CN100448876C - 杂环甲酰胺衍生物 - Google Patents
杂环甲酰胺衍生物 Download PDFInfo
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- CN100448876C CN100448876C CNB2003801016261A CN200380101626A CN100448876C CN 100448876 C CN100448876 C CN 100448876C CN B2003801016261 A CNB2003801016261 A CN B2003801016261A CN 200380101626 A CN200380101626 A CN 200380101626A CN 100448876 C CN100448876 C CN 100448876C
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- 239000000203 mixture Substances 0.000 claims abstract description 41
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- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 239000000460 chlorine Substances 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 10
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Abstract
本发明涉及杀真菌活性的式(I)化合物:其中Het是含有1-3个杂原子的5-或6-元杂环,这些杂原子各自独立地选自氧,氮和硫,条件是所述环不能是1,2,3-***,并且所述环被基团R8,R9和R10取代;X是单键或双键;Y是O,S,N(R11)或(CR12R13)(CR14R15)m(CR16R17)n;m是0或1;n是0或1;且R1-R17各自独立地具有不同的定义。本发明也涉及这些化合物的制备、制备这些化合物用的新中间体、包括至少一种这些新化合物作为活性成分的农药组合物、所述组合物的制备以及所述活性成分或组合物在农业或园艺领域防治或预防植物病原微生物(优选真菌)侵染植物方面的应用。
Description
本发明涉及新的三环胺衍生物,它们具有杀微生物活性,尤其是杀真菌的活性。本发明也涉及这些化合物的制备、制备这些化合物用的新中间体、包括至少一种这些新化合物作为活性成分的农药组合物、所述组合物的制备以及所述活性成分或组合物在农业或园艺领域防治或预防植物病原微生物(尤其是真菌)侵染植物方面的应用。
本发明提供式(I)化合物:
其中Het是含有1-3个杂原子的5-或6-元杂环,这些杂原子各自独立地选自氧,氮和硫,条件是所述环不能是1,2,3-***,并且所述环被基团R8,R9和R10取代;X是单键或双键;Y是O,S,N(R11)或(CR12R13)(CR14R15)m(CR16R17)n;m是0或1;n是0或1;R1是氢,C1-4烷基,C1-4卤代烷基,C1-4烷氧基,C1-4卤代烷氧基,CH2C≡CR18,CH2CR19=CHR20,CH=C=CH2或COR21;R2和R3各自独立地是氢,卤素,C1-4烷基,C1-4烷氧基或C1-4卤代烷氧基;R4,R5,R6和R7是各自独立地是氢,卤素,C1-4烷基,C1-4卤代烷基,C1-4烷氧基,C1-4卤代烷氧基,C1-4烷硫基,C1-4卤代烷硫基,羟甲基,C1-4烷氧基甲基,C(O)CH3或C(O)OCH3,R8,R9和R10各自独立地是氢,卤素,氰基,硝基,C1-4烷基,C1-4卤代烷基,C1-4烷氧基(C1-4)亚烷基或C1-4卤代烷氧基(C1-4)亚烷基,条件是R8,R9和R10中至少一个不是氢;R11是氢,C1-4烷基,苄基(其中的苯基任选被至多三个的取代基取代,这些取代基各自独立地选自卤素,C1-4烷基,C1-4卤代烷基和C1-4烷氧基),甲酰基,C(O)C1-4烷基(任选被卤素或C1-4烷氧基取代),C(=O)OC1-6烷基(任选被卤素、C1-4烷氧基或氰基取代)或C1-4烷氧基(C1-4)亚烷基;R12,R13,R14,R15,R16和R17各自独立地是氢,卤素,羟基,C1-6烷基,C2-6链烯基[后二者任选被卤素,羟基,C1-4烷氧基,=O,芳基或O-C(O)-C1-4烷基或3-7元碳环(carboxylic ring)(其本身任选被至多三个的甲基取代)取代],3-7元饱和环(任选被至多三个的甲基取代,并且任选含有一个选自氮和氧的杂原子)或C1-4烷氧基;或R12和R13与它们相连接的碳原子一起形成基团C=O或3-5元碳环(任选被至多三个的甲基取代,并且任选含有至多2个各自独立地选自O和N的杂原子);或R12和R13一起形成C1-6亚烷基(任选被至多三个的甲基取代)或C3-6亚环烷基(任选被至多三个的甲基取代);R18,R19和R20各自独立地是氢,卤素,C1-4烷基,C1-4卤代烷基或C1-4烷氧基(C1-4)亚烷基;和R21是氢,C1-6烷基,C1-6卤代烷基,C1-4烷氧基(C1-4)亚烷基,C1-4烷基-S-(C1-4)亚烷基,C1-4烷氧基或芳基。
卤素是指氟、氯、溴或碘;优选氟、氯或溴。
各烷基部分是直链或支链的,例如为甲基、乙基、正丙基、正丁基、正戊基、正己基、异丙基、仲丁基、异丁基、叔丁基、新戊基、正庚基、1,3-二甲基丁基、1,3-二甲基戊基,1-甲基-3-乙基-丁基或1,3,3-三甲基丁基。同样,各亚烷基部分也是直链或支链的。
卤代烷基部分是指被一个或多个相同或不同的卤原子取代的烷基部分,例如CF3,CF2Cl,CHF2,CH2F,CCl3,CF3CH2,CHF2CH2,CH2FCH2,CH3CHF或CH3CF2。
链烯基和炔基部分可以是直链或支链的形式。
每个链烯基部分在适当情况下都可以是(E)-或(Z)构型。
3-5元碳环包括三元或五元螺环。
芳基包括苯基、萘基、蒽基、芴基和2,3-二氢化茚基,但优选苯基。
亚烷基部分可以是直链或支链的形式。亚烷基包括亚甲基[CH2=],亚乙基[CH3C(H)=],正丙叉,异丙叉[(CH3)2C=],正丁叉,异丁叉,2-丁叉,正戊叉,异戊叉,新戊叉,2-戊叉,正己叉,2-己叉,3-己叉,异己叉和新己叉。
环烷基包括环丙基,环丁基,环戊基,环己基,环庚基和环辛基。
环烯基包括环丁烯基,环戊烯基,环己烯基和环庚烯基。
亚环烷基包括亚环丙基[c(C3H4)=],亚环丁基,亚环戊基和亚环已基。
在本发明的一个方面中,R11是氢,C1-4烷基,苄基(其中苯基任选被至多三个的取代基取代,这些取代基各自独立地选自卤素,C1-4烷基,C1-4卤代烷基和C1-4烷氧基),甲酰基,C(O)C1-4烷基或C1-4烷氧基(C1-4)亚烷基。
在本发明的另一个方面中,R12,R13,R14,R15,R16和R17各自独立地为氢,C1-4烷基或C1-4烷氧基。
Het优选是吡咯基,吡唑基,噻唑基,噁唑基,吡啶基,嘧啶基,哒嗪基,2,3-二氢-[1,4]氧硫杂环己二烯-6-基,噁嗪基,噻嗪基或三嗪基。
Het较优选是吡咯基,吡唑基,噻唑基,噁唑基,吡啶基,嘧啶基或2,3-二氢-[1,4]氧硫杂环己二烯-基。
Het更优选是吡咯基,吡唑基,噻唑基或吡啶基。
Het最优选是吡咯基或吡唑基。
优选X是单键。
在一个方面中,Y是O,S,N(R11),CH2,CH2CH2,CH2CH2CH2,C(CH3)2,CH(CH3),CH(C2H5),C(CH3)(C2H5),CH(OCH3)或C(OCH3)2;较优选N(R11),O,S,CH2,CH2CH2,CH2CH2CH2,C(CH3)2,CH(CH3)或CH(C2H5);更优选N(R11),O,S,CH2或CH2CH2;且更优选O,CH2或N(R11)。
优选Y是O,N(R11)或(CR12R13)(CR14R15)m(CR16R17)n。
更优选Y是O或(CR12R13)(CR14R15)m(CR16R17)n。
更优选Y是(CR12R13)(CR14R15)m(CR16R17)n。
更加优选Y是(CR12R13)。
优选n为0。
优选m为0。
优选R1是氢,CH2C≡CR18,CH=C=CH2或COR21。
较优选R1是氢,CH2C≡CH,CH=C=CH2,C(O)H或C(O)CH3。
更优选R1是氢,CH2C ≡CH,CH=C=CH2或C(O)CH3。
更优选R1是氢,CH2C≡CH或CH=C=CH2。
最优选R1是氢。
优选R2是氢,卤素或C1-4烷基。
较优选R2是氢或卤素。
最优选R2是氢。
优选R3是氢或甲基。
较优选R3是氢。
优选R4是氢,C1-4烷基,卤素,C1-4卤代烷基,C1-4烷氧基,C(O)CH3或C(O)OCH3。
较优选R4是氢,C1-2烷基,卤素,CF3,甲氧基,C(O)CH3或C(O)OCH3。
更优选R4是氢,甲基,氯,CF3或甲氧基。
最优选R4是氢或甲基。
优选R5是氢,C1-4烷基,卤素,C1-4卤代烷基,C1-4烷氧基,C(O)CH3或C(O)OCH3。
较优选R5是氢,C1-2烷基,氯,CF3,甲氧基,C(O)CH3或C(O)OCH3。
最优选R5是氢或甲基。
优选R6是氢,C1-4烷基,C1-4烷氧基或C(O)CH3。
较优选R6是氢,甲基,甲氧基或C(O)CH3。
最优选R6是氢或甲基。
优选R7是氢,C1-4烷基,C1-4烷氧基或C(O)CH3。
较优选R7是氢,甲基,甲氧基或C(O)CH3。
最优选R7是氢或甲基。
优选R8是氢,卤素,C1-4烷基,C1-4卤代烷基或甲氧基亚甲基。
较优选R8是氢,氯,氟,溴,C1-2烷基,CF3,CF2Cl,CHF2,CH2F或甲氧基亚甲基。
更优选R8是氢,氯,氟,C1-2烷基,CF3,CF2Cl,CHF2,CH2F或甲氧基亚甲基。
最优选R8是氢,氯,氟,甲基,CF3,CHF2或CH2F。
优选R9是氢,卤素,C1-4烷基或C1-4卤代烷基或甲氧基亚甲基。
较优选R9是氢,氯,氟,溴,C1-2烷基,CF3,CF2Cl,CHF2,CH2F或甲氧基亚甲基。
更优选R9是氢,氯,氟,C1-2烷基,CF3,CF2Cl,CHF2,CH2F或甲氧基亚甲基。
最优选R9是氢,氯,氟,甲基,CF3,CHF2或CH2F。
优选R10是氢,卤素,C1-4烷基,C1-4卤代烷基或甲氧基亚甲基。
较优选R10是氢,氯,氟,溴,C1-2烷基,CF3,CF2Cl,CHF2,CH2F或甲氧基亚甲基。
更优选R10是氢,氯,氟,C1-2烷基,CF3,CF2Cl,CHF2,CH2F或甲氧基亚甲基。
最优选R10是氢,氯,氟,甲基,CF3,CHF2或CH2F。
在本发明的一个方面中,R11是氢,C1-4烷基,苄基,甲酰基,C(O)CH3或C(O)OC(CH3)3;较优选氢或C1-2烷基。
优选R11是C1-4烷基,甲酰基,C(O)CH3或C(O)OC1-6烷基(任选被卤素,CN或C1-4烷氧基取代)。
较优选R11是C(O)OC1-4烷基。
在本发明的一个方面中,R12,R13,R14,R15,R16和R17各自独立地为氢,C1-2烷基或甲氧基。
优选R12和R13各自独立地为氢,卤素,C1-5烷基,C1-3烷氧基,CH2OH,CH(O),C3-6环烷基,CH2O-C(=O)CH3,CH2-C3-6环烷基或苄基;或R12和R13与它们相连接的碳原子一起形成基团C=O或3-5元碳环;或者R12和R13一起形成C1-5亚烷基或C3-6亚环烷基。
更优选R12和R13独立地是H,CH3,C2H5,n-C3H7,i-C3H7,n-C4H9,仲-C4H9,i-C4H9,CH(C2H5)2,CH2-环丙基或环戊基;或者R12和R13与它们相连接的碳原子一起形成3-元或5-元碳环。
优选R14是H或CH3。
优选R15是H或CH3。
优选R16是H或CH3。
优选R17是H或CH3。
优选R18是氢,氯,溴,甲基或者甲氧基。
较优选R18是氢,氯或者甲基。
最优选R18是氢。
优选R19是氢,氯,溴,甲基或甲氧基。
较优选R19是氢,氯或者甲基。
最优选R19是氢。
优选R20是氢,氯,溴,甲基或甲氧基。
较优选R20是氢,氯或甲基。
最优选R20是氢。
优选R21是氢,甲基,OC(CH3)3或CH3OCH2。
其中Y,R4,R5,R6和R7如上面式(I)化合物所定义的式(C)化合物:
可用作制备式(I)化合物的中间体。一些式(C)化合物是新的,而某一些却是已知的。
因此,在另一个方面中,本发明提供式(C)化合物,其中Y是O或S;以及R4,R5,R6和R7各自为C(O)OCH3;或者Y是N(R11)或(CR12R13)(CR14R15)m(CR16R17)n;R4,R5,R6,R7,R14,R15,R16,R17,m和n各自如上面式(I)化合物所定义;R11为苄基(其中的苯基任选被至多三个取代基取代,这些取代基各自独立地选自卤素、C1-4烷基、C1-4卤代烷基和C1-4烷氧基);以及R12和R13与它们所连接的碳原子一起形成3-5元碳环(任选地被至多三个甲基取代和包含1或2个各自独立选自O和N的杂原子)。
其中Y,R4,R5,R6和R7如上面式(I)化合物所定义的式(D)化合物:
可用作制备式(I)化合物的中间体。一些式(D)化合物是新的,而某一些却是已知的。
因此,在另一个方面中,本发明提供式(D)化合物,其中Y是O或S;以及R4,R5,R6和R7各自为C(O)OCH3;或者Y是N(R11)或(CR12R13)(CR14R15)m(CR16R17)n;R4,R5,R6,R7,R14,R15,R16,R17,m和n各自如上面式(I)化合物所定义;R11为苄基(其中的苯基任选被至多三个取代基取代,这些取代基各自独立地选自卤素、C1-4烷基、C1-4卤代烷基和C1-4烷氧基);以及R12和R13与它们所连接的碳原子一起形成3-5元碳环(任选地被至多三个甲基取代和包含1或2个各自独立选自O和N的杂原子)。
式(I)、(C)和(D)的化合物可以不同的几何异构体或旋光异构体的形式或以不同的互变异构体的形式存在。对于每种通式化合物,本发明都包括所有这些异构体和互变异构体及其所有比例的混合物以及同位素的形式如氘代化合物。
以下表1-29中的化合物用来说明本发明的化合物。
表1提供了94个式(C)化合物,其中Y,R4,R5,R6和R7如表1中定义。
表1
化合物编号 | R<sup>4</sup> | R<sup>5</sup> | R<sup>6</sup> | R<sup>7</sup> | Y | ||
1.01 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | O | ||
1.02 | CH<sub>3</sub> | H | H | H | O | ||
1.03 | H | CH<sub>3</sub> | H | H | O | ||
1.04 | CH<sub>3</sub> | CH<sub>3</sub> | C(O)CH<sub>3</sub> | H | O | ||
1.05 | CH<sub>3</sub> | CH<sub>3</sub> | H | C(O)CH<sub>3</sub> | O | ||
1.06 | CH<sub>3</sub> | C(O)CH<sub>3</sub> | H | H | O | ||
1.07 | C(O)CH<sub>3</sub> | CH<sub>3</sub> | H | H | O | ||
1.08 | C(O)OCH<sub>3</sub> | H | H | H | O | ||
1.09 | H | C(O)OCH<sub>3</sub> | H | H | O | ||
1.10 | H | H | H | H | O | ||
1.11 | CF<sub>3</sub> | CF<sub>3</sub> | H | H | O | ||
1.12 | OCH<sub>3</sub> | OCH<sub>3</sub> | H | H | O | ||
1.13 | H | H | CH<sub>3</sub> | CH<sub>3</sub> | O | ||
1.14 | C<sub>2</sub>H<sub>5</sub> | C<sub>2</sub>H<sub>5</sub> | H | H | O | ||
1.15 | CH3 | H | CH<sub>3</sub> | H | O | ||
1.16 | H | CH3 | H | CH<sub>3</sub> | O | ||
1.17 | CH<sub>3</sub> | H | CH<sub>3</sub> | H | CH<sub>2</sub> | ||
1.18 | H | CH<sub>3</sub> | H | CH<sub>3</sub> | CH<sub>2</sub> | ||
1.19 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>2</sub> | ||
1.20 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH(CH<sub>3</sub>) | ||
1.21 | H | H | H | H | CH(CH<sub>3</sub>) | ||
1.22 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | CH<sub>2</sub>CH<sub>2</sub> | ||
1.23 | H | H | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>2</sub> | ||
1.24 | H | H | H | H | CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub> | ||
1.25 | H | H | CH<sub>3</sub> | CH<sub>3</sub> | C(CH<sub>3</sub>)<sub>2</sub> | ||
1.26 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | C(CH<sub>3</sub>)<sub>2</sub> | ||
1.27 | CH<sub>3</sub> | H | CH<sub>3</sub> | H | C(CH<sub>3</sub>)<sub>2</sub> | ||
1.28 | H | CH<sub>3</sub> | H | CH<sub>3</sub> | C(CH<sub>3</sub>)<sub>2</sub> | ||
1.29 | H | H | H | H | C(CH<sub>3</sub>)<sub>2</sub> | ||
1.30 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | C(CH<sub>3</sub>)<sub>2</sub> | ||
1.31 | H | H | H | H | C(OCH<sub>3</sub>)<sub>2</sub> | ||
1.32 | H | H | H | H | S | ||
1.33 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | S | ||
1.34 | H | H | CH<sub>3</sub> | CH<sub>3</sub> | S | ||
1.35 | OCH<sub>3</sub> | OCH<sub>3</sub> | H | H | S | ||
1.36 | H | CH<sub>3</sub> | H | H | S | ||
1.37 | CH<sub>3</sub> | H | H | H | S | ||
1.38 | CH<sub>3</sub> | H | CH<sub>3</sub> | H | S | ||
1.39 | H | CH<sub>3</sub> | H | CH<sub>3</sub> | S | ||
1.40 | H | OCH<sub>3</sub> | H | H | S | ||
1.41 | OCH<sub>3</sub> | H | H | H | S |
1.42 | CH<sub>3</sub> | H | CH<sub>3</sub> | CH<sub>3</sub> | S |
1.43 | H | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | S |
1.44 | H | H | CH<sub>3</sub> | H | S |
1.45 | H | H | H | CH<sub>3</sub> | S |
1.46 | H | H | OCH<sub>3</sub> | H | S |
1.47 | H | H | H | OCH<sub>3</sub> | S |
1.48 | H | H | H | H | N(CH<sub>3</sub>) |
1.49 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | N(CH<sub>3</sub>) |
1.50 | H | H | H | H | N(C<sub>2</sub>H<sub>5</sub>) |
1.51 | H | H | H | H | NCH<sub>2</sub>Ph |
1.52 | H | H | H | H | NC(O)CH<sub>3</sub> |
1.53 | H | H | H | H | NC(O)OC(CH<sub>3</sub>)<sub>3</sub> |
1.54 | H | H | H | H | NH |
1.55 | H | H | H | H | NC(O)H |
1.56 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)H |
1.57 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NH |
1.58 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)CH<sub>3</sub> |
1.58 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)OC(CH<sub>3</sub>)<sub>3</sub> |
1.59 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NCH<sub>2</sub>Ph |
1.60 | Cl | Cl | H | H | O |
1.61 | H | H | H | H | NC(O)OCH<sub>3</sub> |
1.62 | H | H | H | H | NCH<sub>2</sub>-4-Cl-Ph |
1.63 | H | H | H | H | NCH<sub>2</sub>-4-CH<sub>3</sub>-Ph |
1.64 | H | H | H | H | NCH<sub>2</sub>-3-Cl-Ph |
1.65 | H | H | H | H | NCH<sub>2</sub>-3-CF<sub>3</sub>-Ph |
1.66 | H | H | H | H | NCH<sub>2</sub>-3-OCH<sub>3</sub>-Ph |
1.67 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)OCH<sub>3</sub> |
1.68 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)OC<sub>2</sub>H<sub>5</sub> |
1.69 | H | H | H | H | NC(O)OC<sub>2</sub>H<sub>5</sub> |
1.70 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)OCH<sub>2</sub>CH<sub>2</sub>Cl |
1.71 | H | H | H | H | NC(O)OCH<sub>2</sub>CH<sub>2</sub>Cl |
1.72 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)OC<sub>4</sub>H<sub>9</sub>-(n) |
1.73 | H | H | H | H | NC(O)OC<sub>4</sub>H<sub>9</sub>-(n) |
1.74 | CH<sub>3</sub> | CH<sub>3</sub> | H | H | NC(O)OC<sub>4</sub>H<sub>9</sub>-(i) |
1.75 | H | H | H | H | NC(O)OC<sub>4</sub>H<sub>9</sub>-(i) |
1.76 | H | H | H | H | CH(C<sub>3</sub>H<sub>7</sub>-(i))顺式或反式 |
1.77 | H | H | H | H | CH(C<sub>3</sub>H<sub>7</sub>-(n))顺式或反式 |
1.78 | H | H | H | H | CH(C<sub>4</sub>H<sub>9</sub>-(i))顺式或反式 |
1.79 | H | H | H | H | CH(C<sub>4</sub>H<sub>9</sub>-(n))顺式或反式 |
1.80 | H | H | H | H | C(C<sub>2</sub>H<sub>4</sub>-(c)) |
1.81 | H | H | H | H | C(C<sub>4</sub>H<sub>8</sub>-(c)) |
1.82 | H | H | H | H | CHCB(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>顺式或反式 |
1.83 | H | H | H | H | CHCH<sub>2</sub>(C<sub>3</sub>H<sub>5</sub>-(c)顺式或反式 |
1.84 | H | H | H | H | CH(C<sub>5</sub>H<sub>9</sub>-(c)顺式或反式 |
1.85 | H | H | H | H | CHCH<sub>2</sub>OAc顺式或反式 |
1.86 | H | H | H | H | CHCHO顺式或反式 |
1.87 | H | H | H | H | CHCH<sub>2</sub>OH顺式或反式 |
1.88 | H | H | H | H | CHCH<sub>2</sub>-C<sub>6</sub>H<sub>5</sub>顺式或反式 |
1.89 | H | H | H | H | C=O |
1.90 | H | H | H | H | C(O-C<sub>3</sub>H<sub>7</sub>-(n))<sub>2</sub> |
1.91 | H | H | H | H | C(O-C<sub>2</sub>H<sub>5</sub>-)<sub>2</sub> |
1.92 | H | H | H | H | CH(C<sub>2</sub>H<sub>5</sub>)顺式或反式 |
1.93 | H | H | H | H | CF<sub>2</sub> |
1.94 | H | H | H | H | CH(Cl)顺式或反式 |
表22提供了111个式(D)化合物,其中Y,R4,R5,R6和R7如表2中定义.
表2
表Z代表表3[当Z是3时],表4[当Z是4时],表5[当Z是5时],表6[当Z是6时],表7[当Z是7时],表8[当Z是8时],表9[当Z是9时],表10[当Z是10时],表11[当Z是11时],表12[当Z是12时],表13[当Z是13时],表14[当Z是14时],表15[当Z是15时],表16[当Z是16时],表17[当Z是17时],表18[当Z是18时],表19[当Z是19时],表20[当Z是20时],表21[当Z是21时],表22[当Z是22时],表23[当Z是23时],表24[当Z是24时],表25[当Z是25时],表26[当Z是26时],表27[当Z是27时],表28[当Z是28时]以及代表表29[当Z是29时].X为单键(-)或双键(=)
表Z
表3提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表3中定义。
表4提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表4中定义。
表5提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表5中定义。
表6提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表6中定义。
表7提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表7中定义。
表8提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表8中定义。
表9提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表9中定义。
表10提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表10中定义。
表11提供235个式(I)化合物,其中Het为
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表11中定义。
表12提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表12中定义。
表13提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表13中定义。
表14提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表14中定义。
表15提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表15中定义。
表16提供235个式(I)化合物,其中Het为
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表16中定义。
表17提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表17中定义。
表18提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表18中定义。
表19提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表19中定义。
表20提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表20中定义。
表21提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表21中定义。
表22提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表22中定义。
表23提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表23中定义。
表24提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表24中定义。
表25提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表25中定义。
表26提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表26中定义。
表27提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表27中定义。
表28提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表28中定义。
表29提供235个式(I)化合物,其中Het为:
R2和R3都为氢;以及X,Y,R1,R4,R5,R6和R7如表29中定义。
在本说明书中,温度以摄氏度表示,″NMR″表示核磁共振光谱;MS表示质谱;″%″指重量百分比,除非相应的浓度以其它单位表示;“顺式”是指相关取代基相对于稠合苯环呈顺式构型;而“反式”则指相关取代基相对于稠合苯环呈反式构型.
本说明书中使用下列缩写:
m.p.=熔点 b.p.=沸点
s=单峰 br=宽峰
d=二重峰 dd=双二重峰
t=三重峰 q=四重峰
m=多重峰 ppm=百万分之一
表30给出表1-29中化合物的精选熔点和精选NMR数据,所有这些NMR数据均以CDCl3为溶剂(另有说明除外;如果存在溶剂混合物,则以例如[CDCl3/d6-DMSO]的方式表示),(在所有情形下都没有打算列出全部特征数据)。
表30
化合物序号 | m.p(/℃) | NMR质子位移(/ppm)(CDCl<sub>3</sub>,另有说明除外) |
1.01 | 92-96 | 6.85和6.7(两个m,2×2H),6.47(t,1H),约5-3(宽峰,可与D<sub>2</sub>O交换,2H),2.07(s,3H),1.85(s,3H). |
1.10 | 121-124 | |
2.01 | 92-93 | 7.05(t,1H),6.7(t,2H),ca.5(brd,可与D<sub>2</sub>O交换,2H),2.0(s,3H),1.9(m,2H),1.8(s,3H),1.7(m,1H),1.5(m,1H). |
2.02 | 92-93 | |
2.03 | 112-114 | |
2.10 | 75-76 | |
2.16 | 63-64 | 6.90(dd(~t),J<sub>1</sub>=7.3Hz,J<sub>2</sub>=8.2Hz,1H),6.65(d,J=7.3Hz,1H),6.46(d,J=8.2Hz,1H),3.46(br.,可与D<sub>2</sub>O发生交换,2H),3.35(br.s,1H), |
3.31(br.s,1H),1.87(m,2H),1.70(m,1H),1.50(m,1H),1.18(m,1H). | ||
2.23 | 74-75 | 6.99(t,1H),6.63(d与三重峰重叠,2H),4.0-3.5(br,可与D<sub>2</sub>O交换,2H),3.08(br.s,1H),2.94(br.s,1H),1.76(m,4H),1.40(m,4H). |
2.53 | 139-140 | 6.97(t,1H),6.69(d,1H),6.51(d,1H),4.12(br s,1H),4.03(br s,1H),3.9-3.1(br,可与D<sub>2</sub>O发生交换,2H),2.06(s,3H)在2.12-2.05(2H)处与多重峰重叠,1.26-1.19(m,2H). |
2.55 | 粘性体 | 6.95(t,1H),6.68(d,1H),6.51(d,1H),4.26(d,1H),4.18(d,1H),3.56(br,可与D<sub>2</sub>O交换,2H),2.22(br d,2H),2.10(br,2H),1.22(m,2+2H),1.03(t,3H). |
2.58 | 89-90 | 6.94(dd(~t),J<sub>1</sub>=7.3Hz,J<sub>2</sub>=7.9Hz,1H),6.68(d,J=7.3Hz,1H),6.49(d,J=7.9Hz,1H),5.11(br,1H),5.04(br,1H),3.5-3.0(br,2H,可与D<sub>2</sub>O交换),2.07(m,2H),1.40(s,9H),1.30(m,2H). |
2.59 | oil | 6.91(dd(~t),J<sub>1</sub>=7.3Hz,J<sub>2</sub>=7.9Hz,1H),6.66(d,J=7.3Hz,1H),6.44(d,J=7.9Hz,1H),4.55(d,J=~1Hz,1H)),4.48(d,J=~1Hz,1H),4.0-3.0(br,可与D<sub>2</sub>O交换,H),2.02(m,2H),1.25(m,2H). |
2.61 | 176-177 | 顺-反式混合物:8.00 & 7.98(s,1H),6.96(t,1H),6.71 & 6.67(d,1H),6.50(d,1H),5.55 & 5.48(brs,1H),5.09 & 5.02(br s,1H),4.0-3.0(br,可与D<sub>2</sub>O交换,2H),2.06(m,2H),1.37-1.47(m,2H). |
2.64 | 110-111 | 6.96(t,1H),6.58(d,1H),6.47(d,1H),3.79(br,2H),2.29(s,3H),2.01(s,6H),1.98(m,2H),1.54(m,1H),1.32(m,1H). |
2.65 | 94-95 | 6.96(t,1H),6.59(d,1H),6.47(d,1H),ca 3.7(br,可与D<sub>2</sub>O交换,2H),2.18(s,3H),1.95(m,2H),1.93(s,3H),1.49(m,1H),1.37(s,9H),1.25(m,1H). |
2.67 | 104-105 | 6.96(t,1H),6.69(d),1H),6.50(d,1H),5.20(br,1H),5.13(br,1H),3.64(s,3H),2.10(m,2H),1.33(m,2H). |
2.73 | 114-115 | 6.97(t.1H),6.60(d,1H),3.80(br,2H),3.55(s,3H),2.20(s,3H),1.97(m,2H),1.95(s,3H),1.50(m,1H),1.29(m,1H). |
2.75 | 粘性体 | 6.95(t,1H),6.70(d,1H),6.50(d,1H),5.20(br,1H),5.13(br,1H),4.07(q,2H),3.33(br,2H),2.10(m,2H),1.32(m,2H),1.22(t,3H). |
2.77 | 粘性体 | 6.97(t,1H),6.72(d,1H),6.53(d,1H),5.24(m,1H),5.16(m,1H),4.27(br,2H),3.64(t,2H),3.18(br,2H),2.12(m,2H),1.35(m,2H). |
2.79 | 粘性体 | 6.96(t,1H),6.71(d,1H),6.52(d,1H),5.20(br, |
1H),5.12(br,1H),4.02(t,2H),3.19(br,2H),2.09(m,2H),1.57(m,2H),1.34(m,4H),0.91(t,3H). | ||
2.81 | 粘性体 | 6.96(t,1H),6.71(d,1H),6.52(d,1H),5.21(br,1H),5.13(br,1H),3.80(d,2H),3.25(br,2H),2.10(m,2H),1.88(m,1H),1.33(m,2H),0.89(d,6H). |
2.82顺式∶反式=86∶14 | 蜡状固体 | 顺式组分的数据:6.91(t,1H),6.65(d,1H),6.49(d,1H),3.5(br,2H),3.20(br,1H),3.15(br,1H),1.92(m,2H),1.54(d,1H),1.19(m,2H),1.03(m,1H),0.81(d,6H). |
2.82顺式∶反式=35∶65 | 油体 | 顺-反式混合物的数据:6.94-6.87(m,1H),6.65(m,1H),6.52和6.46(d,1H),3.52(br,2H),3.21,3.16和3.14(三个m,2H),1.96-1.84(m,2H),1.55和1.49(两个d,1H),1.43和1.03(m,1H),1.22-1.12(m,2H),0.92和0.82(两个m,6H). |
2.84顺式∶反式=12∶88 | 粘性体 | 反式组分的数据:6.89(t,1H),6.64(d,1H),6.48(d,1H),ca4.0-3.75(br,2H),3.03(br,1H),3.00(br,1H),1.96-1.87(m,3H),1.58(m,1H),1.12(m,3H),0.91(d,6H). |
2.84顺式∶反式=82∶18 | 粘性体 | 顺式组分的数据:6.92(t,1H),6.64(d,1H),6.50(t,1H),3.53(br,2H),3.08(m,1H),3.03(m,1H),2.02(t,1H),1.90(m,2H),1.46(m,1H),1.16(m,2H),0.92(m,2H),0.81(d,6H). |
2.86 | 粘性体 | 6.92(t,1H),6.66(d,1H),6.49(d,1H),3.52(br,2H),2.62(m,1H),2.59(m,1H),2.07(m,2H),1.27(m,2H),0.54(m,2H),0.45(m,2H). |
2.88顺式∶反式=46∶54 | 粘性体 | 顺式-反-(1∶1)混合物的数据:6.91和6.89(两个t,1H),6.63(d,1H),6.48和6.46(两个d,1H),3.52(br,2H),3.20,3.16和3.13(三个m,2H),1.93-1.86(m,2H),1.78和1.72(两个d,1H),1.45(m,1H),1.37-1.11(m,6H),0.85和0.76(t两个m,6H). |
2.89顺式∶反式=84∶16 | 粘性体 | 顺式组分的数据:6.90(t,1H),6.64(d,1H),6.48(d,1H),3.51(br,2H),3.19(br s,1H),3.13(br s,1H),2.08(t,1H),1.94(m,2H),1.20(m,2H),0.97(m,1H),0.90(m,1H),0.57(1H),0.35(m,2H),0.13(m,2H). |
2.90顺式∶反式= | 粘性体 | 顺式组分的数据:6.91(t,1H),6.64(d,1H),6.49(d,1H),3.52(br,2H),3.12(br s,1H),3.08(br s,1H),1.91(m,2H), |
74∶26 | 1.8-1.0(m,12H). | |
2.94顺式∶反式=74∶26 | 粘性体 | 顺式组分的数据:7.28(m,2H),7.17(m,1H),7.04(d,2H),6.99(t,1H),6.72(d,1H),6.57(d,1H),3.6(br,2H),3.06(m,2H),2.35(m,2H),2.20(m,1H),1.89(m,2H),1.20(m,2H). |
2.106 | 81-82 | 6.90(t,1H),6.67(d,1H),6.47(d,1H),3.77(m,1H),3.73(m,1H),3.56(br,2H),1.88(m,2H),1.63(s,6H),1.26(m,2H). |
2.107 | 粘性体 | 6.89(t,1H),6.65(d,1H),6.46(d,1H),3.76(m,1H),3.72(m,1H),3.56(br,2H),2.12-1.90(m,4H),1.88(m,2H),1.26(m,2H),0.94(m,6H). |
3.001 | 150-154 | |
3.002 | 163-165 | |
3.023 | 129-133[旋转异构体混合物] | 7.62(br),7.44(d,J~1Hz),7.32(d,J~1Hz),7.2(m),7.0(m);这些信号归于6个质子.其它信号在3.7(s,3H),1.84(s,3H),1.82(s,3H),2.0-1.5(m,4H). |
3.024 | 172-176 | 7.5-7.0(m)和6.8(br.s)共5H,5.7-4.8(两组AB体系,2H),4.1(m,1H),3.35和3.3(两个s,共3H),1.85,1.75,1.70(三个s,共6H),2.0-1.4(m,4H). |
3.027 | 无定形固体 | 7.60br.s,1H),7.34(br.s,1H),7.22-7.07(m,3H),7.01(br.s,1H),5.27(d,1H),3.71(s,3H),2.19(m,1H),1.91(m,1H),1.83(s,3H),1.71(m,1H),1.49(m,1H). |
3.028 | 无定形固体 | 7.68(br.,1H),7.53(d,1H),7.37(br.s,1H),7.17(t,1H),7.00(br.s,1H),6.96(d,1H),5.39(d,1H),3.70(s,3H),2.25(m,1H),1.83(s,3H),1.83-1.66(m,2H),1.48(m,1H). |
3.035 | 无定形固体 | |
3.048 | 无定形固体 | 7.85(d,1H),7.72(br.,1H),7.48(br.s,1H),7.60(t,1H),7.0(br s,1H),9.95(d,1H),3.73(s,3H),3.43(br.s,1H),3.37(br.s,1H),1.9(m,2H),1.75(m,1H),1.55(m,1H),1.2(m,2H). |
3.052 | 136-138 | |
3.076 | 154-155 | |
3.152 | 无定形固体 | 7.71(br,1H),7.69(d,1H),7.39(br s,1H),7.18(t,1H),7.06(d,1H),6.99(br s,1H),4.30(br s,1H),4.18(br s,1H),3.71(s,3H),2.20(m,2H),2.12(s,3H),1.42-1.21(m,2H).. |
3.162 | 无定形固体 | 7.71(d,1H),7.68(br,1H),7.39(br s,1H),7.17(t,1H),7.05(d,1H),7.01(br s,1H),4.40(br s,1H),4.28(br s,1H),3.72(s,3H),2.24(br,2H),2.17(br,2H),1.37(t,1H),1.25(t,1H),1.04(t,3H). |
3.168 | 无定形固体 | 7.71(br,2H),7.37(br.s,1H),7.14(t,1H),7.05(d,1H),7.00(br.s,1H),5.18(br,1H),5.11(br,1H),3.71(s,3H),2.14(m,2H),1.50(m,1H),1.38(s,9H),1.30(m,1H). |
3.172 | 无定形固体 | 顺-反式混合物:8.00(s,1H),7.72(br,1H),7.58 &7..31(d,1H),7.38 & 7.36(br s,1H),7.16(t,1H),7.11 & 7.09(d,1H),7.01(br s,1H),5.61 & 5.53(br s,1H),5.19 & 5.09(br s,1H),3.71(s,3H),2.11(m,2H),1.75-1.61(m,1H),1.50-1.39(m,1H). |
3.176 | 231-232 | 7.48(br,1H),7.22(t,1H),7.09(br,1H),7.06(d,1H),6.96(br s,1H),5.91(br s,1H),3.69(s,3H),2.87(m,1H),2.22(m,2H),1.97(s,3H),ca 1.9(m,1H),1.66(s,3H),1.49(s,3H). |
3.183 | 无定形固体 | 7.71(br,1H),7.3(br d,1H),7.38(br s,1H),7.16(t,1H),7.06(d,1H),7.02(br s,1H),5.25(m,1H),5.18(m,1H),3.72(s,3H),3.62(s,3H),2.16(m,2H),1.55(m,1H),1.35(m,1H). |
3.189 | 无定形物 | 7.65(br,1H),7.31(d,1H),7.30(br s,1H),7.17(t,1H),7.02(d,1H),7.01(br s,1H),3.72(s,3H),3.54(s,3H),2.08(s,3H),1.99(s,3H),1.94(m,2H),1.76(m,1H),1.33(m,1H). |
3.191 | 无定形物 | 7.72(br,1H),7.64(d,1H),7.38(br s,1H),7.16(t,1H),7.07(d,1H),7.02(br s,1H),5.26(m,1H),5.20(m,1H),4.05(q,1H),3.72(s,3H),2.15(m,2H),1.55(m,1H),1.35(m,1H),1.20(t,3H). |
3.193 | 无定形物 | 7.72(br,1H),7.60(d,1H),7.38(br s,1H),7.16(t,1H),7.08(d,1H),7.02(br s,1H),5.29(m,1H),5.22(m,1H),4.24(m,2H),3.73(s,3H),3.61(t,2H),2.18(m,2H),1.59(m,1H),1.37(m,1H). |
3.195 | 无定形物 | 7.72(br,1H),7.65(d,1H),7.38(br s,1H),7.15(t,1H),7.06(d,1H),7.01(br s,1H),5.26(m,1H),5.18(m,1H),4.00(t,2H),3.72(s,3H),2.15(m,2H),1.55(m,3H),1.34(m,3H),0.89(t,3H). |
3.197 | 无定形物 | 7.72(br,1H),7.66(d,1H),7.38(br s,1H),7.16(t,1H),7.07(d,1H),7.01(br s,1H),5.27(m,1H),5.19(m,1H),3.78(dd,2H),3.73(s,3H),2.16(m,2H),1.87(m,1H),1.55(m,1H),1.35(m,1H). |
3.202顺式∶反式=90∶10 | 121-125 | 顺式组分的数据:7.91(d,1H),7.72(br,1H),7.38(br s,1H),7.10(t,1H),7.00(br s,1H),6.97(d,1H),3.72(s,3H),3.32(m,1H),3.22(m,1H),1.95(m,2H),1.58(d,1H),1.20(m,2H),0.90(m,1H),0.81(m,6H). |
3.202顺式∶反式= | 无定形物 | 顺-反式混合物的数据:7.91和7.85(两个d,1H),7.72(br,1H),7.37(m,1H),7.12-7.05(m,1H),6.99(m,1H),6.98-6.94(m, |
34∶66 | 1H),3.71(s,3H),3.32,3.25.3.22和3.19(四个m,2H),1.96-1.88(m,2H),1.58和1.51(两个d,1H),1.44和0.98(两个m,1H),1.26-1.12(m,2H).0.91和0.81(两个m,6H). | |
3.208顺式∶反式=10∶90 | 130-131 | 反式组分的数据:7.85(d,1H),7.70(br,1H),7.38(br s,1H),7.08(t,1H),6.99(br s,1H),6.95(d,1H),3.71(s,3H),3.12(m,1H),3.06(m,1H),2.0-1.9(m,3H),1.6-1.5(m,2H),1.22-1.11(m,3H),0.92(d,6H). |
3.208顺式∶反式=85∶15 | 无定形物 | 顺式组分的数据:7.92(d,1H),7.70(br,1H),7.38(br s,1H),7.11(t,1H),6.99(br s,1H),6.96(d,1H),3.71(s,1H),3.19(m,1H),3.10(m,1H),2.06(t,1H),1,97(m,2H),1.44(m,1H),1.27-1.11(m,2H),0.90(m,2H),0.79(d,6H). |
3.210 | 155-157 | 7.84(d,1H),7.68(br,1H),7.37(br s,1H),7.11(t,1H),6.98(d,1H),3.71(s,3H),2.69(m,1H),2.65(m,1H),2.09(m,2H),1.33(m,1H),1.32(m,1H),0.49(m,4H). |
3.212 | 无定形物 | 顺-反式混合物的数据:7.92和7.85(两个d,1H),7.72(br,1H),7.38(m,1H),7.13-7.06(m,1H),7.00(m,1H),6.96(m,1H),3.72(s,3H),3.32,3.25,3.22和3.19(四个m,2H),1.92(m,2H),1.82和1.72(两个d,1H),1.43(m,1H),1.35-1.05(m,6H),0.84和0.73(两个t,6H). |
3.213顺式∶反式=95∶05 | 115-117 | 顺式组分的数据:7.90(d,1H),7.71br,1H),7.38(br s,1H),7.10(t,1H),6.99(br s,1H),6.96(d,1H),3.71(s,3H),3.31(m,1H),3.18(m,1H),2.12(t,1H),1.98(m,2H),1.28-1.14(m,3H),1.0-0.78(m,2H),0.55(m,1H),0.34(m,2H),0.16(m,2H). |
3.214顺式∶反式=74∶26 | 无定形物 | 顺式组分的数据:7.93(d,1H),7.72(br,1H),7.38(br s,1H),7.11(t,1H),7.00(br s,1H),6.95(d,1H),3.71(s,3H),3.24(m,1H),3.14(m,1H),1.94(m,2H),1.8-0.88(m,12H). |
3.218顺式∶反式=92∶08 | 143-146 | 顺式组分的数据7.96(d,1H),7.70(br,1H),7.37(br s,1H),7.30-6.95(m,8H),3.72(s,3H),3.18(m,1H),3.12(m,1H),2.37-2.07(m,3H),1.93(m,2H),1.25(m,2H). |
3.230 | 无定形物 | 7.82(d,1H),7.75(br,1H),7.39(br s,1H),7.08(t,1H),7.01(br s,1H),6.98(d,1H),3.83(m,1H),3.78(m,1H),3.72(s,3H),1.90(m,2H),1.61(s,6H),1.35-1.21(m,2H). |
3.231 | 无定形物 | 7.81(d,1H),7.75(br,1H),7.38(br s,1H),7.08(t,1H),7.00(br s,1H),6.97(d,1H),3.85(m,1H),3.77(m,1H),3.72(s,3H),2.1-1.9(m,6H),1.38-1.21(m,2H),0.93(m,6H). |
4.048 | 粘性油 | 7.87(br,1H),7.80(d,1H),7.27(m,1H),7.07(t,1H),6.96(d,1H),6.95(t,J=56Hz,1H),6.87(m,1H),3.68(s,3H),3.47(br.s,1H),3.36(br.s,1H),1.90(m,2H),1.74(m,1H),1.50(m,1H),1.16-1.24(m,2H). |
8.048 | 粘性油 | 7.83(br d,1H),7.76(br,1H),7.55(br s,1H),7.12(br s,1H),7.09(t,1H),6.98(d,1H),5.19(s,2H),3.45(br s,1H),3.37(br s,1H),3.32(s,3H),1.92(m,2H),1.77(m,1H),1.52(m,1H),1.22(m,2H). |
11.048 | 粘性油 | 7.90(br d,1H),7.73(br,1H),7.09(t,1H),7.04(brs,1H),6.98(d,1H),3.68(s,3H),3.43(br s,1H),3.38(be s,1H),1.90(m,2H),1.77(m,1H),1.52(m,1H),1.24(m,2H). |
14.002 | 148-151 | |
14.023 | 162-166 | |
14.024 | 148-150 | |
14.027 | 182-184 | |
14.028 | 无定形固体 | 8.04(s,1H),7.66(br.,1H),7.45(d,1H),7.19(t,1H),6.99(d,1H),5.37(d,1H),3.98(s,3H),2.25(m,1H),1.83(s,3H),1.83-1.65(m,2H),1.47(m,1H). |
14.035 | 144-146 | |
14.048 | 无定形固体 | 8.05(s,1H),7.8(d,1H),7.7(br.s,1H),7.6(t,1H),7.0(d,1H),3.98(s,3H),3.43(br.s,1H),3.39(br.s,1H),1.9(m,2H),1.75(m,1H),1.54(m,1H),1.2(m,2H). |
14.052 | 121-122 | |
14.076 | 127-130 | |
14.152 | 无定形固体 | 8.09(s,1H),7.75(br,1H),7.62(d,1H),7.19(t,1H),7.09(d,1H),4.30(br,1H),4.20(br s,1H),3.98(s,3H),2.2-2.1(m,2H),2.11(br s,3H),1.4-1.2(m,2H). |
14.162 | 142-147 | 8.09(s,1H),7.74(br,1H),7.63(d,1H),7.19(t,1H),7.08(d,1H),4.40(br s,1H),4.31(br s,1H),4.00(s,3H),2.26(br,2H),2.15(br,2H),1.38(t,1H),1.26(t,1H),1.05(t,3H). |
14.168 | 无定形固体 | 8.04(s,1H),7.72(br,1H),7.60(d,1H),7.16(t,1H),7.08(d,1H),5.15(br,1H),5.12(br,1H),3.99(s,3H),2.13(m,2H),1.49(m,1H),1.38(s,9H),1.32(m,1H). |
14.172 | 123-124 | 顺-反式混合物;DMS0:9.97(s,1H),8.45 & 8.43(br,1H),7.87(br s,1H),7.21 & 7.12(d,1H),7.06(m,2H),5.42 & 5.29(br,1H),5.24(m,1H),3.88(s,3H),1.87(m,2H),1.45 & 1.39(m,1H),1.21(m,1H). |
14.176 | 232-233 | 8.12(br,1H),7.23(t,1H),7.09-7.05(m,2H),5.93(s,1H),3.97(s,3H),2.90(m,1H),2.32-2.20(m,2H),1.97(s,3H),1.90(m,1H),1.67(s,3H),1.48(s,3H). |
14.178 | 148-150 | 7.98(br,1H),7.67(br,1H),7.30(d,1H),7.19(t,1H),7.04(d,1H),3.99(s,3H),2.05(s,3H),1.97(s,3H)overlapped by a m(2.00-1.89,2H),1.68(m,1H),1.35(s,9H),1.31(m,1H). |
14.183 | 无定形固体 | 8.05(s,1H),7.74(br,1H),7.53(d,1H),7.17(t,1H),7.10(d,1H),5.23(m,1H),5.19(m,1H),4.00(s,3H),3.62(s,3H),2.14(m,2H),1.55(m,1H),1.35(1H). |
14.189 | 无定形物 | 7.99(br s,1H),7.68(br,1H),7.28(d,1H),7.19(t,1H),7.06(d,1H),3.99(s,3H),3.54(s,3H),2.06(s,3H),2.02-1.91(m,2H),1.72(m,1H),1.35(m,1H). |
14.191 | 无定形物 | 8.05(s,1H),7.75(br,1H),7.55(d,1H),7.17(t,1H),7.11(d,1H),5.23(m,1H),5.20(m,1H),4.05(q,2H),4.00(s,3H),2.15(m,2H),1.54(m,1H),1.35(m,1H),1.20(t,3H). |
14.193 | 无定形物 | 8.05(s,1H),7.72(br,1H),7.52(d,1H),7.18(t,1H),7.12(d,1H),5.27(m,1H),5.23(m,1H),4.24(m,2H),4.00(s,3H),3.61(t,2H),2.19(m,2H),1.58(m,1H),1.38(m,1H). |
14.195 | 无定形物 | 8.05(s,1H),7.75(br,1H),7.55(d,1H),7.17(t,1H),7.10(d,1H),5.23(m,1H),5.20(m,1H),4.00(s,3H),4.00(t,2H),2.15(m,2H),1.55(m,3H),1.35(m,3H),0.89(t,3H). |
14.197 | 无定形物 | 8.05(s,1H),7.77(br,1H),7.55(d,1H),5.24(m,1H),5.20(m,1H),3.99(s,3H),3.78(dd,2H),2.17(m,2H),1.86(m,1H),1.55(m,1H),1.36(m,1H),0.87(d,6H). |
14.202顺式∶反式=90∶10 | 145-150 | 顺式组分的数据:8.06(s,1H),7.84(d,1H),7.70(br,1H),7.12(t,1H),7.01(d,1H),3.99(s,3H),3.29(m,1H),3.23(m,1H),1.96(m,2H),1.60(d,1H),1.20(m,2H),0.96(m,1H),0.80(m,6H). |
14.202顺式∶反式=28∶72 | 无定形物 | 顺-反式混合物的数据:8.05(br,1H),7.83和7.78(两个d,1H),7.70(br,1H),7.14-7.07(m,1H),7.0<sub>1-6</sub>.98(m,1H),3.99(s,3H),3.30和3.21(两个m,2H),1.97-1.90(m,2H), |
1.60和1.51(两个d,1H),1.43和0.98(两个m,1H),1.26-1.12(m,2H),0.91和0.82(两个m,6H). | ||
14.208顺式∶反式=10∶90 | 132-133 | 反式组分的数据:8.04(8,1H),7.77(d,1H),7.68(br,1H),7.09(t,1H),6.99(d,1H),3.99(s,3H),3.08(m,2H),2.0-1.91(m,3H),1.63-1.55(m,2H),1.22-1.10(m,3H),0.91(d,6H). |
14.208顺式∶反式=85∶15 | 130-133 | 顺式组分的数据:8.05(br s,1H),7.84(d,1H),7.68(br,1H),7.12(t,1H),7.00(d,1H),3.99(s,3H),3.16(m,1H),3.12(m,1H),2.10(t,1H),1.97(m,2H),1.44(m,1H),1.22(m,2H),0.91(m,2H),0.80(d,6H). |
14.210 | 151-153 | 8.04(br,1H),7.76(d,1H),7.65(br,1H),7.12(t,1H),7.02(d,1H),3.98(s,3H),2.66(m,2H),2.10(m,2H),1.29(m,2H),0.49(m,4H). |
14.212顺式∶反式=48∶52 | 无定形物 | 顺-反式混合物的数据:8.05(br,1H),7.84和7.78(两个d,1H),7.69(br,1H),7.14-7.08(m,1H),6.99(m,1H),3.99(s,3H),3.29,3.24和3.20(三个m,2H),1.95(m,2H),1.83和1.74(两个d,1H),1.44(m,1H),1.35-1.11(m,6H),0.85和0.74(两个t,6H). |
14.213顺式∶反式=90∶10 | 无定形物 | 顺式组分的数据:8.05(s,1H),7.83(d,1H),7.70(br,1H),7.12(t,1H),7.00(d,1H),3.99(s,3H),3.29(m,1H),3.20(m,1H),2.14(t,1H),2.00(m,2H),1.16(m,2H),1.02-0.78(m,2H),0.55(m,1H),0.35(m,2H),-016(m,2H). |
14.214顺式∶反式=74∶26 | 无定形物 | 顺式组分的数据:8.05(s,1H),7.85(d,1H),7.69(br,1H),7.12(t,1H),7.00(d,1H),3.99(s,3H),3.21(m,1H),3.16(m,1H),1.96(m,2H),1.80-0.0.9(m,12H). |
14.218顺式∶反式=78∶22 | 无定形物 | 顺式组分的数据:8.05(s,1H),7.89(d,1H),7.68(br,1H),7.30-6.92(m,7H),4.00(s,3H),3.14(m,2H),2.60-2.10(m,3H),1.94(m,2H),1.29-1.15(m,2H). |
14.230 | 183-187 | 8.06(br s,1H),7.74(d,与br重叠,2H),7.09(t,1H),7.02(d,1H),4.00(s,3H),3.83(m,1H),3.80(m,1H),1.92(m,2H),1.62(s,6H),1.35-1.11(m,2H). |
14.231 | 无定形物 | 8.05(br s,1H),7.73(d,与br重叠,2H),7.09(t,1H),7.01(d,1H),3.99(s,3H),3.82(m,1H),3.79(m,1H),2.1-1.95(m,4H),1.92(m,2H),1.38-1.23(m,2H),0.93(m,6H). |
15.013 | 139-140 | |
15.023 | 无定形固体 | 7.99(s,1H),7.93(br.,1H),7.22-7.16(m,2H), |
7.03(d,1H),6.88(t,J<sub>HF</sub>=54Hz,1H),3.93(s,3H),1.90(m,2H),1.82(s,3H),1.80(s,3H),1.55(m,2H). | ||
15.027 | 168-169 | |
15.028 | 145-147 | |
15.035 | 136-139 | |
15.048 | 132-134 | 8.11(br.,1H),8.03(s,1H),7.83(d,1H),7.08(t,1H),6.98(d,1H),6.88(t,J<sub>HF</sub>=54Hz,1H),3.93(s,3H),3.49(br.s,1H),3.37(br.s,1H),1.91(m,2H),1.74(m,1H),1.51(m,1H),1.22(m,2H). |
15.049 | 107-108 | |
15.050 | 115-117 | |
15.052 | 118-122 | |
15.076 | 148-150 | |
15.086 | 无定形固体 | 8.00(s.1H),7.97(br,1H),7.64(d,1H),7.15(t,1H),6.94(d,1H),6.86(t,J<sub>HF</sub>=54.3Hz,1H),3.92(s,3H),3.25(br.s,1H),3.03(br.s,1H),1.94(d,2H),1.8-1.6(m,8H). |
15.152 | 141-147(分解) | 8.07(br,1H),8.05(s,1H),7.76(d,1H),7.18(t,1H),7.06(d,1H),6.87(t,J<sub>HF</sub>=54.2Hz,1H),4.26(brs,1H),4.12(br s,1H),3.95(s,3H),2.16(m,2H),2.07(s,3H),1.37-1.19(m,2H). |
15.162 | 无定形固体 | 8.17(br,1H),8.09(s,1H),7.72(d,1H),7.20(t,1H),7.07(d,1H),6.90(t,J<sub>HF</sub>=54.2Hz,1H),4.56(brs,1H),4.38(br s,1H),3.96(s,3H),2.32(br,2H),2.23(br,2H),1.42(t,1H),1.30(t,1H),1.08(t,3H). |
15.168 | 粘性物 | 8.12(br,1H),8.04(s,1H),7.72(d,1H),7.15(t,1H),7.06(d,1H),6.89(t,J<sub>HF</sub>=54Hz,1H),5.22(br,1H),5.11(br,1H),3.05(s,3H),2.12(m,2H),1.53-1.24(m,2H),1.37(s,9H). |
15.172 | 无定形固体 | 顺-反式混合物:8.22 & 8.16(br,1H),8.06(br s,1H),8.00(s,1H),7.58 & 7.42(d,1H),7.17(t,1H),7.10(d,1H),6.93 & 6.91(t,J<sub>HF</sub>=54Hz,1H),5.64& 5.53(br s,1H),5.21 & 5.10(br s,1H),3.95(s,3H),2.10(m,2H),1.63(m,1H),1.43(m,1H). |
15.176 | 223-224 | |
15.183 | 无定形固体 | 8.13(br,1H),8.05(s,1H),7.65(d,1H),7.17(t,1H),7.08(d,1H),6.91(t,J<sub>HF</sub>=54Hz,1H),5.29(brs,1H),5.19(br s,1H),3.96(s,3H),3.62(s,3H),2.15(m,2H).1.53(m,1H),1.35(m,1H). |
15.189 | 无定形物 | 7.95(br,2H),7.25(d,1H),7.19(t,1H),7.06(d,1H),6.94(t,J<sub>HF</sub>=54Hz,1H),3.94(s,3H),3.54(s,3H),2.07(s,3H),1.99(s,3H),1.98(m,2H),1.72(m,1H),1.35(m,1H). |
15.191 | 无定形物 | 8.15(br,1H),8.05(s,1H),7.66(d,1H),7.17(t, |
1H),7.08(d,1H),(6.91(t,J<sub>HF</sub>=54Hz,1H),5.30(m,1H),5.20(m,1H),4.05(q,2H),3.95(s,3H),2.14(m,2H),1.52(m,1H),1.35(m,1H),1.20(t,3H). | ||
15.193 | 无定形物 | 8.12(br,1H),8.05(s,1H),7.64(d,1H),7.18(t,1H),7.09(d,1H),6.91(t,J<sub>HF</sub>=54Hz,1H),5.32(m,1H),5.23(m,1H),4.24(m,2H),3.96(s,3H),3.61(t,2H),2.18(m,2H),1.55(m,1H),1.37(m,1H). |
15.195 | 无定形物 | 8.13(br,1H),8.05(s,1H),7.67(d,1H),7.16(t,1H),7.07(d,1H),6.91(t,J<sub>HF</sub>=54Hz,1H),5.29(M,1H),5.18(m,1H),4.01(t,2H),3.95(s,3H),2.16(m,2H),1.53(m,3H),1.33(m,3H),0.88(t,3H). |
15.197 | 无定形物 | 8.14(br,1H),8.05(s,1H),7.69(d,1H),7.15(t,1H),7.08(d,1H),6.91(t,J<sub>HF</sub>=54Hz,1H),5.30(m,1H),5.20(m,1H),3.96(s,3H),3.79(dd,2H),2.16(m,2H),1.86(m,1H),1.53(m,1H),1.35(m,1H),0.87(d,6H). |
15.202顺式∶反式=90∶10 | 110-112 | 顺式组分的数据:8.10(br,1H),8.05(br s,1H),7.92(d,1H),7.11(t,1H),6.98(d,1H),6.87(t,J<sub>HF</sub>=54Hz,1H),3.95(s,3H),3.37(m,1H),3.22(m,1H),1.95(m,2H),1.58(d,1H),1.19(m,2H),0.98(m,1H),0.81(m,6H). |
15.202顺式∶反式=35∶65 | 无定形物 | 顺-反式混合物的数据:8.09(br,1H),8.04(br,1H),7.91和7.84(两个d,1H),7.13-7.06(m,1H),7.02-6.96(m,1H),6.88和6.87(两个t,J<sub>HF</sub>=54Hz,1H),3.95(s,3H),3.38,3.30,3.23和3.20(四个m,2H),1.96-1.89(m,2H),1.58和1.50(两个d,1H),1.44和0.97(两个m,1H),1.20-1.12(m,2H),0.91和0.82(两个m,6H). |
15.208顺式∶反式=12∶88 | 粘性体 | 反式组分的数据:8.07(br,1H),8.03(br s,1H),7.84(d,1H),7.08(t,1H),6.97(d,1H),6.88(t,J<sub>HF</sub>=54Hz,1H),3.94(s,3H),3.17(m,1H),3.07(m,1H),1.93(m,3H),1.59(m,1H),1.28-1.12(m,4H),0.91(d,6H). |
15.208顺式∶反式=93∶7 | 117-119 | 顺式组分的数据:8.08(br,1H),8.04(br s,1H),7.91(d,1H),7.12(t,1H),6.98(d,1H),6.87(t,J<sub>HF</sub>=54Hz,1H),3.94(s,3H),3.25(m,1H),3.11(m,1H),2.07(t,1H),1.96(m,2H),1.45(m,1H),1.19(m,2H),0.89(m,2H),0.80(d,6H). |
15.210 | 158-160 | 8.04(br,2H),7.84(d,1H),7.12(t,1H),7.00(d,1H),6.86(t,J<sub>HF</sub>=54Hz,1H),3.94(s,3H),2.74(m, |
1H),2.66(m,1H),2.11(m,2H),1.33(m,1H),1.26(m,1H),0.48(m,4H). | ||
15.212顺式∶反式=46∶54 | 无定形物 | 顺-反式混合物的数据:8.09(br,1H),8.04(br s,1H),7.92和7.85(两个d,1H),7.13-7.07(m,1H),6.98(m,1H),6.88和6.87(两个t,J<sub>HF</sub>=54Hz,1H),3.95(s,3H),3.37,3.31,3.23和3.20(四个m,2H),1.95(m,2H),1.82和1.73(两个d,1H),1.46(m,1H),1.37-1.10(m,6H),0.85和0.74(两个t,6H). |
15.213顺式∶反式=90∶10 | 131-135 | 顺式组分的数据:8.08(br,1H),8.04(s,1H),7.90(d,1H),7.11(t,1H),6.98(d,1H),6.87(t,J<sub>HF</sub>=54Hz,1H),3.95(s,3H),3.37(m,1H),3.19(m,1H),2.13(t,1H),1.98(m,2H),1.24(m,2H),1.1-0,78(m,2H),0.55(m,1H),0.35(m,2H),-0.16(m,2H). |
15.214顺式∶反式=74∶26 | 无定形物 | 顺式组分的数据:8.09(br,1H),8.04(s,1H),7.92(d,1H),7.12(t,1H),6.98(d,1H),6.87(t,J<sub>HF</sub>=54Hz,1H),3.95(s,3H),3.29(m,1H),3.15(m,1H),1.95(m,2H),1.80-0.90(m,12H). |
15.218顺式∶反式=74∶26 | 无定形物 | 顺式组分的数据:8.08(br,1H),8.05(s,1H),7.96(d,1H),7.3-6.9(m,7H),6.85(t,J<sub>HF</sub>=54Hz,1H),3.96(s,3H),3.23(m,1H),3.13(m,1H),2.4-2.07(m,3H),1.95(m,2H),1.3-1.1(m,2H). |
15.230 | 无定形物 | 8.15(br,1H),8.05(br s,1H),7.83(d,1H),7.09(t,1H),7.00(d,1H),6.90(t,J<sub>HF</sub>=54Hz,1H),3.94(s,3H),3.92(m,1H),3.80(m,1H),1.91(m,2H),1.61(s,6H),1.35-1.22(m,2H). |
15.231 | 无定形物 | 8.13(br,1H),8.04(br s,1H),7.82(d,1H),7.09(t,1H),6.99(d,1H),6.90(t,J<sub>HF</sub>=54Hz,1H),3.94(s,3H),3.91(m,1H),3.78(m,1H),2.1-1.95(m,4H),1.91(m,2H),1.39-1.21(m,2H),0.93(m,6H). |
16.048 | 无定形固体 | 8.16(brd d,1H),7.98(brd s,1H),7.85(d,1H),7.10(t,1H),6.99(d,1H),5.72(AB-信号,1H),5.59(AB-信号,1H),3.94(s,3H),3.47(br s,1H),3.38(brd s,1H),1.91(m,2H),1.76(m,1H),1.52(m,1H),1.23(m,2H). |
16.076 | 粘性体 | 8.13(brd,1H),7.95(brd s,1H),7.70(d,1H),7.19(t,1H),7.02(d,1H),5.64(d,J<sub>HF</sub>=48.7Hz,2H),3.92(s,3H),3.15(br s,1H),3.02(brd s,1H),1.77(d,4H),1.39(d,4H). |
21.023 | 161-165 | |
20.048 | 132-133 | |
21.048 | 136-138 |
22.048 | 粘性油 | 7.78(br.,1H),7.68(d,1H),7.12-7.03(m,2H),3.39(br.s,2H),2.76(s,3H),1.92(m,2H),1.76(m,1H),1.53(m,1H),1.20(m,2H). |
23.048 | 粘性油 | 7.60(br d,1H),7.38(br,1H),7.10(t,1H),7.03(d,1H),3.39(m,2H),2.76(s,3H),1.93(m,2H),1.78(m,1H),1.55(m,1H),1.23(m,2H). |
24.048 | 粘性油 | 7.85(br.,1H),7.72(d,1H),7.12-7.02(m,2H),3.43(br.s,1H),3.40(br.s,1H),2.63(s,3H),1.93(m,2H),1.78(m,1H),1.55(m,1H),1.23(m,2H). |
29.048 | 158-160 | |
29.052 | 151-152 | |
29.202顺式∶反式=90∶10 | 146-147 | 顺式组分的数据:8.53(m,1H),8.28(d,1H),8.17(br,1H),7.82(d,1H),7.42(d,1H),7.15(t,1H),7.05(d,1H),3.37(m,1H),3.26(m,1H),1.98(m,2H),1.62(d,1H),1.24(m,2H),0.97(m,1H),0.82(d,6H). |
29.202顺式∶反式=34∶66 | 无定形物 | 顺-反式混合物的数据:8.53(m,1H),8.27(m,1H),8.15(br,1H),7.82-7.77(m,1H),7.42(m,1H),7.17-7.10(m,1H),7.06-7.02(m,1H),3.38,3.30,3.26和3.23(四个m,2H),1.99-1.90(m,2H),1.62和1.54(两个d,1H),1.46和0.99(两个m,1H),1.30-1.10(m,2H),0.91和0.83(两个m,6H). |
29.208顺式∶反式=82∶18 | 无定形物 | |
29.213顺式∶反式=90∶10 | 无定形物 | 顺式组分的数据:8.52(m,1H),8.29(d,1H),8.20(br,1H),7.81(d,1H),7.43(d,1H),7.15(t,1H),7.04(d,1H),3.36(m,1H),3.23(m,1H),2.16(t,1H),2.00(m,2H),1.29(m,3H),0.98(m,1H),0.86(m,1H),0.57(m,1H),0.35(m,2H),-0.15(m,2H). |
29.208顺式∶反式=15∶85 | 无定形物 | 反式组分的数据:8.52(m,1H),8.28(d,1H),8.16(br,1H),7.78(d,1H),7.41(d,1H),7.12(t,1H),7.02(d,1H),3.17(m,1H),3.10(m,1H),1.96(m,3H),1.59(m,1H),1.26-1.1(m 4H),0.91(d,6H). |
29.212顺式∶反式=47∶53 | 无定形物 | 顺-反式混合物的数据:8.52(m,1H),8.26(m,1H),8.15(br,1H),7.83和7.78(两个d,1H),7.42(m,1H),7.17-7.10(m,1H),7.04(m,1H),3.37.3.30,3.27和3.23(四个m,2H),1.95(m,2H),1.86和1.77(两个d,1H),1.45(m,1H),1.38-1.10(m,6H),0.85和0.74(两个t,6H). |
29.214 | 无定形物 | 顺式组分的数据: |
顺式∶反式=74∶26 | 8.52(m,1H),8.29(d,1H),8.16(br,1H),7.83(d,1H),7.43(d,1H),7.16(t,1H),7.05(d,1H),3.30(m,1H),3.19(m,1H),1.98(m,2H),1.80-0.8(m,12H). | |
29.218顺式∶反式=88∶12 | 无定形物 | |
29.230 | 无定形物 | 8.53(m,1H),8.29(d,1H),8.17(br,1H),7.71(d,1H),7.43(m,1H),7.13(t,1H),7.06(d,1H),3.91(m,1H),3.82(m,1H),1.93(m,2H),1.63(s,6H),1.40-1.23(m,2H). |
29.231 | 无定形物 | 8.53(m,1H),8.26(d,1H),8.16(br,1H),7.73(d,1H),7.43(m,1H),7.13(t,1H),7.05(d,1H),3.91(m,1H),3.81(m,1H),2.1-1.89(m,6H),1.40-1.23(m,2H),0.93(m,6H). |
式(I)化合物可以按照下述反应图式制备。
式(I)化合物的制备
图式1
如J.Wang等人所述(Synlett,2001,1485),在-10℃至室温下,优选在无水THF中,通过式(II)化合物[其中Het如上式(I)化合物所定义,且R’为C1-5烷基]与式(III)苯胺[其中R2,R3,R4,R5,R6,R7,X和Y如上面式(I)化合物所定义]在NaN(TMS)2存在下反应,可以合成得到式(I)化合物[其中R1为氢;而Het,R2,R3,R4,R5,R6,R7,X和Y则如上面式(I)化合物所定义]。
图式2
另一方面,式(I)化合物[其中R1为氢;而Het,R2,R3,R4,R5,R6,R7,X和Y则如上面式(I)化合物所定义]也可以制备如下:在活化剂[如BOP-C1]和两当量的碱[如三乙胺]存在下,使式(II’)化合物[其中Het如上面式(I)化合物所定义]与式(III)的苯胺[[其中R2,R3,R4,R5,R6,R7,X和Y如上面式(I)化合物所定义]反应;或者是在一当量的碱[如NEt3,NaHCO3,KHCO3,Na2CO3或K2CO3]存在下,使式(II”)化合物[其中Het如上面式(I)化合物所定义;且Q为Cl,F或Br]与式(III)苯胺[其中R2,R3,R4,R5,R6,R7,X和Y如上面式(I)化合物所定义]在溶剂[如二氯甲烷、乙酸乙酯或DMF]中反应,反应温度优选为-10℃至30℃,并且其中的式(II”)化合物系用卤化剂如亚硫酰氯、草酰氯、光气、SF4、DAST、Deoxofluor或亚硫酰溴处理式(II’)化合物获得。
图式3
进而,在碱[例如NaH,NEt3,NaHCO3或K2CO3]存在下,于-10至30℃,在适当溶剂[譬如乙酸乙酯]或在两相混合物[譬如二氯甲烷/水混合物]中,使式(I)化合物[其中R1为氢;且Het,R2-R7,X和Y如上面式(I)化合物所定义]与物质Z-R1反应[其中R1如式(I)所定义,只是不为氢;而Z优选为Cl,Br或I;或者Z为能使Z-R1成为酸酐的基团:即当R1为COR*时,Z为OCOR*]。
起始原料
杂环酸与酯[即式(II’)或(II)化合物]普遍是文献中已知的,或者可按照已知方法合成。
式(C)或(D)的邻位取代的氨基苯并降冰片二烯(包括类似物在内)(图 式4)的制备可以包括使就地生成的苯炔[例如以式(A)的6-硝基邻氨基苯甲酸为原料按L.Paquette等描述的方法生成(J.Amer.Chem.Soc.99,3734(1977))或以其它适当的前体为原料生成(参见H.Pellissier等Tetrahedron,59,701(2003))]与5-7元环状1,4-二烯按照以下文献方法或其类似方法进行狄尔斯-阿德耳(Diels-Alder)加成,得到式(B)的硝基苯并降冰片二烯:L.Paquette等,J.Amer.Chem.Soc.99,3734(1977),D.Gravel等,Can.J.Chem.69,1193(1991),J.R.Malpass等,Tetrahedron,48,861(1992),D.E.Lewis等,Synthetic Communications,23,993(1993),R.N.Warrener等,Molecules,6,353(2001),R.N.Warrener等,Molecules,6,194(2001)或I.Fleming等,J.Chem.Soc.,PerkinTrans.1,2645(1998)。用于该步骤的适当溶剂包括乙酸乙酯、二氯甲烷、丙酮、THF和二甲氧基乙烷。反应温度为室温至100℃,优选40-80℃。
随后选择性还原式(B)化合物中的硝基生成式(C)氨基苯并降冰片二烯的反应需要温和条件[例如金属锌/氯化铵,或铝汞合金]。这两种方法都是在质子溶剂如乙醇、水或其混合物中进行。另一方面,在高压(~10巴)和高温(~100℃)下,在甲苯-水中用改性的5%Pt/C催化剂催化氢化还原式(B)化合物,也可以获得式(C)化合物。在标准条件下(例如5%Pd/C或5%Ra/Ni或5%Rh/C),在溶剂[例如甲醇、乙醇THF或乙酸乙酯]中进行催化还原则能够同时还原硝基和双键,从而得到式(D)的苯并降冰片烯。优选的反应条件为常温常压。
图式4
式(B)、(C)和(D)化合物中的某些在文献中已有记载[例如,参见L.A.Paquette等,J.Amer.Chem.Soc.99,3734(1977);D.Gravel等,Canad.J.Chem.69,1193(1991);T.Nishiyama等,Rikagaku-hen,28,37(2000);H.Plieninger等,Chem.Ber.109,2121(1976);和A.J.Kirby等,J.Chem.Soc.,Perkin Trans.2,1997,1081]。
新的式(C)或(D)起始原料可按照图式4的类似方法或按照上面所引用的文献合成。
令人惊奇的是,现已发现式(I)新化合物在实践中具有非常有用的活性谱,用于保护植物抵抗由真菌以及细菌和病毒所致的病害。
式(I)化合物可以作为活性成分在农业方面以及相关领域中用于防治植物病虫害。这些新化合物的突出之处在于它们在低施用剂量下具有优越的活性,良好的植物耐受性和环境安全性。它们具有非常有用的治愈、预防和内吸性质,可用于保护多种栽培植物。式(I)化合物可用于抑制或杀灭出现在各种有用作物的植株或植株部分(果实、花、叶、茎、块茎、根)上的有害生物,同时亦能保护以后生长的植株部分,例如使其免受植物病原微生物的侵害。
也可以使用式(I)化合物作为拌种剂用于处理植物繁殖材料,尤其是种子(果实、块茎、谷粒)和植物扦插物(例如稻),以防御真菌侵染和土壤中存在的植物病原真菌。
此外,本发明的化合物还可以用于防治例如工业材料(包括木材和与木材有关的工业产品)的保护、食物储存、卫生保健管理等相关领域中的真菌。
例如,式(I)化合物对下列种类的植物病原真菌有效:半知菌类(例如葡萄孢属、梨孢属(Pyricularia)、长孺孢属、镰孢属、壳针孢属、尾孢属和链格孢属)和担子菌纲(如丝核菌属、驼孢锈菌属、柄锈菌属)。另外,它们还对子囊菌纲(例如黑星菌属和白粉菌属、叉丝单囊壳属、链核盘菌属、钩丝壳属)以及卵菌纲(如疫霉属、腐霉属、单轴霉属)有效。已经观察到对白粉菌(白粉菌属)具有显著活性。此外,式I新化合物对植物病原细菌和病毒(例如对黄单胞菌属、假单胞菌属、解淀粉欧文氏菌以及烟草花叶病毒)也都有效。
在本发明范围内,欲保护的靶标作物通常包括以下种属植物:禾谷类(小麦、大麦、黑麦、燕麦、水稻、玉米、高粱及有关种类);甜菜(糖用甜菜和饲用甜菜);梨果、核果和浆果(苹果、梨、李、桃、杏、樱桃、草莓、树莓和黑莓);豆科植物(菜豆类、扁豆类、豌豆类、大豆类);油科植物(油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆、落花生);瓜类植物(南瓜、黄瓜、甜瓜);纤维类植物(棉花、亚麻、***、黄麻);桔果(橙、柠檬、葡萄、柑橘);蔬菜类(菠菜、莴苣、芦笋、圆白菜、胡萝卜、洋葱、番茄、马铃薯、红辣椒);樟科(鳄梨、肉桂、樟脑)或诸如烟草、坚果、咖啡、茄、甘蔗、茶、胡椒、葡萄、忽布、香蕉和天然橡胶植物之类植物,以及观赏植物。
式I化合物可以以其原有形式、或者(优选)与加工配制领域常用的辅助剂一起使用。为此,它们可以用已知方法很方便地加工成乳油、可涂布性糊剂、可直接喷雾或可稀释的溶液剂、稀乳剂、可湿性粉剂、可溶性粉剂、撒粉剂、颗粒剂、以及微囊剂(如在聚合物中的微囊剂)。与选择组合物类型的情形一样,根据预定目的和主要条件来选择施用方法,例如喷雾、弥雾、喷粉、撒粉、涂敷或浇泼。所述组合物也可以包含其它助剂如稳定剂、消泡剂、粘度调节剂、粘合剂或增稠剂以及肥料、微量营养元素供体或能获得特定效果的其它制剂。
合适的载体和辅助剂可以是固态或液态的,并且是加工配制领域有用的物质,例如天然或再生矿物质、溶剂、分散剂、湿润剂、粘着剂、增稠剂、粘合剂或肥料。这些载体在例如WO 97/33890中有记载。
式(I)化合物通常以组合物形式使用,并且可以与其它化合物同时或依次施于欲处理的作物区或植物上。这些其它化合物可以是例如肥料或微量营养元素供体或能影响植物生长的其它制剂。它们也可以是选择性的除草剂以及杀虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或数种这些制剂的混合物,如果需要,还含有其它载体、表面活性剂或配制加工领域惯用的促施用助剂。
式I化合物可以与其它杀真菌剂一起混用,结果在一些情形下能产生意想不到的协同活性。特别优选的混用组分为唑类,例如戊环唑、BAY 14120、双苯***醇、糠菌唑、环唑醇、噁醚唑、烯唑醇、氧唑菌、腈苯唑、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、酰胺唑、环戊唑醇、环戊唑菌、腈菌唑、稻瘟酯、戊菌唑、啶斑肟、丙氯灵、丙环唑、simeconazole、戊唑醇、氟醚唑、***酮、唑菌醇、氟菌唑、戊叉唑菌;嘧啶基甲醇类,例如嘧啶醇、异嘧菌醇、氟苯嘧啶醇;2-氨基嘧啶类,例如磺嘧菌灵、甲菌定、乙菌定;吗啉类,例如吗菌灵、苯锈啶、丁苯吗啉、螺噁茂胺、克啉菌;苯氨基嘧啶类,例如环丙嘧啶、嘧菌胺、二甲嘧菌胺;吡咯类,例如拌种咯、氟噁菌;苯基酰胺类,例如苯霜灵、呋氨丙灵、甲霜灵、R-甲霜灵、甲呋酰胺、噁霜灵;苯并咪唑类,例如苯菌灵、多菌灵、双乙氧咪唑威、麦穗宁、涕必灵;二酰胺类,例如乙菌利、菌核利、异丙定、甲菌利、杀菌利、烯菌酮;酰胺类,例如萎锈灵、呋菌胺、氟酰胺、丙氧灭锈胺、氧化萎锈灵、溴氟唑菌;胍类,例如双胍盐、多果定、iminoctadine;strobilurines,例如腈嘧菌酯、亚胺菌、叉氨苯酰胺、SSF-129、trifloxystrobin、picoxystrobin、BAS 500F(建议名pyraclostrobin)、BAS 520;二硫代氨基甲酸类,例如福美铁、代森锰锌、代森锰、代森联、甲基代森锌、福美双、代森锌、福美锌;N-卤素甲硫基邻苯二甲酰亚胺类,例如敌菌丹、克菌丹、抑菌灵、氟菌安、灭菌丹、对甲抑菌灵;铜化合物,例如波尔多液、氢氧化铜、王铜、硫酸铜、氧化亚铜、锰铜混剂、喹啉铜;硝基苯酚衍生物,例如敌螨普、异丙消;有机磷衍生物,例如克瘟散、异稻瘟净、稻瘟灵、双氟苯磷、定菌磷、甲基立枯磷;其他,例如acibenzolar-S-methy1、敌菌灵、benthiavalicarb、灭瘟素、灭螨猛、地茂散、百菌清、cyflufenamid、清菌脲、二氯萘醌、哒菌清、氯硝胺、乙霉威、烯酰吗啉、SYP-L190(建议名flumorph)、二噻农、ethaboxam、氯唑灵、噁唑酮菌、fenamidone、fenoxanil、三苯锡基、嘧菌腙、氟啶胺、磺菌胺、fenhexamid、藻菌磷、土菌消、iprovalicarb、IKF-916(cyazofamid)、春雷霉素、磺菌威、metrafenone、nicobifen、戊菌隆、四氯苯酞、多氧霉素、噻菌灵、百维灵、咯喹酮、喹氧灵、五氯硝基苯、硫、唑菌嗪、三环唑、嗪氨灵、有效霉素、zoxamide(RH7281)。
施用式(I)化合物或包含至少一种所述化合物的农药组合物的优选方法是叶面施用。施用次数和施用量取决于相应病原引起的侵染危险性。但式I化合物也可以通过用液体制剂喷湿植物所在场所,经土壤通过根部进入植物体内(内吸),或者通过将固体形式(如颗粒形式)的化合物施于土壤(土施)。在水稻作物中,这类颗粒剂可以施用到灌水稻田中。式I化合物也可以通过用杀菌剂的液体制剂浸渍种子或块茎、或用固体制剂包涂它们而施药于种子(包衣)。
制剂[即包含式I化合物和如果需要还含有固体或液体助剂的组合物]使用已知方法制备,典型的制法是将化合物与增量剂如溶剂、固体载体以及任选的表面活性化合物(表面活性剂)紧密混合和/或研磨。
农药制剂中通常含有0.1-99%重量、优选0.1-95%重量的式I化合物,99.9-1%重量、优选99.8-5%重量的固体或液体助剂,以及0-25%重量、优选0.1-25%重量的表面活性剂。
有利的施用量通常为每公顷(ha)5g-2kg活性成分(a.i.),优选10g-1kg a.i./ha,最优选为20g-600g a.i./ha。当用作浸种剂时,适宜剂量为每千克种子10mg-1g活性物质。
虽然市售产品优选配制成浓缩物形式,但最终用者通常要使用稀释制剂。
上述本发明用下列非限制性实施例详细说明。
实施例1
本实施例说明化合物2.01的制备。
室温,在RaNi(1.1g)存在下氢化1,4-二甲基-5-硝基-1,4-二氢-1,4-环氧萘(5.49g;25.27mmol)(参见T.Nishiyama等,Rikagaku-hen,28,37-43(2000))的THF(55ml)溶液。18小时后氢气吸收量为2.23升(97%)。滤除催化剂,然后蒸发滤液,再吸收到***中,用碳酸氢钠水溶液洗涤,干燥(Na2SO4)得到4.60g油状粗产物。用己烷和微量***研制,得到总重4.51g(94%)微红色结晶产物。
实施例2
本实施例说明化合物1.01的制备。
于47℃,向1,4-二甲基-5-硝基-1,4-二氢-1,4-环氧萘(4.22g;19.43mmol)(参见实施例1)的乙醇(60ml)溶液中加入氯化铵(2.08g)的水(5.2ml)溶液。在剧烈搅拌下,于5分钟内分批加入锌粉(9.10g;0.14mol)。将悬浮液加热回流5.5小时,随后通过HyfloTM过滤,得到黄色清亮滤液。蒸发得到4.57g粗产物,为粘性油状物。硅胶柱层析(乙酸乙酯-己烷,1∶4)得到1.24g(34%)需要产物,为褐色结晶。
实施例3
本实施例说明化合物2.16的制备。
在5%Pd/C(0.5g)存在下,室温氢化5-硝基苯并降冰片二烯(L.A.Paquette等,J.Amer.Chem.Soc.99,3734(1977))(2.52g;13.46mmol)的甲醇(100ml)溶液。11分钟后吸收1.14升氢气(95%)。过滤溶液与催化剂分开,蒸发得到纯净产物(1.86g;87%),为黄色油状物,室温放置发生固化(m.p.63-64℃)。
实施例4
本实施例说明化合物3.023的制备。
在初始冰冷却下,使1-甲基-4-三氟甲基-1H-吡咯-3-羧酸(1.02g;5.3mmol)和催化量的DMF(3滴)在二氯甲烷(20ml)中的溶液与草酰氯(0.805g;1.2eq)反应2小时。随后在15分钟内,于冷却下(3-7℃),将反应混合物逐滴加到由1,8-二甲基-11-氧杂-三环[6.2.1.0*2,7*]十一碳-2,4,6-三烯-3-基胺(化合物2.01;参见上面的制备)(1.0g;5.284mmol)和三乙胺(1.07g;10.57mmol)在20ml二氯甲烷中形成的溶液内,接着室温搅拌31/4小时。反应混合物然后倒入冰水中,用二氯甲烷萃取,得到2.26g粗产物。利用乙酸乙酯-己烷(1∶1)进行硅胶纯化,进而用***-己烷研制,得到一固体物(1.14g,59%),为异构体混合物。
实施例5
本实施例说明化合物3.024的制备。
在10-15℃下,使NaH(0.107g;60%油分散物,~2.7mmol)的DMF(5ml)悬浮液与1-甲基-4-三氟甲基-1H-吡咯-3-羧酸(1,8-二甲基-11-氧杂-三环[6.2.1.0*2,7*]十一碳-2,4,6-三烯-3-基)-酰胺(化合物3.023;参见上面的制备)(0.65g;1.784mmol)的5ml DMF溶液反应30分钟。加入3-溴-1-丙炔(0.276g;2.32mmol),进一步在室温下反应过夜。在用冰水和乙酸乙酯进行含水处理并经硅胶纯化后,得到0.36g(50%)需要产物,为异构体混合物。
式(I)化合物的制剂实施例
制备式I化合物的制剂如乳油、溶液、颗粒剂、粉剂和可湿性粉剂的加工方法见WO 97/33890中所述。
生物实施例: 杀真菌作用
实施例B-1:抗小麦叶锈病(Puccinia recondita)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理1周龄“Arina”品种小麦植株。施药1天后,向试验植株喷洒孢子悬浮液(1×105夏孢子/ml)对小麦植株进行接种。在20℃和95%相对湿度(r.h.)下培育植株2天后,再在温室中于20℃和60%r.h.下培育8天。接种10天后评价病害发生情况。
下列化合物基本上能完全防止真菌的侵染(0-5%侵染率):化合物3.048,14.048,29.048,15.048,20.048,3.028,22.048,21.048,15.023,15.027,15.028,3.035,14.035,15.035,15.052,14.210,15.210,14.202和15.202。
实施例B-2:抗苹果梢白粉病(Podosphaera leucotricha)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理5周龄“McIntosh”品种苹果幼苗。施药1天后,通过在试验植枝上方振摇侵染了苹果白粉病的枝条对苹果植株进行接种。在14/10小时(明/暗)光照条件下于22℃和60%相对湿度(r.h.)下培育12天后,评价病害发生情况。
化合物3.048,14,048,15.048,22.048,14.210,15.210,14.202,15.202和15.023均显示强大效力(<20%侵染率)。
实施例B-3:抗苹果黑星病(Venturia inaequalis)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理4周龄“McIntosh”品种苹果幼苗。施药1天后,向试验植株喷洒孢子悬浮液(4×105分生孢子/ml)对苹果植株进行接种。在21℃和95%r.h.下培育植株4天后,再在温室中于21℃和60%r.h.下培育4天。经进一步在21℃和95%r.h.下培育4天后,评价病害发生情况。
化合物3.048,14.048,14.210,15.210,14.202,15.202和15.048均显示强大效力(<20%侵染率)。
实施例B-4:抗大麦白粉病(Erysiphe graminis)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理1周龄“Regina”品种大麦植株。施药1天后,通过在试验植株上方振摇侵染了白粉病的植株对大麦植株进行接种。在20℃/18℃(昼/夜)和60%r.h.于温室培育6天后,评价病害发生情况。
化合物3.023,14.023,3.048,14.048,15.048,3.027,3.028,15.023,14.210,15.210,14.202,15.202和15.027均显示强大效力(<20%侵染率)。
实施例B-5:抗葡萄灰霉病(Botrytis cinerea)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理5周龄“Gutedel”品种葡萄幼苗。施药2天后,向试验植株喷洒孢子悬浮液(1×106分生孢子/ml)对葡萄植株进行接种。在温室中于21℃和95%r.h.下培育4天后,评价病害发生情况。
化合物14.048,15.048,3.028,14.210,15.210,14.202,15.202和15.027在本试验中均显示良好活性(<50%病害发生率)。
实施例B-6:抗番茄灰霉病(Botrytis cinerea)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理4周龄“Roter Gnom”品种番茄植株。施药2天后,向试验植株喷洒孢子悬浮液(1×105分生孢子/ml)对番茄植株进行接种。在温室中于20℃和95%r.h.下培育4天后,评价病害发生情况。
化合物3.048,3.052,14.052,15.048,14.210,15.210,14.202,15.202和15.023均显示良好效力(<50%病害发生率)。
实施例B-7:抗小麦叶枯病(Septorian odorum)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理1周龄“Arina”品种小麦植株。施药1天后,向试验植株喷洒孢子悬浮液(5×105分生孢子/ml)对小麦植株进行接种。在20℃和95%r.h.下培育植株1天后,再在温室中于20℃和60%r.h.下培育10天。接种11天后评价病害发生情况。
化合物3.002,3.048,14.048,14.210,15.210,14.202,15.202和15.048在本试验中均显示良好活性(<50%病害发生率)。
实施例B-8:抗大麦网斑病(Helminthosporium teres)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理1周龄“Regina”品种大麦植株。施药两天后,向试验植株喷洒孢子悬浮液(3×104分生孢子/ml)对大麦植株进行接种。在温室中于20℃和95%r.h.下培育4天后,评价病害发生情况。
化合物3.023,14.023,3.048,14.048,15.048,3.027,15.023,15.027,14.210,15.210,14.202,15.202和15.028在本试验中均显示良好活性(<20%病害发生率)。
实施例B-9:抗番茄早疫病(Alternaria solani)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理4周龄“Roter Gnom”品种番茄植株。施药两天后,向试验植株喷洒孢子悬浮液(2×105分生孢子/ml)对番茄植株进行接种。在生长室中于20℃和95%r.h.下培育3天后,评价病害发生情况。
化合物3.023,14.023,3.048,14.048,14.210,15.210,14.202,15.202和15.048在本试验中均显示良好活性(<20%病害发生率)。
实施例B-10:抗葡萄白粉病(Uncinula necator)作用
在喷雾室内,用试验化合物的加工制剂(0.02%活性成分)处理5周龄“Gutedel”品种葡萄幼苗。施药1天后,通过在试验植株上方摇动侵染葡萄白粉病的植株对葡萄植株进行接种。按照14/10小时(明/暗)光照方案于26℃和60%r.h.培育7天后,评价病害发生情况。
化合物14.048,15.048,14.028和15.023在本试验中均显示良好活性(<20%病害发生率)。
实施例B-11:抗大麦白粉病(Erysiphe graminis)的内吸作用(袋囊试
验)(Pouch试验)
将试验化合物的制剂(0.002%活性成分)施加到预先配备滤纸的袋囊内。施药后在滤纸的上断层内播种大麦种子(品种:Express)。然后将制备好的袋囊在23℃/18℃(昼/夜)和80%r.h.下培育。播种一周后,通过在试验植株上方振摇侵染白粉病的植株对大麦植株进行接种。6天培育期后评价病害发生率。采用每种试验化合物的效力作为内吸活性的指标。
化合物14.024,3.002,3.048,29.048,3.027,22.048,21.048,15.023,15.027,15.028和15.035在本试验中均显示良好活性(<50%病害发生率)。
实施例B-12:抗小麦梢首腐病(Fusarium culmorum)作用(袋囊试验)
混合大刀镰孢的分生孢子悬浮液(7×105分生孢子/ml)与试验化合物的制剂(0.002%活性成分)。将该混合物施加到预先配备滤纸的袋囊内。施药后在滤纸的上断层内播种小麦种子(品种:Orestis)。然后将制备好的袋囊在约10-18℃和100%r.h.下培育11天,日光照期为14小时。根据根部棕色损伤的情形评估病害发生程度,从而对化合物的活性作出评价。
化合物14.024,15.048,20.048,14.027,24.048和3.035在本试验中均显示良好活性(<50%病害发生率)。
实施例B-13:抗小麦全蚀病(Gaeumannomyces graminis)作用(袋囊试
验)
将规定量的G.graminis菌丝体与水混合。向菌丝体混悬液中加入试验化合物的制剂(0.002%活性成分)。将所得混合物施加到预先配备滤纸的袋囊内。施药后在滤纸的上断层内播种小麦种子(品种:Orestis)。然后将制备好的袋囊在18℃/16℃(昼/夜)和80%r.h.下培育14天,日光照期为14小时。通过估计根部变成棕色的程度对化合物的活性作出评价。
化合物15.048,20.048,21.048,15.028和15.052在本试验中均显示良好活性(<50%病害发生率)。
实施例B-14:抗小麦叶锈病(Puccinia recondita)作用(袋囊试验)
将试验化合物的制剂(0.002%活性成分)施加到预先配备滤纸的袋囊内。施药后,在滤纸的上断层内播种小麦种子(品种:Arina)。然后将制备好的袋囊在23℃/18℃(昼/夜)和80%r.h.下培育。播种一周后,通过对试验植株喷雾孢子悬浮液(1×105夏孢子)对小麦植株进行接种。在23℃和95%r.h.下培育1天后,将植株进一步在20℃/18℃(昼/夜)和80%r.h.下保持9天。接种后10天评价病害发生率。采用每种试验化合物的效力作为内吸活性的指标。
化合物14.024,3.002,14.002,15.048,20.048,3.027,22.048,15.023,15.027,15.028,3.035,14.035和15.035在本试验中均显示良好活性(<50%病害发生率)。
实施例B-15:抗稻纹枯病(Rhizoctonia solani)作用(袋囊试验)
将规定量的R.solani(茄属丝核菌)菌丝体与水混合。向菌丝体混悬液中加入试验化合物的制剂(0.002%活性成分)。将所得混合物施加到预先配备滤纸的袋囊内。施药后在滤纸的上断层内播种稻种子(品种:Koshihikari)。然后将制备好的袋囊在23℃/21℃(昼/夜)和100%r.h.下培育10天,日光照期为14小时。根据根部棕色损伤的情形估计病害发生程度,对化合物的活性作出评价。
化合物3.048,14.048,29.048,3.052,29.052,14.052,15.048,20.048,3.027,14.028,22.048,21.048,4.048,15.023,3.035,14.035和15.035在本试验中均显示良好活性(<50%病害发生率)。
实施例B-16:抗小麦颍枯病(Septoria nodorum)作用(袋囊试验)
将试验化合物的制剂(0.002%活性成分)施加到预先配备滤纸的袋囊内。施药后,在滤纸的上断层内播种小麦种子(品种:Arina)。然后将制备好的袋囊在23℃/18℃(昼/夜)和80%r.h.下培育。播种一周后,通过对试验植株喷雾孢子悬浮液(5×105分生孢子)对小麦植株进行接种。在23℃和95%r.h.下培育1天后,将植株进一步在20℃/18℃(昼/夜)和80%r.h.下保持9天。接种后8天评价病害发生率。采用每种试验化合物的效力作为内吸活性的指标。
化合物3.048,29.048,15.048,14.027,15.023和15.027在本试验中均显示良好活性(<50%病害发生率)。
实施例B-17:抗小麦叶枯病(Septoria tritici)作用
在喷雾室内,用试验化合物的制剂(0.02%活性成分)处理2周龄“Riband”品种小麦植株。施药1天后,向试验植株喷雾孢子悬浮液(10×105分生孢子/ml)对小麦植株进行接种。在23℃和95%r.h.下培育植株1天后,再在温室中于23℃和60%r.h.下培育16天。接种后18天评价病害发生情况。
化合物14.202和14.210在本试验中均显示良好活性(<20%病害发生率)。
Claims (13)
1.式(I)化合物:
其中Het是吡咯基或吡唑基,其被基团R8、R9和R10取代;
X是单键;
Y是(CR12R13)(CR14R15)m(CR16R17)n;
m是0或1;
n是0或1;
R1是氢;
R2和R3各自独立地是氢、卤素、C1-4烷基、C1-4烷氧基或C1-4卤代烷氧基;
R4、R5、R6和R7是各自独立地是氢、卤素、C1-4烷基、C1-4卤代烷基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、C1-4卤代烷硫基、羟甲基、C1-4烷氧基甲基、C(O)CH3或C(O)OCH3;
R8、R9和R10各自独立地是氢、卤素、氰基、硝基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基(C1-4)亚烷基或C1-4卤代烷氧基(C1-4)亚烷基,条件是R8、R9和R10中至少一个不是氢;
R12和R13各自独立地是氢、卤素、C1-5烷基、C1-3烷氧基、CH2OH、CH(O)、C3-6环烷基、CH2O-C(=O)CH3、CH3-C3-6环烷基或苄基;
或R12和R13与它们相连接的碳原子一起形成基团C=O或3-5元碳环;
或R12和R13一起形成C1-5亚烷基或C3-6亚环烷基;以及
R14、R15、R16和R17各自独立地是氢或CH3。
2.权利要求1所述的式(I)化合物,其中R8、R9和R10各自独立地是氢、氯、氟、甲基、CF3、CHF2或CH2F,条件是R8、R9和R10中至少一个不是氢。
3.权利要求1所述的式(I)化合物,其中n是0,m是0。
4.权利要求3所述的式(I)化合物,其中R12和R13各自独立地是氢、C1-4烷基或C1-4烷氧基。
5.权利要求1所述的式(I)化合物,其中R2是氢、卤素或C1-4烷基。
6.权利要求1所述的式(I)化合物,其中R3是氢或甲基。
7.权利要求1所述的式(I)化合物,其中Het是吡唑基。
9.权利要求1所述的式(I)化合物,其中Het是吡咯基。
10.一种用于防治微生物和预防植物受微生物侵袭和侵染的组合物,其中活性成分是权利要求1所述的式(I)化合物,此外还包括适当载体。
11.一种防治或预防植物病原微生物侵染栽培植物的方法,该方法包括叶面或土壤施用权利要求1所述的式(I)化合物。
12.一种防治或预防植物病原微生物侵染栽培水稻植物的方法,该方法包括施用权利要求1所述的式(I)化合物到灌水稻田中。
13.一种防治或预防植物病原微生物侵染栽培植物的方法,该方法包括施用权利要求1所述的式(I)化合物至其种子。
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US11033029B2 (en) | 2013-11-25 | 2021-06-15 | Shenyang Sinochem Agrochemicals R & D Co., Ltd. | Pyrazole amide compound and use thereof |
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