基等。即使在这些当中,由于X为苯基的化合物药害性低而且防除效果优异,所以特别优选。
即使在这些当中,作为X最优选的还是氢原子。
在用上述通式(2)或者上述通式(3)表示的四唑基中,Y表示烷基。即使在烷基中,优选如甲基、乙基、正丙基、异丙基的碳原子数1~3的烷基。即使在这些当中,由于Y为甲基或者乙基的化合物药害性低而且防除效果优异,所以特别优选。
用上述通式(4)表示的吡啶基中的R表示氢原子;如氯原子、溴原子、碘原子、氟原子的卤原子。即使在这些当中,由于R为氢原子或者氯原子的化合物药害性低而且防除效果优异,所以还特别优选。
用上述通式(1)表示的四唑基肟衍生物中的Het是用上述通式(4)表示的吡啶基或者上述通式(5)表示的噻唑基的任一个,上述通式(4)以及上述通式(5)中的Z表示氢原子、氨基或者用通式QC(=O)NH-表示的基团。
用上述通式QC(=O)NH-表示的基团中的Q表示氢原子、低级烷基、用卤原子取代的低级烷基、碳原子数3~6的环烷基、苄氧基、2-苯基乙氧基、碳原子数1~8烷氧基、碳原子数3~6的环烷氧基、用碳原子数1~6的烷氧基取代的低级烷基,用碳原子数1~4的烷基取代的硫代烷基、用碳原子数1~4的酰胺基取代的碳原子数1~6的烷基、用碳原子数1~4的酰胺基取代的碳原子数1~6的烷氧基、碳原子数1~8的烷基氨基、碳原子数2~6的链烯基、芳烷基或者苯基。
作为Q表示的低级烷基,优选碳原子数1~8的烷基,具体地可以举例为甲基、乙基、正丙基、异丙基、1,1-二甲基丙基、正丁基、异丁基、仲丁基、叔丁基、异戊基、1-甲基丁基、2-甲基丁基、新戊基、1-乙基丙基、正戊基、己基、庚基、辛基等。
作为Q表示的用卤原子取代的低级烷基,优选用卤原子取代的碳原子数1~6的烷基,具体地可以举例为氯甲基、二氟甲基、三氟甲基、二氟氯甲基、五氟乙基、3,3,3-三氟正丙基、1-氯己基等。
作为Q表示的碳原子数3~6的环烷基,具体地可以举例为环丙基、环丁基、环戊基、环己基。
作为Q表示的碳原子数1~8的烷氧基,具体地可以举例为甲氧基、乙氧基、丙氧基、异丙氧基、1,1-二甲基丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、异戊氧基、1-甲基丁氧基、2-甲基丁氧基、新戊氧基、1-乙基丙氧基、正戊氧基、己氧基、庚氧基、辛氧基等。
作为Q表示的碳原子数3~6的环烷氧基,具体地可以举例为环丙氧基、环丁氧基、环戊氧基、环己氧基。
作为Q表示的用碳原子数1~4的烷氧基取代的碳原子数1~2的烷基,可以举例为甲氧基甲基、乙氧基甲基、乙氧基乙基、丁氧基甲基。
作为Q表示的用碳原子数1~4的烷基取代的烷硫基,具体地可以举例为甲硫甲基、甲硫乙基、乙硫甲基、丁硫甲基。
作为Q表示的用碳原子数1~4的酰基氨基取代的碳原子数1~6的烷氧基,具体地可以举例为乙酰基氨基甲氧基、2-(丙酰基氨基)乙氧基、3-(乙酰基氨基)丙氧基、3-(丙酰基氨基)丙氧基、3-(异丙酰基氨基)丙氧基、3-(丁酰基氨基)丙氧基、3-(异丁酰基氨基)丙氧基、3-(仲丁酰基氨基)丙氧基、3-(叔丁酰基氨基)丙氧基、4-(乙酰基氨基)丁氧基、5-(乙酰基氨基)戊氧基以及6-(乙酰基氨基)己氧基等。
作为Q表示的用碳原子数1~4的酰基氨基取代的碳原子数1~6的烷基,具体地可以举例为乙酰基氨基甲基、2-(丙酰基氨基)乙基、3-(乙酰基氨基)丙基、3-(丙酰基氨基)丙基、3-(异丙酰基氨基)丙基、3-(丁酰基氨基)丙基、3-(异丁酰基氨基)丙基、3-(仲丁酰基氨基)丙基、3-(叔丁酰基氨基)丙基、4-(乙酰基氨基)丁基、5-(乙酰基氨基)戊基以及6-(乙酰基氨基)己基等。
作为Q表示的碳原子数1~8的烷基氨基,具体地可以举例为甲基氨基、乙基氨基、丙基氨基、异丙基氨基、丁基氨基、异丁基氨基、仲丁基氨基、叔丁基氨基、新戊基氨基、1-乙基丙基氨基、正戊基氨基、己基氨基、庚基氨基、辛基氨基等。
作为Q表示的碳原子数2~6的链烯基,具体地可以举例为烯丙基、丙烯基、1-丁烯基、2-丁烯基、2-戊烯基、5-己烯基。
作为Q表示的芳烷基,可以举例为苄基、苯乙基等。
用上述通式(6)表示的四唑基氧肟体中的X1表示氢原子、卤原子、烷基或者烷氧基。
作为X1表示的卤原子,可以举例为氯原子、溴原子、碘原子、氟原子。即使在这些当中,特别优选氯原子或者氟原子。
作为X1表示的烷基,优选碳原子数1~4的烷基,具体地可以举例为甲基、乙基、正丙基、异丙基、1,1-二甲基丙基、正丁基、异丁基、仲丁基、叔丁基等。即使在这些当中,特别优选甲基。
作为X1表示的烷氧基,优选碳原子数1~3的烷氧基,具体地可以举例为甲氧基、乙氧基、丙氧基、异丙氧基等。即使在这些当中,还特别优选甲基。
用上述通式(6)表示的四唑基氧肟体中的Y1表示烷基。即使在烷基中,还优选如甲基、乙基、正丙基、异丙基的碳原子数1~3的烷基,特别优选甲基。
用上述通式(7)表示的四唑基氧肟体中的X2表示烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基。
作为X2表示的烷基,优选如甲基、乙基、正丙基、异丙基、1,1-二甲基丙基、正丁基、异丁基、仲丁基、叔丁基的碳原子数1~4的烷基,即使在这些当中,还特别优选甲基或者叔丁基。
作为X2表示的烷氧基,优选如甲氧基、乙氧基、丙氧基、异丙氧基的碳原子数1~3的烷氧基,即使在这些当中,还特别优选甲氧基。
作为X2表示的芳基,具体地可以举例为苯基、4-甲基苯基以及4-氯苯基等,即使在这些当中,还特别优选苯基。
作为Y2表示的烷基,优选如甲基、乙基、正丙基、异丙基的碳原子数1~3的烷基,特别优选甲基。
在用上述通式(1)表示的化合物中,优选Z是用通式QC(=O)NH-表示的基团(式中,Q表示碳原子数1~8的烷基或者碳原子数1~8的烷氧基),而且Het是用上述通式(4)表示的吡啶基或者用上述通式(5)表示的噻唑基的四唑基肟衍生物,而且,特别优选X为氢原子或者卤原子的四唑基肟衍生物。
在用上述通式(1)表示的四唑基肟衍生物以及用上述通式(6)或者上述通式(7)表示的四唑基肟衍生物中存在的肟部位中,存在(E)体和(Z)体的立体结构,这两个立体异构体及其混合物都包含在本发明中。通常,合成物作为只是(Z)体、或者(E)体和(Z)体的混合物获得。
(E)体和(Z)体的混合物通过分离精制可以单独分离两个异构体。
上述通式(1)的四唑基肟衍生物,其(Z)体比(E)体对植物病害的防除活性还优异。但是,(Z)体也可在自然环境下,由于光等的作用,部分变为(E)体,作为(E)体和(Z)体的混合物,由于存在按某一定比率进行稳定化的倾向,所以两者的化合物及其混合物都是有用的。而且,由于(E)体和(Z)体的稳定化比率根据每个化合物而不同,所以不能一律进行特定。
(制造方法)
用上述通式(1)表示的四唑基肟衍生物,当四唑基是用通式(2)表示的四唑基时,可以用制造方法(A)来制造,当四唑基是用通式(3)表示的四唑基时,可以用制造方法(B)来制造。但是,本发明的四唑基肟衍生物的制造方法并不限于这些制造方法。
制造方法(A)
(式中,X、Y以及Het表示与上述通式(1)中已经定义的X、Y以及Het相同的含义,L表示氯原子、溴原子或者碘原子)
在制造方法(A)中,使羟氨与用通式(a-1)表示的四唑基甲醛衍生物反应,从而获得用通式(2’)表示的四唑基肟基衍生物,然后,在碱(例如,氢化钠、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸铯、三乙胺、吡啶、N,N-二甲基氨基吡啶等)的存在下使由通式(b)表示的化合物反应,从而制造用通式(1-a)表示的四唑基肟衍生物。
作为原料的用通式(a-1)表示的四唑基甲醛衍生物可以按照,例如文献(CaN.J.Chem.,49卷,2139页,1971年)中记载的方法,通过1-烷基四唑与酯类的反应很容易制造。
制造方法(B)
(式中,X、Y以及Het表示与上述通式(1)中已经定义的X、Y以及Het相同的含义,L表示氯原子、溴原子或者碘原子)
在制造方法(B)中,在碱(例如,氢化钠、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸铯、三乙胺、吡啶、N,N-二甲基氨基吡啶等)的存在下,使由通式(b)表示的化合物与由通式(7’)表示的四唑基肟基衍生物反应,从而制造了用通式(1-b)表示的四唑基肟衍生物。
作为原料的用通式(7’)表示的四唑基肟基衍生物可以按照,例如文献(Bull.Soc.Chim.Belg.96卷,675页,1987年)中记载的方法,通过在三乙胺的存在下使苯基羟基氯代亚胺与5-烷基四唑反应很容易制造。
用上述方法制造的本发明的用通式(1)表示的四唑基肟衍生物的具体结构示于表1-23。而且,表中的X、Y、Z以及R表示与上述通式(1)中定义的意思相同的意思,cyclo表示环状结构。
表1
化合物编号 | Z | R | X | Y |
(1)-1 | H | H | H | CH3 |
(1)-2 | H2N | H | H | CH3 |
(1)-3 | HCONH | H | H | CH3 |
(1)-4 | CH3CONH | H | H | CH3 |
(1)-5 | CH3CH2CONH | H | H | CH3 |
(1)-6 | CH3CH2CH2CONH | H | H | CH3 |
(1)-7 | (CH3)2CHCONH | H | H | CH3 |
(1)-8 | CH3CH2CH2CH2CONH | H | H | CH3 |
(1)-9 | (CH3)2CHCH2CONH | H | H | CH3 |
(1)-10 | CH3CH2CH(CH3)CONH | H | H | CH3 |
(1)-11 | (CH3)3CCONH | H | H | CH3 |
(1)-12 | CH3CH2CH2CH2CH2CONH | H | H | CH3 |
(1)-13 | (CH3)2CHCH2CH2CONH | H | H | CH3 |
(1)-14 | CH3CH2CH(CH3)CH2CONH | H | H | CH3 |
(1)-15 | CH3CH2CH2CH(CH3)CONH | H | H | CH3 |
(1)-16 | (CH3)3CCH2CONH | H | H | CH3 |
(1)-17 | (CH3CH2)2CHCONH | H | H | CH3 |
(1)-18 | CH3CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(1)-19 | CH3CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(1)-20 | CH3CH2CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(1)-21 | cyclo-C3H5-CONH | H | H | CH3 |
(1)-22 | cyclo-C5H9-CONH | H | H | CH3 |
(1)-23 | cyclo-C6H11-CONH | H | H | CH3 |
表2
化合物编号 | Z | R | X | Y |
(2)-1 | H | H | H | CH3 |
(2)-2 | H2N | H | H | CH3 |
(2)-3 | HCONH | H | H | CH3 |
(2)-4 | CH3CONH | H | H | CH3 |
(2)-5 | CH3CH2CONH | H | H | CH3 |
(2)-6 | CH3CH2CH2CONH | H | H | CH3 |
(2)-7 | (CH3)2CHCONH | H | H | CH3 |
(2)-8 | CH3CH2CH2CH2CONH | H | H | CH3 |
(2)-9 | (CH3)2CHCH2CONH | H | H | CH3 |
(2)-10 | CH3CH2CH(CH3)CONH | H | H | CH3 |
(2)-11 | (CH3)3CCONH | H | H | CH3 |
(2)-12 | CH3CH2CH2CH2CH2CONH | H | H | CH3 |
(2)-13 | (CH3)2CHCH2CH2CONH | H | H | CH3 |
(2)-14 | CH3CH2CH(CH3)CH2CONH | H | H | CH3 |
(2)-15 | CH3CH2CH2CH(CH3)CONH | H | H | CH3 |
(2)-16 | (CH3)3CCH2CONH | H | H | CH3 |
(2)-17 | (CH3CH2)2CHCONH | H | H | CH3 |
(2)-18 | CH3CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(2)-19 | CH3CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(2)-20 | CH3CH2CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(2)-21 | cyclo-C3H5-CONH | H | H | CH3 |
(2)-22 | cyclo-C5H9-CONH | H | H | CH3 |
(2)-23 | cyclo-C6H11-CONH | H | H | CH3 |
表3
化合物编号 | Z | R | X | Y |
(3)-1 | CH3OCONH | H | H | CH3 |
(3)-2 | CH3CH2OCONH | H | H | CH3 |
(3)-3 | CH3CH2CH2OCONH | H | H | CH3 |
(3)-4 | (CH3)2CHOCONH | H | H | CH3 |
(3)-5 | CH3CH2CH2CH2OCONH | H | H | CH3 |
(3)-6 | (CH3)2CHCH2OCONH | H | H | CH3 |
(3)-7 | CH3CH2CH(CH3)OCONH | H | H | CH3 |
(3)-8 | (CH3)3COCONH | H | H | CH3 |
(3)-9 | CH3CH2CH2CH2CH2OCONH | H | H | CH3 |
(3)-10 | (CH3)2CHCH2CH2OCONH | H | H | CH3 |
(3)-11 | CH3CH2CH(CH3)CH2OCONH | H | H | CH3 |
(3)-12 | CH3CH2CH2CH(CH3)OCONH | H | H | CH3 |
(3)-13 | (CH3)3CCH2OCONH | H | H | CH3 |
(3)-14 | (CH3CH2)2CHOCONH | H | H | CH3 |
(3)-15 | CH3CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(3)-16 | CH3CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(3)-17 | CH3CH2CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(3)-18 | C6H5CH2OCONH | H | H | CH3 |
(3)-19 | C6H5CH2CH2OCONH | H | H | CH3 |
(3)-20 | cyclo-C3H5-OCONH | H | H | CH3 |
(3)-21 | CH3CH2C(CH3)2OCONH | H | H | CH3 |
(3)-22 | cyclo-C5H9-OCONH | H | H | CH3 |
(3)-23 | cyclo-C6H11-OCONH | H | H | CH3 |
(3)-24 | CH3CONHCH2CH2OCONH | H | H | CH3 |
(3)-25 | CH3CONHCH2CH2CH2OCONH | H | H | CH3 |
表4
化合物编号 | Z | R | X | Y |
(4)-1 | CH3OCONH | H | H | CH3 |
(4)-2 | CH3CH2OCONH | H | H | CH3 |
(4)-3 | CH3CH2CH2OCONH | H | H | CH3 |
(4)-4 | (CH3)2CHOCONH | H | H | CH3 |
(4)-5 | CH3CH2CH2CH2OCONH | H | H | CH3 |
(4)-6 | (CH3)2CHCH2OCONH | H | H | CH3 |
(4)-7 | CH3CH2CH(CH3)OCONH | H | H | CH3 |
(4)-8 | (CH3)3COCONH | H | H | CH3 |
(4)-9 | CH3CH2CH2CH2CH2OCONH | H | H | CH3 |
(4)-10 | (CH3)2CHCH2CH2OCONH | H | H | CH3 |
(4)-11 | CH3CH2CH(CH3)CH2OCONH | H | H | CH3 |
(4)-12 | CH3CH2CH2CH(CH3)OCONH | H | H | CH3 |
(4)-13 | (CH3)3CCH2OCONH | H | H | CH3 |
(4)-14 | (CH3CH2)2CHOCONH | H | H | CH3 |
(4)-15 | CH3CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(4)-16 | CH3CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(4)-17 | CH3CH2CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(4)-18 | C6H5CH2OCONH | H | H | CH3 |
(4)-19 | C6H5CH2CH2OCONH | H | H | CH3 |
(4)-20 | cyclo-C3H5-OCONH | H | H | CH3 |
(4)-21 | CH3CONHCH2CH2OCONH | H | H | CH3 |
(4)-22 | CH3CONHCH2CH2CH2OCONH | H | H | CH3 |
表5
化合物编号 | Z | R | X | Y |
(5)-1 | CH3OCH2CONH | H | H | CH3 |
(5)-2 | CH3CH2OCH2CONH | H | H | CH3 |
(5)-3 | CH3CH2OCH2CH2CONH | H | H | CH3 |
(5)-4 | CH3CH2CH2CH2OCH2CONH | H | H | CH3 |
(5)-5 | CH3SCH2CONH | H | H | CH3 |
(5)-6 | CH3SCH2CH2CONH | H | H | CH3 |
(5)-7 | CH3C(=CH2)CONH | H | H | CH3 |
(5)-8 | CH3CH=CHCH2CH2CONH | H | H | CH3 |
(5)-9 | CH3CH2CH=CHCH2CONH | H | H | CH3 |
(5)-10 | CH3CH2CH=CHCONH | H | H | CH3 |
(5)-11 | CH3CH2CH2CH=CHCONH | H | H | CH3 |
(5)-12 | C6H5CH2CONH | H | H | CH3 |
(5)-13 | C6H5CH2CH2CONH | H | H | CH3 |
(5)-14 | C6H5CONH | H | H | CH3 |
(5)-15 | ClCH2CONH | H | H | CH3 |
(5)-16 | F2CHCONH | H | H | CH3 |
(5)-17 | F3CCONH | H | H | CH3 |
(5)-18 | F3CCH2CONH | H | H | CH3 |
(5)-19 | CH3CONHCH2CH2CONH | H | H | CH3 |
(5)-20 | CH3CONHCH2CH2CH2CH2CH2CONH | H | H | CH3 |
表6
化合物编号 | Z | R | X | Y |
(6)-1 | CH3OCH2CONH | H | H | CH3 |
(6)-2 | CH3CH2OCH2CONH | H | H | CH3 |
(6)-3 | CH3CH2OCH2CH2CONH | H | H | CH3 |
(6)-4 | CH3CH2CH2CH2OCH2CONH | H | H | CH3 |
(6)-5 | CH3SCH2CONH | H | H | CH3 |
(6)-6 | CH3SCH2CH2CONH | H | H | CH3 |
(6)-7 | CH3C(=CH2)CONH | H | H | CH3 |
(6)-8 | CH3CH=CHCH2CH2CONH | H | H | CH3 |
(6)-9 | CH3CH2CH=CHCH2CONH | H | H | CH3 |
(6)-10 | CH3CH2CH=CHCONH | H | H | CH3 |
(6)-11 | CH3CH2CH2CH=CHCONH | H | H | CH3 |
(6)-12 | C6H5CH2CONH | H | H | CH3 |
(6)-13 | C6H5CH2CH2CONH | H | H | CH3 |
(6)-14 | C6H5CONH | H | H | CH3 |
(6)-15 | CH3CH2CH2OCH2CH2CONH | H | H | CH3 |
(6)-16 | CH3OCH2CH2OCONH | H | H | CH3 |
(6)-17 | F2CHCONH | H | H | CH3 |
(6)-18 | F3CCONH | H | H | CH3 |
(6)-19 | F3CCH2CH2CONH | H | H | CH3 |
(6)-20 | CH3CONHCH2CH2CONH | H | H | CH3 |
(6)-21 | CH3CONHCH2CH2CH2CH2CH2CONH | H | H | CH3 |
表7
化合物编号 | Z | R | X | Y |
(7)-1 | CH3CH2CH2CONH | H | 4-Cl | CH3 |
(7)-2 | (CH3)2CHCONH | H | 4-Cl | CH3 |
(7)-3 | cyclo-C3H5-CONH | H | 4-Cl | CH3 |
(7)-4 | CH3CH2CONH | H | 3-F | CH3 |
(7)-5 | (CH3)2CHCONH | H | 3-F | CH3 |
(7)-6 | cyclo-C3H5-CONH | H | 3-F | CH3 |
(7)-7 | (CH3)3CCONH | H | 3-F | CH3 |
(7)-8 | (CH3)2CHCONH | H | 4-F | CH3 |
(7)-9 | (CH3)2CHCONH | H | 4-CH3O | CH3 |
(7)-10 | (CH3)3CCONH | H | 4-CH3O | CH3 |
(7)-11 | cyclo-C3H5-CONH | H | 4-CH3O | CH3 |
(7)-12 | CH3CH2CH2CH2CH2CONH | H | 4-CH3 | CH3 |
(7)-13 | (CH3)3CCH2CONH | H | 4-CH3 | CH3 |
(7)-14 | (CH3)2CHCONH | Cl | H | CH3 |
(7)-15 | (CH3)2CHCONH | Cl | H | CH3CH2 |
(7)-16 | (CH3)3CCONH | H | H | CH3CH2 |
(7)-17 | (CH3)2CHCONH | H | H | CH3CH2 |
(7)-18 | H | H | 4-F | CH3 |
(7)-19 | H | H | 3-F | CH3 |
(7)-20 | H | H | 4-Cl | CH3 |
表8
化合物编号 | Z | R | X | Y |
(8)-1 | CH3CH2CH2CONH | H | 4-Cl | CH3 |
(8)-2 | (CH3)2CHCONH | H | 4-Cl | CH3 |
(8)-3 | cyclo-C3H5-CONH | H | 4-Cl | CH3 |
(8)-4 | CH3CH2CONH | H | 3-F | CH3 |
(8)-5 | (CH3)2CHCONH | H | 3-F | CH3 |
(8)-6 | cyclo-C3H5-CONH | H | 3-F | CH3 |
(8)-7 | (CH3)3CCONH | H | 3-F | CH3 |
(8)-8 | (CH3)2CHCONH | H | 4-F | CH3 |
(8)-9 | (CH3)2CHCONH | H | 4-CH3O | CH3 |
(8)-10 | (CH3)3CCONH | H | 4-CH3O | CH3 |
(8)-11 | cyclo-C3H5-CONH | H | 4-CH3O | CH3 |
(8)-12 | CH3CH2CH2CH2CH2CONH | H | 4-CH3 | CH3 |
(8)-13 | (CH3)3CCH2CONH | H | 4-CH3 | CH3 |
(8)-14 | (CH3)2CHCONH | Cl | H | CH3 |
(8)-15 | (CH3)2CHCONH | Cl | H | CH3CH2 |
(8)-16 | (CH3)3CCONH | H | H | CH3CH2 |
(8)-17 | (CH3)3CCONH | H | 4-Cl | CH3 |
表9
化合物编号 | Z | R | X | Y |
(9)-1 | (CH3)3COCONH | H | 3-F | CH3 |
(9)-2 | (CH3)2CHOCONH | H | 4-F | CH3 |
(9)-3 | (CH3)3COCONH | H | 4-F | CH3 |
(9)-4 | (CH3)3COCONH | H | 4-CH3 | CH3 |
(9)-5 | CH3CH2CH2CH2CH2OCONH | H | 4-CH3 | CH3 |
(9)-6 | CH3CH2CH2OCONH | H | 3-F | CH3 |
(9)-7 | CH3CH2CH2CH2CH2CONH | H | 3-CH3 | CH3 |
(9)-8 | (CH3)3COCONH | H | 3-CH3 | CH3 |
(9)-9 | CH3CH2C(CH3)2OCONH | H | 4-CH3 | CH3 |
(9)-10 | CH3CH2CH2CH2CH2OCONH | H | 2-CH3 | CH3 |
(9)-11 | CH3CH2CH2CH2OCONH | H | 2-CH3 | CH3 |
表10
化合物编号 | Z | R | X | Y |
(10)-1 | (CH3)3COCONH | H | 3-F | CH3 |
(10)-2 | (CH3)2CHOCONH | H | 4-F | CH3 |
(10)-3 | (CH3)3COCONH | H | 4-F | CH3 |
(10)-4 | (CH3)3COCONH | H | 4-CH3 | CH3 |
(10)-5 | CH3CH2CH2CH2CH2OCONH | H | 4-CH3 | CH3 |
表11
化合物编号 | Z | R | X | Y |
(11)-1 | H | H | H | CH3 |
(11)-2 | H2H | H | H | CH3 |
(11)-3 | HCONH | H | H | CH3 |
(11)-4 | CH3CONH | H | H | CH3 |
(11)-5 | CH3CH2CONH | H | H | CH3 |
(11)-6 | CH3CH2CH2CONH | H | H | CH3 |
(11)-7 | (CH3)2CHCONH | H | H | CH3 |
(11)-8 | CH3CH2CH2CH2CONH | H | H | CH3 |
(11)-9 | (CH3)2CHCH2CONH | H | H | CH3 |
(11)-10 | CH3CH2CH(CH3)CONH | H | H | CH3 |
(11)-11 | (CH3)3CCONH | H | H | CH3 |
(11)-12 | CH3CH2CH2CH2CH2CONH | H | H | CH3 |
(11)-13 | (CH3)2CHCH2CH2CONH | H | H | CH3 |
(11)-14 | CH3CH2CH(CH3)CH2CONH | H | H | CH3 |
(11)-15 | CH3CH2CH2CH(CH3)CONH | H | H | CH3 |
(11)-16 | (CH3)3CCH2CONH | H | H | CH3 |
(11)-17 | (CH3CH2)2CHCONH | H | H | CH3 |
(11)-18 | CH3CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(11)-19 | CH3CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(11)-20 | CH3CH2CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(11)-21 | cyclo-C3H5-CONH | H | H | CH3 |
(11)-22 | cyclo-C5H9-CONH | H | H | CH3 |
(11)-23 | cyclo-C6H11-CONH | H | H | CH3 |
(11)-24 | CH3CONHCH2CH2CONH | H | H | CH3 |
(11)-25 | CH3CONHCH2CH2CH2CH2CH2CONH | H | H | CH3 |
表12
化合物编号 | Z | R | X | Y |
(12)-1 | H | H | H | CH3 |
(12)-2 | H2H | H | H | CH3 |
(12)-3 | HCONH | H | H | CH3 |
(12)-4 | CH3CONH | H | H | CH3 |
(12)-5 | CH3CH2CONH | H | H | CH3 |
(12)-6 | CH3CH2CH2CONH | H | H | CH3 |
(12)-7 | (CH3)3CHCONH | H | H | CH3 |
(12)-8 | CH3CH2CH2CH2CONH | H | H | CH3 |
(12)-9 | (CH3)2CHCH2CONH | H | H | CH3 |
(12)-10 | CH3CH2CH(CH3)CONH | H | H | CH3 |
(12)-11 | (CH3)3CCONH | H | H | CH3 |
(12)-12 | CH3CH2CH2CH2CH2CONH | H | H | CH3 |
(12)-13 | (CH3)2CHCH2CH2CONH | H | H | CH3 |
(12)-14 | CH3CH2CH(CH3)CH2CONH | H | H | CH3 |
(12)-15 | CH3CH2CH2CH(CH3)CONH | H | H | CH3 |
(12)-16 | (CH3)3CCH2CONH | H | H | CH3 |
(12)-17 | (CH3CH2)2CHCONH | H | H | CH3 |
(12)-18 | CH3CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(12)-19 | CH3CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(12)-20 | CH3CH2CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(12)-21 | cyclo-C3H5-CONH | H | H | CH3 |
(12)-22 | cyclo-C5H9-CONH | H | H | CH3 |
(12)-23 | cyclo-C6H11-CONH | H | H | CH3 |
(12)-24 | CH3CONHCH2CH2CONH | H | H | CH3 |
(12)-25 | CH3CONHCH2CH2CH2CH2CH2CONH | H | H | CH3 |
表13
化合物编号 | Z | R | X | Y |
(13)-1 | CH3OCONH | H | H | CH3 |
(13)-2 | CH3CH2OCONH | H | H | CH3 |
(13)-3 | CH3CH2CH2OCONH | H | H | CH3 |
(13)-4 | (CH3)2CHOCONH | H | H | CH3 |
(13)-5 | CH3CH2CH2CH2OCONH | H | H | CH3 |
(13)-6 | (CH3)2CHCH2OCONH | H | H | CH3 |
(13)-7 | CH3CH2CH(CH3)OCONH | H | H | CH3 |
(13)-8 | (CH3)3COCONH | H | H | CH3 |
(13)-9 | CH3CH2CH2CH2CH2OCONH | H | H | CH3 |
(13)-10 | (CH3)2CHCH2CH2OCONH | H | H | CH3 |
(13)-11 | CH3CH2CH(CH3)CH2OCONH | H | H | CH3 |
(13)-12 | CH3CH2CH2CH(CH3)OCONH | H | H | CH3 |
(13)-13 | (CH3)3CCH2OCONH | H | H | CH3 |
(13)-14 | (CH3CH2)2CHOCONH | H | H | CH3 |
(13)-15 | CH3CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(13)-16 | CH3CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(13)-17 | CH3CH2CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(13)-18 | C6H5CH2OCONH | H | H | CH3 |
(13)-19 | C6H5CH2CH2OCONH | H | H | CH3 |
(13)-20 | cyclo-C3H5-OCONH | H | H | CH3 |
(13)-21 | cyclo-C5H9-OCONH | H | H | CH3 |
(13)-22 | cyclo-C6H11-OCONH | H | H | CH3 |
(13)-23 | CH2CONHCH2CH2OCONH | H | H | CH3 |
(13)-24 | CH3CONHCH2CH2CH2OCONH | H | H | CH3 |
表14
化合物编号 | Z | R | X | Y |
(14)-1 | CH3OCONH | H | H | CH3 |
(14)-2 | CH3CH2OCONH | H | H | CH3 |
(14)-3 | CH3CH2CH2OCONH | H | H | CH3 |
(14)-4 | (CH3)2CHOCONH | H | H | CH3 |
(14)-5 | CH3CH2CH2CH2OCONH | H | H | CH3 |
(14)-6 | (CH3)2CHCH2OCONH | H | H | CH3 |
(14)-7 | CH3CH2CH(CH3)OCONH | H | H | CH3 |
(14)-8 | (CH3)3COCONH | H | H | CH3 |
(14)-9 | CH3CH2CH2CH2CH2OCONH | H | H | CH3 |
(14)-10 | (CH3)2CHCH2CH2OCONH | H | H | CH3 |
(14)-11 | CH3CH2CH(CH3)CH2OCONH | H | H | CH3 |
(14)-12 | CH3CH2CH2CH(CH3)OCONH | H | H | CH3 |
(14)-13 | (CH3)3CCH2OCONH | H | H | CH3 |
(14)-14 | (CH3CH2)2CHOCONH | H | H | CH3 |
(14)-15 | CH3CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(14)-16 | CH3CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(14)-17 | CH3CH2CH2CH2CH2CH2CH2CH2OCONH | H | H | CH3 |
(14)-18 | C6H5CH2OCONH | H | H | CH3 |
(14)-19 | C6H5CH2CH2OCONH | H | H | CH3 |
(14)-20 | cyclo-C3H5-OCONH | H | H | CH3 |
(14)-21 | CH3CONHCH2CH2OCONH | H | H | CH3 |
(14)-22 | CH3CONHCH2CH2CH2OCONH | H | H | CH3 |
表15
化合物编号 | Z | R | X | Y |
(15)-1 | C6H5CH2CONH | H | H | CH3 |
(15)-2 | C6H5CH2CH2CONH | H | H | CH3 |
(15)-3 | C6H5CONH | H | H | CH3 |
(15)-4 | F2CHCONH | H | H | CH3 |
(15)-5 | F3CCONH | H | H | CH3 |
(15)-6 | F3CCH2CH2CONH | H | H | CH3 |
表16
化合物编号 | Z | R | X | Y |
(16)-1 | C6H5CH2CONH | H | H | CH3 |
(16)-2 | C6H5CH2CH2CONH | H | H | CH3 |
(16)-3 | C6H5CONH | H | H | CH3 |
(16)-4 | F2CHCONH | H | H | CH3 |
(16)-5 | F3CCONH | H | H | CH3 |
(16)-6 | F3CCH2CH2CONH | H | H | CH3 |
表17
化合物编号 | Z | R | X | Y |
(17)-1 | CH3CH2CH2CONH | H | 4-Cl | CH3 |
(17)-2 | (CH3)2CHCONH | H | 4-Cl | CH3 |
(17)-3 | cyclo-C3H5-CONH | H | 4-Cl | CH3 |
(17)-4 | CH3CH2CONH | H | 3-F | CH3 |
(17)-5 | (CH3)2CHCONH | H | 3-F | CH3 |
(17)-6 | cyclo-C3H5-CONH | H | 3-F | CH3 |
(17)-7 | (CH3)3CCONH | H | 3-F | CH3 |
(17)-8 | (CH3)2CHCONH | H | 4-F | CH3 |
(17)-9 | (CH3)2CHCONH | H | 4-CH3O | CH3 |
(17)-10 | (CH3)3CCONH | H | 4-CH3O | CH3 |
(17)-11 | cyclo-C3H5-CONH | H | 4-CH3O | CH3 |
(17)-12 | CH3CH2CH2CH2CH2CONH | H | 4-CH3 | CH3 |
(17)-13 | (CH3)3CCH2CONH | H | 4-CH3 | CH3 |
(17)-14 | (CH3)2CHCONH | Cl | H | CH3 |
(17)-15 | (CH3)2CHCONH | Cl | H | CH3CH2 |
(17)-16 | (CH3)3CCONH | H | H | CH3CH2 |
(17)-17 | (CH3)2CHCONH | H | H | CH3CH2 |
(17)-18 | H | H | 4-F | CH3 |
(17)-19 | H | H | 3-F | CH3 |
(17)-20 | H | H | 4-Cl | CH3 |
(17)-21 | CH3CH2CH2CH2CH2CONH | H | H | CH3CH2 |
表18
化合物编号 | Z | R | X | Y |
(18)-1 | CH3CH2CH2CONH | H | 4-Cl | CH3 |
(18)-2 | (CH3)2CHCONH | H | 4-Cl | CH3 |
(18)-3 | cyclo-C3H5-CONH | H | 4-Cl | CH3 |
(18)-4 | CH3CH2CONH | H | 3-F | CH3 |
(18)-5 | (CH3)2CHCONH | H | 3-F | CH3 |
(18)-6 | cyclo-C3H5-CONH | H | 3-F | CH3 |
(18)-7 | (CH3)3CCONH | H | 3-F | CH3 |
(18)-8 | (CH3)2CHCONH | H | 4-F | CH3 |
(18)-9 | (CH3)2CHCONH | H | 4-CH3O | CH3 |
(18)-10 | (CH3)3CCONH | H | 4-CH3O | CH3 |
(18)-11 | cyclo-C3H5-CONH | H | 4-CH3O | CH3 |
(18)-12 | CH3CH2CH2CH2CH2CONH | H | 4-CH3 | CH3 |
(18)-13 | (CH3)3CCH2CONH | H | 4-CH3 | CH3 |
(18)-14 | (CH3)2CHCONH | Cl | H | CH3 |
(18)-15 | (CH3)2CHCONH | Cl | H | CH3CH2 |
(18)-16 | (CH3)3CCONH | H | H | CH3CH2 |
(18)-17 | (CH3)2CHCONH | H | H | CH3 |
(18)-18 | CH3CH2CH2CH2CONH | H | 4-Cl | CH3 |
(18)-19 | CH3CH2CH2CH2CH2CONH | H | H | CH3CH2 |
表19
化合物编号 | Z | R | X | Y |
(19)-1 | (CH3)3COCONH | H | 3-F | CH3 |
(19)-2 | (CH3)2CHOCONH | H | 4-F | CH3 |
(19)-3 | (CH3)3COCONH | H | 4-F | CH3 |
(19)-4 | (CH3)3COCONH | H | 4-CH3 | CH3 |
(19)-5 | CH3CH2CH2OCONH | H | 3-F | CH3 |
(19)-6 | CH3CH2CH2OCONH | H | 4-F | CH3 |
(19)-7 | CH3CH2CH2OCONH | H | 3-Cl | CH3 |
(19)-8 | CH3CH2CH2OCONH | H | 4-Cl | CH3 |
(19)-9 | CH3CH2CH2OCONH | H | 3-CH3 | CH3 |
(19)-10 | CH3CH2CH2OCONH | H | 4-CH3 | CH3 |
(19)-11 | CH3CH2CH2CH2OCONH | H | 3-F | CH3 |
(19)-12 | CH3CH2CH2CH2OCONH | H | 4-F | CH3 |
(19)-13 | CH3CH2CH2CH2OCONH | H | 3-Cl | CH3 |
(19)-14 | CH3CH2CH2CH2OCONH | H | 4-Cl | CH3 |
(19)-15 | CH3CH2CH2CH2OCONH | H | 3-CH3 | CH3 |
(19)-16 | CH3CH2CH2CH2OCONH | H | 4-CH3 | CH3 |
(19)-17 | CH3CH2CH2CH2CH2OCONH | H | 3-F | CH3 |
(19)-18 | CH3CH2CH2CH2CH2OCONH | H | 4-F | CH3 |
(19)-19 | CH3CH2CH2CH2CH2OCONH | H | 3-Cl | CH3 |
(19)-20 | CH3CH2CH2CH2CH2OCONH | H | 4-Cl | CH3 |
(19)-21 | CH3CH2CH2CH2CH2OCONH | H | 3-CH3 | CH3 |
(19)-22 | CH3CH2CH2CH2CH2OCONH | H | 4-CH3 | CH3 |
(19)-23 | CH3CH2CH2CH2OCONH | H | 4-CH3O | CH3 |
(19)-24 | CH3CH2CH2CH2CH2OCONH | H | 4-CH3O | CH3 |
表20
化合物编号 | Z | R | X | Y |
(19)-25 | CH3CH2CH2CH2OCONH | H | 4-CN | CH3 |
(19)-26 | CH3CH2CH2CH2CH2OCONH | H | 4-CN | CH3 |
(19)-27 | CH3CH2CH2CH2OCONH | H | 4-CH3SO2 | CH3 |
(19)-28 | CH3CH2CH2CH2CH2OCONH | H | 4-CH3SO2 | CH3 |
(19)-29 | CH3CH2CH2CH2OCONH | H | 4-NO2 | CH3 |
(19)-30 | CH3CH2CH2CH2CH2OCONH | H | 4-NO2 | CH3 |
(19)-31 | CH3CH2CH2CH2OCONH | H | 4-CF3 | CH3 |
(19)-32 | CH3CH2CH2CH2CH2OCONH | H | 4-CF3 | CH3 |
(19)-33 | CH3CH2CH2CH2OCONH | H | H | CH3 |
(19)-34 | CH3CH2CH2CH2OCONH | H | 4-CH3CH2 | CH3 |
(19)-35 | CH3CH2CH2CH2OCONH | H | 4-(CH3)3C | CH3 |
(19)-36 | CH3CH2CH2CH2OCONH | H | 4-C6H5 | CH3 |
(19)-37 | CH3CH2CH2CH2OCONH | H | 2-Cl | CH3 |
(19)-38 | CH3CH2CH2CH2OCONH | H | 2-CH3 | CH3 |
表21
化合物编号 | Z | R | X | Y |
(20)-1 | (CH3)3COCONH | H | 3-F | CH3 |
(20)-2 | (CH3)2CHOCONH | H | 4-F | CH3 |
(20)-3 | (CH3)3COCONH | H | 4-F | CH3 |
(20)-4 | (CH3)3COCONH | H | 4-CH3 | CH3 |
(20)-5 | CH3CH2CH2CH2OCONH | H | 4-CH3 | CH3 |
(20)-6 | CH3CH2CH2CH2CH2OCONH | H | H | CH3CH2 |
表22
化合物编号 | Z | R | X | Y |
(21)-1 | CH3NHCONH | H | H | CH3 |
(21)-2 | CH3CH2NHCONH | H | H | CH3 |
(21)-3 | CH3CH2CH2NHCONH | H | H | CH3 |
(21)-4 | (CH3)2CHNHCONH | H | H | CH3 |
(21)-5 | CH3CH2CH2CH2NHCONH | H | H | CH3 |
(21)-6 | (CH3)2CHCH2NHCONH | H | H | CH3 |
(21)-7 | CH3CH2CH(CH3)NHCONH | H | H | CH3 |
(21)-8 | (CH3)3CNHCONH | H | H | CH3 |
(21)-9 | CH3CH2CH2CH2CH2CONH | H | H | CH3 |
(21)-10 | (CH3)2CHCH2CH2NHCONH | H | H | CH3 |
(21)-11 | CH3CH2CH(CH3)CH2CONH | H | H | CH3 |
(21)-12 | CH3CH2CH2CH(CH3)CONH | H | H | CH3 |
(21)-13 | (CH3)3CCH2NHCONH | H | H | CH3 |
(21)-14 | (CH3CH2)2CHNHCONH | H | H | CH3 |
(21)-15 | CH3CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(21)-16 | CH3CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
(21)-17 | CH3CH2CH2CH2CH2CH2CH2CH2CONH | H | H | CH3 |
表23
化合物编号 | Z | R | X | Y |
(22)-1 | CH3NHCONH | H | H | CH3 |
(22)-2 | CH3CH2NHCONH | H | H | CH3 |
(22)-3 | CH3CH2CH2NHCONH | H | H | CH3 |
(22)-4 | (CH3)2CHNHCONH | H | H | CH3 |
(22)-5 | CH3CH2CH2CH2NHCONH | H | H | CH3 |
(22)-6 | (CH3)2CHCH2NHCONH | H | H | CH3 |
(22)-7 | CH3CH2CH(CH3)NHCONH | H | H | CH3 |
(22)-8 | (CH3)3CNHCONH | H | H | CH3 |
(22)-9 | CH3CH2CH2CH2CH2NHNHCONH | H | H | CH3 |
(22)-10 | (CH3)2CHCH2CH2NHCONH | H | H | CH3 |
(22)-11 | CH3CH2CH(CH3)CH2NHCONH | H | H | CH3 |
(22)-12 | CH3CH2CH2CH(CH3)NHCONH | H | H | CH3 |
(22)-13 | (CH3)3CCH2NHCONH | H | H | CH3 |
(22)-14 | (CH3CH2)2CHNHCONH | H | H | CH3 |
(22)-15 | CH3CH2CH2CH2CH2CH2NHCONH | H | H | CH3 |
(22)-16 | CH3CH2CH2CH2CH2CH2CH2NHCONH | H | H | CH3 |
(22)-17 | CH3CH2CH2CH2CH2CH2CH2CH2NHCONH | H | H | CH3 |
本发明的四唑基肟衍生物对各种植物病原菌具有很强的活性,并可对由植物病原菌引起的植物病害的预防和治疗发挥很强的防除效果。本发明的四唑基肟衍生物即使在植物病原菌中,也是对由丝菌纲引起的各种植物病害特别有效,尤其优选用于卵菌亚纲、接合菌纲、子囊菌纲、担子菌纲以及半知菌亚门产生的植物病害的防除。下面列举了植物病原菌的例子,但是并不限于这些。
作为卵菌亚纲,可以举例为,例如各种作物的如甜菜立枯病菌(Pythium ultium)的腐霉属菌;如马铃薯疫病菌(PhytophthoraiNfestaNs)、番茄灰霉病菌(Phytophthora capsici)的Phytophthora属菌;如黄瓜霜霉病菌(PseudoperoNospora cubeNsis)、律草属霜霉病菌(PseudoperoNospora humuli)的假霜霉属菌;如葡萄霜霉病菌(Plasmopara viticola)的单轴霉属菌;如十字花科蔬菜的霜霉病菌(PeroNospora brassicae)、葱霜霉病菌(PeroNospora destructor)、菠菜霜霉病菌(PeroNospora spiNaciae)的霜霉属菌等。
作为子囊菌纲,可以举例为,例如,如麦类白粉病菌(ErysiphegramiNis)的白粉菌属菌;如蔬菜类白粉病(Sphaerotheca fuligiNea)的单丝壳属菌;如苹果黑星病菌(VeNturia iNaequalis)、梨黑星病菌(VeNturia Nashicola)的黑星菌属菌;如大麦网斑病菌(PyreNophorateres)的PyreNophora属菌;如麦类斑点病(Cochliobolus sativus)的Cochliobolus属菌;如蔬菜类菌核病菌(SclerotiNia sclerotiorum)的核盘菌属菌等。
作为担子菌纲,可以举例为,例如,如小麦叶锈病菌(PucciNiarecoNdita)的双孢锈菌属菌;如小麦腥黑穗病菌(Tilletia caries)的腥黑粉菌属菌;如大麦散黑穗病菌(Ustilago Nuda)的黑粉菌属菌等。
作为半知菌亚门,可以举例为,例如,如天门冬茎枯病菌(Phomaasparagi)的茎点霉属菌;如麦类外皮枯病菌(Septoria Nodorum)的壳针孢属菌;如瓜类炭疽病菌(Colletotrichum lageNarium)的刺盘孢属菌;如枯萎病菌(Pyricularia oryzae)的Pyricularia属菌;如蔬菜类灰霉病菌(Botrytis ciNerea)的葡萄孢属菌;如苹果斑点落叶病菌(AlterNaria mali)、番茄早疫病菌(AlterNaria solaNi)的链格孢属菌;如甜菜褐斑病菌(Cercospora beticola)的尾孢属菌;如桃子黑星病菌(Cladosporium carpophilum)的芽枝霉属菌;如稻属纹枯病菌(RhizoctoNia solaNi)的丝核菌属菌等。
也可以把本发明的四唑基肟衍生物单独用作农药,但是通常把四唑基肟衍生物作为有效成分,通过与农药制剂中使用的惯用的固体载体、液体载体、分散剂、稀释剂、乳化剂、展着剂以及增粘剂等辅助试剂混合,可以制剂为水合剂、液剂、油剂、粉剂、粒剂或者溶胶剂(フロアブル)等剂型进行使用。
作为固体载体或者液体载体,可以举例为,例如滑石、高岭土、皂土、陶土、硅藻土、蒙脱石、云母、蛭石、石膏、碳酸钙、胶态硅石、木粉、淀粉、矾土、硅酸盐、糖聚合物、蜡类、水、醇类(甲醇、乙醇、正丙醇、异丙醇、正丁醇、乙二醇、苄醇等)、石油馏分(石油醚、煤油、溶剂石脑油等)、脂肪族或脂环或烃类(正己环、环己环等)芳香族烃类(苯、甲苯、二甲苯、乙基苯、氯苯、枯烯、甲基萘等)、卤化烃类(氯仿、二氯甲烷等)、醚类(异丙醚、环氧乙烷、四氢呋喃等)、酮类(丙酮、甲乙酮、环己酮、甲基异丁基酮等)、酯类(乙酸乙酯、乙酸丁酯、乙二醇乙酸酯、醋酸戊酯等)、酰胺类(二甲基甲酰胺、二甲基乙酰苯基苯胺等)、腈类(乙腈、丙腈、丙烯腈等)、亚砜类(二甲基亚砜等)、醇醚类(乙二醇单甲醚、乙二醇单乙醚等)等。
作为辅助试剂,可以举例为,例如非离子型表面活性剂(聚氧乙烯烷基醚、聚氧乙烯烷基酯、聚氧乙烯烷基苯基醚、缩聚山梨醇烷基酯、山梨糖醇烷基酯等)、阴离子型表面活性剂(烷基苯磺酸盐、烷基硫代丁二酸盐、聚氧乙烯烷基硫酸盐、芳基磺酸盐等)、阳离子型表面活性剂(烷基胺类、聚氧乙烯烷基胺类、季铵盐类等)、两性型表面活性剂(烷基氨基乙基甘氨酸、烷基二甲基甜菜碱等)、聚乙烯醇、羟丙基纤维素、羧甲基纤维素、阿拉伯胶、龙须胶、黄原胶、聚醋酸乙烯酯、明胶、酪蛋白、海藻酸钠等。
另外,本发明的四唑基肟衍生物也可以与各种公知通用的农园艺用杀菌剂、除草剂、植物生长调节剂、杀虫剂、杀螨剂等农药或肥料等混合使用。本发明的四唑基肟衍生物在农药中的含有量根据制剂形式、施用方法、其它条件而各不相同,但是优选0.5~95质量%,特别优选2~70质量%。
作为本发明农药的施用方法,可以是对植物的施用(茎叶喷洒)对植物的生长土壤的施用(土壤施用)、对水田表面的水的施用(水面施用)、对种子的施用(种子处理)等。
关于本发明农药的施用量,也根据适用植物、适用病害而各不相同,但是当茎叶喷洒时,优选每10公亩施用50~300L作为有效成分浓度的1~10000ppm、优选10~1000ppm的溶液,当土壤施用以及水面施用时,优选以有效成分量计每10公亩施用1~1000g、特别优选10~100g。另外,当种子处理时,优选对于1kg种子,施用0.001~50g的有效成分。
实施例
下面根据制造例、制剂例以及试验例对本发明进行说明,但是本发明并不限于这些。
首先说明四唑基肟基衍生物的制造例。
(制造例1)
将11.1g(59.1毫摩尔)(1-甲基四唑-5-基)苯甲醛、10.3g(148毫摩尔)氯化羟氨加入100ml吡啶中,在45℃下搅拌24小时。反应结束后,减压下浓缩反应液,向得到的残留物中加入水和乙酸乙酯,进而萃取出反应生成物。用稀盐酸、水、碳酸氢钠水溶液按顺序洗涤有机层后,用无水硫酸镁干燥有机层。通过从有机层馏去溶剂,获得用式
表示的12.0g(收率100%)(1-甲基四唑-5-基)苯甲肟。
1H-NMR(CDCl3,δ):4.03(s,3H),7.3~7.55(m,5H),9.0(brd,1H).
(制造例2)
在制造例1中,除了使用560mg(2.52毫摩尔)(1-甲基四唑-5-基)4-氯苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的600mg(1-甲基四唑-5-基)4-氯苯甲肟。
1H-NMR(CDCl3,δ):4.04(s,3H),7.36(m,2H),7.46(m,2H),9.00(brd,1H).
(制造例3)
在制造例1中,除了使用964mg(4.68毫摩尔)(1-甲基四唑-5-基)3-氟苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的999mg(1-甲基四唑-5-基)3-氟苯甲肟。
1H-NMR(CDCl3,δ):4.04(s,3H),7.11(m,1H),7.2~7.5(m,3H),12.31(brd,1H)。
(制造例4)
在制造例1中,除了使用850mg(4.14毫摩尔)(1-甲基四唑-5-基)4-氟苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的930mg(1-甲基四唑-5-基)4-氟苯甲肟。
1H-NMR(CDCl3,δ):4.05(s,3H),7.08(dd,1H,J=8.6,8.6Hz),7.53(m,2H),8.68(brd,1H).
(制造例5)
在制造例1中,除了使用386mg(1.77毫摩尔)(1-甲基四唑-5-基)4-甲氧基苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的410mg(1-甲基四唑-5-基)4-甲氧基苯甲肟。
1H-NMR(CDCl3,δ):3.83(s,3H),4.03(s,3H),6.89(m,2H),7.45(m,2H),8.36(brd,1H).
(制造例6)
在制造例1中,除了使用1.36g(6.78毫摩尔)(1-甲基四唑-5-基)3-甲基苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的1.31g(1-甲基四唑-5-基)3-甲基苯甲肟。
1H-NMR(CDCl3,δ):2.31(s,3H),3.99(s,3H),7.2-7.3(m,5H),9.92(brd,1H).
(制造例7)
在制造例1中,除了使用1.65g(8.16毫摩尔)(1-甲基四唑-5-基)4-甲基苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的1.67g(1-甲基四唑-5-基)4-甲基苯甲肟。
1H-NMR(CDCl3,δ):2.37(s,3H),4.01(s,3H),7.18(m,2H),7.37(m,2H),9.02(brd,1H).
(制造例8)
在制造例1中,除了使用1.90g(9.40毫摩尔)(1-甲基四唑-5-基)2-甲基苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的1.93g(1-甲基四唑-5-基)2-甲基苯甲肟。
1H-NMR(CDCl3,δ):
Z体:2.22(s,3H),4.06(s,3H),7.2~7.4(m,4H),9.05(brd,1H).
E体:2.21(s,3H),4.31(s,3H),7.15~7.45(m,4H),8.43(brd,1H).
(制造例9)
在制造例1中,除了使用1.00g(4.95毫摩尔)(1-乙基四唑-5-基)苯甲醛代替(1-甲基四唑-5-基)苯甲醛以外,与制造例1相同,从而获得了用式
表示的1.00g(1-乙基四唑-5-基)苯甲肟。
1H-NMR(CDCl3,δ):1.51(t,J=7.3Hz,3H),4.35(q,J=7.3Hz,2H),7.33-7.55(m,5H),10.45(brd,1H).
(制造例10)
将2.78g(20毫摩尔)3-氟苯甲醛肟溶解于25ml N,N-二甲基甲酰胺的溶液中,一边将液温保持在45℃以下,一边加入2.80g(21毫摩尔)N-氯琥珀酸酰亚胺,在室温下搅拌1小时后,将反应液注入饱和氯化铵水中,用醋酸乙酯萃取。用水、饱和食盐水按顺序洗涤有机层后,用无水硫酸钠干燥有机层。从有机层馏去溶剂,并向得到的残留物中加入1.70g(20毫摩尔)5-甲基四唑和25ml二氯甲烷。在室温下向该溶液中滴加3.6ml(1.26毫摩尔)三乙胺。在室温下搅拌6小时后,将反应液注入饱和氯化铵水中,用醋酸乙酯萃取。用水、饱和食盐水按顺序洗涤有机层后,用无水硫酸钠使其干燥。馏去溶剂,并使用硅胶柱层析法精制获得的残留物,从而获得了用式
表示的1.40g(5-甲基四唑-1-基)-3-氟苯甲肟。
1H-NMR(CDCl3,δ):2.57(s,3H),7.06~7.09(m,1H),7.18~7.27(m,2H),7.36~7.43(m,1H),8.67(s,1H).
(制造例11)
在制造例10中,除了使用2.78g(20毫摩尔)4-氟苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.00g(5-甲基四唑-1-基)-4-氟苯甲肟。
1H-NMR(CDCl3,δ):2.53(s,3H),7.06~7.12(m,2H),7.38~7.45(m,2H),12.11(s,1H).
(制造例12)
在制造例10中,除了使用3.11g(20毫摩尔)3-氯苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的2.05g(5-甲基四唑-1-基)-3-氯苯甲肟。
1H-NMR(CDCl3,δ):2.58(s,3H),7.20~7.23(m,1H),7.33~7.38(m,2H),7.46~7.51(m,1H),9.22(s,1H).
(制造例13)
在制造例10中,除了使用3.11g(20毫摩尔)4-氯苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的2.17g(5-甲基四唑-1-基)-4-氯苯甲肟。
1H-NMR(CDCl3,δ):2.53(s,3H),7.33~7.39(m,4H),12.07(s,1H).
(制造例14)
在制造例10中,除了使用2.70g(20毫摩尔)4-甲基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的2.50g(5-甲基四唑-1-基)-4-甲基苯甲肟。
1H-NMR(CDCl3,δ):2.39(s,3H),2.56(s,3H),7.20~7.30(m,4H),8.69(s,1H).
(制造例15)
在制造例10中,除了使用3.20g(20毫摩尔)4-甲氧基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.96g(5-甲基四唑-1-基)-4-甲氧基苯甲肟。
1H-NMR(CDCl3,δ):2.55(s,3H),3.84(s,3H),6.89~6.94(m,2H),7.30~7.35(m,2H),8.13(s,1H).
(制造例16)
在制造例10中,除了使用2.92g(20毫摩尔)4-氰基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.70g(5-甲基四唑-1-基)-4-氰基苯甲肟。
1H-NMR(CDCl3,δ):2.54(s,3H),7.53~7.56(m,2H),7.68~7.71(m,2H),12.71(s,1H).
(制造例17)
在制造例10中,除了使用1.30g(6.5毫摩尔)4-甲基磺酰基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.20g(5-甲基四唑-1-基)-4-甲基磺酰基苯甲肟。
1H-NMR(CDCl3,δ):2.55(s,3H),3.08(s,3H),7.62~7.65(m,2H),7.95~7.98(m,2H),12.68(s,1H).
(制造例18)
在制造例10中,除了使用3.32g(20毫摩尔)4-硝基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.00g(5-甲基四唑-1-基)-4-硝基苯甲肟。
1H-NMR(CDCl3,δ):2.55(s,3H),7.61~7.64(m,2H),8.24~8.26(m,2H),12.72(s,1H).
(制造例19)
在制造例10中,除了使用3.78g(20毫摩尔)4-三氟甲基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的0.78g(5-甲基四唑-1-基)-4-三氟甲基苯甲肟。
1H-NMR(CDCl3,δ):2.54(s,3H),7.55(d,2H,J=8.41Hz),7.66(d,2H,J=8.41Hz),12.26(s,1H).
(制造例20)
在制造例10中,除了使用1.49g(10毫摩尔)4-乙基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.35g(5-甲基四唑-1-基)-4-乙基苯甲肟。
1H-NMR(CDCl3,δ):1.34(t,3H,J=7.51Hz),2.56(s,3H),2.69(q,2H,J=7.69H),7.22~7.32(4H,m),8.69(s,1H).
(制造例21)
在制造例10中,除了使用1.77g(10毫摩尔)4-叔丁基苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.35g(5-甲基四唑-1-基)-4-叔丁基苯甲肟。
1H-NMR(CDCl3,δ):1.33(s,9H),2.55(s,3H),7.32(d,2H,J=8.62Hz),7.44(d,2H,J=8.62Hz),7.99(s,1H).
(制造例22)
在制造例10中,除了使用1.97g(20毫摩尔)4-联苯醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.20g(5-甲基四唑-1-基)-4-联苯甲肟。
1H-NMR(CDCl3,δ):2.56(s,3H),7.29~7.49(m,5H),7.58~7.63(m,4H),12.05(s,1H).
(制造例23)
在制造例10中,除了使用2.00g(20.4毫摩尔)5-乙基四唑代替5-甲基四唑,且使用2.70g(22毫摩尔)苯甲醛肟代替3-氟苯甲醛肟以外,与制造例10相同,从而获得了用式
表示的1.93g(5-乙基四唑-1-基)苯甲肟。
1H-NMR(CDCl3,δ):1.37(t,J=7.6Hz,3H),2.88(q,J=7.6Hz,2H),7.35~7.55(m,5H),9.42(s,1H).
下面,说明四唑基肟衍生物的制造例。
(制造例24)
使1.40g(60%iN oil)氢化钠悬浮于30ml干燥N,N-二甲基甲酰胺中后,一边用冰浴冷却,一边滴入由制造例1得到的2.6g(12.6毫摩尔)(1-甲基四唑-5-基)苯甲肟以及15ml干燥N,N-二甲基甲酰胺构成的溶液。连续搅拌10分钟后,再滴入溶解于15ml干燥N,N-二甲基甲酰胺的4.0g(14毫摩尔)2-溴甲基-6-(己酰基氨基)吡啶。滴入结束后,除去冰浴,连续搅拌1.5小时。将反应液注入饱和氯化铵水中,用乙酸乙酯萃取反应生成物。用水、饱和食盐水按顺序洗涤有机层后,用无水硫酸钠干燥有机层。从有机层馏去溶剂,并使用硅胶柱层析法精制获得的残留物,从而获得了用式
表示的3.55g(Z)-(1-甲基四唑-5-基)苯甲肟0-(6-(己酰基氨基)吡啶-2-基)甲基肟(化合物No.(1)-12)。
1H-NMR(CDCl3,δ):0.91(t,3H,J=7.2Hz),1.37(m,4H),1.74(m,2H),2.39(t,2H,J=7.7Hz),3.97(s,3H),5.26(s,2H),7.00(d,1H,J=7.3Hz),7.3~7.55(m,5H),7.70(dd,1H,J=7.3,8.1Hz),7.86(brd,1H),8.15(d,1H,J=8.1Hz).
(制造例25)
将由制造例1得到的60mg(0.30毫摩尔)(1-甲基四唑-5-基)苯甲肟、85mg(0.32毫摩尔)4-氯甲基-2-(正戊氧基羰基氨基)噻唑溶解于4ml干燥N,N-二甲基甲酰胺中后,一边用冰浴冷却,一边加入40mg(60%iN oil)氢化钠。除去冰浴后,连续搅拌3小时后,将反应液注入饱和氯化铵水中,用乙酸乙酯萃取。用水、饱和食盐水按顺序洗涤有机层后,用无水硫酸镁干燥有机层。从有机层馏去溶剂,并使用硅胶柱层析法精制获得的残留物,从而获得了用式
表示的120mg(Z)-(1-甲基四唑-5-基)苯甲肟0-(2-(正戊氧基羰基氨基)噻唑-4-基)甲基肟(化合物No.(4)-9)。
1H-NMR(CDCl3):0.89(t,3H,J=7.0Hz),1.34(m,4H),1.68(m,2H),3.87(s,3H),4.23(t,2H,J=6.9Hz),5.30(s,2H),6.89(s,1H),7.30~7.55(m,5H),10.21(brd,1H).
(制造例26)
使1.79g(60%油状物)氢化钠悬浮于60ml干燥N,N-二甲基甲酰胺中,一边用冰浴冷却,一边向该悬浮液中滴入由8.24g(40.6毫摩尔)(Z)-(5-甲基四唑-1-基)苯甲肟以及30ml干燥N,N-二甲基甲酰胺构成的溶液,连续搅拌10分钟后,滴入由12.7g(44.5毫摩尔)2-溴甲基-6-(己酰基氨基)吡啶以及40ml干燥N,N-二甲基甲酰胺构成的溶液。滴入结束后,除去冰浴,再连续搅拌2小时。将反应液注入饱和氯化铵水中,用乙酸乙酯萃取反应生成物。用水、饱和食盐水按顺序洗涤有机层后,用无水硫酸钠干燥有机层。从有机层馏去溶剂,并使用硅胶柱层析法精制获得的残留物,从而获得了用式
表示的10.5g(Z)-(5-甲基四唑-1-基)苯甲肟0-(6-(己酰基氨基)吡啶-2-基)甲基肟(化合物No.(11)-12)。
1H-NMR(CDCl3,δ):0.91(t,3H,J=7.1Hz),1.31~1.38(m,4H),1.70~1.77(m,2H),2.45(t,2H,J=7.5Hz),2.46(s,3H),5.23(s,2H),6.92(s,1H),7.34-7.53(m,5H),9.10(brd,1H).
(制造例27)
将100mg(0.42毫摩尔)(Z)-(5-甲基四唑-1-基)苯甲肟以及120mg(0.51毫摩尔)4-氯甲基-2-(正己酰基氨基)噻唑溶解于2ml干燥N,N-二甲基甲酰胺中,一边用冰浴冷却,一边向该溶液中加入40mg(60%iN oil)氢氧化钠后,除去冰浴,再连续搅拌3小时。将反应液注入饱和氯化铵水中,用乙酸乙酯萃取反应生成物。用水、饱和食盐水按顺序洗涤有机层后,用无水硫酸镁干燥有机层。从有机层馏去溶剂,并使用硅胶柱层析法精制获得的残留物,从而获得了用式
表示的117mg(Z)-(5-甲基四唑-1-基)苯甲肟0-(2-(正己酰基氨基)噻唑-4-基)甲基肟(化合物No.(12)-12)。
1H-NMR(CDCl3):0.91(t,3H,J=7.1Hz),1.31~1.38(m,4H),1.70~1.77(m,2H),2.45(t,J=7.5Hz,2H),2.46(s,3H),5.23(s,2H),6.92(s,1H),7.34~7.53(m,5H),9.10(brd,1H).
把与这些制造例相同制造的四唑基肟衍生物的1NMR光谱数据归纳起来,并示于下面的表24~45中。表中化合物的标注表示,例如(1)-1的化合物是表1的1化合物。另外,表中的“Z/E”的栏表示(Z)体或者(E)体。
表24
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(1)-1 | Z | 4.00(s,3H),5.41(s,1H),7.22~7.28(m,2H),7.3~7.47(m,3H),7.51~7.55(m,2H),7.67(t,d,J=7.7Hz,J=1.7Hz.1H),8.58(d,d,J=7.5Hz,J=1,7Hz,1H). |
(1)-2 | Z | 3.4(s,3H),5.25(s,2H),7.15(d,J=7.1Hz,1H),7.35~7.53(m,5H),7.80(d,d,J=7.1Hz,J=8.0Hz,1H),8.10(d,J=8.0Hz.1H). |
(1)-5 | Z | 1.26(t,J=7.5Hz,3H),2.44(q,J=7.5Hz,2H),4.10(s,3H),5.27(s,2H),7.00(d,J=7.5Hz,1H),7.35~7.52(m,5H),7.70(d,d,J=7.5Hz,J=8.1Hz,1H),8.14(d,J=8.1Hz,1H). |
(1)-7 | Z | 1.27(d,6H,J=7.0Hz),2.55(seq,1H,J=7.0Hz),3.97(s,3H),5.27(s,2H),6.99(d,1H,J=7.5Hz),7.3~7.55(m,5H),7.70(dd,1H,J=7.5,8.4Hz),7.85(brd,1H),8.17(d,1H,J=8.4Hz). |
(1)-8 | Z | 0.93(t,J=7.3Hz,3H),1.40(sept,J=7.3Hz,2H),1.72(sept,7.3Hz,2H),2.41(t,J=7.3Hz,2H),3.97(s,3H),5.26(s,2H),7.00(d,J=7.5Hz,1H),7.35~7.52(m,5H),7.70(d,d,J=7.5Hz,J=8.2Hz,1H),8.16(d,J=8.2Hz.1H). |
(1)-11 | Z | 1.34(s,9H),3.98(s,3H),5.27(s,2H),7.00(d,J=6.8Hz,1H),7.35~7.53(m,5H),7.72(d,d,J=6.8Hz,J=8.2Hz,1H),8.18(d,J=8.2Hz,1H). |
表25
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(1)-12 | Z | 0.91(t,J=6.9Hz,3H),1.33~1.41(m,3H),1.69~1.79(m,3H),2.3(t,J=7.2Hz,2H),3.98(s,3H),5.26(s,2H),7.00(d,J=7.0Hz,1H),7.35~7.52(m,5H),7.69(d,d,J=7.0Hz,J=8.3Hz,1H),8.15(d,J=8.3Hz,1H). |
(1)-16 | Z | 1.11(s,9H),2.26(s,2H),3.97(s,3H),5.26(s,2H),7.00(d,1H,J=7.5Hz),7.3~7.55(m,5H),7.69(dd,1H,J=7.5,8.2Hz),7.80(brd,1H),8.16(d,1H,J=8.2Hz). |
(1)-18 | Z | 0.89(t,3H,J=6.8Hz),1.25~1.5(m,6H),1.73(m,2H),2.40(t,2H,J=7.6Hz),3.97(s,3H),5.26(s,2H),7.00(d,1H,J=7.0Hz),7.3~7.55(m,5H),7.70(dd,1H,J=7.0,8.2Hz),7.86(brd,1H),8.15(d,1H,J=8.2Hz). |
(1)-21 | Z | 0.87~0.93(m,2H),1.08~1.13(m,2H),1.52~1.55(m,1H),3.97(s,3H),5.27(s,2H),7.00(d,J=7.5Hz,1H),7.35~7.53(m,5H),7.68(d,d,J=7.5Hz,J=8.0Hz,1H),8.11(d,J=8.0Hz,1H). |
(1)-23 | Z | 1.31~2.05(m,10H),2.262.31(m,1H),3.97(s,3H),5.26(s,2H),6.99(d,J=7.5Hz,1H),7.35~7.52(m,5H),7.72(d,d,J=7.5Hz,J=8.3Hz,1H),8.15(d,J=8.3Hz,1H). |
表26
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(2)-7 | Z | 1.29(d,6H,J=6.8Hz),2.63(seq,1H,J=6.8Hz),3.95(s,3H),5.25(s,2H),6.92(s,1H),7,3~7.5(m,3H),7.52(m,2H),8.78(brd,1H). |
(2)-11 | Z | 1.33(s,9H),3.95(s,3H),5.27(s,2H),6.92(s,1H),7.3~7.5(m,3H),7.52(m,2H),8.89(brd,1H). |
(2)-12 | Z | 0.90(t,3H,J=7.1Hz),1.2~1.4(m,4H),1.73(m,2H),2.44(t,2H,J=7.5Hz),3.93(s,3H),5.24(s,2H),6.91(s,1H),7.3~7.55(m,5H),9.17(brd,1H). |
(2)-18 | Z | 0.87(t,3H,J=6.8Hz),1.30(m,6H),1.72(m,4H),2.44(t,2H,J=7.5Hz),3.92(s,3H),5.24(s,2H),6.91(s,1H),7.3~7.55(m,5H),9.35(brd,1H). |
(2)-19 | Z | 0.87(t,1H,J=6.8Hz),1.2~1.4(m,8H),1.71(m,2H),2.44(t,2H,J=7.5Hz),3.92(s,3H),5.23(s,2H),6.91(s,1H),7.3~7.55(m,5H),9.48(brd,1H). |
表27
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(3)-2 | Z | 1.26(t,J=7.2Hz,3H),3.98(s,3H),4.12(q,J=7.2Hz,2H),5.26(s,2H),6.95(d,J=7.7Hz,1H),7.26~7.52(m,5H),7.68(d,d,J=7.7Hz,J=8.2Hz,1H),7.90(d,J=8.2Hz,1H). |
(3)-2 | E | 1.33(t,J=7.2Hz,3H),4.00(s,3H),5.13(s,2H),7.15(d,J=7.3Hz,1H),7.26~7.52(m,5H),7.80(d,d,J=7.3Hz,J=8.1Hz,1H),8.10(d,J=8.1Hz,1H). |
(3)-3 | Z | 0.97(t,3H,J=7.4Hz),1.70(tq,2H,J=6.7,7.4Hz),3.97(s,3H),4.14(t,2H,J=6.7Hz),5.26(s,2H),6.96(d,1H,J=7.0Hz),7.3~7.55(m,6H),7.68(dd,1H,J=7.0,8.4Hz),7.90(d,1H,J=8.4Hz). |
(3)-4 | Z | 1.30(d,6H,J=6.2Hz),3.98(s,3H),5.03(seq,1H,J=6.2Hz),5.26(s,2H),6.95(d,1H,J=7.0Hz),7.3~7.55(m,6H),7.67(dd,1H,J=7.0,8.3Hz),7.89(d,1H,J=8.3Hz). |
(3)-5 | Z | 0.95(t,3H,J=7.3Hz),1.40(tq,2H,J=7.3,7.3Hz),1.66(tt,2H,J=6.6,7.3Hz),3.97(s,3H),4.18(t,2H,J=6.6Hz),5.26(s,2H),6.95(d,1H,J=7.3Hz),7.25~7.6(m,6H),7.68(dd,1H,J=7.3,8.3Hz),7.90(d,1H,J=8.3Hz). |
(3)-8 | Z | 1.5(s,9H),3.97(s,3H),5.25(s,2H),6.92(d,J=7.5Hz,1H),7.34~7.53(m,5H),7.64(d,d,J=7.5Hz,J=8.2Hz,1H),7.86(d,J=8.2Hz,1H). |
表28
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(3)-9 | Z | 0.91(t,3H,J=7.1Hz),1.35(m,4H),1.68(m,2H),3.98(s,3H),4.18(t,2H,J=6.7Hz),5.26(s,2H),6.95(d,1H,J=6.8Hz),7.3~7.55(m,6H),7.68(dd,1H,J=6.8,8.3Hz),7.90(d,1H,J=8.3Hz). |
(3)-15 | Z | 0.90(t,3H,J=7.0Hz),1.25~1.45(m,6H),1.68(m,2H),3.98(s,3H),4.18(t,2H,J=6.8Hz),5.26(s,2H),6.95(d,1H,J=7.7Hz),7.3~7.55(m,6H),7.68(dd,1H,J=7.7,8.4Hz),7.90(d,1H,J=8.4Hz). |
(3)-16 | Z | 0.89(t,3H,J=6.8Hz),1.2~1.4(m,8H),1.68(m,2H),3.97(s,3H),4.18(t,J=6.8Hz,2H),5.26(s,2H),6.95(s,1H),7.3~7.55(m,6H),7.68(dd,1H,J=7.3.7.9Hz),7.90(d,J=7.9Hz,1H). |
(3)-18 | Z | 3.96(s,3H),5.22(s,2H),5.24(s,2H),6.95(d,1H,J=7.3Hz),7.3~7.55(m,5H),7.68(dd,1H,J=7.3,8.2Hz),7.91(d,1H,J=8.2Hz). |
(3)-21 | Z | 0.92(t,3H,J=7.5Hz),1.49(s,6H),1.83(q,2H,J=7.5Hz),3.97(s,3H),5.25(s,2H),6.93(d,1H,J=7.0Hz),7.2~7.55(m,6H),7.65(dd,1H,J=7.0,8.2Hz),7.86(d,1H,J=8.2Hz). |
(3)-22 | Z | 1.21.6(m,6H),1.75(m,2H),1.89(m,2H),3.97(s,3H),4.77(m,1H),5.26(s,2H),6.95(d,1H,J=6.8Hz),7.3~7.55(m,6H),7.67(dd,1H,J=6.8,8.3Hz),7.89(d,1H,J=8.3Hz). |
表29
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(4)-3 | Z | 3.36(s,3H),3.61(t,J=4.6Hz,2H),3.87(s,3H),4.37(t,J=4.6Hz,2H),5.31(s,2H),6.91(s,1H),7.31~7.51(m,5H). |
(4)-5 | Z | 0.93(t,J=7.3Hz,3H),1.32~1.45(m,2H),1.63~1.73(m,2H),3.87(s,3H),4.27(t,J=6.8Hz,2H),5.29(s,2H),6.89(s,1H),7.32~7.61(m,5H),10.18(brd,1H). |
(4)-9 | Z | 0.89(t,3H,J=7.0Hz),1.34(m,4H),1.68(m,2H),3.87(s,3H),4.23(t,2H,J=6.9Hz),5.30(s,2H),6.89(s,1H),7.3~7.55(m,5H),10.21(brd,1H). |
(4)-15 | Z | 0.87(t,3H,J=6.7Hz),1.2~1.45(m,6H),1.69(m,2H),3.86(s,3H),4.22(t,2H,J=6.9Hz),5.31(s,2H),6.89(s,1H),7.25~7.55(m,5H),10.50(brd,1H). |
(4)-16 | Z | 0.87(t,J=6.9Hz,3H),1.24~1.31(m,7H),1.64~1.72(m,3H),3.88(s,3H),4.23(t,J=6.8Hz,2H),5.29(s,2H),6.89(s,1H),7.31~7.52(m,5H),9.94(brd,1H) |
(4)-18 | Z | 3.79(s,3H),5.10(s,2H),5.22(s,2H),6.85(s,1H),7.2~7.55(m,10H),10.89(brd,1H). |
(5)-1 | Z | 3.52(s,3H),3.99(s,3H),4.04(s,2H),5.29(s,2H),7.04(d,J=7.1Hz),7.34~7.53(m,4H),7.72(dd,J=7.9Hz,J=7.9Hz,1H),8.18(d,J=8.3Hz),8.81(brd,1H). |
(5)-2 | Z | 1.32(t,J=7.0Hz),3.67(q,J=7.0Hz,2H),4.00(s,3H),4.07(s,2H),5.30(s,2H),7.04(d,J=7.5Hz,1H),7.34~7.55(m,4H),7.72(dd,J=7.9,J=7.9Hz,1H),8.18(d,J=8.3Hz),8.85(brd,1H). |
表30
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(5)-10 | Z | 1.08(t,J=7.3Hz,3H),2.24~2.31(m,2H),3.96(s,3H),5.26(s,2H),5.95(d,J=15.2Hz,1H),7.01(d,J=7.3Hz,1H),7.10(t,J=6.4Hz,1H),7.33~7.51(m,5H),7.69(d,d,J=7.3Hz,J=8.2Hz,1H),8.22(d,J=8.2Hz,1H). |
(5)-12 | Z | 3.76(s,2H),3.89(s,3H),5.20(s,2H),6.99(d,1H,J=7.0Hz),7.25~7.55(m,10H),7.68(dd,1H,J=7.0,J=8.3Hz),7.82(brd,1H),8.15(d,1H,J=8.3Hz). |
(6)-1 | Z | 3.51(s,3H),3.95(s,3H),4.12(s,2H),5.27(s,2H),6.95(s,1H),7.35~7.55(m,5H),9.65(brd,1H). |
(6)-2 | Z | 1.29(t,J=7.1Hz,3H),3.66(q,J=7.0Hz,2H),3.95(s,3H),4.17(s,2H),5.28(s,2H),6.93(s,1H),7.35~7.54(m,5H),9.65(brd,1H). |
(6)-3 | Z | 1.27(t,J=6.7Hz,3H),2.73(t,J=5.6Hz,2H),3.62(q,J=7.0Hz),3.77(t,J=5.6Hz,2H),3.96(s,2H),6.91(s,1H),7.34~7.61(m,5H). |
(6)-6 | Z | 2.15(s,3H),2.76(t,J=6.7Hz,2H),2.89(t,J=7.1Hz,2H),3.93(s,3H),5.24(s,2H),6.93(s,1H),7.33~7.53(m,5H),9.70(brd,1H). |
(6)-7 | Z | 2.06(s,3H),3.91(s,3H),5.24(s,2H),5.58(s,1H),5.93(s,1H),6.94(s,1H),7.33~7.52(m,5H). |
表31
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(7)-1 | Z | 1.01(t,3H,J=7.3Hz),1.76(qt,2H,J=7.3,7.4Hz),2.37(t,2H,J=7.4Hz),3.97(s,3H),5.26(s,2H),6.99(d,1H,J=7.5Hz),7.35(m,2H),7.47(m,2H),7.70(dd,1H,J=7.5,8.4Hz),7.86(brd,1H),8.17(d,1H,J=8.4Hz). |
(7)-2 | Z | 1.27(d,2H,J=7.0Hz),2.56(seq,1H,J=7.0Hz),3.98(s,3H),5.27(s,2H),6.98(d,1H,J=7.0Hz),7.35(m,2H),7.47(m,2H),7.70(dd,1H,J=7.0,8.1Hz),7.8(brd,1H),8.17(d,1H,J=8.1Hz). |
(7)-3 | Z | 0.90(m,2H),1.11(m,2H),1.55(m,1H),3.98(s,3H),5.27(s,2H),6.98(d,1H,J=6.6Hz),7.36(m,2H),7.47(m,2H),7.69(dd,1H,J=6.6,8.1Hz),8.05(brd,1H),8.12(d,1H,J=8.1Hz). |
(7)-4 | Z | 1.26(t,3H,J=7.5Hz),2.44(q,2H,J=7.5Hz),3.98(s,3H),5.27(s,2H),7.00(d,1H,J=7.3Hz),7.1~7.25(m,2H),7.3~7.4(m,2H),7.71(dd,1H,J=7.3,8.4Hz),7.85(brd,1H),8.16(d,1H,J=8.4Hz). |
(7)-5 | Z | 1.27(d,6H,J=7.0Hz),2.56(seq,1H,J=7.0Hz),3.98(s,3H),5.28(s,2H),7.00(d,1H,J=7.5Hz),7.1~7.25(m,2H),7.3~7.4(m,2H),7.70(dd,1H,J=7.5,8.1Hz),7.87(brd,1H),8.18(d,1H,J=8.1Hz). |
(7)-6 | Z | 1.92(m,2H),1.11(m,2H),1.56(m,1H),3.98(s,3H),5.28(s,2H),6.99(d,1H,J=6.6Hz),7.1~7.25(m,2H),7.25~7.45(m,2H),7.69(dd,1H,J=6.6,8.1Hz),8.13(d,1H,J=8.1Hz),8.1(brd,1H). |
表32
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(7)-8 | Z | 1.26(d,6H,J=7.0Hz),2.55(seq,1H,J=7.0Hz),3.98(s,3H),5.26(s,2H),7.00(d,1H,J=7.7Hz),7.07(m,2H),7.52(m,2H),7.70(dd,1H,J=7.7,8.4Hz),7.91(brd,1H),8.18(d,1H,J=8.4Hz). |
(7)-9 | Z | 1.27(d,6H,J=7.0Hz),2.56(seq,1H,J=7.0Hz),3.82(s,3H),3.97(s,3H),5.23(s,2H),6.90(m,2H),6.99(d,1H,J=6.8Hz),7.44(m,2H),7.69(dd,1H,J=6.8,J=7.9Hz),7.86(brd,1H),8.15(d,1H,J=7.9Hz). |
(7)-11 | Z | 1.90(m,2H),1.18(m,2H),1.56(m,1H),3.82(s,3H),3.97(s,3H),5.23(s,2H),6.88(m,2H),6.98(d,1H,J=6.8Hz),7.44(m,2H),7.67(dd,1H,J=6.8,7.9Hz),8.10(d,1H,J=7.9Hz),8.14(brd,1H). |
(7)-12 | Z | 1.91(t,3H,J=7.0Hz),1.35(m,4H),1.73(m,2H),2.37(s,3H),2.39(t,2H,J=7.5Hz),3.96(s,3H),5.24(s,2H),6.99(d,1H,J=7.3Hz),7.17(m,2H),7.38(m,2H),7.69(dd,1H,J=7.3,8.4Hz),7.89(brd,1H),8.14(d,1H,J=8.4Hz). |
(7)-13 | Z | 1.11(s,9H),2.26(s,2H),2.37(s,3H),3.96(s,3H),5.24(s,2H),7.00(d,1H,J=7.0Hz),7.17(m,2H),7.38(m,2H),7.68(dd,1H,J=7.0,8.2Hz),7.85(brd,1H),8.16(d,1H,J=8.2H). |
表33
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(7)-14 | Z | 1.28(d,6H,J=7.0Hz),2.64(seq,1H,J=7.0Hz),4.04(s,3H)5.40(s,2H),7.3~7.5(m,3H),7.55(m,2H),7.78(d,1H,J=86Hz),8.07(d,1H,J=8.6Hz),8.38(brd,1H). |
(7)-17 | Z | 1.27(d,6H,J=6.8Hz),1.45(t,3H,J=7.3Hz),2.56(seq,1H,J=6.8Hz),4.28(q,2H,J=7.3Hz),5.25(s,2H),7.00(d,1H,J=6.8Hz),7.3~7.5(m,5H),7.69(dd,1H,J=6.8,8.0Hz),7.88(brd,1H),8.16(d,1H,J=8.0Hz). |
(7)-18 | Z | 4.02(s,3H),5.41(s,2H),7.07(m,2H),7.25(m,2H),7.54(m,2H),7.70(ddd,1H,J=2.0,7.7Hz,7.7Hz),8.59(d,1H,J=4.8Hz). |
(7)-19 | Z | 4.02(s,3H),5.42(s,2H),7.14(dddd,1H,J=1.0Hz,2.6Hz,7.7Hz,7.7Hz),7.18~7.4(m,5H),7.70(ddd,1H,J=1.8Hz,7.7Hz,7.7Hz),8.59(m,1H). |
(7)-20 | Z | 4.01(s,3H),5.41(s,2H),7.24(m,2H),7.35(m,2H),7.48(m,2H),7.70(ddd,1H,J=1.8Hz,7.7Hz,7.7Hz),8.59(ddd,1H,J=1.5Hz,1.8Hz,4.4Hz). |
(8)-2 | Z | 1.27(d,6H,J=7.0Hz),2.64(seq,1H,J=7.0Hz),3.92(s,3H),5.24(s,2H),6.93(s,1H),7.34(m,2H),7.47(m,2H),9.20(brd,1H). |
表34
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(8)-7 | Z | 1.33(s,9H),3.96(s,3H),5.27(s,2H),6.93(s,1H),7.1~7.43(m,4H),8.95(brd,1H). |
(8)-9 | Z | 1.29(d,6H,J=7.0Hz),2.63(seq,1H,J=7.0Hz),3.83(s,3H),3.94(s,3H),5.22(s,2H),6.88(m,3H),7.46(m,2H),8.87(brd,1H). |
(8)-10 | Z | 1.33(s,9H),3.83(s,3H),3.94(s,3H),5.22(s,2H),6.89(m,3H),7.46(m,2H),8.99(brd,1H). |
(8)-12 | Z | 0.91(t,J=7.1Hz,3H),1.31~1.38(m,4H),1.70~1.77(m,2H),5.23(s,2H),6.92(s,1H),7.34~7.53(m,5H),9.10(brd,1H) |
(8)-15 | Z | 1.26(d,6H,J=7.0Hz),1.42(t,3H,J=7.3Hz),2.65(seq,1H,J=7.0Hz),4.26(q,2H,J=7.3Hz),5.19(s,2H),7.3~7.5(m,5H),9.12(brd,1H). |
(9)-1 | Z | 1.52(s,9H),3.98(s,3H),5.26(s,2H),6.92(d,1H,J=7.7Hz),7.17.4(m,5H),7.66(dd,1H,J=7.7,8.4Hz),7.88(d,1H,J=8.4Hz). |
(9)-2 | Z | 1.31(d,6H,J=6.4Hz),3.99(s,3H),5.03(seq,1H,J=6.4Hz),5.25(s,2H),6.93(d,1H,J=7.2Hz),7.07(m,2H),7.28(brd,1H),7.53(m,2H),7.68(d,1H,J=7.2,8.4Hz),7.90(d,1H,J=8.4Hz). |
(9)-3 | Z | 1.52(s,9H),3.98(s,3H),5.24(s,2H),6.91(d,1H,J=7.3Hz),7.07(m,2H),7.19(brd,1H),7.53(m,2H),7.65(dd,1H,J=7.3,8.4Hz),7.87(d,1H,J=8.4Hz). |
表35
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(9)-4 | Z | 1.52(s,9H),2.36(s,3H),3.95(s,3H),5.23(s,2H),6.92(d,1H,J=7.2Hz),7.17(m,2H),7.31(brd,1H),7.39(m,2H),7.64(dd,1H,J=7.2,8.4Hz),7.86(d,1H,J=8.4Hz). |
(9)-5 | Z | 0.92(t,3H,J=7.0Hz),1.36(m,4H),1.68(m,2H),2.36(s,3H),3.96(s,3H),4.17(t,2H,J=6.7Hz),5.24(s,2H),6.95(d,1H,J=7.5Hz),7.17(m,2H),7.38(m,2H),7.46(brd,1H),7.67(dd,1H,J=7.5,8.1Hz),7.89(d,1H,J=8.1Hz). |
(9)-6 | Z | 0.98(t,3H,J=7.4Hz),1.71(tq,2H,J=6.7,7.4Hz),3.99(s,3H),4.15(q,2H,J=6.7Hz),6.95(d,1H,J=7.0H),7.1~7.25(m,2H),7.3~7.45(m,3H),7.69(dd,1H,J=7.0,8.3Hz),7.91(d,1H,J=8.3Hz). |
(9)-7 | Z | 0.91(t,3H,J=7.1Hz),1.36(m,4H),1.73(m,2H),2.33(s,3H),2.39(q,2H,J=7.5Hz),3.96(s,3H),5.26(s,2H),7.00(d,1H,J=7.5Hz),7.27(m,4H),7.69(dd,1H,J=7.5,8.3Hz),7.89(brd,1H),8.15(d,1H,J=8.3Hz). |
(9)-8 | Z | 1.52(s,9H),2.33(s,3H),3.96(s,3H),5.24(s,2H),6.92(d,1H,J=6.8Hz),7.2~7.35(m,5H),7.65(dd,1H,J=6.8,8.3Hz),7.86(d,1H,J=8.3Hz). |
(9)-9 | Z | 0.93(t,3H,J=7.5Hz),1.49(s,6H),1.83(q,2H,J=7.5Hz),2.36(s,3H),3.96(s,H),5.23(s,2H),6.92(d,1H,J=7.0Hz),7.19(m,3H),7.39(m,2H),7.64(dd,1H,J=7.0,8.3Hz),7.85(d,1H,J=8.3Hz). |
表36
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(11)-4 | Z | 2.21(s,3H),2.49(s,3H),5.24(s,2H),7.00(d,J=7.5Hz,1H),7.34~7.53(m,5H),7.71(dd,J=7.9Hz,1H),7.90(brd,1H),8.13(d,J=8.3Hz,1H). |
(11)-5 | Z | 1.26(t,J=7.5Hz,3H),2.44(q,J=7.5Hz,2H),2.49(s,3H),5.24(s,2H),6.99(d,J=7.5Hz,1H),7.34~7.50(m,5H),7.71(dd,J=7.8Hz,1H),7.79(brd,1H),8.16(d,J=8.2Hz,1H). |
(11)-6 | Z | 1.02(t,J=7.3Hz,7.5Hz,3H),1.78(m,2H),2.38(t,J=7.3Hz,7.5Hz,2H),2.49(s,3H),5.24(s,2H),6.99(d,J=6.8Hz,1H),7.34~7.52(m,5H),7.70(dd,J=7.7Hz,8.0Hz,1H),7.77(brd,1H),8.16(d,J=8.4Hz,1H). |
(11)-7 | Z | 1.27(d,J=7.0Hz,6H),2.49(s,3H),2.51(qq,J=6.8Hz,1H),5.24(s,2H),6.99(d,J=7.5Hz,1H),7.35~7.55(m,5H),7.70(dd,J=7.7Hz,8.3Hz,1H),7.80(brd,1H),8.17(d,J=8.4Hz,1H). |
(11)-8 | Z | 0.95(t,J=7.3Hz,3H),1.42(m,2H),1.2(m,2H),2.40(t,J=7.3Hz,2H),2.49(s,3H),5.24(s,2H),6.99(d,J=7.5Hz,2H),7.34~7.53(m,5H),7.70(dd,J=7.9Hz,1H),7.80(brd,1H),8.16(d,J=8.3Hz,1H). |
(11)-11 | Z | 1.33(s,9H),2.50(s,3H),5.25(s,2H),6.99(d,J=7.5Hz,1H),7.35~7.53(m,5H),7.70(dd,J=7.7Hz,8.0Hz,1H),7.97(brd,1H),8.19(d,J=8.3Hz,1H). |
表37
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(11)-18 | Z | 0.89(t,J=6.6Hz,7.1Hz,3H),1.26~1.42(m,6H),1.68~1.75(m,2H),2.40(t,J=7.4Hz,7.7Hz,2H),2.49(s,3H),5.24(s,2H),6.99(d,J=7.5Hz,1H),7.34~7.52(m,5H),7.70(dd,J=7.9Hz,8.1Hz,1H),7.86(brd,1H),8.16(d,J=8.2Hz,1H). |
(11)-19 | Z | 0.88(t,J=7.00,3H),1.23~1.36(m,8H),1.68~1.78(m,2H),2.42(t,J=7.5Hz,2H),2.49(s,3H),5.24(s,2H),6.98(d,J=7.5Hz,1H),7.37~7.52(m,5H),7.70(dd,J=7.5Hz,J=8.2Hz,1H),7.79(brd,1H),8.15(d,J=8.2Hz,1H). |
(11)-21 | Z | 0.87~0.93(m,2H),1.09~1.14(m,2H),1.51~1.62(m,1H),2.49(s,3H),5.25(s,2H),6.98(d,J=7.5Hz,1H),7.35~7.52(m,5H),7.69(dd,J=7.8Hz,7.9Hz,1H),8.03(brd,1H),8.12(d,J=8.6Hz,1H). |
(11)-22 | Z | 1.62~2.16(m,8H),2.49(s,3H),2.73(tt,J=7.7Hz,8.0Hz,1H),5.24(s,2H),6.99(d,J=6.7Hz),7.34~7.53(m,5H),7.70(dd,J=7.7Hz,8.0Hz,1H),7.81(brd,1H),8.17(d,J=8.4Hz,1H). |
(11)-23 | Z | 1.22~1.99(m,10H),2.27(tt,J=3.5Hz,11.6Hz,1H),2.49(s,3H),5.24(s,2H),6.98(d,J=7.4Hz,1H),7.34~7.53(m,5H),7.69(dd,J=7.9Hz,1H),7.83(brd,1H),8.17(d,J=7.9Hz,1H). |
(12)-3 | Z | 2.43(s,3H),5.25(s,2H),7.02(s,1H)7.32~7.52(m,5H),8.54(s,1H),11.50(brd,1H). |
表38
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(12)-7 | Z | 1.25~1.28(m,6H),2.46(s,3H),2.58~2.73(m,1H),5.23(s,2H),6.93(s,1H),7.20~7.54(m,5H),9.43(brd,1H). |
(12)-8 | Z | 0.95(t,3H,J=7.33Hz),1.35~1.47(m,2H),1.68~1.78(m,2H),2.43~2.48(m,5H),5.23(s,1H),6.91(s,1H),7.35~7.52(m,5H),8.74(brd,1H). |
(12)-9 | Z | 1.62(d,6H,J=6.43Hz),2.20~2.30(m,1H),2.32(d,2H,J=6.58Hz),2.47(s,3H),5.23(s,2H),6.91(s,1H),7.38~7.50(m,5H),8.62(brd,1H). |
(12)-16 | Z | 1.10(s,9H),2.31(s,2H),2.47(s,3H),5.23((s,2H),6.91(s,1H),7.36~7.61(m,5H),8.60(brd,1H). |
(12)-18 | Z | 0.84~0.88(m,3H),1.23~1.40(m,6H),1.67~1.77(m,2H),2.45~2.55(m,5H),5.23(s,2H),6.93(s,1H),7.33~7.73(m,5H),9.80(brd,1H). |
(12)-19 | Z | 0.85~0.90(m,3H),1.23~1.39(m,8H),1.66~1.78(m,2H),2.24~2.48(m,5H),5.23(s,2H),6.91(s,1H),7.34~7.52(m,5H),8.95(brd,1H). |
(13)-1 | Z | 2.50(s,3H),3.80(s,3H),,5.24(s,2H),6.94(d,J=7.0Hz,1H),7.34~7.43(m,5H),7.72(dd,J=7.0Hz,J=8.6Hz,1H),7.93(d,J=8.6Hz,1H). |
(13)-2 | Z | 1.32(t,J=7.0Hz,3H),2.50(s,3H),4.31(q,J=7.0Hz,2H),5.24(s,2H),6.96(d,J=7.1Hz,1H),7.33~7.45(m,5H),7.74(dd,J=7.1Hz,J=8.6Hz,1H),7.96(d,J=8.6Hz,1H). |
表39
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(13)-3 | Z | 0.93(t,J=6.8Hz,3H),1.72(tq.J=6.7Hz,J=6.8Hz,2H),2.49(s,3H),4.14(t,J=6.7Hz,2H),5.25(s,2H),6.94(d,J=6.8Hz,1H),7.34~7.53(m,5H),7.69(dd,J=6.8Hz,J=8.4Hz,1H),7.90(d,J=8.4Hz,1H). |
(13)-5 | Z | 0.95(t,J=7.3Hz,3H),1.43~1.72(m,4H),2.49(s,3H),4.19(t,J=6.6Hz,2H),5.23(s,2H),6.93(d,7.5Hz,1H),7.35~7.52(m,5H),7.68(dd,J=7.5Hz,J=8.2Hz,1H),7.90(d,J=8.2Hz,1H). |
(13)-6 | Z | 0.96(d,J=6.8Hz,6H),1.98(sept,J=6.8Hz,1H),2.49(s,3H),3.95(d,J=6.6Hz,2H),5.24(s,1H),6.94(d,J=8.0Hz,1H),7.32~7.52(m,5H),7.68(dd,J=8.0Hz,J=8.2Hz,1H),7.90(d,J=8.2Hz,1H). |
(13)-6 | E | 0.96(d,J=6.8Hz,6H),1.98(sept,J=6.8Hz,1H),2.49(s,3H),3.95(d,J=6.6Hz,2H),5.22(s,1H),6.92(d,J=8.0Hz,1H),7.32~7.52(m,5H),7.66(dd,J=8.0Hz,J=8.2Hz,1H),7.78(d,J=8.2Hz,1H). |
(13)-15 | Z | 0.90(t,J=6.6Hz,3H),1.33~1.43(m,6H),1.63~1.72(m,2H),2.50(s,3H),4.18(t,J=6.6Hz,2H),5.24(s,2H),6.93(d,J=7.0Hz,J=8.2Hz,1H),7.90(d,J=8.2Hz,1H). |
(13)-21 | Z | 1.61~1.95(m,8H),2.49(s,3H),5.20(m,1H),5.23(s,2H),6.92(d,J=7.0Hz,1H),7.357.52(m,5H),7.68(dd,J=7.0Hz,J=8.3Hz,1H),7.89(d,J=8.3Hz,1H). |
表40
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(13)-22 | Z | 1.23~1.94(m,10H),2.50(,s,3H),4.73~4.81(m,1H),5.24(s,2H),6.93(d,J=7.0Hz,1H),7.35~7.52(m,5H),7.65(dd,J=7.7Hz,8.1Hz,1H),7.90(d,J=8.3Hz,1H). |
(14)-3 | Z | 0.94(t,3H,J=7.5Hz),1.73(m,2H),2.34(s,3H),4.15(m,2H),5.33(s,2H),6.94(s,1H),7.29~7.49(m,5H),11.28(brs,1H). |
(14)-5 | Z | 0.94(t,3H,J=7.33Hz),1.33~1.46(m,2H),1.591.73(m,2H),2.42(s,3H),4.25(t,2H,J=6.76Hz),5.25(s,2H),6.88(s,1H),7.33~7.50(m,5H),9.40(brd,1H). |
(14)-9 | Z | 0.90(t,J=6.8Hz3H),1.32~1.38(m,4H),1.65~1.72(m,2H),2.38(s,3H),4.26(q,J=7.0Hz,2H),5.39(s,2H),6.93(s,1H),7.31~7.61(m,5H). |
(14)-15 | Z | 0.88(t,3H,J=6.61Hz),1.24~1.32(m,6H),1.65~1.72(m,2H),2.44(s,1H),4.24(t,2H,J=6.79Hz),5.25(s,2H),6.88(s,1H),7.34~7.50(m,5H),9.05(brd,1H). |
(16)-3 | Z | 2.46(s,3H),5.25(s,2H),6.99(s,1H),7.36~7.65(m,8H),7.91~7.94(m,2H),9.63(brd,1H). |
(17)-21 | Z | 0.91(t,J=7.1Hz,3H),1.32(t,J=7.6Hz,3H),1.34(m,4H),1.74(m,2H),2.39(t,J=7.5Hz,2H),2.79(q,J=7.6Hz,2H),5.23(s,2H),6.99(d,J=7.5Hz,1H),7.2~7.6(m,5H),7.70(dd,J=7.5Hz,J=8.4Hz,1H),7.81(brd,1H),8.16(d,J=8.4Hz,1H). |
表41
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(18)-19 | Z | 0.89(t,J=7.0Hz,3H),1.27(t,J=7.7Hz,3H),1.2~1.4(m,4H),1.73(m,2H),2.46(t,J=7.3Hz,2H),2.76(q,J=7.7Hz,2H),5.22(s,2H),6.91(s,1H),7.2~7.55(m,5H),9.47(brd,1H). |
(19)-11 | Z | 0.96(t,3H,J=7.33Hz),1.361.48(m,2H),1.63~1.72(m,2H),2.50(s,3H),4.19(t,2H,J=6.61Hz),5.23(s,2H),6.93(d,1H,J=7.33Hz),7.02~7.05(m,1H),7.16~7.26(m,3H),7.33~7.41(m,1H),7.69(t,1H,J=7.69Hz),7.92(d,1H,J=8.44Hz). |
(19)-12 | Z | 0.95(t,3H,J=7.33Hz),1.35~1.48(m,2H),1.64~1.72(m,2H),2.50(s,3H),4.19(t,2H,J=6.79Hz),5.23(s,2H),6.92(d,1H,J=6.79Hz),7.05~7.13(m,2H),7.32(brd,1H),7.35~7.41(m,2H),7.68(t,1H,J=6.34Hz),7.91(d,1H,J=8.26Hz). |
(19)-13 | Z | 0.96(t,3H,J=7.33Hz),1.36~1.48(m,2H),1.62~1.72(m,2H),2.50(s,3H),4.19(t,2H,J=6.58Hz),5.25(s,2H),6.92(d,1H,J=7.51Hz),7.15~7.18(m,1H),7.26~7.36(m,2H),7.44~7.49(m,1H),7.69(t,1H,J=8.05Hz),7.92(d,1H,J=8.23Hz). |
(19)-14 | Z | 0.96(t,3H,J=7.33Hz),1.36~1.48(m,2H),1.62~1.72(m,2H),2.49(s,3H),4.19(t,2H,J=6.61Hz),5.23(s,2H),6.92(d,1H,J=7.51Hz),7.30~7.40(m,4H),7.68(t,1H,J=7.51Hz),7.91(d,1H,J=8.26Hz). |
表42
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(19)-16 | Z | 0.95(t,3H,J=7.15Hz),1.35~1.48(m,2H),1.62~1.71(m,2H),2.38(s,3H),2.48(s,3H),4.19(t,2H,J=6.58Hz),5.22(s,2H),6.93(d,1H,J=7.33Hz),7.20~7.30(m,5H),7.68(t,1H,J=7.90Hz),7.89(d,1H,J=8.41Hz). |
(19)-23 | Z | 0.96(t,3H,J=7.48Hz),1.36~1.48(m,2H),1.62~1.72(m,2H),2.49(s,3H),3.83(s,3H),4.19(t,2H,J=6.79Hz),5.20(s,2H),6.88~6.94(m,3H),7.26~7.31(m,3H),7.68(t,1H,J=7.87Hz),7.92(d,1H,J=8.23Hz). |
(19)-25 | Z | 0.96(t,3H,J=7.33Hz),1.36~1.48(m,2H),1.63~1.72(m,2H),2.51(s,3H),4.19(t,2H,J=6.61Hz),5.28(s,2H),6.92(d,1H,J=7.15Hz),7.49~7.53(m,2H),7.67~7.72(m,3H),7.93(d,1H,J=8.26Hz). |
(19)-28 | Z | 0.90~0.94(m,3H),1.34~1.40(m,4H),1.65~1.69(m,2H),2.52(s,3H),3.07(s,3H),4.18(t,2H,J=6.79Hz),5.29(s,2H),6.93(d,1H,J=7.51Hz),7.58~7.62(m,2H),7.70(t,1H,J=7.90Hz),7.92~8.00(m,3H). |
(19)-29 | Z | 0.96(t,3H,J=7.33Hz),1.36~1.48(m,2H),1.63~1.72(m,2H),2.52(s,3H),4.20(t,2H,J=6.61Hz),5.30(s,2H),6.93(d,1H,J=6.97Hz),7.56~7.61(m,2H),7.70(t,1H,J=7.69Hz),7.94(d,1H,J=8.23Hz),8.24~8.27(m,2H). |
表43
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(19)-31 | Z | 0.96(t,3H,J=7.33Hz),1.34~1.48(m,2H),1.63~1.72(m,2H),2.51(s,3H),4.19(t,2H,J=6.61Hz),5.27(s,2H),6.93(d,1H,J=7.33Hz),7.28(brd,1H),7.51(d,1H,J=8.26),7.65~7.72(m,3H),7.93(d,1H,J=8.26Hz). |
(19)-33 | Z | 0.95(t,J=7.3Hz,3H),1.32(t,J=7.6Hz,3H),1.41(m,2H),2.80(q,J=7.6Hz,2H),4.19(t,J=6.6Hz,2H),5.24(s,2H),6.93(d,J=7.0Hz,1H),7.2~7.6(m,6H),7.68(dd,J=7.0Hz,8.3Hz,1H),7.90(d,J=8.3Hz,1H). |
(19)-34 | Z | 0.96(t,3H,J=7.33Hz),1.23(t,3H,J=7.51),1.35~1.48(m,2H),1.67~1.72(m,2H),2.49(s,3H),2.68(q,2H,J=7.51),4.19(t,2H,J=6.58Hz),5.21(s,2H),6.92(d,1H,J=7.33Hz),7.20~7.29(m,5H),7.67(t,1H,J=7.51Hz),7.89(d,1H,J=8.26Hz). |
(19)-36 | Z | 0.96(t,3H,J=7.33Hz),1.36~1.48(m,2H),1.62~1.72(m,2H),2.52(s,3H),4.19(t,2H,J=6.61Hz),5.25(s,2H),6.95(d,1H,J=7.54Hz),7.37~7.48(m,6H),7.57~7.63(m,4H),7.69(t,1H,J=8.05Hz),7.91(d,1H,J=8.26Hz). |
(19)-37 | Z | 0.94(t,3H,J=7.33Hz),1.36~1.46(m,2H),1.61~1.71(m,2H),2.64(s,3H),4.19(t,2H,J=6.79Hz),5.29(s,2H),6.98(d,1H,J=7.33Hz).7.34~7.48(m,3H),7.59(brd,1H),7.64~7.71(m,2H),7.95(d,1H,J=8.08Hz). |
表44
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(19)-38 | Z | 0.94(t,3H,J=7.33Hz),1.34~1.46(m,2H),1.61~1.68(m,2H),2.59(s,3H),3.50(s,3H),4.18(t,2H,J=6.79Hz),5.25(s,2H),6.84(d,1H,J=8.05Hz),6.90~7.11(m,2H),7.38~7.48(m,1H),7.62~7.73(m,3H),7.93(d,1H,J=8.27Hz). |
(20)-6 | Z | 0.87(t,J=7.0Hz,3H),1.23(t,J=7.7Hz,3H),1.2~1.4(m,6H),1.69(m,2H),2.71(q,J=7.7Hz,2H),4.24(t,J=7.0Hz,2H),5.30(s,2H),6.87(s,1H),7.2~7.5(m,5H),10.53(brd,1H). |
(21)-5 | Z | 0.94(t,J=7.3Hz,3H),1.40(m,2H),1.56(m,2H),3.35(dt,J=6.3,6.3Hz,2H),3.93(s,3H),5.27(s,2H),6.77(d,J=7.5Hz,1H),6.83(d,J=7.5Hz,1H),7.3~7.6(m,5H),7.58(dd,J=7.5,8.3Hz,1H),8.72(brd,1H),9.31(brd,1H). |
(21)-15 | Z | 0.88(t,J=6.8Hz,3H),1.2~1.4(m,6H),1.56(m,2H),3.35(dt,J=6.6,6.6Hz,2H),3.93(s,3H),5.27(s,2H),6.78(d,J=8.3Hz,1H),6.82(d,J=7.5Hz,1H),7.3~7.6(m,5H),7.57(dd,J=7.5,8.3Hz,1H),8.82(brd,1H),9.31(brd,1H). |
(22)-15 | Z | 0.88(t,J=6.9Hz,3H),1.2~1.4(m,6H),1.57(m,2H),2.46(s,3H),3.36(td,J=6.5,6.5Hz,2H),5.25(s,2H),6.81(d,J=7.5Hz,1H),6.84(d,J=8.6Hz,1H),7.3~7.6(m,5H),7.58(dd,J=7.5,8.6Hz,1H),9.28(brd,1H),9.34(brd,1H). |
表45
化合物编号 | Z/E | 1H-NMR(CDCl3)δ |
(3)-25 | Z | 1.64(m,2H),2.00(s,3H),3.64(q,J=6.2Hz,2H),3.99(s,3H),4.18(t,J=6.7Hz,2H),5.22(s,2H),6.94(d,J=7.0Hz,1H),7.3~7.55(m,6H),7.65(dd,J=7.0,8.4Hz,1H),7.88(d,J=8.4Hz,1H). |
(5)-19 | Z | 2.03(s,3H),2.25(q,J=6.0Hz,2H),3.45(q,J=6.0Hz,1H),4.13(s,3H),5.25(s,2H),7.04(d,J=7.3Hz,1H),7.31~7.51(m,5H),7.76(dd,J=7.5Hz,8.0Hz,1H),8.16(d,J=8.0Hz,1H). |
(11)-24 | Z | 2.01(s,3H),2.22(q,J=6.0Hz,2H),2.51(s,3H),3.47(q,J=6.0Hz,2H),5.27(s,2H),6.92(d,J=7.3Hz,1H),7.35~7.52(m,5H),7.75(dd,J=7.6,8.2Hz,1H),7.76(brd,1H),8.19(J=8.1Hz,1H). |
(13)-24 | Z | 1.62(m,2H),2.02(s,3H),2.51(s,3H),3.62(q,J=6.1Hz,2H),4.17(t,J=6.7Hz,2H),5.23(s,3H),6.91(d,J=6.8Hz,1H),7.37~7.59(m,5H),7.63(dd,J=6.8,8.4Hz,1H),7.86(d,J=8.4Hz,1H). |
下面,说明使用本发明化合物的制剂的例子。制剂例以及防除试验中使用的本发明的化合物除非有特别地记载,否则就是(Z)体和(E)体的混合物。
(制剂例1)水合剂
将上述表1~23中所示的20质量份四唑基肟衍生物分别吸附在30质量份胶态硅石上。向其中加入3质量份聚氧乙烯月桂基硫酸钠、8质量份50质量%粉末聚氧乙烯烷基苯基醚硫酸铵、1质量份木质磺酸钠以及38质量份高岭土并进行混合后,使用喷射式磨机进行粉碎,从而成为水合剂。
(制剂例2)粉剂
将上述表1~23中所示的2质量份四唑基肟衍生物分别与98质量份高岭土混合后,进行粉碎,从而成为粉剂。
(制剂例3)粒剂
将上述表1~23中所示的5质量份四唑基肟衍生物分别与90质量份皂土和滑石的等量混合物以及5质量份烷基苯磺酸钠混合,并进行粉碎后,成形为粒剂。
下面用试验例说明本发明的化合物作为各种植物病害防除剂的有效成分是有用的。还有,使用以下表示调查时发病状态的发病指数分别调查发病程度,由下式算出发病度以及防除值,并记载于以下的表47~56中。
发病指数
0:没有发病
1:发病面积为不足25%
2:发病面积为25%以上、不足50%
3:发病面积为50%以上
发病度(%)=【(发病程度不同的叶数×指数)÷(调查叶数×3(发病度指数最高值))】×100
防除值(%)=(无处理区的发病度-处理区的发病度)÷无处理区的发病度×100
另外,提供以下化合物作为对照剂。
对照剂1:代森锰锌水合剂(广泛使用的霜霉病、疫病防除剂)
对照剂2:特开平11-269176号公报(WO99/29689号公报、欧洲专利公开第1038874号公报)中记载的代表化合物A
对照剂3和4:特开2001-55387号公报(WO00/75138号公报、欧洲专利公开第1184382号公报)中记载的代表化合物B以及C
对照剂1中使用的代森锰锌水合剂的有效成分是美国的ロ-ム·アンド·ハ-ス社进行开发,并于1969年登记的园艺用的杀菌剂,是用式
表示的锌配位亚乙基双二硫代氨基甲酸酯。
另外,对照剂2、3以及4是由下述通式和下表特定的化合物。
表46
R | X | Y | Z | Q | |
对照剂2 | H | CH | S | CH | H |
对照剂3 | Cl | N | S | CH | H |
对照剂4 | H | CH | CH | N | Cl |
作为对于葡萄霜霉病、番茄疫病的防除效果,主要列举为防护效果和治疗效果。防护效果是通过向试验用植物花盆苗喷洒被验物质,风干后,接种目标植物病原菌的胞子悬浮液,然后将花盆苗置于多湿条件下并使其发病后,在温室等中在一定期间培育植物花盆苗所获得的效果;治疗效果是通过向试验用植物花盆苗接种目标植物病原菌的胞子悬浮液,置于多湿条件下并使其发病后,向花盆苗喷洒被验物质并风干后,在温室等中在一定期间培育植物花盆苗所获得的效果。
关于本发明化合物防护效果的试验,相对于葡萄霜霉病、番茄疫病,与对照剂1、2、3、4一起实施。本发明的各化合物都显示出了超过对照剂1的效果,而且相对于对照剂2、3、4显示出相等或者其以上的效果。关于治疗效果的试验按照以下的葡萄霜霉病防除试验(试验例1)和番茄疫病防除试验(试验例2)进行。
(试验例1)葡萄霜霉病防除试验(治疗效果)
向1/10000公亩在瓦格纳盆中育苗的5~6叶期的葡萄(品种:ネオマスカツト)接种葡萄霜霉病菌(Plasmopara viticola)的胞子悬浮液,在25℃的湿室中放置18小时。使叶风干后,按照制剂例1的方法调制的水合剂,以水稀释使成为有效成分浓度为100ppm的药液,并以滴下药液的程度进行喷洒,然后在温室中使其发病。接种10天后调查发病程度。其结果示于以下的表47~56中。
表47
化合物No. | 浓度(ppm) | 防除值(%) |
(1)-6(1)-7(1)-8(1)-12(1)-16(1)-18(1)-21(2)-7(2)-11(2)-12(2)-16(3)-2(3)-3(3)-4(3)-5(3)-8(3)-9(3)-15(3)-16(3)-18(3)-21(3)-22(3)-23 | 100100100100100100100100100100100100100100100100100100100100100100100 | 701007010070100709010090907090901001001001001001007010080 |
表48
化合物No. | 浓度(ppm) | 防除值(%) |
(4)-9(4)-15(4)-18(5)-12(5)-14(6)-2(6)-6(6)-7(6)-15(7)-1(7)-3(7)-11(7)-12(8)-2(8)-7(8)-10(8)-17 | 100100100100100100100100100100100100100100100100100 | 8070701009070701007070807010070707090 |
表49
化合物No. | 浓度(ppm) | 防除值(%) |
(9)-1(9)-2(9)-3(9)-4(9)-5(9)-6(9)-7(9)-9(9)-10(9)-11(11)-4(11)-5(11)-6(11)-7(11)-8(11)-11(11)-12(11)-21(12)-6(12)-7(12)-12(12)-18 | 100100100100100100100100100100100100100100100100100100100100100100 | 100707010010070100100100100707070100100701007080909090 |
表50
化合物No. | 浓度(ppm) | 防除值(%) |
(13)-5(13)-8(13)-9(13)-15(13)-21(13)-22(14)-5(16)-3(17)-1(18)-1 | 100100100100100100100100100100 | 709010080801007070100100 |
表51
化合物No. | 浓度(ppm) | 防除值(%) |
(19)-1(19)-11(19)-12(19)-13(19)-14(19)-16(19)-23(19)-25(19)-28(19)-29(19)-31(19)-33(19)-34(19)-35(20)-1(22)-2(22)-5(22)-15 | 100100100100100100100100100100100100100100100100100100 | 1008090100801007090100809010080707070100100 |
对照剂1对照剂2对照剂3对照剂4 | 750100100100 | 0503020 |
(试验例2)番茄疫病防除效果(治疗效果)
向直径9cmd的塑料花盆中育苗的4叶期的番茄(品种:丰福)接种番茄疫病菌(Phytophthora iNfestaNs)的胞子悬浮液,在20℃的湿室中放置18小时。使叶风干后,按照制剂例1的方法调制的水合剂,以水稀释使便成为有效成分浓度为100ppm的药液,并以滴下药液的程度进行喷洒,然后在温室中使其发病。接种7天后调查发病程度。其结果示于以下的表52~56中。
表52
化合物No. | 浓度(ppm) | 防除值(%) |
(1)-6(1)-7(1)-8(1)-12(1)-16(1)-18(1)-21(2)-7(2)-11(2)-12(2)-16(3)-2(3)-3(3)-4(3)-5(3)-8(3)-9(3)-15(3)-16(3)-18(3)-21(3)-22(3)-23 | 100100100100100100100100100100100100100100100100100100100100100100100 | 90100901001001009010010010010090100100100100100100100100100100100 |
表53
化合物No. | 浓度(ppm) | 防除值(%) |
(4)-9(4)-15(4)-18(5)-12(5)-14(6)-2(6)-6(6)-7(6)-15(7)-1(7)-3(7)-11(7)-12(8)-2(8)-7(8)-10(8)-17 | 100100100100100100100100100100100100100100100100100 | 100809010010080801009080808010090809080 |
表54
化合物No. | 浓度(ppm) | 防除值(%) |
(9)-1(9)-2(9)-3(9)-4(9)-5(9)-6(9)-7(9)-9(9)-10(9)-11(11)-4(11)-5(11)-6(11)-7(11)-8(11)-11(11)-12(11)-21(12)-6(12)-7(12)-12(12)-18 | 100100100100100100100100100100100100100100100100100100100100100100 | 10080901001001001001001001008080801001008010090100100100100 |
表55
化合物No. | 浓度(ppm) | 防除值(%) |
(13)-5(13)-8(13)-9(13)-15(13)-21(13)-22(14)-5(16)-3(17)-1(18)-1 | 100100100100100100100100100100 | 90100100901001008080100100 |
表56
化合物No. | 浓度(ppm) | 防除值(%) |
(19)-1(19)-11(19)-12(19)-13(19)-14(19)-16(19)-23(19)-25(19)-28(19)-29(19)-31(19)-33(19)-34(19)-35(20)-1(22)-2(22)-5(22)-15 | 100100100100100100100100100100100100100100100100100100 | 100901001001001008090100100100100100808090100100 |
对照剂1对照剂2对照剂3对照剂4 | 750100100100 | 10604030 |
由上表所示的结果显而易见的是,本发明的四唑基肟衍生物与以往的杂环取代肟衍生物和通用的植物病害防除剂相比,具有优异的治疗效果。含有治疗效果优异的本发明的四唑基肟衍生物的植物病害防除剂,由于即使在确认了植物病原菌的发病后进行喷洒,也能发挥充分的植物病害的防除效果,所以可以减少农药的喷洒次数,从而省力、省成本性方面的优点显而易见。
产业上的可利用性
本发明的用上述通式(1)表示的四唑基肟衍生物对于有用植物体的药害小,可用作农药,特别是植物病害防除剂。另外,把本发明的四唑基肟衍生物作为有效成分含有的农药比以往的杂环取代肟衍生物对于植物病害的治疗效果还优异。另外,本发明的用通式(6)以及通式(7)表示的四唑基肟基衍生物可用作本发明的用通式(1)表示的四唑基肟衍生物的中间体。
Claims (11)
1.通式(1)表示的四唑基肟衍生物:
式中,X表示氢原子、卤原子、烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基;A表示用通式(2)表示的四唑基
(式中,Y表示烷基)
或者用通式(3)表示的四唑基
(式中,Y表示烷基);
Het表示用通式(4)表示的吡啶基
【式中,R表示氢原子或者卤原子,Z表示氢原子、氨基、用通式QC(=O)NH-表示的基团
(式中,Q表示氢原子、碳原子数1~8的烷基、用卤原子取代的碳原子数1~6的烷基、碳原子数3~6的环烷基、碳原子数1~8烷氧基、碳原子数3~6的环烷氧基、苄氧基、2-苯基乙氧基、用碳原子数1~4的烷基取代的硫代烷基、用碳原子数1~4的烷氧基取代的碳原子数1~2的烷基、用碳原子数1~4的酰胺基取代的碳原子数1~6的烷基、用碳原子数1~4的酰胺基取代的碳原子数1~6的烷氧基、碳原子数1~8的烷基氨基、碳原子数2~6的链烯基、芳烷基或者苯基)】
或者用通式(5)表示的噻唑基
式中,R以及Z表示与上述通式(4)中定义的意思相同的意思。
2.权利要求1中记载的四唑基肟衍生物,其中,Z是用通式QC(=O)NH-表示的基团(式中,Q表示碳原子数1~8的烷基或者碳原子数1~8的烷氧基),
而且,Het是用上述通式(4)表示的吡啶基。
3.权利要求2中记载的四唑基肟衍生物,其中,X是氢原子或者卤原子。
4.权利要求2或者3中记载的四唑基肟衍生物,其中,Y是甲基。
5.权利要求1中记载的四唑基肟衍生物,其中,Z是用通式QC(=O)NH-表示的基团(式中,Q表示碳原子数1~8的烷基或者碳原子数1~8的烷氧基),
而且,Het是用上述通式(5)表示的噻唑基。
6.权利要求5中记载的四唑基肟衍生物,其中,X是氢原子或者卤原子。
7.权利要求5或者6中记载的四唑基肟衍生物,其中,Y是甲基。
9.通式(7)表示的四唑基肟基衍生物:
X2表示烷基、烷氧基、氰基、甲磺酰基、硝基、三氟甲基或者芳基,Y2表示烷基。
10.农药,其含有权利要求1~7任一项中记载的四唑基肟衍生物作为有效成分。
11.植物病害防除剂,其含有权利要求1-7任一项中记载的四唑基肟衍生物作为有效成分。
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Also Published As
Publication number | Publication date |
---|---|
EP1426371A4 (en) | 2004-12-22 |
MXPA04001507A (es) | 2004-05-31 |
RU2004104638A (ru) | 2005-07-10 |
KR100855652B1 (ko) | 2008-09-03 |
PL204568B1 (pl) | 2010-01-29 |
CN1259318C (zh) | 2006-06-14 |
NZ531160A (en) | 2005-12-23 |
CA2457061A1 (en) | 2003-02-27 |
TW577883B (en) | 2004-03-01 |
AU2002328627B2 (en) | 2007-09-20 |
IL160439A (en) | 2010-06-16 |
DE60230164D1 (de) | 2009-01-15 |
HUP0401103A3 (en) | 2005-11-28 |
ATE416172T1 (de) | 2008-12-15 |
IL160439A0 (en) | 2004-07-25 |
KR20040027895A (ko) | 2004-04-01 |
BRPI0212034B1 (pt) | 2018-01-30 |
HU226907B1 (en) | 2010-03-01 |
ZA200401272B (en) | 2005-03-18 |
PL368238A1 (en) | 2005-03-21 |
EP1426371A1 (en) | 2004-06-09 |
US20070105926A1 (en) | 2007-05-10 |
WO2003016303A1 (fr) | 2003-02-27 |
DK1426371T3 (da) | 2009-01-26 |
CA2457061C (en) | 2011-03-08 |
PT1426371E (pt) | 2008-12-31 |
CY1109016T1 (el) | 2014-07-02 |
HUP0401103A2 (hu) | 2004-09-28 |
US20050070439A1 (en) | 2005-03-31 |
ES2315392T3 (es) | 2009-04-01 |
BR0212034A (pt) | 2004-08-03 |
EP1426371B1 (en) | 2008-12-03 |
US7183299B2 (en) | 2007-02-27 |
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