CN1171863C - 氨基甲酸酯衍生物及农用、园艺用杀菌剂 - Google Patents

氨基甲酸酯衍生物及农用、园艺用杀菌剂 Download PDF

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CN1171863C
CN1171863C CNB008112495A CN00811249A CN1171863C CN 1171863 C CN1171863 C CN 1171863C CN B008112495 A CNB008112495 A CN B008112495A CN 00811249 A CN00811249 A CN 00811249A CN 1171863 C CN1171863 C CN 1171863C
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halogen atom
replaced
carbonyl
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CN1368956A (zh
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尾崎正美
����һ
福本俊一郎
玉井龙二
米仓范久
池谷和弘
川岛隆弘
境润悦
ϲһ
村松宪通
高垣真喜一
永山孝三
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Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
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Kumiai Chemical Industry Co Ltd
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Abstract

本发明提供了对作物不会产生不良影响，但对植物病害、特别是禾白粉菌和黄瓜灰霉菌具有较高预防除治效果的新颖的杀菌剂。即，本发明提供了通式[I]表示的氨基甲酸酯衍生物及以这些氨基甲酸酯衍生物为有效组分的农用、园艺用杀菌剂，式中，X表示卤原子、C1～C6烷基等，n表示0或1～4的整数，R1表示C1～C6烷基，R2表示氢原子、C1～C6烷基等，R3表示氢原子或C1～C6烷基，G表示氧原子、硫原子等，Y表示氢原子、C1～C6烷基、C2～C10链烯基等，Q表示氢原子、C1～C6卤代烷基、苯基等。

Description

氨基甲酸酯衍生物及农用、园艺用杀菌剂
技术领域
本发明涉及新颖的氨基甲酸酯衍生物及以该衍生物为有效组分的农用、园艺用杀虫剂。
背景技术
以往，虽然对氨基甲酸衍生物有许多报道，但对本发明的化合物的苯基上具有肟醚基的氨基甲酸酯衍生物具有良好的杀菌作用却没有任何报道。
本发明的目的是提供新颖的氨基甲酸酯衍生物及以此为有效组分的农用、园艺用杀菌剂。
发明的揭示
本发明者们为获得新颖的农用、园艺用杀菌剂进行了认真研究后的结果是，本发明的氨基甲酸酯衍生物(以下称为本发明的化合物)是文献中未记载过的新颖化合物，且作为农用、园艺用杀菌剂使用时显现出很好的效果，从而完成了本发明。即，本发明(1)为通式[I]表示的氨基甲酸酯衍生物及(2)以此为有效成分的农用、园艺用杀菌剂，
式中，X表示卤原子、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6卤代烷氧基，n表示0或1～4的整数，R1表示C1～C6烷基，R2表示氢原子、C1～C6烷基、C2～C6链烯基、C2～C6炔基、C1～C6烷氧基、C1～C6烷氧基C1～C6烷基、C1～C6烷基羰基、C1～C6烷氧基羰基、C1～C6烷基羰基C1～C6烷基或可取代的苄基，R3表示氢原子或C1～C6烷基，G表示氧原子、硫原子或-NR4-基[R4表示氢原子或C1～C6烷基]，Y表示氢原子、C1～C10烷基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、羟基、C3～C6环烷基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6烷基亚磺酰基、羧基、C1～C6烷基羰基、C1～C6烷氧基羰基、C1～C6烷氧基亚氨基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、C2～C10链烯基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、C2～C10炔基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、环烷基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、C3～C6环烷基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、C2～C6炔基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、C3～C6环烯基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、羟基、C2～C6炔基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷氧基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、苯甲酰甲基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基、C1～C6烷基羰基或C1～C6烷氧基羰基)、芳基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、C2～C6炔基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、杂芳基(所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、C2～C6炔基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、芳基-C1～C6烷基(所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、C2～C6炔基、可被取代的苯氧基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6卤代烷氧基、C1～C6烷基羰基、C1～C6烷氧基羰基、C1～C6烷氧基亚氨基C1～C6烷基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、芳基-C2～C6链烯基(所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、C2～C6炔基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))、杂环-C1～C6烷基(所述基团中的杂环可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C2～C6链烯基、C2～C6炔基、羟基、C1～C6烷氧基、氨基、一C1～C6烷基氨基、二C1～C6烷基氨基、C1～C6烷基硫代基、C1～C6卤代烷基、C1～C6烷基羰基、C1～C6烷氧基羰基或C(O)NR5R6(R5和R6可相同或不同表示氢原子或C1～C6烷基))，Q表示氢原子、卤代烷基、氰基、C1～C6烷基、C3～C6环烷基、C1～C4烷基硫代基、C1～C4烷基亚磺酰基、C1～C4烷基磺酰基或苯基(所述基团可被至少1个选自卤原子、氰基、硝基、C1～C4烷基、C2～C4链烯基、C2～C4炔基、羟基、C1～C4烷氧基、C1～C4卤代烷基、C1～C4卤代烷氧基、C1～C4烷基羰基或C1～C4烷氧基羰基的基团取代)。
本说明书中记载的符号及用语的说明如下。
卤原子表示氟原子、氯原子、溴原子或碘原子。
C1～C10等的描述是指其后的取代基的碳原子数为1～10。
C1～C6烷基表示直链或支链状烷基，例如，甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基、1，1-二甲基丙基、1，1-二甲基丁基等基团。
C1～C10烷基表示前述C1～C6烷基、庚基、辛基、1，1-二乙基丁基、壬基、癸基等基团。
C3～C6环烷基表示环丙基、环丁基、环戊基、环己基等基团。
C3～C6环烯基表示1-环戊烯-1-基、2-环戊烯-1-基、1-环己烯-1-基、2-环己烯-1-基等基团。
C1～C6卤代烷基表示被卤原子取代的直链或支链状烷基，例如，氟甲基、氯甲基、二氟甲基、二氯甲基、三氟甲基、五氟乙基等基团。
C2～C10链烯基表示直链或支链状链烯基，例如，乙烯基、1-丙烯基、2-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、1-己烯基、1-辛烯基等基团。
C2～C10炔基表示直链或支链状炔基，例如，乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、4-甲基-1-戊炔基、3-甲基-1-戊炔基等基团。
C1～C6烷氧基表示烷基部分如前所述的烷氧基，例如，甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、异戊氧基、正己氧基等基团。
C1～C6卤代烷氧基表示卤代烷基部分如前所述的卤代烷氧基，例如，氟甲氧基、二氟甲氧基、三氟甲氧基、五氟乙氧基等基团。
C1～C6烷氧基亚氨基表示烷氧基部分如前所述的烷氧基亚氨基，例如，甲氧基亚氨基等。
C1～C6烷氧基亚氨基C1～C6烷基表示烷氧基部分、烷基部分如前所述的烷氧基亚氨基烷基，例如，1-甲氧基亚氨基乙基等基团。
C1～C6烷基羰基表示烷基部分如前所述的烷基羰基，例如，乙酰基、丙酰基、丁酰基、异丁酰基、三甲基乙酰基、己酰基等基团。
C1～C6烷氧基羰基表示烷氧基部分如前所述的烷氧基羰基，例如，甲氧基羰基、乙氧基羰基、异丙氧基羰基、己氧基羰基等基团。
C1～C6烷基羰基C1～C6烷基表示烷基部分如前所述的烷基羰基烷基，例如，2-羰丙基、3-羰丁基、3-羰戊基、3，3-二甲基-2-羰丁基等基团。
芳基表示芳香族烃基，例如，苯基、1-萘基、2-萘基等基团。
杂环-C1～C6烷基表示烷基部分为-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH(Me)-、-C(Me)2-、-CH(Et)-等，杂环部分表示由2～9个碳原子、0～3个氮原子、0～3个氧原子、0～3个硫原子构成的3～10元环，例如，吡咯基、呋喃基、噻吩基、吡唑基、异噁唑基、异噻唑基、咪唑基、噁唑基、噻唑基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、吲哚基、苯并呋喃基、苯并噻吩基、苯并咪唑基、苯并噁唑基、苯并噻唑基、喹啉基、异喹啉基、吗啉基、环氧乙基、二氧杂环戊基等基团。
杂芳基表示多个由2～9个碳原子、0～3个氮原子、0～3个氧原子、0～3个硫原子构成的5～10元芳香环基，例如，吡咯基、呋喃基、噻吩基、吡唑基、异噁唑基、异噻唑基、咪唑基、噁唑基、噻唑基、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、吲哚基、苯并呋喃基、苯并噻吩基、苯并咪唑基、苯并噁唑基、苯并噻唑基、喹啉基、异喹啉基等杂环基。
C1～C6烷氧基C1～C6烷基表示烷基部分及烷氧基部分如前所述的基团，例如，甲氧基甲基、乙氧基甲基、异丙氧基甲基、戊氧基甲基、甲氧基乙基、丁氧基乙基等基团。
一C1～C6烷基氨基表示烷基部分如前所述的基团，例如，甲基氨基、乙基氨基、异丙基氨基、丁基氨基、叔丁基氨基等基团。
二C1～C6烷基氨基表示烷基部分如前所述的基团，其中的2个烷基可以相同也可以不同，例如，二甲基氨基、二乙基氨基、甲基乙基氨基、甲基异丙基氨基、二己基氨基等基团。
C1～C6烷基硫代基表示烷基部分如前所述的基团，例如，甲基硫代基、乙基硫代基、异丙基硫代基、丁基硫代基、己基硫代基等基团。
C1～C6烷基亚磺酰基表示烷基部分如前所述的基团，例如，甲基亚磺酰基、乙基亚磺酰基、异丙基亚磺酰基、丁基亚磺酰基、己基亚磺酰基等基团。
C1～C6烷基磺酰基表示烷基部分如前所述的基团，例如，甲基磺酰基、乙基磺酰基、异丙基磺酰基、丁基磺酰基、己基磺酰基等基团。
芳基C1～C6烷基的芳基部分如前所述，烷基部分为-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH(Me)-、-C(Me)2-、-CH(Et)-等基团。
芳基C1～C6链烯基的芳基部分如前所述，链烯基部分为-CH＝CH-、-CH＝CHCH2-、-C(Me)＝CH-、-CH(Et)＝CH-、-C(Me)＝CHCH2-等基团。
杂芳基C1～C6烷基的杂芳基部分如前所述，烷基部分为-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH(Me)-、-C(Me)2-、-CH(Et)-等基团。
实施发明的最佳方式
通式[I]表示的本发明化合物的具体例示于表1～表13。但是，本发明化合物并不仅限于这些化合物。此外，其后的说明中参考这些化合物编号。
表中符号的含义如下。Me表示甲基，Et表示乙基，Pr表示正丙基，Pr-i表示异丙基，Bu表示正丁基，Bu-i表示异丁基，Bu-s表示仲丁基，Bu-t表示叔丁基，Hex表示正己基，Pr-c表示环丙基，Pen-c表示环戊基，Hex-c表示环己基，Ph表示苯基。例如，Ph(4-Cl)表示4-氯苯基。
通式[1]表示的本发明化合物的分子内具有与E/Z异构体有关的1个或2～3个双键时，这种化合物存在E/Z异构体混合物。本发明化合物包括纯粹的E体、Z体及它们的混合物。以下所示的化合物是与肟部分的双键有关的几何异构体(A-80和A-206、A-84和A-207、A-85和A-208、A-86和A-209、A-286和A-448)。
                                    表1
                                        表2
化合物编号 G    R1  R2  R3 X1   X3 X3  X4 Q        Y 熔点(℃)或折射率(nD 20)
A-42A-43A-44A-45A-46A-47A-48A-49A-50A-51A-52A-53A-64A-55A-56A-57A-58A-59A-60A-61A-62A-63A-64A-65A-66A-67A-68A-69A-70A-71A-72A-73A-74A-75A-76A-77A-78A-79A-80A-81A-82A-83A-84A-85A-86A-87A-88A-89A-90A-91A-92A-93A-94A-95A-96 O    Me   H    H  H     H  H    H Ph      MeO    Me   H    H  H     H  H    H Ph      EtO    Me   H    H  H     H  H    H Ph(4-Cl)EtO    Me   H    H  Cl    H  H    H Me      HO    Me   H    H  Cl    H  H    H Me      MeO    Et   H    H  Cl    H  H    H Me      MeO    Pr   H    H  Cl    H  H    H Me      MeO    Me   H    H  Cl    H  H    H Me      EtO    Me   H    H  Cl    H  H    H Me      PrO    Me   H    H  Cl    H  H    H Me      Pr-iO    Me   H    H  Cl    H  H    H Me      BuO    Me   H    H  Cl    H  H    H Me      Bu-sO    Me   H    H  Cl    H  H    H Me      Bu-iO    Me   H    H  Cl    H  H    H Me      Bu-tO    Me   H    H  Cl    H  H    H Me      CH2Pr-cO    Me   H    H  Cl    H  H    H Me      Pen-cO    Me   H    H  Cl    H  H    H Me      CH2CH＝CH2O    Me   H    H  Cl    H  H    H Me      CH2C(Me)＝CH2O    Me   H    H  Cl    H  H    H Me      CH2CH＝CHCO2EtO    Me   H    H  Cl    H  H    H Me      CH2C≡CHO    Me   H    H  Cl    H  H    H Me      CH2CH2CH2PhO    Me   H    H  Cl    H  H    H Me      CH2COOEtO    Me   H    H  Cl    H  H    H Me      CH2COOBu-tO    Me   H    H  Cl    H  H    H Me      CH2CON(Me)2O    Me   H    H  Cl    H  H    H Me      CH2CO2HO    Me   H    H  Cl    H  H    H Me      CH2OMeO    Me   H    H  Cl    H  H    H Me      CH2SMeO    Me   H    H  Cl    H  H    H Me      CH2SOMeO    Me   H    H  Cl    H  H    H Me      CH2CF3O    Me   H    H  Cl    H  H    H Me      CH2CNO    Me   H    H  Cl    H  H    H Me      CH＝CH2O    Me   H    H  Cl    H  H    H Me      PhO    Me   H    H  Cl    H  H    H Me      Ph(3-Cl)O    Me   H    H  Cl    H  H    H Me      Ph(4-Cl)O    Me   H    H  Cl    H  H    H Me      Ph(3-Me)O    Me   H    H  Cl    H  H    H Me      Ph(4-Me)O    Me   H    H  Cl    H  H    H Me      Ph(3-CF3)O    Me   H    H  Cl    H  H    H Me      Ph(4-CF3)O    Me   H    H  Cl    H  H    H Me      CH2PhO    Me   H    H  Cl    H  H    H Me      CH2Ph(2-F)O    Me   H    H  Cl    H  H    H Me      CH2Ph(3-F)O    Me   H    H  Cl    H  H    H Me      CH2Ph(4-F)O    Me   H    H  Cl    H  H    H Me      CH2Ph(2-Cl)O    Me   H    H  Cl    H  H    H Me      CH2Ph(3-Cl)O    Me   H    H  Cl    H  H    H Me      CH2Ph(4-Cl)O    Me   H    H  Cl    H  H    H Me      CH2Ph(2-Br)O    Me   H    H  Cl    H  H    H Me      CH2Ph(3-Br)O    Me   H    H  Cl    H  H    H Me      CH2Ph(4-Br)O    Me   H    H  Cl    H  H    H Me      CH2Ph(2-Me)O    Me   H    H  Cl    H  H    H Me      CH2Ph(3-Me)O    Me   H    H  Cl    H  H    H Me      CH2Ph(4-Me)O    Me   H    H  Cl    H  H    H Me      CH2Ph(2-OMe)O    Me   H    H  Cl    H  H    H Me      CH2Ph(3-OMe)O    Me   H    H  Cl    H  H    H Me      CH2Ph(4-OMe)O    Me   H    H  Cl    H  H    H Me      CH2Ph(2-Bu-t)     1.59391.5795124-12769-7271-741.54331.539238-401.53321.53331.52691.553169-7285-881.55971.54021.521162-6591-9493-9587-9065-6880-8288-91101-10388-9168-71103-10680-8379-81108-11088-911.572297-100116-1191.57891.5762
                                        表3
Figure C0081124900131
                                        表4
化合物编号 G  R1 R2  R2 X1   X2 X3  X4 Q      Y 熔点(℃)或折射率(nD 20)
 A-146A-147A-148A-149A-150A-151A-152A-153A-154A-155A-156A-157A-158A-159A-160A-161A-162A-163A-164A-165A-166A-167A-168A-169A-170A-171A-172A-173A-174A-175A-176A-177A-178A-179A-180A-181A-182A-183A-184A-185A-186A-187A-188A-189A-190A-191A-192A-193A-194A-195A-196A-197 O  Me H    H  Cl    Me H    H  Me    CH2CNO  Me H    H  Cl    Me H    H  Me    CH2COOMeO  Me H    H  Cl    Me H    H  Me    CH2COOEtO  Me H    H  Cl    Me H    H  Me    CH2CO2HO  Me H    H  Cl    Me H    H  Me    CH2PhO  Me H    H  Cl    Me H    H  Me    CH2Ph(3-F)O  Me H    H  Cl    Me H    H  Me    CH2Ph(4-F)O  Me H    H  Cl    Me H    H  Me    CH3Ph(3-Cl)O  Me H    H  Cl    Me H    H  Me    CH2Ph(4-Cl)O  Me H    H  Cl    Me H    H  Me    CH2Ph(3-Me)O  Me H    H  Cl    Me H    H  Me    CH2Ph(4-Me)O  Me H    H  Cl    Me H    H  Me    CH2Ph(3-OMe)O  Me H    H  Cl    Me H    H  Me    CH2Ph(4-OMe)O  Me H    H  Cl    Me H    H  Me    CH3Ph(3-CF3)O  Me H    H  Cl    Me H    H  Me    CH2Ph(4-CF3)O  Me H    H  Me    H  Me   Me Me    CH2CO2MeO  Me H    H  Me    H  Me   Me Me    CH2C≡CHO  Me H    H  Cl    H  H    Cl Me    CH2CH＝CH2O  Me H    H  Cl    H  H    Cl Me    CH2PhO  Me H    H  OMe   H  H    H  Me    EtO  Me H    H  OMe   H  H    H  Me    Pr-iO  Me H    H  CF3  H  H    H  Me    MeO  Me H    H  CF3  H  H    H  Me    CH2PhO  Me H    H  OCF3 H  H    H  Me    MeO  Me H    H  OCF3 H  H    H  Me    CH2PhO  Me H    H  Cl    H  H    H  CF3  MeO  Me H    H  Cl    H  H    H  CF3  CH2PhO  Me H    H  Cl    H  H    H  Pr-c  CH2CNO  Me H    H  Cl    H  H    H  Pr-c  CH2OMeO  Me H    H  Cl    H  H    H  Me    CH2OHO  Me H    H  Me    H  H    H  Me    CH2OHO  Me H    H  Cl    H  H    H  Me    CH2CH2NH2O  Me H    H  Me    H  H    H  Me    CH2CH2NH2O  Me H    H  Cl    H  H    H  Me    CH2CH2N(Me)2O  Me H    H  Me    H  H    H  Me    CH2CH2N(Me)2O  Me H    H  Cl    H  H    H  Me    CH2COMeO  Me H    H  Me    H  H    H  Me    CH2COMeO  Me H    H  Cl    H  H    H  Me    CH2CONHMeO  Me H    H  Me    H  H    H  Me    CH2CONHMeO  Me H    H  Cl    H  H    H  Me    CH2CH＝CCl2O  Me H    H  Me    H  H    H  Me    CH2CH＝CCl2O  Me H    H  Cl    H  H    H  Me    CH2(CH2)2CH＝CH2O  Me H    H  Me    H  H    H  Me    CH2(CH2)2CH＝CH2O  Me H    H  Cl    H  H    H  Me    CH2CH＝CHMeO  Me H    H  Me    H  H    H  Me    CH2CH＝CHMeO  Me H    Me Cl    H  H    H  Me    CH2PhO  Me H    Me Cl    H  H    H  Me    PrO  Me H    Me Me    H  H    H  Me    CH2PhO  Me H    Me Me    H  H    H  Me    PrO  Me H    H  Cl    H  H    H  Me    CH2C≡CCH2CH2OMeO  Me H    H  Cl    H  H    H  Me    CH2C≡CCH2OHO  Me H    H  Cl    H  H    H  Me    CH2C≡CC(O)Me 1.582164-6785-8888-91107-1101.576175-7873-761.578886-89100-10365-681.5529
                                        表5
Figure C0081124900151
                                        表6
                                            表7
Figure C0081124900171
                                    表8
Figure C0081124900181
                                    表9
                                                表10
Figure C0081124900201
                                        表11
Figure C0081124900211
                                            表12
表13
Figure C0081124900231
作为本发明化合物的通式[1]表示的氨基甲酸酯衍生物的具有代表性的制备方法如下所述。通式[1]表示的新颖化合物由于具有C＝N双键，所以在制备时会生成E/Z异构体混合物。该异构体混合物中的各成分可通过结晶化和柱色谱法等精制方法分离。各异构体及它们的混合物都包括在本发明中。
制备方法1
Figure C0081124900232
式中，G、R1、R2、R3、Q、X、Y及n分别如前所述。
使化合物[II]和化合物[III]在惰性溶剂中反应，能够制得本发明化合物[I](例如，参考实验化学讲座第4版，第20卷，349～355页(日本化学会编))。此外，本制备方法中所用的原料化合物[III]可与盐酸、硫酸等形成盐。化合物[III]可采用公知方法制得(例如，参考实验化学讲座第4版，第20卷，342～349页)。
本反应所用的原料化合物的用量，化合物[III]可对应于化合物[II]在1～50当量的范围内作适当选择，较好为1～10当量。本制备方法中所用的惰性溶剂包括甲醇、乙醇、丙醇、异丙醇等醇类，乙醚、二异丙醚、四氢呋喃、二噁烷、二甲氧基乙烷、二甘醇二甲醚等醚类，苯、氯苯、硝基苯和甲苯等芳香族烃类及水等，这些惰性溶剂可单独使用也可混合使用。
本制备方法中的盐酸、乙酸等酸类可与乙酸钠、碳酸钠、碳酸氢钠等碱类共存下使用。它们可单独使用也可组合使用。对应于化合物[II]，其用量在0.001～50当量的范围内，较好为0.01～10当量。反应温度在-10℃～所用惰性溶剂的沸点的范围内，较好为0℃～所用惰性溶剂的沸点。反应时间由反应温度和反应量等决定，一般在1～48小时的范围内。反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
制备方法2
式中，G、R1、R2、R3、X及n分别如前所述，Q’表示氰基或硝基，A表示C1～C10烷基。
在碱存在下使化合物[IV]和亚硝酸酯[V]反应，能够制得本发明化合物[I-a](例如，参考Organic Syntheses，第6卷，199页(1988年))。本反应所用的原料化合物的用量是对应于化合物[IV]，化合物[V]在1～50当量的范围内，较好为1～10当量。
本制备方法所用的碱包括甲醇钠、乙醇钠、叔丁醇钾等碱金属的醇盐，氢氧化钠、氢氧化钾、碳酸钠和碳酸钾等无机盐类。碱的用量是对应于化合物[IV]在0.5～50当量的范围内，较好为1～10当量。
本制备方法所用的惰性溶剂只要不影响本制备方法的进行即可，包括乙醚、二异丙醚、四氢呋喃、二噁烷、1，2-二甲氧基乙烷、二甘醇二甲醚等醚类，二氯甲烷、氯仿、四氯化碳、四氯乙烷等卤化烃类，苯、氯苯和甲苯等芳香族烃类等，甲醇、乙醇、丙醇、异丙醇等醇类。这些惰性溶剂可单独使用也可混合使用。
反应温度在-70℃～所用惰性溶剂的沸点范围内，较好为-20℃～所用惰性溶剂的沸点。反应时间由反应温度和反应量等决定，一般在1～100小时的范围内，较好为12～75小时。
反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
制备方法3
式中，G、R1、R2、R3、X、Q及n分别如前所述，Y’除氢以外与前述Y所述含义相同，L表示作为脱离基团的卤原子或对甲苯磺酰氧基、甲磺酰氧基等磺酸酯。
在碱存在下使本发明化合物[I-b]和化合物[VI]反应，能够制得本发明化合物[I-e]。
本反应所用的原料化合物的用量是对应于化合物[I-b]，化合物[VI]在1～50当量的范围内，较好为1～5当量。
本制备方法可根据不同情况使用惰性溶剂。惰性溶剂只要不妨碍本反应进行即可，例如，丙酮、甲基乙基甲酮、环己酮等酮类，乙醚、二异丙醚、四氢呋喃、噁烷、二甲氧基乙烷、二甘醇二甲醚等醚类，乙酸乙酯、乙酸甲酯等酯类，二氯甲烷、氯仿和四氯化碳等卤代烃类，苯、氯苯、硝基苯和甲苯等芳香族烃类，乙腈等腈类，N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、1，3-二甲基-2-咪唑啉酮和二甲亚砜等，这些惰性溶剂可单独使用也可混合使用。
所用碱包括氢化钠等碱金属氢化物，叔丁氧基钾等碱金属醇盐，碳酸钠和碳酸钾等无机盐类。碱的用量对应于化合物[I-b]在1～50当量的范围内，较好为1～10当量。
反应温度在-70℃～所用惰性溶剂的沸点范围内，较好为0℃～所用惰性溶剂的沸点。反应时间由反应温度和反应量等决定，一般在1～72小时的范围内。反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
制备方法4
Figure C0081124900261
式中，G、Q、R1、R2、R3、X、Y及n分别如前所述，L’表示卤原子。
采用公知方法使化合物[VII]卤化可制得化合物[VIII](例如，参考实验化学讲座第4版，第19卷，416-482页(日本化学会编))(步骤4.1)。在碱存在下、在惰性溶剂中使化合物[VIII]和化合物[IX]反应可制得本发明化合物[I-c](步骤4.2)。此外，在惰性溶剂中使化合物[VIII]和氰酸碱金属盐类及化合物[X]反应能够制得本发明化合物[I-d](例如，参考日本化学杂志，第87卷，第5号，486页(1966年))(步骤4.3)。
本制备方法的步骤4.1中可使用的卤化剂包括N-溴琥珀酰亚胺、N-氯琥珀酰亚胺、三氯三聚异氰酸等。卤化剂的用量对应于化合物[VII]在0.5～10当量的范围内，较好为1～3当量。本步骤中可使用偶氮二异丁腈、过氧化苯甲酰等催化剂，其用量对应于化合物[VII]在0.001～10当量的范围内，较好是在0.001～1当量的范围内。
所用惰性溶剂只要不影响步骤4.1的进行即可，例如，可使用二氯甲烷、氯仿、四氯化碳等卤化烃类，苯和氯苯等芳香族烃类。
反应温度在0℃～所用惰性溶剂的沸点范围内。反应时间由反应温度和反应量等决定，一般在数分钟～48小时的范围内。反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
本制备方法的步骤4.2所用的原料化合物[IX]的用量对应于化合物[VIII]在1～50当量的范围内，较好为1～10当量。
可使用的碱包括碳酸钠、碳酸钾、碳酸氢钠等无机盐类，氢化钠等碱金属氢化物类，碱的用量是对应于化合物[VIIII]在0.5～100当量的范围内，较好为1～10当量。
所用惰性溶剂只要不影响步骤4.2的进行即可，可使用丙酮、甲基乙基甲酮、环己酮等酮类，乙醚、二异丙醚、四氢呋喃、二噁烷、甘醇二甲醚、二甘醇二甲醚等醚类，乙酸乙酯、乙酸甲酯等酯类，二氯甲烷、氯仿和四氯化碳等卤代烃类，苯、氯苯、硝基苯和甲苯等芳香族烃类，乙腈等腈类，甲醇、乙醇、丁醇等醇类，N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、1，3-二甲基-2-咪唑啉酮、二甲亚砜等，这些惰性溶剂可单独使用也可混合使用。
反应温度在-70℃～所用惰性溶剂的沸点范围内，较好为-10℃～所用惰性溶剂的沸点。反应时间由反应温度和反应量等决定，一般在数分钟～48小时的范围内。反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
可用于本制备方法的步骤4.3的氰酸的碱金属盐类包括氰酸钾和氰酸钠。所用氰酸金属盐类的用量对应于化合物[VIII]在1～50当量的范围内，较好为1～10当量，化合物[X]的用量对应于化合物[VIII]在1～100当量的范围内，较好为1～20当量。可使用的惰性溶剂只要不影响步骤4.3的进行即可，包括丙酮、甲基乙基甲酮、环己酮等酮类，乙醚、二异丙醚、四氢呋喃、二噁烷、甘醇二甲醚、二甘醇二甲醚等醚类，乙酸乙酯、乙酸甲酯等酯类，二氯甲烷、氯仿和四氯化碳等卤代烃类，苯、氯苯、硝基苯和甲苯等芳香族烃类，乙腈等腈类，甲醇、乙醇、丁醇等醇类，N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、1，3-二甲基-2-咪唑啉酮、二甲亚砜等，这些惰性溶剂可单独使用也可混合使用。
反应温度在0℃～所用惰性溶剂的沸点范围内。反应时间由反应温度和反应量等决定，一般在1小时～48小时的范围内。反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
制备方法5
Figure C0081124900281
式中，G、R1和R3的含义如前所述，X1、X2、X3及X4分别表示氢原子、卤原子、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6卤代烷氧基，Q”表示氢原子、卤代烷基、C1～C6烷基、C3～C6环烷基或苯基(所述基团可被至少1个选自卤原子、氰基、硝基、C1～C4烷基、C2～C4链烯基、C2～C4炔基、羟基、C1～C4烷氧基、C1～C4卤代烷基、C1～C4卤代烷氧基、C1～C4烷基羰基或C1～C4烷氧基羰基的基团取代)。
按照公知的方法，在盐酸存在下，利用亚硝酸钠使化合物[XVIII]重氮化，然后在乙酸钠和硫酸铜存在下，使其与化合物[XIX]反应就可制得本发明化合物[I-f](例如，参考0rganic Syntheses，第5卷，139页(1973年))。
本反应所用的原料化合物的用量是，化合物[XIX]对应于化合物[XVIII]在1～50当量的范围内，较好为1～5当量。
可用于本制备方法的溶剂只要不影响本反应的进行即可，例如，可使用乙醚、二异丙醚、四氢呋喃、二噁烷、二甲氧基乙烷、二甘醇二甲醚等醚类，乙酸乙酯、乙酸甲酯等酯类，二氯甲烷、氯仿和四氯化碳等卤化烃类，苯、氯苯、硝基苯和甲苯等芳香族烃类，乙酸、三氟乙酸等有机酸类和水等，这些惰性溶剂可单独使用也可混合使用。
本制备方法的重氮化步骤1)中所用的酸可用硫酸、氢氟硼酸、氢溴酸、三氟乙酸等强酸代替前述盐酸，其用量对应于化合物[XVIII]在1～50当量的范围内，较好为2～4当量。此外，可用亚硝酸异戊酯、亚硝酸甲酯等亚硝酸酯类代替前述亚硝酸钠，其用量对应于化合物[XVIII]在1～50当量的范围内，较好为1～2当量。反应温度在-20℃～30℃的范围内，较好为-5℃～5℃。反应时间由反应温度和反应量等决定，一般在30分钟～2小时的范围内。本反应的偶合步骤2)中所用的铜化合物可用氯化亚铜、乙酸铜等铜盐代替前述硫酸铜，其用量对应于化合物[XVIII]在0.02～2当量的范围内，较好为0.02～0.5当量。此外，乙酸钠的用量对应于化合物[XVIII]在1～50当量的范围内，较好为4～10当量。反应温度在-20℃～30℃的范围内，较好为-5℃～25℃。反应时间由反应温度和反应量等决定，一般在30分钟～2小时的范围内。反应结束后，采用常规方法将目的产物从反应系统中分离出来，根据需要用柱色谱法、重结晶等方法精制。
作为本发明化合物[I]的中间体的化合物[II]可通过以下所示的公知方法制得，但其制备方法并不仅限于此。
Figure C0081124900291
式中，L’、G、Q、R1、R2、R3、X及n的含义如前所述。
使化合物[XI]卤化可制得化合物[XII](例如，参考实验化学讲座第4版，第19卷，416～482页(日本化学会编))(步骤A-1)。在碱(例如，碳酸钠、碳酸钾、碳酸氢钠等无机盐类，氢化钠等碱金属氢化物类等)的存在下，使化合物[XII]与化合物[IX]反应就可制得中间体[II](步骤A-2)。此外，在惰性溶剂中使化合物[XII]和氰酸碱金属盐类及化合物[X]反应，可制得中间体[II-a](例如，参考日本化学杂志，第87卷，第5号，486页(1966年))(步骤A-3)。
作为本发明化合物[I]的中间体的化合物[II]及[IV-a]可通过以下所示公知方法制得，但其制备方法并不仅限于此。
式中，G、Q、R1、R2、R3、X、L’及n的含义如前所述，T表示C1～C6的烷基。
使化合物[XIII]卤化可制得化合物[XIV](例如，参考实验化学讲座第4版，第19卷，416～482页(日本化学会编))(步骤B-1)。然后，使化合物[XIV]和化合物[X]及氰酸碱金属盐类反应，可制得化合物[XV](例如，参考日本化学杂志，第87卷，第5号，486页(1966年))(步骤B-2)。或者，在碳酸钠、碳酸钾、碳酸氢钠等无机盐类，氢化钠等碱金属氢化物类等碱的存在下，使化合物[XIV]与化合物[IX]反应可制得化合物[XV](步骤B-3)。按照常规方法使化合物[XV]还原，可制得化合物[XVI](例如，参考实验化学讲座第4版，第26卷，159～266页(日本化学会编))(步骤B-4)。接着，按照常规方法使化合物[XVI]氧化，制得化合物[II-b](例如，参考实验化学讲座第4版，第21卷，2～23页(日本化学会编))(步骤B-5)。然后，按照常规方法使化合物[XVI]卤化，可制得化合物[XVII](例如，参考实验化学讲座第4版，第19卷，416～482页(日本化学会编))(步骤B-6)。
最后，按照常规方法使化合物[XVII]氰基化，可制得化合物[IV-a](例如，参考实验化学讲座第4版，第20卷，437～462页(日本化学会编))(步骤B-7)。
作为本发明化合物[I]的中间体的化合物[VII]可通过以下所示公知的方法制得，但其制备方法并不仅限于此。
Figure C0081124900311
式中，R3、Q、X、Y及n的含义分别如前所述。
使化合物[XI]与化合物[III]反应可制得本发明化合物[VII](例如，参考实验化学讲座第4版，第20卷，349～355页(日本化学会编))。此外，本制备方法所用的原料化合物[III]可以是与盐酸、硫酸等形成的盐。
作为本发明化合物[I]的中间体的化合物[XVIII]可通过以下所示公知的方法制得，但其制备方法并不仅限于此。
Figure C0081124900312
式中，G、R1、R3、L’、X1、X2、X3及X4的含义如前所述。
在惰性溶剂中使化合物[XX]与氰酸碱金属盐类及化合物[X]反应，可制得中间体[XXI](例如，参考日本化学杂志，第87卷，第5号，486页(1966年))(步骤C-1)。然后，通过硝酸、硝酸乙酰酯、硝酸钠等使化合物[XXI]硝基化，可制得中间体[XXII](例如，参考实验化学讲座第4版，第20卷，394～399页(日本化学会编))(步骤C-2)。接着，按照常规方法使化合物[XXII]还原，可制得中间体[XVIII](例如，参考实验化学讲座第4版，第26卷，159～266页(日本化学会编))(步骤C-3)。
实施例
以下，举出实施例对本发明化合物的制备方法、制剂方法及用途进行具体说明。
本说明书中其他符号的含义如下所述。
1H-NMR：质子核磁共振，CDCl3：氘代氯仿，TMS：四甲基硅烷，s：单峰，d：双峰，t：三重峰，q：四重峰，quint：五重峰，m：多重峰，br：宽谱，dd：双双峰。
制备例1
2-[4-氯-3-(甲氧基羰基氨基甲基)苯基]-2-羟基亚氨基乙腈的制备(化合物编号A-2)
在5ml乙醇中加入0.15g氢氧化钠、0.60g的N-(2-氯-5-氰基甲基苄基)氨基甲酸甲酯。室温下，在该混合物中添加0.40g亚硝酸叔丁酯，搅拌72小时。反应结束后，在反应液中注水，用乙酸乙酯萃取，水洗后，有机层用无水硫酸镁干燥。减压蒸去溶剂后，用硅胶柱色谱法(ヮコ-ゲルC-200，洗脱溶剂：己烷/乙酸乙酯＝3/1)对残渣进行精制，获得0.46g为无色粘稠液体的2-[4-氯-3-(甲氧基羰基氨基甲基)苯基]-2-羟基亚氨基乙腈。
1H-NMR：(CDCl3/TMS，δ(ppm))
3.72(s，3H)，4.48(d，2H)，5.43(br，1H)，7.43-8.21(m，3H)，10.51，11.15(br，1H)。
制备例2
2-[4-氯-3-(甲氧基羰基氨基甲基)苯基]-2-甲氧基亚氨基乙腈的制备(化合物编号A-3)
在5ml甲醇中加入0.36g的2-[4-氯-3-(甲氧基羰基氨基甲基)苯基]-2-羟基亚氨基乙腈、28％的甲醇钠的甲醇溶液0.54g。室温下，再添加0.49g甲基碘，搅拌24小时。然后，浓缩反应液，蒸去溶剂，在残渣中加水，用乙酸乙酯萃取后，有机层用无水硫酸镁干燥。减压蒸去溶剂后，用硅胶柱色谱法(ヮコ-ゲルC-200，洗脱溶剂：己烷/乙酸乙酯＝4/1～5/1)对残渣进行精制，获得0.18g为无色结晶(熔点104～107℃)的2-[4-氯-3-(甲氧基羰基氨基甲基)苯基]-2-甲氧基亚氨基乙腈。
1H-NMR：(CDCl3/TMS，δ(ppm))
3.71(s，3H)，4.22(s，3H)，4.48(d，2H)，5.23(br，1H)，7.43-8.05(m，3H)。
制备例3
N-[2-氯-5-(1-羟基亚氨基乙基)苄基]氨基甲酸甲酯的制备(化合物编号A-45)
使5.0g的N-(2-氯-5-乙酰基苄基)氨基甲酸甲酯溶于10ml乙醇中，再添加1.5g的羟胺盐酸盐、3.0g的乙酸钠和5ml水，加热回流4小时。反应结束后加水，用乙酸乙酯萃取，有机层用无水硫酸镁干燥后，减压蒸去溶剂。所得结晶用己烷洗涤，获得5.2g为无色结晶(熔点124～127℃)的N-[2-氯-5-(1-羟基亚氨基乙基)苄基]氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，6(ppm))
2.25(s，3H)，3.70(s，3H)，4.46(d，2H)，5.31(br，1H)，7.27-7.63(m，3H)。
制备例4
N-[3-(1-甲氧基亚氨基乙基)苄基]氨基甲酸甲酯的制备(化合物编号A-40)
使0.40g的N-(3-乙酰基苄基)氨基甲酸甲酯溶于10ml乙醇中，再添加0.36g的甲氧基胺盐酸盐、5ml含有0.54g乙酸钠的水溶液，加热回流8小时。反应结束后加水，用乙酸乙酯萃取，有机层用无水硫酸镁干燥后，减压蒸去溶剂。所得结晶用己烷洗涤，获得0.40g为淡黄色油状物的N-[3-(1-甲氧基亚氨基乙基)苄基]氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.22(s，3H)，3.69(s，3H)，3.99(s，3H)，4.37(d，2H)，5.12(br，1H)，7.27-7.56(m，4H)。
制备例5
N-{2-氯-5-[1-(4-氟苄氧基亚氨基)乙基]苄基}氨基甲酸甲酯的制备(化合物编号A-83)
使0.70g的N-[2-氯-5-(1-羟基亚氨基乙基)苄基]氨基甲酸甲酯溶于10ml的N，N-二甲基甲酰胺中。然后，在冰冷却下添加60％的氢化钠0.13g，搅拌1小时。接着，在2ml的N，N-二甲基甲酰胺中溶解0.57g的4-氟苄基溴，在冰冷却下，将其滴加入反应混合物中。滴加结束后，室温搅拌16小时。反应结束后，将反应液注入水中，用乙酸乙酯萃取，水洗后有机层用无水硫酸镁干燥。减压蒸去溶剂，所得残渣用硅胶柱色谱法(ヮコ-ゲルC-200，洗脱溶剂：己烷/乙酸乙酯＝5/1)精制，获得0.75g为无色结晶(熔点101～103℃)的N-{2-氯-5-[1-(4-氟苄氧基亚氨基)乙基]苄基}氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.22(s，3H)，3.69(s，3H)，4.45(d，2H)，5.10(br，1H)，5.18(s，2H)，7.02-7.65(m，7H)。
制备例6
N-[2-氯-5-(1-羟基亚氨基乙基)苄基]氨基甲酸甲酯的制备(化合物编号A-45)
使10.7g的N-[5-氨基-2-氯苄基]氨基甲酸甲酯溶于33g的14％盐酸中，室温搅拌1小时。在搅拌下于0～5℃在该溶液中滴加7ml含有3.8g亚硝酸钠的水溶液。在0～5℃下，一边剧烈搅拌一边在21.7g乙酸钠、2.6g硫酸铜及5.9g乙醛肟的水/乙酸乙酯/甲苯(80ml/40ml/40ml)的混合溶剂中滴加以上生成的重氮盐，历时15分钟，室温下继续搅拌2小时。用盐酸将反应液调整为酸性后，用乙酸乙酯萃取，水洗后，有机层用无水硫酸镁干燥。减压蒸去溶剂，所得粗结晶用乙醚/乙酸乙酯的混合溶剂洗涤，获得2.8g为无色结晶(熔点124～127℃)的N-[2-氯-5-(1-羟基亚氨基乙基)苄基]氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.25(s，3H)，3.70(s，3H)，4.46(d，2H)，5.31(br，1H)，7.27-7.63(m，3H)。
制备例7
N-{2-甲基-5-[1-(6-甲基吡啶-2-基甲氧基)亚氨基乙基]苄基}氨基甲酸甲酯的制备(化合物编号A-434)
使0.43g的N-{2-甲基-5-(1-羟基亚氨基乙基)苄基}氨基甲酸甲酯溶于15ml的N，N-二甲基甲酰胺中。然后，添加0.75g的碳酸钾和0.32g的2-氯-6-甲基吡啶盐酸盐，于90～100℃加热搅拌8小时。反应结束后，将反应液注入水中，用乙酸乙酯萃取，水洗后，有机层用无水硫酸镁干燥。减压下蒸去溶剂，所得残渣用硅胶柱色谱法(ヮコ-ゲルC-200，洗脱溶剂：己烷/乙酸乙酯＝4/1)精制，获得0.30g为淡黄色结晶(熔点72～75℃)的N-{2-甲基-5-[1-(6-甲基吡啶-2-基甲氧基)亚氨基乙基]苄基}氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.30(s，3H)，2.32(s，3H)，2.56(s，3H)，3.69(s，3H)，4.35(d，2H)，4.94(br，1H)，5.33(s，2H)，7.04-7.59(m，6H)。
本发明化合物的具体例的一部分的1H-NMR(CDCl3/TMS，δ(ppm))数据如表14～表20所示。
                                      表14
化合物编号     1H-NMRδ值(ppm)溶剂CDCl3/TMS
  A-2A-37A-38A-39A-40A-41A-42A-43A-50A-51A-53A-54A-55   3.72(s，3H)；4.48(d，H)；5.43(br，1H)；7.43-8.21(m，3H)2.20，2.25(a，3H)；3.70(s，3H)；4.37(d，2H)；4.54，4.71(d，2H)；5.08(br，1H)；5.20-5.38(m，2H)；6.00-6.11(m，1H)；729-7.56(m，4H)2.17，2.25(s，3H)；3.68(s，3H)；4.35(d，2H)；5.05(br，1H)；5.09，5.24(s，2H)；7.28-7.55(m，9H)1.24，1.33(t，3H)；2.18，2.22(s，3H)；3.69(s，3H)；4.09，4.24(q，2H)；4.37(d，2H)；5.14(br，1H)；7.26-7.56(m，4H)2.22(s，3H)；3.69(s，3H)；3.99(s，3H)；4.37(d，2H)；5.12(br，1H)；7.27-7.56(m，4H)3.67(s，3H)；4.35(dd，2H)；4.66-4.69(m，2H)；5.17(br，1H)；5.95-6.08(m，2H)；7.25-7.48(m，9H)3.67(s，3H)；3.96(s，3H)；4.11(dd，2H)；5.30(br，1H)；7.25-7.80(m，9H)1.27，1.29(t，3H)；3.67(s，3H)；4.22，4.23(q，2H)；4.34(dd，2H)；5.15(br，1H)；7.27-7.48(9H)0.98(t，3H)；1.75(quint，2H)；2.21(s，3H)；3.69(s，3H)；4.15(t，2H)；4.46(d，2H)；5.19(br，1H)；7.34(d，1H)；7.51(d，1H)；7.66(s，1H)1.30(d，6H)；2.19(s，3H)；3.69(s，3H)；4.41-4.49(m，3H)；5.20(br，1H)；7.34(d，1H)；7.52(dd，1H)；7.65(s，1H)0.95(t，3H)；1.27(d，3H)；1.52-1.78(m，2H)；2.19(s，3H)；3.68(s，3H)；4.21-4.28(m，1H)；4.44(d，2H)；5.27(br，1H)；7.30-7.65(m，3H)0.96(d，6H)；2.04(m，1H)；2.21(s，3H)；3.68(s，3H)；3.96(d，2H)；4.45(d，2H)；5.24(br，1H)；7.33(d，1H)；7.50(dd，1H)；7.65(s，1H)1.35(t，9H)；2.18(d，3H)；3.69(s，3H)；4.45(d，2H)；5.20(br，1H)；7.27-7.63(m，3H)
                                          表15
化合物编号 1H-NMRδ值(ppm)溶剂CDCl3/TMS
  A-56A-62A-63A-64A-91A-94A-95A-98A-100A-150A-155A-158A-189A-198   0.30-0.35(m，2H)；0.54-0.60(m，2H)；1.14-1.27(m，1H)；2.23(s，3H)；3.69(s，3H)；4.01(d，2H)；4.45(d，2H)；5.20(br，1H)；7.34(d，1H)；7.51(dd，1H)；7.66(s，1H)2.05(quint，2H)；2.21(s，3H)；2.74(t，2H)；3.69(s，3H)；4.22(t，2H)；4.46(d，2H)；5.18(br，1H)；7.17-7.67(m，8H)1.29(t，3H)；2.29(s，3H)；3.69(s，3H)；4.25(q，2H)；4.47(d，2H)；4.73(s，2H)；5.22(br，1H)；7.34(d，1H)；7.50(dd，1H)；7.64(s，1H)1.49(s，9H)；2.28(s，3H)；3.69(s，3H)；4.46(d，2H)；4.63(s，2H)；5.19(br，1H)；7.35(1H)；7.5(dd，1H)；7.64(br，1H)2.25(s，3H)；2.39(s，3H)；3.70(s，3H)；4.45(d，2H)；5.22(s，2H)；5.31(br，1H)；7.13-7.54(m，7H)2.24(s，3H)；3.69(s，3H)；3.82(s，3H)；4.45(d，2H)；5.19(br，1H)；5.21(s，3H)；6.84-7.66(m，7H)2.21(s，3H)；3.70(s，3H)；3.81(s，3H)；4.45(d，2H)；5.16(s，3H)；5.21(br，1H)；6.89-7.66(m，7H)1.33，1.35(a，9H)；2.23，2.24(s，3H)；3.69(s，3H)4.45(d，2H)；5.21，5.23(s，2H)；5.26(br，1H)；7.32-7.67(m，7H)2.25(s，3H)；3.68(s，3H)；4.44(d，2H)；5.22(br，1H)；5.27(s，2H)；7.32-7.65(m，7H)2.23(s，3H)；2.40(s，3H)；3.69(s，3H)；4.46(d，2H)；5.18(br，1H)；5.24(s，2H)；7.30-7.49(m，7H)2.22(s，3H)；2.36(s，3H)；2.39(s，3H)；3.67(s，3H)；4.44(d，2H)；5.20(br，1H)；5.21(s，2H)；7.10-7.48(m，6H)2.20(s，3H)；2.40(s，3H)；2.39(s，3H)；3.69(s，3H)3.81(s，3H)；4.46(d，2H)；5.15(br，1H+s，2H)；6.89-7.49(m，6H)1.39，1.74(d，3H)；2.21(s，3H)；3.69(s，3H)；4.46(d，2h)；4.63，4.77(d，2H)；5.14-5.29(br，1H)；5.67-6.03(m，2H)；7.33-7.65(m，3H)2.20(s，3H)；2.48(q，2H)；3.69(s，3H)；4.24(t，2H)；4.46(d，2H)；5.05-5.16(m，2H)；5.20(br，1H)；5.80-5.94(m，1H)；7.33-7.66(m，3H)
                                      表16
化合物编号     1H-NMRδ值(ppm)溶剂CDCl3/TMS
 A-206A-207A-215A-216A-219A-229A-234A-240A-241A-251A-266A-269A-273A-286 2.17(s，3H)；3.68(s，3H)；4.44(d，2H)；5.09(s，2H)；5.23(br，1H)；7.26-7.53(m，8H)2.18(s，3H)；3.68(s，3H)；4.46(d，2H)；5.17(br，1H)；5.20(s，2H)；7.22-7.56(m，7H)2.21(s，3H)；3.69(s，3H)；4.46(d，2H)；5.17(br，1H)；5.69(s，2H)；7.26-8.18(m，10H)1.61(d，3H)；2.26(s，3H)；4.43(d，2H)；5.15(br，1H)；5.37(q，1H)；7.26-7.60(m，8H)2.25(br，3H)；3.75，3.79(s，3H)；4.53(br，4H)；5.47，5.53(s，2H)；7.19-7.78(m，1H)2.20(s，3H)；2.56(t，4H)；2.75(t，2H)；3.69(s，3H)；3.73(t，4H)；4.34(t，2H)；4.45(d，2H)；5.34(br，1H)；7.28-7.65(m，3H)2.32(s，3H)；2.68(t，2H)；3.68(s，3H)；4.30(t，2H)；4.45(d，2H)；5.40(br，1H)；7.33-7.65(m，3H)2.24(s，3H)；2.68(m，1H)；2.87(m，1H)；3.32(m，1H)；3.69(s，3H)；4.08-4.47(m，2H)；4.46(d，2H)；5.23(br，1H)；7.35(d，1H)；7.51(dd，1H)；7.66(s，1H)2.24(s，3H)；3.69(s，3H)；3.90-4.05(m，4H)；4.25(d，2H)；4.45(d，2H)；5.25(t，br，2H)；7.34(d，1H)；7.51(dd，1H)；7.65(s，1H)0.89(t，3H)；1.23-1.41(m，8H)；1.71(quintet，2H)；2.19(s，3H)；3.68(s，3H)；4.17(q，2H)；4.45(d，2H)；5.23(br，1H)；7.34(dd，1H)；7.51(dd，1H)；7.65(s，1H)2.27(s，3H)；3.68(s，3H)；4.44(d，2H)；5.25(br，1H)；5.31(s，2H)；7.33-8.27(m，7H)2.25(s，3H)；2.62(s，3H)；3.69(s，3H)；4.46(d，2H)；5.22(br，1H)；5.28(s，2H)；7.33-8.01(m，7H)1.30(d，6H)；3.70(s，3H)；4.41-4.49(m，3H)；5.18(br，1H)；7.35(d，1H)；7.62(dd，1H)；7.57(s，1H)；8.00(s，1H)2.29(s，3H)；2.56(s，3H)；3.67(s，3H)；4.44(d，2H)；5.33(br，3H)；7.05(d，1H)；7.19(d，1H)；7.32(d，1H)；7.49-7.64(m，3H)
                                            表17
化合物编号 1H-NMRδ值(ppm)溶剂CDCl3/TMS
 A-289A-290A-291A-292A-293A-297A-298A-299A-300A-303A-304A-305A-309A-310 3.17(s，3H)；3.69(s，3H)；4.48(d，2H)；5.18(br，1H)；5.35(s，2H)；7.27-7.69(m，7H)3.17(s，3H)；3.68(s，3H)；4.49(d，2H)；5.26(br，1H)；5.37(s，2H)；7.24-7.77(m，6H)；8.60(d，1H)2.23(s，3H)；3.69(s，3H)；4.00(s，3H)；4.45(d，2H)；5.19(br，1H)；5.24(s，2H)；7.33-7.68(m，7H)1.18(t，3H)；2.21(s，3H)；2.81(q，2H)；3.69(s，3H)；4.46(d，2H)；4.67(s，2H)；5.18(br，1H)；7.36d，1H)；7.50(dd，1H)；7.65(s，1H)1.09-1.22(m，3H)；1.92(s，3H)；2.70-2.79(m，2H)；3.69(s，3H)；3.85，3.90(s，3H)；4.46(d，2H)；4.68，4.99(s，2H)；5.17(br，1H)；7.34-7.64(m，3H)1.41(t，3H)；2.79(q，2H)；3.68(s，3H)；4.45(d，2H)；5.20(br，1H)；5.43(s，2H)；7.33-7.73(m，7H)1.17(t，3H)；1.43(d，3H)；2.19(s，3H)；2.80(q，2H)；3.70(s，3H)；4.45(d，2H)；4.65(q，1H)；5.17(br，1H)；7.35(d，1H)；7.50(dd，1H)；7.62(s，1H)1.09-1.16(m，3H)；1.38，1.43(d，3H)；1.82，1.83(s，3H)；2.68，2.82(m，2H)；3.69(s，3H)；3.84，3.88(s，3H)；4.45(d，2H)；4.84，5.54(q，1H)；5.21(br，1H)；7.34(d，1H)；7.49(d，1H)；7.61(s，1H)1.09-1.16(m，3H)；1.23-1.29(m，3H)；1.38，1.42(d，3H)；1.83(s，3H)；2.68-2.82(m，2H)；3.69(s，3H)；4.03-4.16(m，2H)；4.45(d，2H)；4.84，5.54(q，1H)；5.21(br，1H)；7.34(dd，1H)；7.52(dd，1H)；7.65(s，1H)1.11(t，3H)；2.75(q，2H)；3.69(s，3H)；4.45(d，2H)；5.22(br，3H)；7.28-7.65(m，8H)1.12(t，3H)；2.76(q，2H)；3.69(s，3H)；3.82(s，3H)；4.46(d，2H)；5.20(br，3H)；3.84(dd，1H)；6.95-6.99(m，2H)；7.25-7.36(m，2H)；7.50(dd，1H)；7.65(s，1H)1.17(t，3H)；2.82(q，2H)；3.68(s，3H)；4.45(d，2H)；5.18(br，1H)；5.36(s，2H)；7.19-7.73(m，6H)；8.59(d，1H)1.59(d，3H)；3.00(s，3H)；3.68(s，3H)；4.43(d，2H)；5.14(br，1H)；5.75(q，1H)；7.16-7.59(m，7H)1.58(d，3H)；2.25(s，3H)；3.67(s，3H)；4.42(d，2H)；5.21(br，1H)；5.32(q，1H)；7.24-7.59(m，7H)
                                                表18
化合物编号     1H-NMRδ值(ppm)溶剂CDCl3/TMS
A-312A-313A-315A-322A-329A-332A-333A-338A-339A-341A-343A-344A-348A-349 1.49，1.60(d，3H)；2.26(s，3H)；3.68(s，3H)；3.81(s，3H)；4.43(d，2H)；5.15(br，1H)；5.34(q，1H)；6.81(dd，1H)；6.92-6.97(m，2H)；7.24-7.32(m，2H)；7.48(dd，1H)；7.60(s，1H)1.62(d，3H)；2.27(s，3H)；3.68(s，3H)；4.43(d，3H)；4.43(d，2H)；5.15(br，1H)；5.40(q，1H)；7.30-7.61(m，7H)2.49(s，3H)；2.33(s，3H)；3.70(s，3H)；3.82(s，3H)；4.37(d，2H)；4.86(br，1H)；5.21(s，2H)；6.83-7.53(m，7H)2.23(br，6H)；3.74-3.81(br，9H)；4.33-4.54(br，4H)；5.21(s，2H)；6.68-7.48(m，11H)2.25(s，3H)；3.69(s，3H)；3.82(s，3H)；4.41(d，2H)；5.07(br，1H)；5.20(s，2H)；6.84-7.63(m，7H)2.29(s，3H)；3.69(s，3H)；4.46(d，2H)；5.26(br，1H)；5.37(s，2H)；7.19-7.73(m，5H)；8.60(d，1H)2.31(s，3H)；2.33(s，3H)；3.70(s，3H)；4.37(d，2H)；4.86(br，1H)；5.36(s，2H)；7.15-7.72(m，6H)；8.59(d，1H)2.30(s，3H)；3.71(s，3H)；4.38(d，2H)；4.99(br，1H)；5.36(s，2H)；7.22-7.56(m，8H)2.27(s，3H)；3.71(s，3H)；4.38(d，2H)；5.00(br，1H)；5.21(s，2H)；7.26-7.54(m，8H)0.60-0.70(m，2H)；0.93-0.99(m，2H)；2.19-2.28(m，1H)；3.69(s，3H)；4.44(d，2H)；5.14(br，1H)；5.32(s，2H)；7.21-7.55(m，7H)2.25(s，3H)；2.40(s，3H)；3.70(s，3H)；4.37(d，2H)；5.03(br，1H)；5.26(s，2H)；7.17-7.56(m，8H)2.25(s，3H)；2.37(s，3H)；3.70(s，3H)；4.37(d，2H)；5.04(br，1H)；5.20(s，2H)；7.11-7.56(m，8H)2.30(s，3H)；3.69(s，3H)；4.37(d，2H)；5.06(br，1H)；5.45(s，2H)；7.26-7.68(m，8H)2.27(s，3H)；3-69(s，3H)；4.37(d，2H)；5.07(br，1H)；5.27(s，2H)；7.25-7.67(m，8H)
                                        表19
化合物编号     1H-NMRδ值(ppm)溶剂CDCl3/TMS
 A-350A-361A-366A-368A-369A-373A-378A-379A-383A-394A-398A-399A-400A-405 2.27(s，3H)；3.68(s，3H)；4.35(d，2H)；5.11(br，1H)；5.28(s，2H)；7.25-7.62(m，8H)2.23，2.27(s，6H)；3.79(s，3H)；4.50-4.75(br，4H)；5.40(s，2H)；7.11-7.70(m，11H)2.21(br，6H)；3.80(s，3H)；4.25-4.52(br，4H)；5.18(s，2H)；7.13-7.45(m，11H)1.93(s，3H)；2.22，2.24(s，3H)；2.34(s，3H)；3.70(s，3H)；3.84，3.90(s，3H)；4.33(d，2H)；4.69，5.00(s，2H)；4.89(br，1H)；7.17(d，1H)；7.46(d，1H)；7.52(s，1H)2.19(s，3H)；2.34(s，3H)；3.04(t，2H)；3.70(s，3H)；4.32-4.41(m，4H)；4.86(br，1H)；7.16-7.58(m，8H)2.22(s，3H)2.35(s，3H)；3.69(s，3H)；4.41(d，2H)；5.07(br，1H)；5.18(s，2H)；6.98-7.63(m，7H)1.58(d，3H)；2.30(s，3H)；3.68(s，3H)；4.39(d，2H)；5.05(br，1H)；5.74(q，1H)；6.96-7.57(m，7H)1.58(d，3H)；2.26(s，3H)；3.68(s，3H)；4.39(d，2H)；5.05(br，1H)；5.31(q，1H)；6.97-7.57(m，7H)0.61，0.92(m，4H)；2.21(m，1H)；3.69(s，3H)；4.44(d，2H)；5.14(br，1H)；5.21(s，2H)；7.26-7.47(m，8H)2.32(s，3H)；3.68(s，3H)；4.44(d，2H)；5.18(br，1H)；5.42(s，2H)；7.31-7.98(m，8H)2.26(s，3H)；3.70(s，3H)；4.38(d，2H)；5.00(br，1H)；5.31(s，2H)；7.04-7.56(m，8H)2.27(s，3H)；3.70(s，3H)；4.38(d，2H)；5.01(br，1H)；5.23(s，2H)；6.96-7.55(m，8H)1.90(s，6H)；2.26(s，3H)；3.68(s，3H)；3.89(s，6H)；4.43(d，2H)；5.26(s，2H)；5.41(br，1H)；7.32-7.63(m，3H)0.66，0.97(m，4H)；2.28(m，1H)；3.69(s，3H)；4.43(d，2H)；5.16(br，1H)；5.34(s，2H)；7.18-7.74(m，6H)；8.58(d，1H)
                                         表20
化合物编号     1H-NMRδ值(ppm)溶剂CDCl3/TMS
 A-406A-407A-408A-412A-420A-428A-429A-430A-435A-439A-440A-443A-445 1.58(d，3H)；2.25(s，3H)；2.39(s，3H)；3.69(s，3H)；4.41(d，2H)；5.19(br，1H)；5.58(q，1H)；7.15-7.60(m，7H)1.59(d，3H)；2.25(s，3H)；2.36(s，3H)；3.68(s，3H)；4.42(d，2H)；5.17(br，1H)；5.33(q，1H)；7.07-7.60(m，7H)1.59(d，3H)；2.24(s，3H)；2.34(s，3H)；3.68(s，3H)；4.43(d，2H)；5.16(br，1H)；5.33(q，1H)；7.14-7.60(m，7H)1.90(s，6H)；2.26(s，3H)；3.68(s，3H)；3.89(s，6H)；4.43(d，2H)；5.26(s，1H)；5.41(br，1H)；7.33(d，1H)；7.52(dd，1H)；7.62(d，1H)2.32(s，3H)；2.57(s，3H)；3.70(s，3H)；4.37(d，2H)；5.05(br，1H)；5.34(s，2H)；7.04-7.60(m，7H)2.26(s，3H)；3.68(s，3H)；4.41(d，2H)；5.15(br，1H)；5.24(s，2H)；7.00-8.21(m，7H)2.29(s，3H)；2.38(s，3H)；2.56(s，3H)；3.67(s，3H)；4.44(d，2H)；5.27(br，1H)；5.33(s，2H)；7.06(d，1H)；7.19(d，1H)；7.47(br，2H)；7.57(t，1H)2.30(s，3H)；2.56(s，3H)；3.68(s，3H)；4.41(d，2H)；5.15(br，1H)；5.32(s，2H)；6.99-7.62(m，6H)2.26(s，3H)；2.40(s，3H)；2.88，2.95(br，3H)；3.71，3.76(br，3H)；4.63，4.57(br，2H)；5.35(s，2H)；7.22-7.47(m，6H)2.57(s，3H)；3.69(s，3H)；4.44(d，2H)；5.30(br，3H)；7.06-7.61(m，6H)；8.16(s，1H)2.31(s，3H)；3.64(s，3H)；4.37(d，2H)；5.37(hr，1H)；5.52(s，2H)；6.94-8.27(m，9H)1.62-2.09(m，4H)；2.23(s，3H)；3.69(s，3H)；3.78-3.97(m，2H)；4.15-4.30(m，3H)；4.45(d，2H)；5.06-5.23(br，1H)；7.33-7.65(m，3H)1.40(t，3H)；2.25(s，3H)；3.05(q，2H)；3.69(s，3H)；4.46(d，2H)；5.20(br，1H)；5.31(s，2H)；7.13-7.66(m，4H)
以下所示为作为参考例的本发明化合物的合成中间体的制备例
参考例1
4-氯-3-(甲氧基羰基氨基甲基)苯甲酸甲酯的制备
在300ml四氯化碳中加入4-氯-3-甲基苯甲酸甲酯40.4g、N-溴琥珀酰亚胺39g和偶氮二异丁腈1g，加热回流4小时。反应结束后冷却至室温，滤出不溶物，浓缩滤液。所得粗结晶用己烷洗涤，获得34.3g为白色结晶的3-溴甲基-4-氯苯甲酸甲酯。
在200ml的N，N-二甲基甲酰胺中加入以上制得的3-溴甲基-4-氯苯甲酸甲酯16.0g、氰酸钾15.0g和甲醇35ml，于90℃搅拌4小时。反应结束后，在反应混合物中加水，用乙酸乙酯萃取后，有机层用无水硫酸镁干燥。减压下蒸去溶剂，所得粗结晶用异丙醇洗涤，获得25.2g为白色结晶的4-氯-3-(甲氧基羰基氨基甲基)苯甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
3.70(s，3H)，3.90(s，3H)，4.48(d，2H)，5.29(br，1H)，7.43(d，1H)，7.89(dd，1H)，8.05(s，1H)。
参考例2
N-(2-氯-5-羟基甲基苄基)氨基甲酸甲酯的制备方法
使10.3g的4-氯-3-(甲氧基羰基氨基甲基)苯甲酸甲酯溶于80ml无水四氢呋喃中。然后，在氮氛围气中于-50℃～-30℃的温度下滴加100ml氢化二异丁基铝(0.95M己烷溶液)，滴加结束后，于室温搅拌16小时。反应结束后，于0℃在反应混合物中滴加稀盐酸，加水，用乙酸乙酯萃取后，有机层用无水硫酸镁干燥。减压蒸去溶剂，残渣用硅胶柱色谱法(ヮコ-ゲル C-200，洗脱溶剂：己烷/乙酸乙酯＝1/1)精制，获得6.5g为白色结晶的N-(2-氯-5-羟基甲基苄基)氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.20(br，1H)，3.67(s，3H)，4.43(d，2H)，4.65(s，2H)，5.26(br，1H)，7.21-7.37(m，3H)。
参考例3
N-(5-溴甲基-2-氯苄基)氨基甲酸甲酯的制备方法
使6.2g的N-(2-氯-5-羟基甲基苄基)氨基甲酸甲酯溶于50ml乙二醇二甲醚中。然后，在-20℃的温度下在该溶液中滴加2.7g三溴化磷，室温搅拌1小时。反应结束后，在反应液中加水，用乙酸乙酯萃取，再用碳酸氢钠水溶液洗涤，有机层用无水硫酸镁干燥。减压下蒸去溶剂，获得6.1g为白色结晶的N-(5-溴甲基-2-氯苄基)氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
3.70(s，3H)，4.37(d，2H)，4.49(s，2H)，5.20(br，1H)，7.25-7.40(m，3H)。
参考例4
N-(2-氯-5-氰基甲基苄基)氨基甲酸甲酯的制备
使2.3g参考例3获得的N-(5-溴甲基-2-氯苄基)氨基甲酸甲酯溶于20ml的N，N-二甲基甲酰胺中。于0℃在其中添加氰化钠0.43g。于0℃搅拌1小时后，室温下再搅拌4小时。然后，在该反应混合物中加水，用乙酸乙酯萃取，有机层用无水硫酸镁干燥。减压下蒸去溶剂，所得粗结晶用己烷洗涤，获得1.3g为白色结晶的N-(2-氯-5-氰基甲基苄基)氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
3.70(s，3H)，3.73(s，2H)，4.44(d，2H)，5.21(br，1H)，7.24-7.40(m，3H)。
参考例5
N-(2-氯-5-乙酰基苄基)氨基甲酸甲酯的制备
将25.0g的4-氯-3-甲基乙酰苯、26.6g的N-溴琥珀酰亚胺、催化剂量的偶氮二异丁腈加入150ml四氯化碳中，加热回流2小时。反应结束后，冷却至室温，滤出不溶物后，减压下浓缩滤液。将所得残渣、18.0g氰酸钾和38ml甲醇加入150ml的N，N-二甲基甲酰胺中，于90℃搅拌4小时。反应结束后，在反应混合物中加水，用乙酸乙酯萃取后，有机层用无水硫酸镁干燥。减压下蒸去溶剂，所得残渣用硅胶柱色谱法(ヮコ-ゲルC-200，洗脱溶剂：己烷/乙酸乙酯)精制，获得6.8g为无色结晶的N-(2-氯-5-乙酰基苄基)氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.59(s，3H)，3.70(s，3H)，4.50(d，2H)，5.31(br，1H)，7.46(d，1H)，7.81(dd，1H)，7.97(s，1H)。
参考例6
N-(2-氯-5-乙酰基苄基)氨基甲酸甲酯的制备
使25.0g的4-氯-3-甲基乙酰苯、13.9g的三氯三聚异氰酸悬浮于150ml氯苯中。然后，在其中添加催化剂量的偶氮二异丁腈，于85～90℃加热搅拌12小时。反应结束后，冷却至室温，滤出不溶物。滤液依次用氢氧化钠水溶液和水洗涤后，有机层用无水硫酸镁干燥。减压下蒸去溶剂，将所得残渣、氰酸钾12.2g、14.4g甲醇加入150ml的N，N-二甲基甲酰胺中，于90℃加热搅拌4小时。反应结束后，在反应混合物中加水，用乙酸乙酯萃取后，有机层用无水硫酸镁干燥。减压下蒸去溶剂，所得残渣用硅胶柱色谱法(ヮコ-ゲルC-200，洗脱溶剂：己烷/乙酸乙酯＝3/1)精制，获得6.0g为无色结晶的N-(2-氯-5-乙酰基苄基)氨基甲酸甲酯。
1H-NMR：(CDCl3/TMS，δ(ppm))
2.59(s，3H)，3.70(s，3H)，4.50(d，2H)，5.31(br，1H)，7.46(d，1H)，7.81(dd，1H)，7.97(s，1H)。
本发明的农用、园艺用杀菌剂中以通式[I]表示的氨基甲酸酯衍生物为有效组分。使用本发明化合物为农用、园艺用杀菌剂时，根据不同目的使有效组分以适当制剂使用。通常用惰性液体或固体载体稀释有效组分，再根据需要在其中添加表面活性剂等添加剂，制成粉剂、水和剂、乳剂、颗粒剂等。有效组分的配比可根据需要作适当选择，为粉剂和颗粒剂时，有效组分含量为0.1～20重量％，为乳剂和水和剂时，其含量为5～80重量％。
理想的载体包括滑石粉、皂土、粘土、高岭土、硅藻土、胶态硅石、蛭石、消石灰、硅砂、硫酸铵、尿素等固体载体，异丙醇、二甲苯、环己酮、甲基萘等液体载体等。作为表面活性剂及分散剂包括二萘基甲磺酸盐、醇硫酸酯盐、烷基芳基磺酸盐、木质磺酸盐、聚氧乙烯二醇醚、聚氧乙烯烷基芳基醚、聚氧乙烯山梨糖醇一烷基化物等。助剂包括羧甲基纤维素等。
本发明的农用、园艺用杀菌剂可以上述制剂的形式直接使用，也可稀释后散布于叶茎、用于种子的处理、施加于土壤和水面或在育苗箱中使用等。其用量可根据所用化合物的种类、需消灭的病害、病害发展倾向、消灭程度、环境条件、所用剂型等发生变化。例如，以粉剂及颗粒剂使用时，10公亩的有效组分用量为0.1g～5kg，较好为1g～1kg。以乳剂及水和剂等液体制剂使用时，有效组分用量为0.1ppm～10,000ppm，较好为10～3,000ppm。
本发明的化合物以上述施用方式可对属于卵菌类、子囊菌类、担子菌类及半知菌类的菌引发的植物病害进行预防和除治。以下是具体的菌名，但并不仅限于此。例如，假霜霉菌属中的古巴假霜霉，黑星菌属中的苹果黑星菌，白粉菌属中的禾白粉菌，枯萎菌(Pyricularia)属中的稻米枯萎菌(Pyriculariaoryzae)，灰霉菌(Botrytis)属中的黄瓜灰霉菌，丝核菌属中的立枯丝核菌，柄锈菌属中的隐匿柄锈菌，壳针孢属中的颖枯壳针孢，核盘菌属中的核盘菌。
此外，根据需要本发明化合物还可与杀虫剂、其他杀菌剂、除草剂、植物生长调节剂、肥料等混合。以下，举出本发明的农用、园艺用杀菌剂的具有代表性的制剂例，对制剂方法进行具体说明。以下说明中的[％]表示重量百分率。
制剂例1 粉剂
均匀混合粉碎2％化合物(A-30)、5％硅藻土及93％粘土，制得粉剂。
制剂例2 水和剂
均匀混合粉碎50％化合物(A-31)、45％硅藻土、2％二萘基甲烷二磺酸钠及3％木质磺酸钠，制得水和剂。
制剂例3 乳剂
使30％化合物(A-109)、20％环己酮、11％聚氧乙烯烷基芳基醚、4％烷基苯磺酸钙及35％甲基萘均匀溶解，制得乳剂。
制剂例4 颗粒剂
均匀混合粉碎5％化合物(A-45)、2％月桂醇硫酸酯的钠盐、5％木质磺酸钠、2％羧甲基纤维素及86％粘土。在此混合物中加入20％水，用挤压式造粒机将其混炼加工成14～32目的颗粒后，干燥获得颗粒剂。
以下，举出试验例对本发明的农用、园艺用杀菌剂的效果进行具体说明。
试验例1 对禾白粉菌的预防效果试验
分别在直径6cm的塑料钵中播种10粒小麦种子(品种：农林61号)，温室内培养。用水稀释制剂例2中制成的水和剂，使其中的有效组分浓度达到500ppm，将该经过稀释的水和剂撒在有2片叶子展开的小麦苗上，每个塑料钵中撒10ml。风干后，接种禾白粉菌的孢子，温室内放置。接种10天后观察所有塑料钵的第1片病害叶子的病害面积，按照表21的基准进行评估，其结果如表22所示。
            表21
  评估
    A 未发现病害
    B 病害面积低于5％
    C 病害面积在5％以上10％以下
    D 病害面积在10％以上
        表22
  化合物编号    评估
    A-3A-30A-31A-37A-38A-39A-40A-41A-42A-43A-46A-49A-50A-51A-55A-58A-61A-62A-64A-80A-81A-82A-83A-84A-85A-86A-87A-88A-89A-90A-91A-92A-98A-99A-100A-101A-112A-113     ABBAAAABAAAAAAAAAABAAAAAAAAAAAAAAAAAAA
试验例2 颖枯壳针孢的预防效果试验
分别在直径6cm的塑料钵中播种10粒小麦种子(品种：农林61号)，温室内培养。用水稀释制剂例2中制成的水和剂，使其中的有效组分浓度达到50ppm，将该经过稀释的水和剂撒在有2片叶子展开的小麦苗上，每个塑料钵中撒10ml。风干后，接种颖枯壳针孢的柄孢子，温室内放置。接种10天后观察所有塑料钵的第1片病害叶子的病害面积，按照表21的基准进行评估，其结果如表23所示。
                                      表23
化合物编号 评估 化合物编号 评估 化合物编号 评估 化合物编号 评估 化合物编号 评估
  A-3A-7A-8A-20A-21A-51A-52A-53A-54A-56A-58A-61A-62A-64A-70A-73A-80A-81A-82A-83A-85A-87A-88A-89A-90A-91A-92A-93A-94A-95A-98A-99A-102A-103A-111A-112A-113A-150A-151A-152 BABBABAAABBBBAAAABBABBBBABBAAAABABABABAA   A-153A-154A-155A-156A-157A-158A-159A-160A-185A-189A-198A-201A-206A-207A-208A-215A-216A-217A-218A-220A-225A-227A-228A-241A-242A-248A-251A-252A-254A-256A-257A-258A-266A-269A-277A-278A-279A-283A-285A-286 AAAAAAABAAAABABAAAAAABBBABAAAAABBABBBBAA A-291A-293A-294A-295A-296A-297A-303A-304A-305A-306A-309A-310A-311A-312A-313A-314A-315A-320A-321A-322A-323A-324A-325A-326A-327A-328A-329A-330A-331A-332A-333A-334A-338A-339A-340A-341A-342A-343A-344A-345 AABBABAAAABAAAAAAABAAAAAAAABAAAAAABAAAAB   A-346A-347A-348A-349A-354A-355A-356A-358A-359A-360A-361A-362A-363A-364A-365A-367A-368A-369A-370A-371A-372A-373A-374A-375A-376A-377A-378A-379A-380A-381A-382A-384A-385A-386A-387A-388A-389A-392A-396A-397   AABABBAABABAAABAAAAAAAABBAAAAABABBBAAAAA   A-398A-400A-403A-404A-405A-406A-407A-410A-411A-412A-413A-414A-415A-416A-417A-418A-428A-429A-430A-431A-432A-433A-438A-440A-441A-443A-444   ABAAAAAAAAAAAAAAAAAAABBBABB
试验例3 黄瓜灰霉菌的预防效果试验
分别在直径6cm的塑料钵中播种4粒黄瓜种子(品种：相模半白)，温室内培养。用水稀释制剂例2中制成的水和剂，使其中的有效组分浓度达到500ppm，将该经过稀释的水和剂撒在子叶展开的黄瓜幼苗上，每个塑料钵中撒10ml。风干后，用浸有黄瓜灰霉菌的孢子悬浮液的纸盘覆盖在黄瓜子叶表面进行接种，然后马上放入22℃的温室内。接种3天后观察所有塑料钵中的子叶病害面积，按照表24的基准进行评估，其结果如表25所示。
           表24
  评估
    A 未发现病害
    B 病害面积不足无处理区的25％
    C 病害面积在无处理区的25％以上50％以下
    D 病害面积在50％以上
                                  表25
 化合物编号  评估 化合物编号 评估  化合物编号 评估
    A-3A-7A-37A-38A-39A-40A-46A-49A-50A-51A-62A-81A-82A-83A-84A-87A-88A-90A-99A-100A-112A-113A-150A-157A-206A-220A-225A-254A-255A-256A-258A-279A-285A-286A-291A-294A-295A-296A-297A-300   BBBABBBBAABABBBBBBBBABBBBBBBBBBBBABABABB   A-305A-306A-309A-310A-311A-312A-313A-314A-315A-322A-323A-324A-325A-326A-327A-328A-329A-330A-331A-333A-334A-338A-341A-342A-343A-348A-355A-363A-367A-370A-371A-373A-375A-377A-384A-396A-404A-405A-406A-407   BAABBBAAABAAAABABABBBBBBBAABBABBAABABBBA     A-410A-412A-413A-415A-416A-417A-420A-424A-425A-427A-428A-429A-430A-432A-437A-438A-443   BAAABAAAAABAABBBB
产业上利用的可能性
由于本发明的农用、园艺用杀菌剂对古巴假霜霉、苹果黑星菌、禾白粉菌、稻米枯萎菌、黄瓜灰霉菌、立枯丝核菌，隐匿柄锈菌，颖枯壳针孢，核盘菌具有较高的预防和除治效果。而且，不会对作物产生药害，还兼具残效性和耐雨性良好的特征，所以可作为农用、园艺用杀菌剂使用。

Claims (8)

1.通式[I]表示的氨基甲酸酯衍生物，
式中，X表示卤原子、C1～C6烷基、C1～C6烷氧基；n表示0或1～4的整数；R1表示C1～C6烷基；R2表示氢原子、C1～C6烷基或可取代的苄基；R3表示氢原子；G表示氧原子；Y表示氢原子，C1～C10烷基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C3～C6环烷基、C1～C6烷氧基、二C1～C6烷基氨基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基，C2～C10链烯基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子，C2～C10炔基，苯甲酰甲基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基或C1～C6烷氧基，芳基，杂芳基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基、C1～C6烷氧基或C1～C6卤代烷基，芳基-C1～C6烷基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基、C1～C6卤代烷氧基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基C1～C6烷基，芳基-C2～C6链烯基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子，或者杂环-C1～C6烷基，所述基团中的杂环可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6烷基羰基；Q表示氢原子，氰基，C1～C6烷基，C3～C6环烷基，C1～C4烷基磺酰基，或苯基，所述基团可被至少1个选自卤原子的基团取代。
2.如权利要求1所述的氨基甲酸酯衍生物，其中，Y表示氢原子，C1～C10取代烷基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C3～C6环烷基、C1～C6烷氧基、二C1～C6烷基氨基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基，C2～C10链烯基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子，C2～C10炔基，苯甲酰甲基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基或C1～C6烷氧基，芳基，杂芳基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基、C1～C6烷氧基或C1～C6卤代烷基，芳基-C1～C6烷基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基、C1～C6卤代烷氧基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基C1～C6烷基，芳基-C2～C6链烯基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子，或者杂环-C1～C6烷基，所述基团中的杂环可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6烷基羰基。
3.如权利要求1所述的氨基甲酸酯衍生物，其中，Y表示氢原子，C2～C10链烯基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子，C2～C10炔基，苯甲酰甲基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基或C1～C6烷氧基，芳基，杂芳基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、C1～C6烷基、C1～C6烷氧基或C1～C6卤代烷基，芳基-C1～C6烷基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基、C1～C6卤代烷氧基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基C1～C6烷基，芳基-C2～C6链烯基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子，或者杂环-C1～C6烷基，所述基团中的杂环可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6烷基羰基。
4.如权利要求1所述的氨基甲酸酯衍生物，其中，Y表示芳基-C1～C6烷基，所述基团中的芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基、C1～C6卤代烷氧基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基C1～C6烷基。
5.如权利要求1所述的氨基甲酸酯衍生物，其中，Y表示杂环-C1～C6烷基，所述基团中的杂环可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6烷基羰基。
6.如权利要求1所述的氨基甲酸酯衍生物，其中，Y表示杂芳基-C1～C6烷基，所述基团中的杂芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6烷基羰基。
7.如权利要求1所述的氨基甲酸酯衍生物，其中，Y表示苄基，所述基团可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、硝基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基、C1～C6卤代烷氧基、C1～C6烷基羰基、C1～C6烷氧基羰基或C1～C6烷氧基亚氨基C1～C6烷基，或者表示含有1个以上氮原子的5～6元环表示的杂芳基-C1～C6烷基，所述基团中的杂芳基可被至少1个相同或不同的基团取代，取代基包括卤原子、氰基、C1～C6烷基、C1～C6烷氧基、C1～C6卤代烷基或C1～C6烷基羰基。
8.农用、园艺用杀菌剂，所述杀菌剂以权利要求1～7中的任一项所述的氨基甲酸酯衍生物为有效成分。
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