CN101835772B - 新的咪唑衍生物 - Google Patents
新的咪唑衍生物 Download PDFInfo
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- CN101835772B CN101835772B CN2008801132706A CN200880113270A CN101835772B CN 101835772 B CN101835772 B CN 101835772B CN 2008801132706 A CN2008801132706 A CN 2008801132706A CN 200880113270 A CN200880113270 A CN 200880113270A CN 101835772 B CN101835772 B CN 101835772B
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Classifications
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明涉及作为活性成分的式I的新咪唑衍生物,其具有杀微生物活性,尤其是杀真菌活性:其中R1是卤素,C1-C4烷基或C1-C4卤代烷基;R2是任选经取代的芳基或杂芳基;R3是卤素;R4是氢,卤素,C1-C4烷基,C1-C4卤代烷基,羟基,C1-C4烷氧基,OR6,C1-C4卤代烷氧基或氰基;R5是卤素;R6是氢,C3-C7环烷基,C3-C10烷基环烷基,C1-C6卤代烷基,C2-C6烯基,C2-C6卤代烯基,C3-C7环烯基,C2-C6炔基,C2-C6卤代炔基或C2-C6烷氧基烷基;X是N或C(R);和R是氢,卤素,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基,C1-C4卤代烷氧基或氰基;或其农业化学上可使用的盐;条件是当X是C(R)时R2不能是任选经取代的芳基。
Description
本发明涉及新的咪唑衍生物作为活性成分,其具有杀微生物活性,尤其是杀真菌活性。本发明还涉及这些活性成分的制备;涉及新的杂环衍生物,在这些活性成分的制备中用作中间体;涉及这些新的中间体的制备;涉及农业化学组合物,其包含至少一种所述新的活性成分;涉及这些组合物的制备和涉及活性成分或组合物在农业或园艺用于防治或预防致植物病微生物,优选真菌对植物、收获的植物作物、种子或非生命材料(non-living materials)的侵染。
此外,本发明还涉及这些新的咪唑衍生物作为植物生长调节剂(PGRs)的用途。
此外,本发明还涉及包含改善植物的新的咪唑衍生物的组合物,该改善过程一般地且在后文中称为“植物保健”。
本发明还涉及这些新的咪唑衍生物在治疗癌症中的用途并涉及包含至少一种这些活性组分的化合物的杀真菌组合物或药用组合物。
这些目的通过下述式I化合物来实现:
其中
R1是卤素、C1-C4烷基或C1-C4卤代烷基;
R2是任选经取代的芳基或杂芳基;
R3是卤素;
R4是氢、卤素、C1-C4烷基、C1-C4卤代烷基、羟基、C1-C4烷氧基、OR6、C1-C4卤代烷氧基或氰基;
R5是卤素;
R6是氢、C3-C7环烷基、C3-C10烷基环烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C3-C7环烯基、C2-C6炔基、C2-C6卤代炔基或C2-C6烷氧基烷基;
X是N或C(R);和
R是氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或氰基;
或其农业化学上可使用的盐;
条件是
当X是C(R)时,R2不能是任选经取代的芳基。
在上述定义中芳基包括芳烃环,比如苯基、萘基、蒽基、菲基和联苯基,优选苯基。
杂芳基代表包含单-、二-或三环体系的芳环体系,其中存在至少一个氧、氮或硫原子作为环成员。实例是呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、三唑基、四唑基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、四嗪基、吲哚基、苯并噻吩基、苯并呋喃基、苯并咪唑基、吲唑基、苯并三唑基、苯并噻唑基、苯并噁唑基、喹啉基、异喹啉基、酞嗪基、喹喔啉基、喹唑啉基、噌啉基和萘啶基。
上下文提及的稠环、碳环、杂环、芳基和杂芳基可以任选地被取代。这是指它们可以带有一个或多个相同或不同的取代基。通常不同时存在超过三个取代基。取代基实例是:卤素、烷基、卤代烷基、环烷基、环烷基烷基、烯基、卤代烯基、环烯基、炔基、卤代炔基、烷氧基、卤代烷氧基、环烷氧基、烯氧基、卤代烯氧基、炔氧基、卤代烯氧基、烷硫基、卤代烷硫基、环烷硫基、烯硫基、炔硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烯基羰基、炔基羰基、烷氧基烷基、氰基、硝基、羟基、巯基、氨基、烷基氨基、二烷基氨基。任选经取代的的芳基的典型实例包括2-氟苯基、3-氟苯基、4-氟苯基、2-氯苯基、3-氯苯基、4-氯苯基、3-溴苯基、4-溴苯基、间-甲苯基、对-甲苯基、3-三氟甲基苯基、4-三氟甲基苯基、3-甲氧基苯基、4-甲氧基苯基、3-三氟甲氧基苯基、4-三氟甲氧基苯基、3-氰基苯基、4-氰基苯基、2,4-二氟苯基、2,5-二氟苯基、2,6-二氟苯基、3,4-二氟苯基、2,4-二氯苯基、2,5-二氯苯基、2,6-二氯苯基、3,4-二氯苯基、3,4-二甲基苯基、3,4-二甲氧基苯基、2-氯-4-氟苯基、2-氯-5-氟苯基、2-氯-6-氟苯基、3-氯-4-氟苯基、3-氯-6-氟苯基、3-氯-4-甲基苯基、3-氯-4-甲氧基苯基、4-氯-2-氟苯基、4-氯-3-氟苯基、4-氯-3-甲基苯基、4-氯-3-甲氧基苯基、3-氟-4-甲氧基苯基、3-氟-4-甲基苯基、4-氟-3-甲氧基苯基、4-氟-3-甲基苯基、3-甲氧基-4-甲基苯基、4-甲氧基-3-甲基苯基、2,6-二氟-4-甲基苯基、2,6-二氟-4-三氟甲基苯基、2,6-二氟-4-甲氧基苯基、2,6-二氟-4-三氟甲氧基苯基、2,6-二氟-4-氰基苯基、2,4,6-三氟苯基、2,5,6-三氟苯基。任选经取代的杂芳基的典型实例包括6-氯吡啶-2-基、6-氟吡啶-2-基、6-甲氧基吡啶-2-基、6-甲基吡啶-2-基、6-氯吡啶-3-基、6-氟吡啶-3-基、6-甲氧基吡啶-3-基、6-甲基吡啶-3-基、2-氯吡啶-4-基、2-氟吡啶-4-基、2-甲氧基吡啶-4-基、2-甲基吡啶-4-基、3,5-二氯吡啶-2-基、3,5-二氟吡啶-2-基、3-氯-5-氟吡啶-2-基、3-氯-5-甲基吡啶-2-基、3-氯-5-三氟甲基吡啶-2-基、3-氯-5-甲氧基吡啶-2-基、3-氯-5-三氟甲氧基吡啶-2-基、3-氯-5-氰基吡啶-2-基、5-氯-3-氟吡啶-2-基、3-氟-5-甲基吡啶-2-基、3-氟-5-三氟甲基吡啶-2-基、3-氟-5-甲氧基吡啶-2-基、3-氟-5-三氟甲氧基吡啶-2-基、3-氟-5-氰基吡啶-2-基、5-氯噻吩-2-基、5-溴噻吩-2-基、5-甲氧基噻吩-2-基、4-甲氧基喹啉-2-基、4-甲基喹啉-2-基。
在上述定义中卤素是氟、氯、溴或碘。
烷基、烯基或炔基自由基可以是直链或分支的。
烷基自身或作为其它取代基的一部分取决于提及的碳原子数是,例如,甲基、乙基、丙基、丁基、戊基、己基和其异构体、例如、异丙基、异丁基、仲-丁基、叔-丁基、异戊基或叔-戊基。
卤代烷基可以含有一个或多个相同或不同的卤素原子和,例如,可以表示CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CF3CH2、CH3CF2、CF3CF2或CCl3CCl2。
环烷基自身或作为其它取代基的一部分取决于提及的碳原子数是,例如,环丙基、环丁基、环戊基或环己基。
烯基自身或作为其它取代基的一部分取决于提及的碳原子数是,例如,乙烯基、烯丙基、1-丙烯基、丁烯-2-基、丁烯-3-基、戊烯-1-基、戊烯-3-基、己烯-1-基或4-甲基-3-戊烯基。
炔基自身或作为其它取代基的一部分取决于提及的碳原子数是,例如,乙炔基、丙炔-1-基、丙炔-2-基、丁炔-1-基、丁炔-2-基、1-甲基-2-丁炔基、己炔-1-基或1-乙基-2-丁炔基。
式I化合物存在一个或多个可能的不对称碳原子意味着所述化合物可以出现光学异构体,也即对映异构体或非对映异构体形式。存在可能的脂族C=C双键导致几何异构,也即还可以出现顺-反或(E)-(Z)异构。另外围绕单键的旋转阻碍还导致出现阻转异构体。式I意在包括所有这些可能的异构体及其混合物。本发明意在包括式I化合物的所有这些可能异构体形式及其混合物。
在各种情况下,根据本发明的式I化合物是游离形式或农业上可用的盐形式。
在第一种实施方式中,根据本发明的式I化合物具有的R1是卤素,C1-C3烷基或C1-C3卤代烷基。
在第二种实施方式中,根据本发明的式I化合物具有的R2是任选经取代的苯基、萘基、噻吩基、吡啶基、喹啉基或异喹啉基。
在第三种实施方式中,根据本发明的式I化合物具有的R3是氟、氯、溴或碘。
在第四种实施方式中,根据本发明的式I化合物具有的R4是氢,卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、OR6、C1-C4卤代烷氧基或氰基。
在第五种实施方式中,根据本发明的式I化合物具有的R5是氟、氯、溴或碘。
在第六种实施方式中,根据本发明的式I化合物具有的R6是氢,C3-C7环烷基、C3-C10烷基环烷基、C1-C6卤代烷基、C2-C6烯基、C3-C7环烯基、C2-C6炔基或C2-C6烷氧基烷基。
在第七种实施方式中,根据本发明的式I化合物具有的X是N、C(H)、C(卤素)、C(C1-C4烷基)、C(C1-C4卤代烷基)、C(C1-C4烷氧基)或C(C1-C4卤代烷氧基)。
根据本发明的式I化合物的优选小组是这些,其中
R1是氟,氯,溴,碘,C1-C2烷基或C1-C2卤代烷基;
R2是任选经取代的苯基,萘基,噻吩基,吡啶基或喹啉基;R3是氟,氯或溴;
R4是氢,氟,氯,溴,C1-C3烷基,C1-C3卤代烷基,C1-C3烷氧基,C1-C3卤代烷氧基或氰基;
R5是氟,氯或溴;和
X是N,C(H),C(Cl),C(F),C(Br),C(I),C(C1-C3烷基),C(C1-C3卤代烷基),C(C1-C3烷氧基)或C(C1-C3卤代烷氧基)。
根据本发明的式I化合物的更优选小组是这些,其中
R1是氟,氯,溴,甲基或乙基;
R2是苯基,3-氟苯基,4-氟苯基,3-氯苯基,4-氯苯基,3-溴苯基,4-溴苯基,间-甲苯基,对-甲苯基,3-三氟甲基苯基,4-三氟甲基苯基,3-甲氧基苯基,4-甲氧基苯基,3-三氟甲氧基苯基,4-三氟甲氧基苯基,3-氰基苯基,4-氰基苯基,3,4-二氟苯基,3,4-二氯苯基,3,4-二甲基苯基,3,4-二甲氧基苯基,3-氯-4-氟苯基,3-氯-4-甲基苯基,3-氯-4-甲氧基苯基,4-氯-3-氟苯基,4-氯-3-甲基苯基,4-氯-3-甲氧基苯基,萘-2-基,3-氟-4-甲氧基苯基,3-氟-4-甲基苯基,4-氟-3-甲氧基苯基,4-氟-3-甲基苯基,3-甲氧基-4-甲基苯基,4-甲氧基-3-甲基苯基,吡啶-2-基,吡啶-3-基,吡啶-4-基,6-氯吡啶-2-基,6-氟吡啶-2-基,6-甲氧基吡啶-2-基,6-甲基吡啶-2-基,6-氯吡啶-3-基,6-氟吡啶-3-基,6-甲氧基吡啶-3-基,6-甲基吡啶-3-基,2-氯吡啶-4-基,2-氟吡啶-4-基,2-甲氧基吡啶-4-基,2-甲基吡啶-4-基,5-氯噻吩-2-基,5-溴噻吩-2-基,5-甲氧基噻吩-2-基,喹啉-2-基,喹啉-3-基,4-甲氧基喹啉-2-基或4-甲基喹啉-2-基;
R3是氟或氯;
R4是氢,氟,氯,C1-C2烷基,C1-C2卤代烷基,C1-C2烷氧基,C1-C2卤代烷氧基或氰基;
R5是氟或氯;和
X是N,C(H),C(Cl),C(F),C(Br),C(C1-C2烷基),C(C1-C2卤代烷基),C(C1-C2烷氧基)或C(C1-C2卤代烷氧基)。
根据本发明的式I化合物的最优选小组是这些,其中
R1是氟,氯,甲基或乙基;
R2是4-氟苯基,4-氯苯基,4-溴苯基,对-甲苯基,6-氯吡啶-3-基,6-氟吡啶-3-基,6-甲氧基吡啶-3-基,6-甲基吡啶-3-基,2-氯吡啶-4-基,2-氟吡啶-4-基,2-甲氧基吡啶-4-基,2-甲基吡啶-4-基,喹啉-2-基,喹啉-3-基,4-甲氧基喹啉-2-基或4-甲基喹啉-2-基;
R3是氟或氯;
R4是氢,氟,氯,C1-C2烷基,C1-C2卤代烷基或C1-C2烷氧基;
R5是氟或氯;和
X是N,C(H),C(Cl)或C(F)。
根据本发明的式I化合物的特别优选小组是这些,其中
R1是氯或甲基;
R2是6-氯吡啶-3-基,6-甲基吡啶-3-基,6-甲氧基吡啶-3-基或喹啉-3-基;
R3是氯;
R4是氟或甲氧基;
R5是氟;和
X是C(F)。
优选的单个化合物是:
2-氯-5-[2,4-二氯-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶;
2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶;
5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-甲氧基-吡啶;
2-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-喹啉;
2-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-4-甲氧基-喹啉;
3-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-喹啉;
3-[2,4-二氯-5-(2,4,6-三氟-苯基)-咪唑-1-基]-喹啉;
3-[2,4-二氯-5-(2,6-二氟-4-甲氧基-苯基)-咪唑-1-基]-喹啉;
2-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-4-甲氧基-喹啉;
3-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-喹啉;
2-氯-5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-吡啶;
2-氯-5-[2,4-二氯-5-(2,6-二氟-4-甲氧基-苯基)-咪唑-1-基]-吡啶;
5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲氧基-吡啶;
5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲基-吡啶;
3,5-二氯-2-[5-氯-3-(6-氯-吡啶-3-基)-2-甲基-3H-咪唑-4-基]-吡啶;和
2-[4-氯-5-(3,5-二氯-吡啶-2-基)-2-甲基-咪唑-1-基]-喹啉。
式I.1化合物,其中R2,R3,R4和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,和R1是C1-C4烷基或C1-C4卤代烷基,可以通过将式II化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,和R1是C1-C4烷基或C1-C4卤代烷基,与N-氯琥珀酰亚胺或分子氯反应来获得。
式I.2化合物,其中R2和R6如对式I化合物的定义,条件是R2不能是任选经取代的芳基,和R1是C1-C4烷基,可以通过将式I.3化合物,其中R2是如对式I化合物的定义,条件是R2不能是任选经取代的芳基,和R1是C1-C4烷基,与式NaOR6试剂,其中R6是如对式I化合物的定义反应来获得。
式II化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,和R1是C1-C4烷基,可以通过将式III化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,用式(R1)3Al试剂,其中R1是C1-C4烷基,优选甲基,在过渡金属催化剂存在下转化来获得。
式II化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,和R1是C1-C4烷基或C1-C4卤代烷基,可以可选地通过将式IV化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,用强碱,例如二异丙基胺化锂,随后是式R1Hal试剂,其中R1是C1-C4烷基或C1-C4卤代烷基,和Hal是卤素,优选溴或碘转化来获得。
式I化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,和R1是卤素,优选氯或溴,可以通过将式IV化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,与至少2当量N-氯琥珀酰亚胺,N-溴琥珀酰亚胺,分子氯或溴反应来获得。
式III化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,可以通过将式IV化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,用N-溴琥珀酰亚胺转化来获得。
式IV化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,可以通过将式V化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,与甲苯磺酰基甲基异氰化物在碱例如无水碳酸钾存在下反应来获得,如同Journal of Medicinal Chemistry2003,46,3463中的描述。
式V化合物,其中R2,R4,R5和X如对式I化合物的定义,条件是当X是C(R)时R2不能是任选经取代的芳基,可以通过将式VI醛,其中R4,R5和X如对式I化合物的定义,与式VII胺,其中R2是如对式I化合物的定义,条件是当在式VI中X是C(R)时在式VII中R2不能是任选经取代的芳基反应来获得,如同Journal of MedicinalChemistry 2003,46,3463已有的描述。
令人惊讶地,现在发现新型式I化合物对于实用目的具有非常有利的生物活性水平,其用于保护植物对抗由真菌以及由细菌和病毒引起的病害。
式I化合物可以在农业领域和相关应用领域用作活性成分,用于防治植物病害,或者在非生命物质上用于防治腐败微生物或对人潜在有害的生物体。新的化合物的特性是在低施用率下的优异活性,被植物良好耐受和对环境安全。它们具有非常有用治疗、预防和内吸特性,并且用于保护许多栽培植物。式I化合物可以用来抑制或消灭在不同有用植物作物的植物或植物部分(果实、花、叶、茎、块茎、根)发生的病害,与此同时还保护之后生长的那些植物部分,例如免于致植物病微生物。
还可以将式I化合物用作拌种试剂来处理植物繁殖材料,例如种子如果实、块茎或谷物或者植物插条如稻,以保护对抗真菌侵染以及对抗土壤中存在的致植物病真菌。繁殖材料可以在种植前用包含式I化合物的组合物处理:例如可以在播种前拌种种子。本发明的活性成分还可以被施用于谷物(包衣),通过将种子浸入液体制剂或者用固体制剂将它们包衣。所述组合物还可以在种植繁殖材料时被施用于种植场所,例如在播种期间施用至播种沟。本发明还涉及这样处理植物繁殖材料的方法和涉及这样处理的植物繁殖材料。
此外,本发明化合物可以用来在相关领域防治真菌,例如在工业材料包括木材和木材相关工业产品的保护中,在食物储存中,在卫生管理中。
另外,本发明可以用来保护非生命材料如木材、墙板和涂料免受真菌侵袭。
式I化合物有效对抗例如下述纲的致植物病真菌:半知菌类(Fungi imperfecti)(例如链格孢属(Alternaria spp.),担子菌纲(Basidiomycetes)(例如Corticium spp.,Ceratobasidium spp.,Waitea spp.,Thanatephorus spp.,丝核菌属(Rhizoctonias pp.),驼孢锈菌属(Hemileia spp.),柄锈菌属(Puccinia spp.),层锈菌属(Phakopsora spp.),黑粉菌属(Ustilago spp.),腥黑粉菌属(Tilletia spp.)),子囊菌纲(Ascomycetes)(例如黑星菌属(Venturiaspp.),白粉菌属(Blumeria spp.),白粉菌属(Erysiphe spp.),叉丝单囊壳属(Podosphaera spp.),钩丝壳属(Uncinula spp.),链核盘菌属(Monilinia spp.),核盘霉属(Sclerotinia spp.),刺盘孢属(Colletotrichum spp.),小丛壳属(Glomerellas pp.),镰孢属(Fusarium spp.),赤霉属(Gibberellas pp.),明梭孢属(Monographella spp.),Phaeosphaeria spp.,球腔菌属(Mycosphaerella spp.),尾孢属(Cercospora spp.),核腔菌属(Pyrenophora spp.),喙孢属(Rhynchosporium spp.),Magnaporthespp.,顶囊壳属(Gaeumannomyces spp.),Oculimacula spp.,隔柱孢属(Ramularia spp.),Botryotinia spp.)和卵菌纲(Oomycetes)(例如疫霉属(Phytophthora spp.),腐霉属(Pythium spp.),单轴霉属(Plasmopara spp.),霜霉属(Peronospora spp.),假霜霉属(Pseudoperonospora spp.)盘梗霉属(Bremia spp.)。观察到对抗白粉病(如葡萄钩丝壳(Uncinula necator))、锈病(如柄锈菌属(Puccinias pp.))和叶斑病(如球腔菌属(Mycosphaerella spp.))的优秀活性。此外,新的式I化合物有效对抗致植物病革兰氏阴性和革兰氏阳性的菌类(例如黄单胞杆菌属(Xanthomonas spp)、假单胞杆菌属(Pseudomonas spp)、梨火疫病菌(Erwinia amylovora)、Ralstoniaspp.)和病毒(例如烟草花叶病毒)。
在本发明范围内,要保护的有用植物和/或靶标作物通常包含下述植物物种:谷物(小麦、大麦、黑麦、燕麦、稻、玉米、高梁和相关种);甜菜(糖用甜菜和饲料甜菜);梨果、核果和浆果(苹果、梨、李、桃、扁桃、樱桃、草莓、覆盆子和欧洲黑莓);豆科植物(菜豆、小扁豆、豌豆、大豆);油用植物(油菜、芥末、罂粟、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生);黄瓜植物(南瓜、黄瓜、甜瓜);纤维植物(棉花、亚麻、大麻、黄麻);柑橘类水果(橙、柠檬、葡萄柚、柑);蔬菜(菠菜、莴苣、芦笋、卷心菜、胡萝卜、蒜、西红柿、马铃薯、辣椒);樟科(鳄梨、肉桂、樟脑)或植物如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄、啤酒花、香蕉和天然橡胶植物,以及草坪和观赏植物。
本发明有用植物和/或靶标作物包括常规品种以及基因增强品种或基因工程品种,比如例如昆虫抗性品种(例如Bt.和VIP品种)以及病害抗性品种、除草剂耐受品种(例如草甘膦-和草铵膦-抗性玉米品种,可按商品名和购得)和线虫耐受品种。举例来说,适宜的基因增强或基因工程作物品种包括Stoneville5599BR棉花和Stoneville 4892BR棉花品种。
术语“有用植物”和/或“靶标作物”应理解为还包括由于常规育种方法或基因工程方法使其耐受除草剂如溴苯腈或多类除草剂(比如,例如,HPPD抑制剂,ALS抑制剂,例如氟嘧磺隆、氟磺隆和三氟啶磺隆,EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸-合成酶)抑制剂,GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)的有用植物。已通过常规育种方法(诱变)使其耐受咪唑啉酮类如甲氧咪草烟的作物的实例是夏季油菜(芸苔(Canola))。通过基因工程方法使之耐除草剂或除草剂类的作物的实例包括抗草甘膦和抗草铵膦的玉米,该品种可根据商品名Herculex和购得。
术语“有用植物”和/或“靶标作物”应理解为还包括已通过使用重组DNA技术转化使其能合成一种或多种选择性作用毒素的有用植物,所述毒素如已知来自于毒素产生细菌,特别是芽孢杆菌属的那些细菌。
术语“有用植物”和/或“靶标作物”应理解为还包括已通过使用重组DNA技术转化使其能合成选择性作用抗病原物质,比如,例如所谓的“致病相关蛋白”(PRPs,见例如EP-A-0392225)的有用植物。所述抗病原物质和能合成所述抗病原物质的转基因植物的实例已知于例如EP-A-0392225、WO 95/33818和EP-A-0353191。所述转基因植物的制造方法是本领域技术人员通常已知的,并且描述于例如上述出版物中。
文中使用的术语有用植物的“所在地”意在涵盖有用植物生长的地点、有用植物的植物繁殖材料播种的地点或有用植物的植物繁殖材料放入土壤中的地点。这种所在地的实施例是作物植物生长的大田。
术语“植物繁殖材料”应理解为表示植物的生殖部分,比如可以用于后者繁殖的种子,以及植物材料,比如插条或块茎,例如马铃薯。可以提及例如种子(严格意义的)、根、果实、块茎、鳞茎、根茎和植物部分。还可提及,发芽后或从土壤中出苗后要移植的发芽植物和幼苗。在移植前通过整体或部分浸渍处理可以保护这些幼苗。优选地“植物繁殖材料”应理解为表示种子。
式I化合物以未修饰的形式使用或优选与制剂领域常规的助剂一起使用。为此,它们以已知方式方便地制剂为乳油、可包衣糊剂、直接可喷雾或可稀释的溶液或悬浮剂、稀释乳剂、可湿性粉剂、可溶性粉剂、粉剂、颗粒剂以及例如在聚合物质中胶囊化。与组合物的类型类似,根据目标对象和主要环境来选择施用方法,比如喷雾、雾化、喷粉、撒播、被覆或浇注。该组合物还可以包含其它助剂比如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂以及肥料、微量营养素供体或其它用来获得特殊效果的制剂。
适宜的载体和助剂可以是固体或液体并且是制剂技术中有用的物质,例如天然或再生矿物质、溶剂、分散剂、湿润剂、增粘剂、增稠剂、粘合剂或肥料。这些载体例如描述于WO 97/33890。
式I化合物通常以组合物形式使用并且可以被同时地或与其它化合物连续地施用至作物区域或要处理的植物。这些其它化合物可以是例如肥料或微量营养素供体或其它影响植物生长的制剂。它们还可以是选择性除草剂或非选择性除草剂以及杀虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种这些制剂的混合物,视需要还有制剂领域惯用的其它载体、表面活性剂或施用促进助剂。
式I化合物通常以杀真菌组合物形式使用,上述组合物用于防治或保护对抗致植物病微生物,包含至少一种式I化合物或至少一种上文所定义的优选的单个化合物作为活性成分,其是游离形式或农业化学可使用盐的形式,以及至少一种上述提及的助剂。
上述杀真菌组合物用于防治或保护对抗致植物病微生物,包含至少一种式I化合物或至少一种上文所定义的优选的单个化合物作为活性成分,其是游离形式或农业化学可使用盐的形式,以及至少一种上述提及的助剂,该杀真菌组合物可以与其它杀真菌剂混合,在某些情况下引起无法预料的增效活性。特别优选的混合成分是:
唑类,比如氧环唑、BAY 14120、联苯三唑醇、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、抑霉唑、亚胺唑、种菌唑、叶菌唑、腈菌唑、稻瘟酯、戊菌唑、丙硫菌唑、啶斑肟、咪鲜胺、丙环唑、硅氟唑、戊唑醇、四氟醚唑、三唑酮、三唑醇、氟菌唑、灭菌唑;
嘧啶醇类(Pyrimidinyl carbinoles),比如环丙嘧啶醇、氯苯嘧啶醇、氟苯嘧啶醇;
2-氨基-嘧啶类,比如乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚;
吗啉类,比如十二环吗啉、苯锈啶、丁苯吗啉、螺环菌胺、十三吗啉;
苯胺基嘧啶类,比如嘧菌环胺、嘧菌胺、嘧霉胺;
吡咯类,比如拌种咯、咯菌腈;
苯基酰胺类,比如苯霜灵、呋霜灵、甲霜灵、R-甲霜灵、呋酰胺、噁霜灵;
苯并咪唑类,比如苯菌灵、多菌灵、咪菌威、麦穗宁、噻菌灵;
二甲酰亚胺类,比如乙菌利、菌核利、异菌脲、甲菌利、腐霉利、乙烯菌核利;
甲酰胺类,比如啶酰菌胺、萎锈灵、甲呋酰胺、氟酰胺、灭锈胺、氧化萎锈灵、吡噻菌胺(Penthiopyrad)、噻呋酰胺;胍类、比如双胍辛乙酸盐、多果定、双胍辛胺;
甲氧丙烯酸酯类,比如嘧菌酯、醚菌胺、烯肟菌酯(enestrobin)、氟嘧菌酯、醚菌酯、苯氧菌胺、肟菌酯、肟醚菌胺、啶氧菌酯、唑菌胺酯;
二硫代氨基甲酸酯类,比如福美铁、代森锰锌、代森锰、代森联、丙森锌、福美双、代森锌、福美锌;
N-卤代甲硫基四氢酞酰亚胺类,比如敌菌丹、克菌丹、苯氟磺胺、氟氯菌核利、灭菌丹、甲苯氟磺胺;
铜化合物,比如波尔多液、氢氧化铜、氯氧化铜、硫酸铜、氧化亚铜、代森锰铜、8-羟基喹啉铜;
硝基苯酚衍生物类,比如敌螨普、酞菌酯;
有机磷衍生物,比如敌瘟磷、异稻瘟净、稻瘟灵、氯瘟磷、吡菌磷、甲基立枯磷;
已知且可通过描述于WO 05/121104、WO 06/001175和WO07/066601中的方法制备的哒嗪衍生物,比如3-氯-5-(4-氯-苯基)-6-甲基-4-(2,4,6-三氟-苯基)-哒嗪(式P.1)、3-氯-6-甲基-5-对甲苯基-4-(2,4,6-三氟-苯基)-哒嗪(式P.2)和3-氯-4-(3-氯-5-甲氧基-吡啶-2-基)-5-(4-氯-苯基)-6-甲基-哒嗪(式P.3);
已知且可通过描述于WO98/46607中的方法制备的三唑并嘧啶衍生物,比如5-氯-7-(4-甲基-哌啶-1-基)-6-(2,4,6-三氟-苯基)-[1,2,4]三唑并[1,5-a]嘧啶(式T.1);
已知且可通过描述于WO04/035589和WO06/37632中的方法制备的甲酰胺衍生物,比如3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(9-异丙基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(式U.1);或
N-(3′,4′-二氯-5-氟-1,1′-联苯基-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺(化合物F-13);
已知并可通过描述于WO2004/016088中的方法制备的苯甲酰胺衍生物,比如N-{-2-[3-氯-5-(三氟甲基)-2-吡啶基]乙基}-2-三氟甲基苯甲酰胺,其还称为氟啶胺(fluopyram)(式V.1);
和
各种其它成分,比如活化酯-S-甲酯、敌菌灵、苯噻菌胺、灭瘟素、灭螨猛、氯苯甲醚、百菌清、环氟菌胺、霜脲氰、二氯萘醌、双氯氰菌胺、哒菌酮、氯硝胺、乙霉威、烯酰吗啉、氟吗啉、二氰蒽醌、噻唑菌胺、土菌灵、噁唑菌酮、咪唑菌酮、氰菌胺、三苯锡、嘧菌腙、氟啶胺、氟吡菌胺(fluopicolide)、磺菌胺、环酰菌胺、三乙膦酸铝、噁霉灵、异丙菌胺、氰霜唑、春雷霉素、双炔酰菌胺、磺菌威、表苯菌酮、啶酰菌胺(nicobifen)、戊菌隆、四氯苯酞、多氧霉素、烯丙苯噻唑、霜霉威、丙氧喹啉、咯喹酮、苯氧喹啉、五氯硝苯、硫、噻酰菌胺、咪唑嗪、三环唑、嗪氨灵、有效霉素、苯酰菌胺和草甘膦。
本发明的另一方面涉及式I化合物的用途或上述优选单个化合物的用途,包含至少一种式I化合物或至少一种上述优选单个化合物的组合物的用途,包含至少一种式I化合物或至少一种上述优选单个化合物与上述其它杀真菌剂混合的杀真菌混合物的用途,用于防治或预防致植物病微生物,优选真菌生物体对植物、收获的植物作物、种子或非生命物质的侵染。
本发明的另一方面涉及防治或预防致植物病的或腐败微生物或者潜在对人有害的生物特别是真菌体侵染作物植物、收获的食物作物或者非生命材料的方法,其包含将式I化合物或上述优选单个化合物作为活性成分施用至植物、植物部分或其所在地,或者所述非生命材料的任意部分。
防治或预防是指将致植物病的或腐败微生物或者潜在对人有害的生物特别是真菌体对作物植物或者非生命材料的侵染减少至能显示改善的水平。
防治或预防致植物病微生物特别是真菌体侵染作物植物的优选方法是叶面施用,其包括施用式I化合物或包含至少一种所述化合物的农业化学组合物。施用频率和施用率将取决于被相应病原菌侵染的风险。然而,通过用液体制剂浸透植物所在地或将该化合物以如颗粒形式的固体形式施用至土壤(土壤施用),式I化合物可以经由土壤通过根透入植物(内吸作用)。在水稻作物中,这种颗粒剂可以被施用至淹灌的稻田。也可以通过用杀真菌剂液体制剂浸渍种子或块茎或用固体制剂将它们包衣,从而将式I化合物施用至种子(包衣)。
制剂[即包含式I化合物的组合物]以及视需要的固体或液体助剂或者用来包囊式I化合物的单体是以已知方法制备的,一般通过将所述化合物与增容剂如溶剂、固体载体和可选的表面活性化合物(表面活性剂)紧密混合和/或研磨来制备。
农业化学制剂通常包括0.1到99%重量、优选0.1到95%重量的式I化合物,99.9到1%重量、优选99.8到5%重量的固体或液体助剂,以及0到25%重量、优选0.1到25%重量的表面活性剂。
有利的施用率通常是5g到2kg的活性成分(a.i.)每公顷(ha),优选10g到1kg a.i./ha,最优选20g到600g a.i./ha。当用作种子处理试剂时,适宜的剂量是10mg到1g活性成分每千克种子。
尽管优选将商业产品制剂为浓缩物,但终端用户一般使用稀释制剂。
令人惊讶地,根据本发明的式I咪唑化合物,尤其是在上文的描述中优选的单个咪唑化合物,还表现植物生长调节剂(PGR)活性。因此,本发明还涉及这些新咪唑衍生物作为植物生长调节剂(PGRs)的用途。
植物生长调节剂(PGRs)通常是用于加速或阻滞植物或它们的产品的生长或成熟或者改变其发育的任何物质或物质的混合物。
植物生长调节剂(PGRs)影响植物生长和分化。
更明确地,各种植物生长调节剂(PGRs)可以,例如,降低植物高度、刺激种子萌芽、引起开花、加深叶片着色、改变植物生长速率和修饰结果的时机和效率。
此外,本发明还涉及包含改善植物的本发明的新咪唑衍生物的组合物,该改善过程一般地并且在后文中成为“植物保健”。
例如,可提及的有利特性是经改善的作物特征,包括:出苗、作物产量、蛋白质含量、增加的活力、更快的成熟(maturation)、增加的种子出苗速度、增加的氮利用效率、增加的用水效率、经改善的油含量和/或品质、经改善的可消化性、更快的成熟(ripening)、经改善的香味、经改善的淀粉含量、更发达的根系(经改善的根生长)、经改善的压力耐受(例如对抗干旱、炎热、盐分、光照、UV、水分、寒冷)、减少的乙烯(减少产生和/或抑制接受)、分蘖增加、植物高度增加、更大的叶片、更少的枯死基叶、更强壮的分蘖、更绿的叶色、色素含量、光合作用、更少的输入需求(比如肥料或水)、更少的种子需求、更多产的分蘖、更早的开花、更高的谷物成熟、更少的植物倾倒(倒伏)、增加的植株地上部生长、经增进的植物活力、增加的植物密度和早期更好的萌芽。
特别地得自经处理种子的有利特性,是例如经改善的萌芽和齐苗,更佳的活力,更均匀的齐苗。
特别地得自叶面和/或沟内施用的有利特性,是例如经改善的植物生长和植物发育、更佳的生长、更多分蘖、更绿的叶片、更大的叶片、更多的生物质、更佳的根、经改善的植物压力耐受、更多的谷物产量,更多的收获生物质、经改善的收获品质(脂肪酸、代谢产物、油等的含量)、更易销售的产品(例如经改善的大小)、经改善的工序(例如更长的贮藏期限,对化合物的更佳提取),经改善的种子品质(在随后的季节播种用于种子生产);或本领域技术人员熟悉的任何其他优势。
因此,本发明目的是提高解决前文描述的问题的方法。
本发明涉及植物保护活性成分,其是根据本发明的式I咪唑化合物,尤其是上文描述的优选单个咪唑化合物,以及具有增加的效力的混合物,和涉及通过施用所述化合物和混合物至植物或其所在地来改善植物保健的方法。
式I化合物的作用超越已知的杀真菌作用。根据本发明的式I咪唑化合物,尤其是上文描述为优选化合物的单个咪唑化合物化合物,展示植物保健。
术语植物保健包含与防治有害真菌无关的各种植物改善。
在另一方面中,本发明涉及组合物,其包含至少一种式I化合物或至少一种上述定义的优选单个化合物和/或至少其一种药学上可接受的盐、至少一种药学上可接受的载体和/或至少一种药学上可接受的稀释剂。
在另一方面,本发明还涉及式I化合物或上述定义的优选单个化合物,或其药学上可接受的盐,用作药物。
在优选的方面,本发明还涉及式I化合物或上述定义的优选单个化合物,或其药学上可接受的盐,用与治疗癌症。
在另一方面,本发明还涉及式I化合物或上述定义的优选单个化合物,或其药学上可接受的盐,在治疗癌症的药物的生产中的用途。
在特定方面,本发明还涉及在有此需要的受试者中治疗癌症的方法,包括以治疗上述癌症的有效量将式I化合物或上述定义的优选单个化合物给药至上述受试者。
本发明还提供杀真菌组合物或药用组合物,其包含式I化合物或上述定义的优选单个化合物,和/或他们农业上或药学上可接受的盐和适宜的载体。
适宜的药学上可接受的载体描述如下。
根据本发明的式I咪唑化合物,尤其是上文描述的优选单个咪唑化合物,和/或它们的药学上可接受的盐适用于治疗、抑制或防治肿瘤细胞生长和/或繁殖和相关病症。
因此,它们适用于温血脊椎动物的癌症疗法,上述动物是例如哺乳动物和鸟类,尤其是人,但还是其他哺乳动物,尤其是益兽和家畜,比如狗、猫、猪、反刍动物(牛、绵羊、山羊、野牛等),马和鸟,比如鸡、火鸡、鸭、鹅、珍珠鸡等。
根据本发明的式I咪唑化合物,尤其是上文描述的优选单个咪唑化合物,和/或它们的药学上可接受的盐适宜于下述器官的癌症或癌性病症的治疗:乳房,肺,肠,前列腺,皮(黑色素瘤),肾,膀胱,口,喉,食道,胃,卵巢,胰,肝和脑。
除根据本发明的式I咪唑化合物,尤其是上文描述的优选单个咪唑化合物,和/或其药学上可接受的盐之外,根据本发明的药用组合物包含至少任选的适宜载体。
“药学上可接受的”表示这样的化合物、材料、组合物和/或剂型,其在良好的药学判断范围内,适宜用于人类和动物的组织接触,同时不具过分的毒性、刺激性、变态反应或者其他问题或并发症,与合理的利益/风险比相称。
适宜的载体是,例如,惯用于药物制剂的溶剂、载体、赋形剂、粘合剂等,其在下文中对单独给药类型示例性地描述。
“药学上可接受的载体”如本文所用表示药学上可接受的材料、组合物或媒介物,比如液体或固体填充剂、稀释剂、赋形剂、溶剂或包囊材料,牵涉于将目标试剂从一个器官或身体部分负载或输运至另一个器官或身体部分。各载体必须是“可接受的”,意思是与制剂的其它成分相容并且对患者无害。可以充当药学上可接受载体的材料的一些实例包括:
糖类,比如乳糖,葡萄糖和蔗糖;
淀粉,比如玉米淀粉和马铃薯淀粉;
纤维素,和它的衍生物,比如钠羰甲基纤维素,乙基纤维和乙酸纤维素;
粉末黄蓍胶;
麦芽;
明胶;
滑石;
赋形剂,比如可可脂和栓剂蜡;
油,比如花生油、棉花籽油、红花油、芝麻油、橄榄油、玉米油和大豆油;
二醇类,比如丙二醇;
多元醇,比如甘油、山梨糖醇、甘露糖醇和聚乙二醇;
酯类,比如油酸乙酯和月桂酸乙酯;
琼脂;缓冲剂,比如氢氧化镁和氢氧化铝;
藻酸;
无热原水;
等渗盐水;
林格氏溶液;
乙醇;
磷酸盐缓冲溶液;和
用于药物制剂中的其它无毒性相容物质。
根据本发明的式I咪唑化合物,尤其是上文描述的优选单个咪唑化合物(活性化合物),可以惯用方式给药,例如口服、静脉内、肌内或皮下。
对于口服给药,活性化合物可以例如,与惰性稀释剂或与可食用载体混合;它可以包埋入硬的或软的明胶囊中,它可以压成片剂或者它可以直接与食品/饲料混合。
活性化合物可以与赋形剂混合并以下述形式给药:难消化片剂,颊片剂,软锭剂,丸剂,胶囊剂,悬浮剂,饮剂,糖浆等。
这种制剂应包含至少0.1%的活性化合物。
当然,制剂的组成可以变化。
它通常包含2-60%按重量计的活性化合物,基于所述制剂(剂量单元)的总重量。
根据本发明的式I咪唑化合物,尤其是上文描述的优选单个咪唑化合物的优选制剂,包含10-1000mg活性化合物/口部计量单元。
此外片剂,软锭剂,丸剂,胶囊剂等还可以包含以下组分:粘合剂,比如胺黄树胶、阿拉伯胶、玉米淀粉或明胶,赋形剂,比如磷酸二钙,崩解剂,比如玉米淀粉、马铃薯淀粉、藻酸等,助流剂,比如硬脂酸镁,增甜剂,比如蔗糖、乳糖或糖精,和/或调味剂,比如胡椒薄荷、香草等。
胶囊剂可以进一步包含液体载体。
也可以使用改变剂量单元特性的其它物质。
例如,片剂,丸剂和胶囊剂可以用虫胶、糖或其混合物包衣。
除活性化合物外,糖浆或饮剂还可以包含糖(或其他增甜剂),作为防腐剂的对羟基苯甲酸甲酯或对羟基苯甲酸丙酯、着色剂和/或调味剂。
活性化合物制剂的组分当然必须是药学上纯净的并且在所用量下无毒。
此外,活性化合物可以制剂为具备活性化合物控释的制剂,例如作为缓释制剂。
活性化合物还可以肠胃外或腹膜内给药。
活性化合物或它们的盐的溶液或悬浮液可以使用适宜的湿润剂比如羟丙纤维素用水制备。
分散体还可以用甘油、液体聚乙二醇及其混合物在油中制备。
通常,这些制剂还包含防腐剂从而预防微生物生长。
用于注射的制剂包含无菌水溶液和分散体,以及用于制备无菌溶液和分散体的无菌粉末。
制剂必须充分液化以用于注射。
它必须在配制和贮藏条件下稳定,并且必须保护它免受微生物污染。
载体可以是溶剂或分散介质,例如,水,乙醇,多元醇(例如甘油,丙二醇或液体聚乙二醇),其混合物和/或植物油。
适于肠胃外给药的本发明药物组合物包含根据本发明的式I咪唑化合物,尤其是在上文描述中优选的单个咪唑化合物与下述试剂的组合:一种或多种药学上可接受的无菌等渗的水溶液或非水溶液、分散剂、悬浮剂或乳剂,或在使用之前可以重构为无菌可注射溶液剂或分散剂的无菌粉剂,其可以包含抗氧化剂、缓冲剂、抑菌剂、溶剂,使得制剂与目标接受者的血液等渗,或者悬浮或增稠试剂。
可用于本发明药物组合物中的适宜含水和非水载体的实例包括水、乙醇、多元醇(比如甘油、丙二醇、聚乙二醇等)及其适宜的混合物,植物油,比如橄榄油,和可注射的有机酯,比如油酸乙酯。可以例如通过使用包衣物质,比如卵磷脂,在分散剂的情况中通过保持所需的粒径,和通过使用表面活性剂来保持合适的流动性。这些组合物还可以包含助剂比如防腐剂、湿润剂、乳化剂和分散剂。对微生物作用的预防可以通过包含入各种抗菌剂和其它抗真菌剂,例如对羟基苯甲酸酯、氯丁醇、苯酚山梨酸等来确保。还可以希望在组合物中包括等渗剂,比如糖、氯化钠等。另外,可注射药物形式的延缓吸收可以通过包括入延缓吸收的试剂比如单硬脂酸铝和明胶来引起。
本发明的药物组合物可以通过任何适宜给药方式包括口服、肠胃外、局部、经皮或经直肠来提供。它们当然以适于各种给药途径的形式提供。例如,它们通过注射、吸入以片剂或胶囊形式给药,通过注射、输注或吸入以洗眼剂、膏剂、栓剂形式给药;通过局部以洗剂或膏剂形式给药;和通过直肠以栓剂形式给药。优选局部或肠胃外给药。
下述非限制性实施例以更多细节举例说明上文描述的发明。
实施例1:该实施例举例说明制备2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶(化合物No.I.j.210)
a)制备(6-氯-吡啶-3-基)-[1-(2,4,6-三氟-苯基)-亚甲-(E)-基]-胺
将6-氯-吡啶-3-基胺(5g)和2,4,6-三氟-苯甲醛(6.226g)溶于甲苯(190ml)。随后,混合物在Dean-Stark装置中与回流下搅拌16.0h。减压蒸发反应混合物,获得9.92g的(6-氯-吡啶-3-基)-[1-(2,4,6-三氟-苯基)-亚甲-(E)-基]-胺。1H NMR(300Mhz,CDCl3)8.58ppm,1H,s;8.25ppm,1H,d,J=2.16Hz;7.51ppm,1H,dd,J=2.47和8.36Hz;7.36ppm,1H,d,J=8.39Hz;6.79ppm,2H,t,J=8.69Hz。
b)制备2-氯-5-[5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶
将9.92g的(6-氯-吡啶-3-基)-[1-(2,4,6-三氟-苯基)-亚甲-(E)-基]-胺溶于120ml的N,N-二甲基-甲酰胺和100ml的1,2-二甲氧基-乙烷。加入10.73g的甲苯磺酰基甲基异氰化物和10.13g的无水碳酸钾,和所得反应混合物在100℃下加热90分钟。冷却后,过滤混合物,蒸发溶剂,所得固体吸附于HM-N上兵通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯3∶1-7∶3-2∶1和1∶1的混合物作为连续洗脱液获得9.320g的中间体,分子量相当于465.88g/mol。将此中间体溶于80ml的N,N-二甲基-甲酰胺和70ml的1,2-二甲氧基-乙烷,向此溶液加入6.645g的无水碳酸钾。所得反应混合物在100℃下加热24h。冷却后,过滤混合物,蒸发溶剂,所得固体吸附于HM-N上通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯2∶1和1∶1的混合物作为连续洗脱液,获得4.782g的2-氯-5-[5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶。1H NMR(300Mhz,CDCl3)8.26ppm,1H,d,J=2.57Hz;7.81ppm,1H,s;7.48ppm,1H,dd,J=2.7和8.44Hz;7.38ppm,1H,d,J=8.41Hz;7.35ppm,1H,s;6.69ppm,2H,t,J=8Hz。
c)制备5-[2-溴-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-氯-吡啶
将3.290g的2-氯-5-[5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶,2.203g的N-溴琥珀酰亚胺和30ml的氯仿的混合物加热4h至80℃。随后,混合物冷却至室温,HM-N加至反应混合物,蒸发氯仿。粗混合物通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯4∶1的混合物作为洗脱液,获得1.520g的5-[2-溴-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-氯-吡啶,是淡黄橙色固体。1H NMR(300Mhz,CDCl3)8.23ppm,1H,d,J=2.58Hz;7.54ppm,1H,dd,J=2.71和8.43Hz;7.40ppm,1H,d,J=8.41Hz;7.27ppm,1H,s;6.66ppm,2H,t,J=7.85Hz。
d)制备2-氯-5-[2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶
将5-[2-溴-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-氯-吡啶(0.959g)溶于50ml的四氢呋喃。向此溶液,加入0.040g的四(三苯基膦)钯,随后回流所得混合物10分钟。此时间后,除去油浴并立即缓慢加入3.7ml的(三甲基)铝。反应混合物准确回流95分钟,随后冷却至0℃。滴加2ml甲醇(气体发生),5分钟后加入HM-N,减压除去溶剂。残余物通过色谱法在硅胶上纯化,使用庚烷/乙酸乙酯1∶4的混合物作为洗脱液,提供0.218g的2-氯-5-[2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶,是白色固体。1H NMR(300Mhz,CDCl3)8.23ppm,1H,d,J=2.53Hz;7.47ppm,1H,dd,J=2.62和8.53Hz;7.39ppm,1H,d,J=8.4Hz;7.20ppm,1H,s;6.64ppm,2H,t,J=7.46Hz;2.38ppm,3H,s。作为副产物,获得0.312g的2-甲基-5-[2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶。1H NMR(300Mhz,CDCl3)8.23ppm,1H,d,J=2.22Hz;7.30ppm,1H,dd,J=2.4和8.22Hz;7.12ppm,1H,d,J=8.24Hz;7.09ppm,1H,s;6.53ppm,2H,t,J=7.38Hz;2.51ppm,3H,s;2.27ppm,3H,s。
e)制备2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶(化合物No.I.j.210)
0.310g的2-氯-5-[2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶,0.134g的N-氯琥珀酰亚胺和3ml的氯仿的混合物加热3h至80℃。随后,混合物冷却至室温,将HM-N加至反应混合物,蒸发氯仿。粗混合物通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯2∶1的混合物作为洗脱液,获得2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶。将此白色固体溶于二乙基醚(10ml),用5ml的1N氢氧化钠溶液萃取两次,有机相在硫酸钠上干燥,过滤,减压蒸发,获得0.195g的2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶(化合物No.I.j.210),是白色固体。1H NMR(300Mhz,CDCl3)8.23ppm,1H,d,J=2.49Hz;7.47ppm,1H,dd,J=2.63和8.43Hz;7.40ppm,1H,d,J=8.41Hz;6.68ppm,2H,t,J=7.45Hz;2.34ppm,3H,s。
实施例2:该实施例举例说明制备2-氯-5-[2,4-二氯-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶(化合物No.I.j.209)
0.15g的2-氯-5-[5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶,0.164g的N-氯琥珀酰亚胺和1.56ml的氯仿的混合物加热16h至80℃。随后,混合物冷却至室温,将HM-N加至反应混合物,蒸发氯仿。粗混合物通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯6∶1的混合物作为洗脱液,获得0.136g的2-氯-5-[2,4-二氯-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶(化合物No.I.j.209)。1H NMR(300Mhz,CDCl3)8.23ppm,1H,d,J=2.7Hz;7.54ppm,1H,dd,J=2.7和8.5Hz;7.43ppm,1H,d,J=8.36Hz;6.71ppm,2H,t,J=7.97Hz。
实施例3:该实施例举例说明制备5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲基-吡啶(化合物No.I.m.225)
a)制备5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-甲基-吡啶(化合物No.I.j.225)
将0.448g的2-甲基-5-[2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶,0.217g的N-氯琥珀酰亚胺和5ml的氯仿的混合物加热1.5h至80℃。随后,混合物冷却至室温,将HM-N加至反应混合物,蒸发氯仿。粗混合物通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯1∶1的混合物作为洗脱液,获得的5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-甲基-吡啶(化合物No.I.j.225),杂质含琥珀酰亚胺。将此白色固体溶于二乙基醚(10ml),用5ml的1N氢氧化钠溶液萃取两次,有机相在硫酸钠上干燥,过滤,减压蒸发,获得0.265g的纯5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-甲基-吡啶(化合物No.I.j.225),是白色固体。1H NMR(300Mhz,CDCl3)8.32ppm,1H,d,J=2.26Hz;7.39ppm,1H,dd,J=2.41和8.21Hz;7.21ppm,1H,d,J=8.21Hz;6.65ppm,2H,t,J=7.51Hz;2.60ppm,3H,s;2.32ppm,3H,s。
b)制备5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲基-吡啶化合物No.I.m.225)
将0.280g的5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-2-甲基-吡啶(化合物No.I.j.225)溶于5ml的四氢呋喃,该混合物在0℃下冷却。加入305μl的甲醇钠(30%)甲醇溶液,反应在室温下搅拌16h。加入5ml的乙酸乙酯,随后是5ml水,分层。水相用乙酸乙酯萃取两次,经合并的有机相在硫酸钠上干燥,过滤,减压蒸发,获得0.260g的5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲基-吡啶(化合物No.I.m.225)。1H NMR(300Mhz,CDCl3)8.22ppm,1H,d,J=2.26Hz;7.31ppm,1H,dd,J=2.39和8.21Hz;7.10ppm,1H,d,J=8.21Hz;6.32ppm,2H,d,J=9.1Hz;3.69ppm,3H,s;2.50ppm,3H,s;2.22ppm,3H,s。
实施例4:该实施例举例说明制备5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲氧基-吡啶(化合物No.I.m.220)
将0.102g的2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶(化合物No.I.j.210)溶于1.75ml的四氢呋喃,该混合物在0℃下冷却。加入132μl的甲醇钠(30%)甲醇溶液,反应在室温下搅拌16h。加入2ml的乙酸乙酯,随后是3ml水,分层。水相用乙酸乙酯萃取两次,经合并的有机相在硫酸钠上干燥,过滤,减压蒸发,获得0.099g的5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲氧基-吡啶(化合物No.I.m.220)。1H NMR(300Mhz,CDCl3)7.90ppm,1H,d,J=2.6Hz;7.28ppm,1H,dd,J=2.72和8.72Hz;6.67ppm,1H,d,J=8.78Hz;6.33ppm,2H,d,J=9.1Hz;3.86ppm,3H,s;3.69ppm,3H,s;2.21ppm,3H,s。
实施例5:该实施例举例说明制备2-氯-5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-吡啶(化合物No.I.m.210)
将0.089g的5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲氧基-吡啶(化合物No.I.m.220)溶于1ml的三氯氧化磷并回流24小时。将溶液倾至冷水中,搅拌30分钟,然后加入1M的氢氧化钠溶液从而达到中性。水溶液用二氯甲烷萃取三次,合并的有机馏分在硫酸钠上干燥,减压除去溶剂。粗混合物通过色谱柱在硅胶上纯化,使用庚烷/乙酸乙酯3∶1的混合物作为洗脱液,获得0.041g的2-氯-5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-吡啶(化合物No.I.m.210)。1H NMR(300Mhz,CDCl3)8.15ppm,1H,d,J=2.7Hz;7.39ppm,1H,dd,J=2.7和8.4Hz;7.31ppm,1H,d,J=8.4Hz;6.34ppm,2H,d,J=9.25Hz;3.71ppm,3H,s;2.25ppm,3H,s。
下述表1举例说明根据本发明的单个式I化合物的实例。
表1:根据本发明的单个式I化合物
化合物编号 | R1 | R2 | R3 |
001 | F | 苯基 | F |
002 | CH3 | 苯基 | F |
003 | F | 苯基 | Cl |
004 | Cl | 苯基 | Cl |
005 | CH3 | 苯基 | Cl |
006 | F | 3-氟苯基 | F |
007 | CH3 | 3-氟苯基 | F |
008 | F | 3-氟苯基 | Cl |
009 | Cl | 3-氟苯基 | Cl |
010 | CH3 | 3-氟苯基 | Cl |
011 | F | 4-氟苯基 | F |
化合物编号 | R1 | R2 | R3 |
012 | CH3 | 4-氟苯基 | F |
013 | F | 4-氟苯基 | Cl |
014 | Cl | 4-氟苯基 | Cl |
015 | CH3 | 4-氟苯基 | Cl |
016 | F | 3-氯苯基 | F |
017 | CH3 | 3-氯苯基 | F |
018 | F | 3-氯苯基 | Cl |
019 | Cl | 3-氯苯基 | Cl |
020 | CH3 | 3-氯苯基 | Cl |
021 | F | 4-氯苯基 | F |
022 | CH3 | 4-氯苯基 | F |
023 | F | 4-氯苯基 | Cl |
024 | Cl | 4-氯苯基 | Cl |
025 | CH3 | 4-氯苯基 | Cl |
026 | F | 3-溴苯基 | F |
027 | CH3 | 3-溴苯基 | F |
028 | F | 3-溴苯基 | Cl |
029 | Cl | 3-溴苯基 | Cl |
030 | CH3 | 3-溴苯基 | Cl |
031 | F | 4-溴苯基 | F |
032 | CH3 | 4-溴苯基 | F |
033 | F | 4-溴苯基 | Cl |
034 | Cl | 4-溴苯基 | Cl |
035 | CH3 | 4-溴苯基 | Cl |
036 | F | 间-甲苯基 | F |
037 | CH3 | 间-甲苯基 | F |
038 | F | 间-甲苯基 | Cl |
039 | Cl | 间-甲苯基 | Cl |
化合物编号 | R1 | R2 | R3 |
040 | CH3 | 间-甲苯基 | Cl |
041 | F | 对-甲苯基 | F |
042 | CH3 | 对-甲苯基 | F |
043 | F | 对-甲苯基 | Cl |
044 | Cl | 对-甲苯基 | Cl |
045 | CH3 | 对-甲苯基 | Cl |
046 | F | 3-三氟甲基苯基 | F |
047 | CH3 | 3-三氟甲基苯基 | F |
048 | F | 3-三氟甲基苯基 | Cl |
049 | Cl | 3-三氟甲基苯基 | Cl |
050 | CH3 | 3-三氟甲基苯基 | Cl |
051 | F | 4-三氟甲基苯基 | F |
052 | CH3 | 4-三氟甲基苯基 | F |
053 | F | 4-三氟甲基苯基 | Cl |
054 | Cl | 4-三氟甲基苯基 | Cl |
055 | CH3 | 4-三氟甲基苯基 | Cl |
056 | F | 3-甲氧基苯基 | F |
057 | CH3 | 3-甲氧基苯基 | F |
058 | F | 3-甲氧基苯基 | Cl |
059 | Cl | 3-甲氧基苯基 | Cl |
060 | CH3 | 3-甲氧基苯基 | Cl |
061 | F | 4-甲氧基苯基 | F |
062 | CH3 | 4-甲氧基苯基 | F |
063 | F | 4-甲氧基苯基 | Cl |
064 | Cl | 4-甲氧基苯基 | Cl |
065 | CH3 | 4-甲氧基苯基 | Cl |
066 | F | 3-三氟甲氧基苯基 | F |
067 | CH3 | 3-三氟甲氧基苯基 | F |
化合物编号 | R1 | R2 | R3 |
068 | F | 3-三氟甲氧基苯基 | Cl |
069 | Cl | 3-三氟甲氧基苯基 | Cl |
070 | CH3 | 3-三氟甲氧基苯基 | Cl |
071 | F | 4-三氟甲氧基苯基 | F |
072 | CH3 | 4-三氟甲氧基苯基 | F |
073 | F | 4-三氟甲氧基苯基 | Cl |
074 | Cl | 4-三氟甲氧基苯基 | Cl |
075 | CH3 | 4-三氟甲氧基苯基 | Cl |
076 | F | 3-氰基苯基 | F |
077 | CH3 | 3-氰基苯基 | F |
078 | F | 3-氰基苯基 | Cl |
079 | Cl | 3-氰基苯基 | Cl |
080 | CH3 | 3-氰基苯基 | Cl |
081 | F | 4-氰基苯基 | F |
082 | CH3 | 4-氰基苯基 | F |
083 | F | 4-氰基苯基 | Cl |
084 | Cl | 4-氰基苯基 | Cl |
085 | CH3 | 4-氰基苯基 | Cl |
086 | F | 3,4-二氟苯基 | F |
087 | CH3 | 3,4-二氟苯基 | F |
088 | F | 3,4-二氟苯基 | Cl |
089 | Cl | 3,4-二氟苯基 | Cl |
090 | CH3 | 3,4-二氟苯基 | Cl |
091 | F | 3,4-二氯苯基 | F |
092 | CH3 | 3,4-二氯苯基 | F |
093 | F | 3,4-二氯苯基 | Cl |
094 | Cl | 3,4-二氯苯基 | Cl |
095 | CH3 | 3,4-二氯苯基 | Cl |
化合物编号 | R1 | R2 | R3 |
096 | F | 3,4-二甲基苯基 | F |
097 | CH3 | 3,4-二甲基苯基 | F |
098 | F | 3,4-二甲基苯基 | Cl |
099 | Cl | 3,4-二甲基苯基 | Cl |
100 | CH3 | 3,4-二甲基苯基 | Cl |
101 | F | 3,4-二甲氧基苯基 | F |
102 | CH3 | 3,4-二甲氧基苯基 | F |
103 | F | 3,4-二甲氧基苯基 | Cl |
104 | Cl | 3,4-二甲氧基苯基 | Cl |
105 | CH3 | 3,4-二甲氧基苯基 | Cl |
106 | F | 3-氯-4-氟苯基 | F |
107 | CH3 | 3-氯-4-氟苯基 | F |
108 | F | 3-氯-4-氟苯基 | Cl |
109 | Cl | 3-氯-4-氟苯基 | Cl |
110 | CH3 | 3-氯-4-氟苯基 | Cl |
111 | F | 3-氯-4-甲基苯基 | F |
112 | CH3 | 3-氟-4-甲基苯基 | F |
113 | F | 3-氯-4-甲基苯基 | Cl |
114 | Cl | 3-氯-4-甲基苯基 | Cl |
115 | CH3 | 3-氯-4-甲基苯基 | Cl |
116 | F | 3-氯-4-甲氧基苯基 | F |
117 | CH3 | 3-氯-4-甲氧基苯基 | F |
118 | F | 3-氯-4-甲氧基苯基 | Cl |
119 | Cl | 3-氯-4-甲氧基苯基 | Cl |
120 | CH3 | 3-氯-4-甲氧基苯基 | Cl |
121 | F | 4-氯-3-氟苯基 | F |
122 | CH3 | 4-氯-3-氟苯基 | F |
123 | F | 4-氯-3-氟苯基 | Cl |
化合物编号 | R1 | R2 | R3 |
124 | Cl | 4-氯-3-氟苯基 | Cl |
125 | CH3 | 4-氯-3-氟苯基 | Cl |
126 | F | 4-氯-3-甲基苯基 | F |
127 | CH3 | 4-氯-3-甲基苯基 | F |
128 | F | 4-氯-3-甲基苯基 | Cl |
129 | Cl | 4-氯-3-甲基苯基 | Cl |
130 | CH3 | 4-氯-3-甲基苯基 | Cl |
131 | F | 4-氯-3-甲氧基苯基 | F |
132 | CH3 | 4-氯-3-甲氧基苯基 | F |
133 | F | 4-氯-3-甲氧基苯基 | Cl |
134 | Cl | 4-氯-3-甲氧基苯基 | Cl |
135 | CH3 | 4-氯-3-甲氧基苯基 | Cl |
136 | F | 3-氟-4-甲氧基苯基 | F |
137 | CH3 | 3-氟-4-甲氧基苯基 | F |
138 | F | 3-氟-4-甲氧基苯基 | Cl |
139 | Cl | 3-氟-4-甲氧基苯基 | Cl |
140 | CH3 | 3-氟-4-甲氧基苯基 | Cl |
141 | F | 3-氟-4-甲基苯基 | F |
142 | CH3 | 3-氟-4-甲基苯基 | F |
143 | F | 3-氟-4-甲基苯基 | Cl |
144 | Cl | 3-氟-4-甲基苯基 | Cl |
145 | CH3 | 3-氟-4-甲基苯基 | Cl |
146 | F | 4-氟-3-甲氧基苯基 | F |
147 | CH3 | 4-氟-3-甲氧基苯基 | F |
148 | F | 4-氟-3-甲氧基苯基 | Cl |
149 | Cl | 4-氟-3-甲氧基苯基 | Cl |
150 | CH3 | 4-氟-3-甲氧基苯基 | Cl |
151 | F | 4-氟-3-甲基苯基 | F |
化合物编号 | R1 | R2 | R3 |
152 | CH3 | 4-氟-3-甲基苯基 | F |
153 | F | 4-氟-3-甲基苯基 | Cl |
154 | Cl | 4-氟-3-甲基苯基 | Cl |
155 | CH3 | 4-氟-3-甲基苯基 | Cl |
156 | F | 3-甲氧基-4-甲基苯基 | F |
157 | CH3 | 3-甲氧基-4-甲基苯基 | F |
158 | F | 3-甲氧基-4-甲基苯基 | Cl |
159 | Cl | 3-甲氧基-4-甲基苯基 | Cl |
160 | CH3 | 3-甲氧基-4-甲基苯基 | Cl |
161 | F | 4-甲氧基-3-甲基苯基 | F |
162 | CH3 | 4-甲氧基-3-甲基苯基 | F |
163 | F | 4-甲氧基-3-甲基苯基 | Cl |
164 | Cl | 4-甲氧基-3-甲基苯基 | Cl |
165 | CH3 | 4-甲氧基-3-甲基苯基 | Cl |
166 | F | 萘-2-基 | F |
167 | CH3 | 萘-2-基 | F |
168 | F | 萘-2-基 | Cl |
169 | Cl | 萘-2-基 | Cl |
170 | CH3 | 萘-2-基 | Cl |
171 | F | 吡啶-2-基 | F |
172 | CH3 | 吡啶-2-基 | F |
173 | F | 吡啶-2-基 | Cl |
174 | Cl | 吡啶-2-基 | Cl |
175 | CH3 | 吡啶-2-基 | Cl |
176 | F | 吡啶-3-基 | F |
177 | CH3 | 吡啶-3-基 | F |
178 | F | 吡啶-3-基 | Cl |
179 | Cl | 吡啶-3-基 | Cl |
化合物编号 | R1 | R2 | R3 |
180 | CH3 | 吡啶-3-基 | Cl |
181 | F | 吡啶-4-基 | F |
182 | CH3 | 吡啶-4-基 | F |
183 | F | 吡啶-4-基 | Cl |
184 | Cl | 吡啶-4-基 | Cl |
185 | CH3 | 吡啶-4-基 | Cl |
186 | F | 6-氯吡啶-2-基 | F |
187 | CH3 | 6-氯吡啶-2-基 | F |
188 | F | 6-氯吡啶-2-基 | Cl |
189 | Cl | 6-氯吡啶-2-基 | Cl |
190 | CH3 | 6-氯吡啶-2-基 | Cl |
191 | F | 6-氟吡啶-2-基 | F |
192 | CH3 | 6-氟吡啶-2-基 | F |
193 | F | 6-氟吡啶-2-基 | Cl |
194 | Cl | 6-氟吡啶-2-基 | Cl |
195 | CH3 | 6-氟吡啶-2-基 | Cl |
196 | F | 6-甲氧基吡啶-2-基 | F |
197 | CH3 | 6-甲氧基吡啶-2-基 | F |
198 | F | 6-甲氧基吡啶-2-基 | Cl |
199 | Cl | 6-甲氧基吡啶-2-基 | Cl |
200 | CH3 | 6-甲氧基吡啶-2-基 | Cl |
201 | F | 6-甲基吡啶-2-基 | F |
202 | CH3 | 6-甲基吡啶-2-基 | F |
203 | F | 6-甲基吡啶-2-基 | Cl |
204 | Cl | 6-甲基吡啶-2-基 | Cl |
205 | CH3 | 6-甲基吡啶-2-基 | Cl |
206 | F | 6-氯吡啶-3-基 | F |
207 | CH3 | 6-氯吡啶-3-基 | F |
化合物编号 | R1 | R2 | R3 |
208 | F | 6-氯吡啶-3-基 | Cl |
209 | Cl | 6-氯吡啶-3-基 | Cl |
210 | CH3 | 6-氯吡啶-3-基 | Cl |
211 | F | 6-氟吡啶-3-基 | F |
212 | CH3 | 6-氟吡啶-3-基 | F |
213 | F | 6-氟吡啶-3-基 | Cl |
214 | Cl | 6-氟吡啶-3-基 | Cl |
215 | CH3 | 6-氟吡啶-3-基 | Cl |
216 | F | 6-甲氧基吡啶-3-基 | F |
217 | CH3 | 6-甲氧基吡啶-3-基 | F |
218 | F | 6-甲氧基吡啶-3-基 | Cl |
219 | Cl | 6-甲氧基吡啶-3-基 | Cl |
220 | CH3 | 6-甲氧基吡啶-3-基 | Cl |
221 | F | 6-甲基吡啶-3-基 | F |
222 | CH3 | 6-甲基吡啶-3-基 | F |
223 | F | 6-甲基吡啶-3-基 | Cl |
224 | Cl | 6-甲基吡啶-3-基 | Cl |
225 | CH3 | 6-甲基吡啶-3-基 | Cl |
226 | F | 2-氟吡啶-4-基 | F |
227 | CH3 | 2-氯吡啶-4-基 | F |
228 | F | 2-氯吡啶-4-基 | Cl |
229 | Cl | 2-氯吡啶-4-基 | Cl |
230 | CH3 | 2-氯吡啶-4-基 | Cl |
231 | F | 2-氟吡啶-4-基 | F |
232 | CH3 | 2-氟吡啶-4-基 | F |
233 | F | 2-氟吡啶-4-基 | Cl |
234 | Cl | 2-氟吡啶-4-基 | Cl |
235 | CH3 | 2-氟吡啶-4-基 | Cl |
化合物编号 | R1 | R2 | R3 |
236 | F | 2-甲氧基吡啶-4-基 | F |
237 | CH3 | 2-甲氧基吡啶-4-基 | F |
238 | F | 2-甲氧基吡啶-4-基 | Cl |
239 | Cl | 2-甲氧基吡啶-4-基 | Cl |
240 | CH3 | 2-甲氧基吡啶-4-基 | Cl |
241 | F | 2-甲基吡啶-4-基 | F |
242 | CH3 | 2-甲基吡啶-4-基 | F |
243 | F | 2-甲基吡啶-4-基 | Cl |
244 | Cl | 2-甲基吡啶-4-基 | Cl |
245 | CH3 | 2-甲基吡啶-4-基 | Cl |
246 | F | 5-氯噻吩-2-基 | F |
247 | CH3 | 5-氯噻吩-2-基 | F |
248 | F | 5-氯噻吩-2-基 | Cl |
249 | Cl | 5-氯噻吩-2-基 | Cl |
250 | CH3 | 5-氯噻吩-2-基 | Cl |
251 | F | 5-溴噻吩-2-基 | F |
252 | CH3 | 5-溴噻吩-2-基 | F |
253 | F | 5-溴噻吩-2-基 | Cl |
254 | Cl | 5-溴噻吩-2-基 | Cl |
255 | CH3 | 5-溴噻吩-2-基 | Cl |
256 | F | 5-甲氧基噻吩-2-基 | F |
257 | CH3 | 5-甲氧基噻吩-2-基 | F |
258 | F | 5-甲氧基噻吩-2-基 | Cl |
259 | Cl | 5-甲氧基噻吩-2-基 | Cl |
260 | CH3 | 5-甲氧基噻吩-2-基 | Cl |
261 | F | 喹啉-2-基 | F |
262 | CH3 | 喹啉-2-基 | F |
263 | F | 喹啉-2-基 | Cl |
化合物编号 | R1 | R2 | R3 |
264 | Cl | 喹啉-2-基 | Cl |
265 | CH3 | 喹啉-2-基 | Cl |
266 | F | 喹啉-3-基 | F |
267 | CH3 | 喹啉-3-基 | F |
268 | F | 喹啉-3-基 | Cl |
269 | Cl | 喹啉-3-基 | Cl |
270 | CH3 | 喹啉-3-基 | Cl |
271 | F | 4-甲氧基喹啉-2-基 | F |
272 | CH3 | 4-甲氧基喹啉-2-基 | F |
273 | F | 4-甲氧基喹啉-2-基 | Cl |
274 | Cl | 4-甲氧基喹啉-2-基 | Cl |
275 | CH3 | 4-甲氧基喹啉-2-基 | Cl |
276 | F | 4-甲基喹啉-2-基 | F |
277 | CH3 | 4-甲基喹啉-2-基 | F |
278 | F | 4-甲基喹啉-2-基 | Cl |
279 | Cl | 4-甲基喹啉-2-基 | Cl |
280 | CH3 | 4-甲基喹啉-2-基 | Cl |
其中
a)110个式(I.a)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
b)110个式(I.b)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
c)110个式(I.c)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
d)110个式(I.d)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
e)110个式(I.e)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
f)110个式(I.f)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
g)110个式(I.g)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
h)110个式(I.h)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
i)110个式(I.i)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
j)110个式(I.j)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
k)110个式(I.k)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
l)110个式(I.l)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
m)110个式(I.m)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
n)110个式(I.n)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
o)110个式(I.o)化合物:
其中R1,R2和R3如表1中对化合物171-280的定义。
p)280个式(I.p)化合物:
其中R1,R2和R3如表1中的定义。
q)280个式(I.q)化合物:
其中R1,R2和R3如表1中的定义。
r)280个式(I.r)化合物:
其中R1,R2和R3如表1中的定义。
s)280个式(I.s)化合物:
其中R1,R2和R3如表1中的定义。
t)280个式(I.t)化合物:
其中R1,R2和R3如表1中的定义。
u)280个式(I.u)化合物:
其中R1,R2和R3如表1中的定义。
v)280个式(I.v)化合物:
其中R1,R2和R3如表1中的定义。
w)280个式(I.w)化合物:
其中R1,R2和R3如表1中的定义。
x)280个式(I.x)化合物:
其中R1,R2和R3如表1中的定义。
y)280个式(I.y)化合物:
其中R1,R2和R3如表1中的定义。
z)280个式(I.z)化合物:
其中R1,R2和R3如表1中的定义。
aa)280个式(I.aa)化合物:
其中R1,R2和R3如表1中的定义。
ab)280个式(I.ab)化合物:
其中R1,R2和R3如表1中的定义。
ac)280个式(I.ac)化合物:
其中R1,R2和R3如表1中的定义。
说明书全文中,以摄氏度标记温度;“m.p.”表示熔点,“NMR”表示核磁共振谱;并且″%″是重量百分比,除非相应浓度以其它单位表示。
在说明书全文中使用下述缩写:
m.p.= 熔点 br = 宽峰
s = 单峰 dd = 双二重峰
d = 二重峰 dt = 双三重峰
t = 三重峰 q = 四重峰
m = 多重峰 ppm= 百万分之一
表2显示表中的化合物的经选择的NMR数据,都用CDCl3作溶剂(除非另有说明,并不试图列出全部情况下的全部表征数据)。
表2:对于表1化合物所选的NMR数据
化合物编号 | 1H-NMR数据(ppm/H的数量/重度) |
I.j.209 | 8.23ppm,1H,d,J=2.70Hz;7.54ppm,1H,dd,J=2.70和8.50Hz;7.43ppm,1H,d,J=8.36Hz;6.71ppm,2H,t,J=7.97Hz |
I.j.210 | 8.23ppm,1H,d,J=2.49Hz;7.47ppm,1H,dd,J=2.63和8.43Hz;7.40ppm,1H,d, |
化合物编号 | 1H-NMR数据(ppm/H的数量/重度) |
J=8.41Hz;6.68ppm,2H,t,J=7.45Hz;2.34ppm,3H,s | |
I.j.225 | 8.32ppm,1H,d,J=2.26Hz;7.39ppm,1H,dd,J=2.41和8.21Hz;7.21ppm,1H,d,J=8.21Hz;6.65ppm,2H,t,J=7.51Hz;2.60ppm,3H,s;2.32ppm,3H,s |
I.j.269 | 8.70ppm,1H,d,J=2.27Hz;8.17ppm,1H,d,J=8.37Hz;8.06ppm,1H,s;7.86ppm,2H,m;7.67ppm,1H,t,J=7.34Hz;6.64ppm,2H,t,J=7.82Hz |
I.j.270 | 8.61ppm,1H,d,J=2.24Hz;8.08ppm,1H,d,J=8.40Hz;7.92ppm,1H,d,J=2.13Hz;7.77ppm,1H,d,J=7.54Hz;7.76ppm,1H,t,J=8.25Hz;7.58ppm,1H,t,J=7.57Hz;6.52ppm,2H,t,J=7.79Hz;2.29ppm,3H,s |
I.m.210 | 1H NMR(300Mhz,CDCl3)8.15ppm,1H,d,J=2.7Hz;7.39ppm,1H,dd,J=2.7和8.4Hz;7.31ppm,1H,d,J=8.4Hz;6.34ppm,2H,d,J=9.25Hz;3.71ppm,3H,s;2.25ppm,3H,s。 |
I.m.220 | 1H NMR(300Mhz,CDCl3)7.90ppm,1H,d,J=2.6Hz;7.28ppm,1H,dd,J=2.72和8.72Hz;6.67ppm,1H,d,J=8.78Hz;6.33ppm,2H,d,J=9.1Hz;3.86ppm,3H,s;3.69ppm,3H,s;2.21ppm,3H,s。 |
I.m.225 | 8.22ppm,1H,d,J=2.26Hz;7.31ppm,1H, |
化合物编号 | 1H-NMR数据(ppm/H的数量/重度) |
dd,J=2.39和8.21Hz;7.10ppm,1H,d,J=8.21Hz;6.32ppm,2H,d,J=9.1Hz;3.69ppm,3H,s;2.50ppm,3H,s;2.22ppm,3H,s。 |
本发明化合物可以按照前面提及的反应流程制备,除非另有说明其中各变量的定义如之前对式(I)化合物的定义。
生物实施例
茄链格孢(Alternaria solani)/番茄/预防(对抗番茄上的链格孢
属(Alternaria)的作用)
在喷雾室中,用经制剂的测试化合物处理4周龄的番茄植株RoterGnom品种。施用两天后,通过在测试植株上喷雾孢子悬浮剂来接种番茄植株。在温室中22℃/18℃和95%r.h.下温育4天后,评价病害发生率。
根据本发明的化合物I.j.209、I.j.210、I.j.225、I.j.269、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
灰葡萄孢(Botrytis cinerea)/番茄/预防(对抗番茄上的葡萄孢
属(Botrytis)的作用)
在喷雾室中,用经制剂的测试化合物处理4周龄的番茄植株RoterGnom品种。施用两天后,通过在测试植株上喷雾孢子悬浮剂来接种番茄植株。在温室中20℃和95%r.h.下温育3天后,评价病害发生率。
根据本发明的化合物I.j.209、I.j.210、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
隐匿柄锈菌(Puccinia recondita)/小麦/预防(对抗小麦上的褐
锈病的作用)
在喷雾室中,用经制剂的测试化合物处理1周龄的小麦植株Arina品种。施用一天后通过在测试植株上喷雾孢子悬浮剂(1x105夏孢子/ml)来接种小麦植株。在20℃和95%r.h.下温育1天后,在温室中将植株在20℃/18℃(白天/夜晚)和60%r.h.下保持10天。在接种11天后评价病害发生率。
根据本发明的化合物I.j.210、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
稻瘟梨孢霉(Magnaporthe grisea)(稻瘟梨孢霉(Pyricularia
oryzae))/稻/预防(对抗稻瘟病的作用)
在喷雾室中,用经制剂的测试化合物处理3周龄的稻植株Koshihikari品种。施用两天后通过在测试植株上喷雾孢子悬浮剂(1x105分生孢子/ml)来接种稻植株。在25℃和95%r.h.下温育6天后评价病害发生率。
根据本发明的化合物I.j.209、I.j.210、I.j.225、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
圆核腔菌(Pyrenophora teres)(圆核腔菌(Helminthosporium
teres))/大麦/预防(对抗大麦上的网斑病的作用)
在喷雾室中,用经制剂的测试化合物处理1周龄的大麦植株Regina品种。施用两天后通过在测试植株上喷雾孢子悬浮剂(2.6x104分生孢子/ml)来接种大麦植株。在20℃和95%r.h.下温育4天后评价病害发生率。
根据本发明的化合物I.j.209、I.j.210、I.j.269、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
小麦壳针孢(Septoria tritici)/小麦/预防(对抗小麦上的壳针
孢属(Septoria)叶斑病的作用)
在喷雾室中,用经制剂的测试化合物处理2周龄的小麦植株Riband品种。施用一天后,通过在测试植株上喷雾孢子悬浮剂(106分生孢子/ml)来接种小麦植株。在22℃/21℃和95%r.h.下温育1天后,在温室中将植株保持在22℃/21℃和70%r.h.下。在接种16-18天后评价病害发生率。
根据本发明的化合物I.j.209、I.j.210、I.j.225、I.j.269、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
葡萄钩丝壳(Uncinula necator)/葡萄/预防(对抗葡萄上的白粉
病的作用)
在喷雾室中,用经制剂的测试化合物处理5周龄的葡萄幼苗Gutedel品种。施用一天后,通过在测试植株上方抖动被葡萄白粉病感染的植株来接种葡萄植株。在14/10h(光照/黑暗)的光照制度下、在24℃/22℃和70%r.h.下温育7天后,评价病害发生率。
根据本发明的化合物I.j.210、I.j.225、I.j.269、I.j.270、I.m.210、I.m.220和I.m.225在200ppm抑制本测试中的真菌侵染的至少80%,而在相同条件下未经处理的对照植物被致植物病真菌的侵染为大于80%。
Claims (17)
1.式I化合物:
其中
R1是卤素、C1-C4烷基或C1-C4卤代烷基;
R2是任选经取代的芳基或杂芳基,其中所述任选的取代基选自卤素、烷基、卤代烷基、环烷基、环烷基烷基、烯基、卤代烯基、环烯基、炔基、卤代炔基、烷氧基、卤代烷氧基、环烷氧基、烯氧基、卤代烯氧基、炔氧基、卤代烯氧基、烷硫基、卤代烷硫基、环烷硫基、烯硫基、炔硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烯基羰基、炔基羰基、烷氧基烷基、氰基、硝基、羟基、巯基、氨基、烷基氨基和二烷基氨基;
R3是卤素;
R4是氢、卤素、C1-C4烷基、C1-C4卤代烷基、羟基、C1-C4烷氧基、OR6或氰基;
R5是卤素;
R6是氢、C3-C7环烷基、C3-C10烷基环烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C3-C7环烯基、C2-C6炔基、C2-C6卤代炔基或C2-C6烷氧基烷基;
X是N或C(R);和
R是氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或氰基;
或其农业化学上可使用的盐;
条件是
当X是C(R)时,R2不能是任选经取代的芳基。
2.根据权利要求1的化合物,其中R1是卤素、C1-C3烷基或C1-C3卤代烷基。
3.根据权利要求1或2的化合物,其中R2是任选经取代的苯基、萘基、噻吩基、吡啶基、喹啉基或异喹啉基,其中所述任选的取代基选自卤素、烷基、卤代烷基、环烷基、环烷基烷基、烯基、卤代烯基、环烯基、炔基、卤代炔基、烷氧基、卤代烷氧基、环烷氧基、烯氧基、卤代烯氧基、炔氧基、卤代烯氧基、烷硫基、卤代烷硫基、环烷硫基、烯硫基、炔硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烯基羰基、炔基羰基、烷氧基烷基、氰基、硝基、羟基、巯基、氨基、烷基氨基和二烷基氨基。
4.根据权利要求1-3中任一项的化合物,其中R3是氟、氯、溴或碘。
5.根据权利要求1-4中任一项的化合物,其中R4是氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、OR6或氰基。
6.根据权利要求1-5中任一项的化合物,其中R5是氟、氯、溴或碘。
7.根据权利要求1-6中任一项的化合物,其中R6是氢、C3-C7环烷基、C3-C10烷基环烷基、C1-C6卤代烷基、C2-C6烯基、C3-C7环烯基、C2-C6炔基或C2-C6烷氧基烷基。
8.根据权利要求1-7中任一项的化合物,其中X是N、C(H)、C(卤素)、C(C1-C4烷基)、C(C1-C4卤代烷基)、C(C1-C4烷氧基)或C(C1-C4卤代烷氧基)。
9.根据权利要求1-8中任一项的化合物,其中
R1是氟、氯、溴、碘、C1-C2烷基或C1-C2卤代烷基;
R2是任选经取代的苯基、萘基、噻吩基、吡啶基或喹啉基,其中所述任选的取代基选自卤素、烷基、卤代烷基、环烷基、环烷基烷基、烯基、卤代烯基、环烯基、炔基、卤代炔基、烷氧基、卤代烷氧基、环烷氧基、烯氧基、卤代烯氧基、炔氧基、卤代烯氧基、烷硫基、卤代烷硫基、环烷硫基、烯硫基、炔硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烯基羰基、炔基羰基、烷氧基烷基、氰基、硝基、羟基、巯基、氨基、烷基氨基和二烷基氨基;
R3是氟、氯或溴;
R4是氢、氟、氯、溴、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基或氰基;
R5是氟、氯或溴;和
X是N、C(H)、C(Cl)、C(F)、C(Br)、C(I)、C(C1-C3烷基)、C(C1-C3卤代烷基)、C(C1-C3烷氧基)或C(C1-C3卤代烷氧基)。
10.根据权利要求1-9中任一项的化合物,其中
R1是氟、氯、溴、甲基或乙基;
R2是苯基、3-氟苯基、4-氟苯基,3-氯苯基,4-氯苯基,3-溴苯基,4-溴苯基,间-甲苯基,对-甲苯基,3-三氟甲基苯基,4-三氟甲基苯基,3-甲氧基苯基,4-甲氧基苯基,3-三氟甲氧基苯基,4-三氟甲氧基苯基,3-氰基苯基,4-氰基苯基,3,4-二氟苯基,3,4-二氯苯基,3,4-二甲基苯基,3,4-二甲氧基苯基,3-氯-4-氟苯基,3-氯-4-甲基苯基,3-氯-4-甲氧基苯基,4-氯-3-氟苯基,4-氯-3-甲基苯基,4-氯-3-甲氧基苯基,萘-2-基,3-氟-4-甲氧基苯基,3-氟-4-甲基苯基,4-氟-3-甲氧基苯基,4-氟-3-甲基苯基,3-甲氧基-4-甲基苯基,4-甲氧基-3-甲基苯基,吡啶-2-基,吡啶-3-基,吡啶-4-基,6-氯吡啶-2-基,6-氟吡啶-2-基,6-甲氧基吡啶-2-基,6-甲基吡啶-2-基,6-氯吡啶-3-基,6-氟吡啶-3-基,6-甲氧基吡啶-3-基,6-甲基吡啶-3-基,2-氯吡啶-4-基,2-氟吡啶-4-基,2-甲氧基吡啶-4-基,2-甲基吡啶-4-基,5-氯噻吩-2-基,5-溴噻吩-2-基,5-甲氧基噻吩-2-基,喹啉-2-基,喹啉-3-基,4-甲氧基喹啉-2-基或4-甲基喹啉-2-基;
R3是氟或氯;
R4是氢、氟、氯、C1-C2烷基、C1-C2卤代烷基、C1-C2烷氧基、C1-C2卤代烷氧基或氰基;
R5是氟或氯;和
X是N、C(H)、C(C l)、C(F)、C(Br)、C(C1-C2烷基)、C(C1-C2卤代烷基)、C(C1-C2烷氧基)或C(C1-C2卤代烷氧基)。
11.根据权利要求1-10中任一项的化合物,其中
R1是氟、氯、甲基或乙基;
R2是4-氟苯基、4-氯苯基、4-溴苯基、对-甲苯基、6-氯吡啶-3-基、6-氟吡啶-3-基、6-甲氧基吡啶-3-基、6-甲基吡啶-3-基、2-氯吡啶-4-基、2-氟吡啶-4-基、2-甲氧基吡啶-4-基、2-甲基吡啶-4-基、喹啉-2-基、喹啉-3-基、4-甲氧基喹啉-2-基或4-甲基喹啉-2-基;
R3是氟或氯;
R4是氢、氟、氯、C1-C2烷基、C1-C2卤代烷基或C1-C2烷氧基;
R5是氟或氯;和
X是N、C(H)、C(Cl)或C(F)。
12.根据权利要求1-11中任一项的化合物,其中
R1是氯或甲基;
R2是6-氯吡啶-3-基、6-甲基吡啶-3-基、6-甲氧基吡啶-3-基或喹啉-3-基;
R3是氯;
R4是氟或甲氧基;
R5是氟;和
X是C(F)。
13.化合物,选自:
2-氯-5-[2,4-二氯-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶;
2-氯-5-[4-氯-2-甲基-5-(2,4,6-三氟-苯基)-咪唑-1-基]-吡啶;
2-氯-5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-吡啶;
5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲氧基-吡啶;和
5-[4-氯-5-(2,6-二氟-4-甲氧基-苯基)-2-甲基-咪唑-1-基]-2-甲基-吡啶。
14.用于防治或保护对抗致植物病微生物的杀真菌组合物,其包含作为活性成分的权利要求1到13任一项中所定义的至少一种化合物,为游离形式或农业化学可使用盐的形式,和至少一种助剂。
15.权利要求1到13中任一项定义的化合物的用途,其用于防治或预防致植物病微生物对植物、收获的粮食作物、种子或非生命材料的侵染。
16.防治或预防致植物病微生物或有害微生物或潜在对人有害的生物侵染作物植物、收获的粮食作物或非生命材料的方法,其包含将权利要求1到13中任一项定义的化合物作为活性成分施用至植物、植物部分或其所在地、种子或者所述非生命材料的任何部分。
17.权利要求16的方法,其中所述致植物病微生物是真菌。
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US (1) | US20110311649A1 (zh) |
EP (2) | EP2053046A1 (zh) |
JP (1) | JP2011500749A (zh) |
KR (1) | KR20100101579A (zh) |
CN (1) | CN101835772B (zh) |
AR (1) | AR069036A1 (zh) |
AT (1) | ATE524457T1 (zh) |
AU (1) | AU2008315561A1 (zh) |
BR (1) | BRPI0818863A2 (zh) |
CA (1) | CA2702786A1 (zh) |
CL (1) | CL2008003179A1 (zh) |
EA (1) | EA201000604A1 (zh) |
GT (1) | GT200800230A (zh) |
IL (1) | IL205149A0 (zh) |
MA (1) | MA31784B1 (zh) |
MX (1) | MX2010004052A (zh) |
NZ (1) | NZ584575A (zh) |
TW (1) | TW200930295A (zh) |
WO (1) | WO2009053101A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PE20091953A1 (es) * | 2008-05-08 | 2010-01-09 | Du Pont | Azoles sustituidos como fungicidas |
WO2010032874A1 (ja) * | 2008-09-19 | 2010-03-25 | 住友化学株式会社 | 農業用組成物 |
JP2013503129A (ja) * | 2009-08-26 | 2013-01-31 | ノバルティス アーゲー | テトラ−置換ヘテロアリール化合物ならびにmdm2および/またはmdm4モジュレーターとしてのそれらの使用 |
US8680121B2 (en) * | 2010-11-03 | 2014-03-25 | Dow Agrosciences, Llc. | Pesticidal compositions and processes related thereto |
CN102499218B (zh) * | 2011-10-21 | 2014-04-09 | 福建农林大学 | 农药毒理实验预处理装置及方法 |
CN109810062B (zh) * | 2019-01-24 | 2022-06-17 | 云南农业大学 | 一种苯基咪唑衍生物及其合成方法和在农药中的应用 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3261873A (en) * | 1961-08-04 | 1966-07-19 | Dow Chemical Co | Substituted 2-halo-4-aminoimidazoles and preparatory process |
CA1340685C (en) | 1988-07-29 | 1999-07-27 | Frederick Meins | Dna sequences encoding polypeptides having beta-1,3-glucanase activity |
ES2199931T3 (es) | 1989-03-24 | 2004-03-01 | Syngenta Participations Ag | Plantas transgenicas resistentes a enfermedades. |
US5639949A (en) | 1990-08-20 | 1997-06-17 | Ciba-Geigy Corporation | Genes for the synthesis of antipathogenic substances |
US6262058B1 (en) | 1996-03-11 | 2001-07-17 | Syngenta Crop Protection, Inc. | Pyrimidin-4-one derivatives as pesticide |
TWI252231B (en) | 1997-04-14 | 2006-04-01 | American Cyanamid Co | Fungicidal trifluorophenyl-triazolopyrimidines |
EP1003726A1 (de) * | 1997-07-24 | 2000-05-31 | Bayer Aktiengesellschaft | Nitrophenyl-sulfonyl-imidazole und deren verwendung zur bekämpfung von pflanzlichen und tierischen schädlingen |
RU2316548C2 (ru) | 2002-08-12 | 2008-02-10 | Байер Кропсайенс С.А. | Новое производное 2-пиридилэтилбензамида, способ его получения, фунгицидная композиция, способ профилактического или лечебного подавления фитопатогенных грибков |
GB0224316D0 (en) | 2002-10-18 | 2002-11-27 | Syngenta Participations Ag | Chemical compounds |
WO2004052280A2 (en) | 2002-12-10 | 2004-06-24 | Imclone Systems Incorporated | Anti-angiogenic compounds and their use in cancer treatment |
EP1720862A1 (en) * | 2004-02-03 | 2006-11-15 | Eli Lilly And Company | Kinase inhibitors |
ES2324883T3 (es) | 2004-06-09 | 2009-08-18 | Sumitomo Chemical Company, Limited | Compuesto de piridazina y su utilizacion. |
WO2006001175A1 (ja) | 2004-06-28 | 2006-01-05 | Sumitomo Chemical Company, Limited | ピリダジン化合物及びその用途 |
GB0422401D0 (en) | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
AU2006322707B2 (en) | 2005-12-07 | 2011-09-15 | Sumitomo Chemical Company, Limited | Pyridazine compound and use thereof |
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2008
- 2008-04-10 EP EP08007093A patent/EP2053046A1/en not_active Ceased
- 2008-10-24 AU AU2008315561A patent/AU2008315561A1/en not_active Abandoned
- 2008-10-24 EA EA201000604A patent/EA201000604A1/ru unknown
- 2008-10-24 AR ARP080104657A patent/AR069036A1/es not_active Application Discontinuation
- 2008-10-24 US US12/739,852 patent/US20110311649A1/en not_active Abandoned
- 2008-10-24 JP JP2010530349A patent/JP2011500749A/ja not_active Withdrawn
- 2008-10-24 CN CN2008801132706A patent/CN101835772B/zh not_active Expired - Fee Related
- 2008-10-24 KR KR1020107011564A patent/KR20100101579A/ko not_active Application Discontinuation
- 2008-10-24 CL CL2008003179A patent/CL2008003179A1/es unknown
- 2008-10-24 MX MX2010004052A patent/MX2010004052A/es not_active Application Discontinuation
- 2008-10-24 GT GT200800230A patent/GT200800230A/es unknown
- 2008-10-24 EP EP08842112A patent/EP2201001B1/en not_active Not-in-force
- 2008-10-24 BR BRPI0818863 patent/BRPI0818863A2/pt not_active IP Right Cessation
- 2008-10-24 NZ NZ584575A patent/NZ584575A/en not_active IP Right Cessation
- 2008-10-24 WO PCT/EP2008/009042 patent/WO2009053101A1/en active Application Filing
- 2008-10-24 TW TW097140815A patent/TW200930295A/zh unknown
- 2008-10-24 AT AT08842112T patent/ATE524457T1/de not_active IP Right Cessation
- 2008-10-24 CA CA2702786A patent/CA2702786A1/en not_active Abandoned
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2010
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- 2010-04-22 MA MA32784A patent/MA31784B1/fr unknown
Also Published As
Publication number | Publication date |
---|---|
MA31784B1 (fr) | 2010-10-01 |
EP2201001A1 (en) | 2010-06-30 |
EA201000604A1 (ru) | 2010-12-30 |
AU2008315561A1 (en) | 2009-04-30 |
GT200800230A (es) | 2009-11-24 |
AR069036A1 (es) | 2009-12-23 |
US20110311649A1 (en) | 2011-12-22 |
JP2011500749A (ja) | 2011-01-06 |
WO2009053101A1 (en) | 2009-04-30 |
ATE524457T1 (de) | 2011-09-15 |
IL205149A0 (en) | 2010-11-30 |
EP2053046A1 (en) | 2009-04-29 |
NZ584575A (en) | 2011-07-29 |
KR20100101579A (ko) | 2010-09-17 |
MX2010004052A (es) | 2010-04-30 |
TW200930295A (en) | 2009-07-16 |
CN101835772A (zh) | 2010-09-15 |
EP2201001B1 (en) | 2011-09-14 |
BRPI0818863A2 (pt) | 2015-05-05 |
CL2008003179A1 (es) | 2009-06-05 |
CA2702786A1 (en) | 2009-04-30 |
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