CN108503587B - 一种酰胺类化合物及其应用 - Google Patents

一种酰胺类化合物及其应用 Download PDF

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CN108503587B
CN108503587B CN201810368391.0A CN201810368391A CN108503587B CN 108503587 B CN108503587 B CN 108503587B CN 201810368391 A CN201810368391 A CN 201810368391A CN 108503587 B CN108503587 B CN 108503587B
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pyrazol
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杜永磊
吕亮
李宏伟
刘世勤
刘吉永
侯爽
马文
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Shanghai Xiaoming Testing Technology Service Co ltd
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Abstract

本发明提供一种酰胺类化合物及其应用，所述化合物与现有技术的化合物相比，杀菌活性得到显著改进的酰胺类化合物。以期开发一种结构新颖的杀菌剂，将其用于农业、林业或卫生上病害的防治。

Description

一种酰胺类化合物及其应用
技术领域
本发明属于杀菌剂领域，涉及一种酰胺类化合物及其用途。
背景技术
由于杀菌剂在使用一段时间后，病害会对其产生抗性，因此，需要不断发明新型的和改进的具有杀菌活性的化合物和组合物。
某些具有杀菌活性的酰胺类化合物已有报道。WO2010106071A1公开了具有杀真菌特性的N-羟基-1-甲基-1H-吡唑-4-甲酰胺类化合物及其杀菌活性，如该专利中的化合物1.001(KC1)和化合物2.001(KC2)。
Figure BDA0001637890800000011
本发明所示的酰胺类化合物未见公开。
发明内容
为解决现有技术存在的技术问题，本发明提供一种酰胺类化合物及其用途，所述化合物与现有化合物相比，杀菌活性得到显著改进的酰胺类化合物。以期开发一种结构新颖的杀菌剂，将其用于农业、林业或卫生上病害的防治。
为达到上述目的，本发明采用以下技术方案：
一种酰胺类化合物，所述化合物为式I所示化合物或式I所示化合物的盐：
Figure BDA0001637890800000021
其中，Q1为取代或未取代的烷基、取代或未取代的芳基、取代或未取代的杂芳基或取代或未取代的稠环杂芳基；Q2为取代或未取代的杂芳基、取代或未取代的稠环杂芳基或2、5位分别被取代的苯基中的任意一种；R1为氢或取代或未取代的烷基，R2为氢、卤素或取代或未取代的烷基。
作为本发明优选的技术方案，所述Q1为C1～C12的烷基、C1～C12的卤代烷基、苯基、5～6元杂芳基、6～20元稠环杂芳基、被1个或1个以上相同或不同的R3取代的苯基、被1个或1个以上相同或不同的R3取代的5～6元杂芳基或被1个或1个以上相同或不同的R3取代的6～20元稠环杂芳基中的任意一种。
优选地，所述Q2为5～6元杂芳基、6～20元稠环杂芳基、被1个或1个以上相同或不同的R3取代的5～6元杂芳基、被1个或1个以上相同或不同的R3取代的6～20元稠环杂芳基或2、5位分别被R4和R5取代的苯基中的任意一种。
优选地，所述5～6元杂芳基为吡唑基、呋喃基、噻唑基、噁唑基、异噁唑基、咪唑基、三唑基、噻吩基、噻二唑基、吡啶基、嘧啶基、吡嗪基或哒嗪基中的任意一种。
作为本发明优选的技术方案，所述Q1为被1个或1个以上相同或不同R3取代的苯基、吡唑基、呋喃基、噻唑基、噻吩基、噻二唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、苯并噻二唑基，所述苯基、吡唑基、呋喃基、噻唑基、噻吩基、噻二唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基或苯并噻二唑基中的任意一种。
优选地，所述Q2为吡唑基、被1个或1个以上相同或不同R3取代的吡唑基或2、5位分别被R4和R5取代的苯基中的任意一种。
作为本发本发明优选的技术方案，所述R1为氢、C1～C6烷基或C1～C6卤代烷基中的任意一种。
优选地，所述R2为氢、卤素、C1～C6烷基或C1～C6卤代烷基中的任意一种。
优选地，所述R3为卤素、C1～C6烷基、C1～C6卤代烷基、C1～C6烷氧基、C1～C6卤代烷氧基、C3～C8环烷基、C3～C8卤代环烷基、氰基、硝基、氨基、C1～C6烷基氨基、羟基、羟甲基、羧基、巯基、磺酰基、被1个或1个以上R6取代的C6～C10芳基或被1个或1个以上R6取代的3～12元杂环基中的任意一种或至少两种的组合，所述组合典型但非限制性实例有：卤素和C1～C6烷基的组合、C1～C6烷基和C1～C6卤代烷基的组合、C1～C6卤代烷基和C1～C6烷氧基的组合、C1～C6烷氧基和C1～C6卤代烷氧基的组合、C3～C8环烷基和C3～C8卤代环烷基的组合、氰基和硝基的组合、硝基和氨基的组合、氨基和C1～C6烷基氨基的组合、氨基和羟基的组合、羟基和羟甲基的组合、羟基和羧基的组合、羟基和巯基的组合、巯基和磺酰基的组合、被1个或1个以上R6取代的C6～C10芳基和被1个或1个以上R6取代的3～12元杂环基的组合或卤素、C1～C6烷基和羟基的组合等。
优选地，所述R4和所述R5分别独立地为卤素、C1～C6烷基、C1～C6卤代烷基、C1～C6烷氧基、C1～C6卤代烷氧基、C3～C8环烷基、C3～C8卤代环烷基、氰基、硝基、氨基、C1～C6烷基氨基、羟基、羟甲基、羧基、巯基、磺酰基、被1个或1个以上R6取代的C6～C10芳基或被1个或1个以上R6取代的3～12元杂环基中的任意一种。
优选地，所述卤素为氟、氯、溴或碘中的任意一种或至少两种的组合，所述组合典型但非限制性实例有：氟和氯的组合、氯和溴的组合、溴和碘的组合或碘和氯的组合等。
作为本发本发明优选的技术方案，所述R1为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或特丁基中的任意一种。
优选地，所述R2为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或特丁基中的任意一种。
优选地，R3为氟、氯、溴、碘、C1～C6烷基、C1～C6卤代烷基或被1个或1个以上R6取代的苯基中的任意一种或至少两种的组合。
优选地，所述R4和所述R5分别独立地为C1～C6烷基、C1～C6卤代烷基、C1～C6烷氧基、C1～C6卤代烷氧基、C3～C8环烷基或C3～C8卤代环烷基中的任意一种。
作为本发明优选的技术方案，所述R6为氢、氟、氯、溴、碘、C1～C6烷基、C1～C6卤代烷基、C1～C6烷氧基、C1～C6卤代烷氧基、C3～C8环烷基、C3～C8卤代环烷基、氰基、硝基、氨基、C1～C6烷基氨基、羟基、羟甲基、羧基、巯基或磺酰基中的任意一种或至少两种的组合，所述组合典型但非限制性实例有：氟和氯的组合、氯和溴的组合、溴和碘的组合、碘和氯的组合、C1～C6烷基和C1～C6卤代烷基的组合、C1～C6烷氧基和C1～C6卤代烷氧基的组合、C3～C8环烷基和C3～C8卤代环烷基的组合、氰基和硝基的组合、硝基和氨基的组合、氨基和C1～C6烷基氨基的组合、氨基和羟基的组合、羟基和羟甲基的组合、羟基和羧基的组合、羟基和巯基的组合或巯基和磺酰基的组合等。
作为本发明优选的技术方案，所述式I所示化合物的盐为式I所示化合物的盐酸盐、硫酸盐、硝酸盐、碳酸氢盐、碳酸盐、磷酸盐、甲酸盐、醋酸盐、三氟乙酸盐、苯磺酸盐、对甲苯磺酸盐、甲基磺酸盐、苯甲酸盐、柠檬酸盐、苹果酸盐、酒石酸盐、马来酸盐、琥珀酸盐、抗坏血酸盐或草酸盐中的任意一种。
上述说明书内容中汇集所用术语一般定义如下：
如本文所用，烷基是指直链或支链形式，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、特丁基、正戊基、异戊基、正己基等基团。卤代烷基是指烷基被一个或多个卤原子取代的基团。烷氧基是指烷基末端连有氧原子的基团，例如甲氧基、乙氧基、正丙氧基、异丙氧基、特丁氧基等。卤代烷氧基是指烷氧基被一个或多个卤原子取代的基团。卤素为F、Cl、Br或I。
如本文所用，术语“C1～C6烷基”是指具有1至6个碳原子的直链或支链烷基，非限制性地包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、特丁基、正戊基、异戊基、正己基等。术语“C1～C6烷氧基”是指具有1至6个碳原子的直链或支链烷氧基，非限制性地包括甲氧基、乙氧基、正丙氧基、异丙氧基和特丁氧基等。术语“C1～C12烷基”具有类似的含义。
如本文所用，术语“C3～C8环烷基”是指在环上具有3至8个碳原子的环状烷基，非限制性地包括环丙基、环丁基、环戊基、环己基、环庚基、环辛基等。
如本文所用，术语“C6～C10芳基”是指在环上不含杂原子的具有6至10个碳原子的芳香族环基，如苯基、萘基等。
如本文所用，术语“3～12元杂环基”是指在环上含有1～3个选自氧、硫和氮中的杂原子的饱和或不饱和的3～12元环基，例如二氧杂环戊基等。
在本发明中，除非特别指出，所用术语具有本领域技术人员公知的一般含义。
本发明的式I所示化合物，可按式II所示化学方程式的方法制备：
Figure BDA0001637890800000061
通式化合物A与酰氯在适宜的溶剂中，温度为室温到溶剂沸点下反应0.5～48小时制得式I所示化合物。
所述适宜的溶剂选自二氯甲烷、氯仿、乙酸乙酯、乙腈、四氢呋喃、二氧六环、乙醇、甲醇、N,N-二甲基甲酰胺或二甲基亚砜等中的任意一种或至少两种的组合。
加入适宜的碱类物质对反应有利。适宜的碱选自有机碱和/或无机碱，所述有机碱可以是三乙胺、N,N-二甲基苯胺、吡啶、甲醇钠、乙醇钠、叔丁醇钠或叔丁醇钾等中的任意一种或至少两种的组合，所述无机碱可以是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾或氢化钠等中的任意一种或至少两种的组合。
化合物A制备方法如式III所示：
Figure BDA0001637890800000062
步骤a：化合物B溶于有机溶剂，室温下滴加化合物C，反应得化合物D；所述有机溶剂可以是二氯甲烷、氯仿、乙酸乙酯、乙腈、四氢呋喃、二氧六环、乙醇、甲醇、N,N-二甲基甲酰胺或二甲基亚砜等中的任意一种或至少两种的组合。
加入适宜的碱类物质对反应有利。适宜的碱选自有机碱和/或无机碱，所述有机碱可以是三乙胺、N,N-二甲基苯胺、吡啶、甲醇钠、乙醇钠、叔丁醇钠或叔丁醇钾等中的任意一种或至少两种的组合，所述无机碱可以是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾或氢化钠等中的任意一种或至少两种的组合。
步骤b：化合物D溶于适宜溶剂，回流条件下加入化合物E，反应得化合物F；所述适宜溶剂可以是水、二氯甲烷、氯仿、乙酸乙酯、乙腈、四氢呋喃、二氧六环、乙醇、甲醇、N,N-二甲基甲酰胺或二甲基亚砜等中的任意一种或至少两种的组合。
加入适宜的碱类物质对反应有利。适宜的碱选自有机碱和/或无机碱，所述有机碱可以是三乙胺、N,N-二甲基苯胺、吡啶、甲醇钠、乙醇钠、叔丁醇钠或叔丁醇钾等中的任意一种或至少两种的组合，所述无机碱可以是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾或氢化钠等中的任意一种或至少两种的组合。
步骤c：化合物F溶于有机溶剂，室温下加入还原剂，反应得化合物A；所述有机溶剂可以是二氯甲烷、氯仿、乙酸乙酯、乙腈、四氢呋喃、二氧六环、乙醇、甲醇、N,N-二甲基甲酰胺或二甲基亚砜等中的任意一种或至少两种的组合；所述还原剂可以是氢化铝锂、硼氢化钠、硼氢化锂、硼氢化钾、三仲丁基硼氢化锂、硫代硼氢化钠、氰基硼氢化钠、铁粉、锌粉、氯化亚锡、水合肼、金属锂或金属钠等中的任意一种或至少两种的组合。
加入适宜的酸对反应有利，适宜的酸选自无机酸(可以是硫酸或盐酸等)和/或有机酸(可以是乙酸或对甲苯磺酸等)。
表1列出了部分式I所示化合物的结构和理化性质。
Figure BDA0001637890800000071
表1
Figure BDA0001637890800000072
Figure BDA0001637890800000081
Figure BDA0001637890800000091
Figure BDA0001637890800000101
Figure BDA0001637890800000111
Figure BDA0001637890800000121
Figure BDA0001637890800000131
Figure BDA0001637890800000141
Figure BDA0001637890800000151
Figure BDA0001637890800000161
Figure BDA0001637890800000171
Figure BDA0001637890800000181
Figure BDA0001637890800000191
Figure BDA0001637890800000201
Figure BDA0001637890800000211
部分化合物的1H NMR数据如下：
化合物21：1H NMR(400MHz,CDCl3)δ7.68(d,J＝2.6Hz,1H),7.57–7.53(m,1H),7.53–7.50(m,1H),7.38–7.36(m,1H),7.36–7.32(m,1H),5.88(d,J＝2.6Hz,1H),4.85(s,1H),4.40(dd,J＝10.6,8.4Hz,1H),4.26(dd,J＝10.6,5.2Hz,1H),3.78(s,3H),2.43(s,2H),1.64(dt,J＝15.1,7.7Hz,2H),1.37–1.28(m,9H),0.88(t,J＝6.8Hz,3H).
化合物22：1H NMR(400MHz,CDCl3)δ7.72–7.65(m,1H),7.48(d,J＝5.5Hz,2H),7.40–7.32(m,2H),7.31–7.24(m,2H),7.18(d,J＝7.2Hz,2H),5.90(s,1H),4.51–4.39(m,1H),4.15(dd,J＝20.6,18.5Hz,2H),3.83(s,3H),2.40(s,3H),1.35(s,3H).
化合物23：1H NMR(400MHz,CDCl3)δ7.66(d,J＝1.6Hz,1H),7.54–7.38(m,3H),7.35(d,J＝8.8Hz,3H),7.07(dd,J＝18.3,9.3Hz,2H),5.90(s,1H),4.44(s,1H),4.37–4.02(m,2H),3.75(s,3H),1.41(s,3H).
化合物24：1H NMR(400MHz,DMSO-d6)δ8.34(d,J＝2.7Hz,1H),7.72(d,J＝9.0Hz,2H),7.55–7.46(m,2H),7.28(d,J＝5.3Hz,1H),7.02(d,J＝5.3Hz,1H),6.03(d,J＝2.7Hz,1H),4.52(s,1H),4.32(t,J＝10.1Hz,1H),4.14(dd,J＝10.6,4.1Hz,1H),3.64(s,3H),2.46(s,3H),1.29(d,J＝6.8Hz,3H).
化合物25：1H NMR(400MHz,DMSO-d6)δ8.35(d,J＝2.7Hz,1H),8.05(s,1H),7.80–7.69(m,2H),7.55–7.42(m,2H),6.04(d,J＝2.7Hz,1H),4.80(dd,J＝12.8,7.6Hz,1H),4.37(dd,J＝10.6,8.8Hz,1H),4.23(dd,J＝10.6,5.0Hz,1H),3.76(s,3H),3.67(s,3H),2.29(s,3H),1.28(d,J＝6.9Hz,3H).
化合物26：1H NMR(400MHz,DMSO-d6)δ8.34(d,J＝2.7Hz,1H),7.74–7.65(m,2H),7.57–7.45(m,4H),7.44–7.33(m,3H),6.06(d,J＝2.7Hz,1H),4.58(s,1H),4.34(t,J＝10.1Hz,1H),4.17(dd,J＝10.7,4.4Hz,1H),3.64(s,3H),1.29(d,J＝6.8Hz,3H).
化合物27：1H NMR(400MHz,DMSO-d6)δ8.34(d,J＝2.7Hz,1H),7.68(d,J＝8.9Hz,2H),7.49(dd,J＝6.9,2.2Hz,4H),7.43(d,J＝8.5Hz,2H),6.05(d,J＝2.7Hz,1H),4.61(s,1H),4.32(t,J＝10.0Hz,1H),4.17(dd,J＝10.8,4.2Hz,1H),3.63(s,3H),1.30(d,J＝6.8Hz,3H).
化合物28：1H NMR(400MHz,DMSO-d6)δ8.83(d,J＝8.1Hz,1H),8.36(d,J＝5.9Hz,1H),8.22(d,J＝2.4Hz,1H),7.88–7.79(m,1H),7.63(d,J＝8.9Hz,2H),7.53–7.40(m,2H),5.87(s,1H),4.92(s,1H),4.43(t,J＝10.1Hz,1H),4.24(dd,J＝10.9,3.9Hz,1H),3.77(s,3H),1.43(d,J＝6.9Hz,3H).
化合物29：1H NMR(400MHz,DMSO-d6)δ8.42–8.34(m,1H),7.78(d,J＝8.8Hz,1H),7.74–7.67(m,1H),7.54–7.44(m,4H),7.27(s,1H),6.12(d,J＝2.4Hz,1H),4.91(dd,J＝12.2,7.4Hz,1H),4.45(t,J＝9.7Hz,1H),4.33(dd,J＝10.7,4.8Hz,1H),3.44(s,3H),1.38(d,J＝6.9Hz,3H).
化合物30：1H NMR(400MHz,DMSO-d6)δ8.33(d,J＝2.7Hz,1H),7.74–7.70(m,2H),7.64(d,J＝1.5Hz,1H),7.54–7.45(m,2H),6.45(d,J＝1.5Hz,1H),5.97(d,J＝2.6Hz,1H),4.83–4.72(m,1H),4.33(t,J＝8Hz,1H),4.19(dd,J＝10.7,4.5Hz,1H),3.73(s,3H),2.18(s,3H),1.32(d,J＝6.8Hz,3H).
化合物31：1H NMR(400MHz,DMSO-d6)δ8.35(d,J＝2.7Hz,1H),7.77–7.72(m,2H),7.67(d,J＝5.0Hz,1H),7.52–7.48(m,2H),6.97(d,J＝5.0Hz,1H),6.02(d,J＝2.7Hz,1H),4.81–4.69(m,1H),4.39(dd,J＝10.6,9.2Hz,1H),4.23(dd,J＝10.6,4.7Hz,1H),3.68(s,3H),2.39(s,3H),1.32(d,J＝6.9Hz,3H).
化合物32：1H NMR(400MHz,DMSO-d6)δ8.82(d,J＝8.2Hz,1H),8.35(d,J＝5.7Hz,1H),8.23(d,J＝2.0Hz,1H),7.84(t,J＝7.8Hz,1H),7.64(d,J＝8.8Hz,2H),7.53–7.43(m,2H),5.87(s,1H),4.91(s,1H),4.43(t,J＝10.1Hz,1H),4.24(d,J＝7.1Hz,1H),3.95(q,J＝7.0Hz,2H),1.43(d,J＝6.9Hz,3H),1.16(t,J＝7.0Hz,3H).
化合物33：1H NMR(400MHz,DMSO-d6)δ8.35(d,J＝2.7Hz,1H),7.77–7.72(m,2H),7.65(d,J＝5.0Hz,1H),7.53–7.47(m,2H),6.96(d,J＝5.0Hz,1H),6.02(d,J＝2.7Hz,1H),4.81–4.68(m,1H),4.38(t,J＝10.6Hz,1H),4.23(dd,J＝10.6,4.6Hz,1H),3.96–3.78(m,2H),2.37(s,3H),1.31(d,J＝6.9Hz,3H),1.14(t,J＝7.1Hz,3H).
化合物34：1H NMR(500MHz,DMSO-d6)δ8.37(d,J＝2.7Hz,1H),7.74(d,J＝8.9Hz,2H),7.56–7.48(m,2H),6.96(t,JH-F＝53.7Hz,1H),5.99(d,J＝1.8Hz,1H),4.69(s,1H),4.33(t,J＝9.9Hz,1H),4.20(d,J＝7.3Hz,1H),3.84(dd,J＝13.9,7.0Hz,2H),3.75(s,3H),1.31(d,J＝6.8Hz,3H),1.08(t,J＝6.2Hz,3H).
化合物39：1H NMR(500MHz,DMSO-d6)δ8.36(d,J＝2.7Hz,1H),8.21(s,1H),7.75(d,J＝8.9Hz,2H),7.50(d,J＝8.9Hz,2H),7.21(t,JH-F＝54.1Hz,1H),6.03(d,J＝2.6Hz,1H),4.86–4.72(m,1H),4.38(t,J＝10.5Hz,1H),4.25(dd,J＝10.6,4.6Hz,1H),3.91(s,3H),3.90–3.81(m,2H),1.31(d,J＝6.9Hz,3H),1.20–1.15(m,3H).
化合物44：1H NMR(500MHz,DMSO-d6)δ8.38(d,J＝2.7Hz,1H),8.24(s,1H),7.75(d,J＝8.9Hz,2H),7.51(d,J＝8.9Hz,2H),6.05(d,J＝2.6Hz,1H),4.72(s,1H),4.35(t,J＝9.8Hz,1H),4.23(dd,J＝10.4,4.1Hz,1H),3.92(s,3H),3.87–3.77(m,2H),1.29(d,J＝6.9Hz,3H),1.09(t,J＝7.0Hz,3H).
化合物49：1H NMR(400MHz,DMSO-d6)δ8.84(d,J＝8.2Hz,1H),8.46–8.31(m,1H),8.21(d,J＝1.9Hz,1H),7.84(t,J＝7.8Hz,1H),7.61(d,J＝8.0Hz,2H),7.41(t,J＝8.0Hz,2H),7.21(t,J＝7.4Hz,1H),5.85(s,1H),4.93(s,1H),4.43(t,J＝10.0Hz,1H),4.24(d,J＝7.3Hz,1H),3.77(s,3H),1.44(d,J＝6.9Hz,3H).
化合物50：1H NMR(400MHz,DMSO-d6)δ8.33(d,J＝2.6Hz,1H),7.80–7.61(m,3H),7.49–7.39(m,2H),7.22(t,J＝7.4Hz,1H),6.98(d,J＝5.0Hz,1H),6.00(d,J＝2.6Hz,1H),4.84–4.66(m,1H),4.39(t,J＝10.6Hz,1H),4.23(dd,J＝10.6,4.6Hz,1H),3.68(s,3H),2.39(s,3H),1.32(d,J＝6.9Hz,3H).
化合物51：1H NMR(400MHz,DMSO-d6)δ8.34(d,J＝2.7Hz,1H),8.30(s,1H),7.77–7.69(m,2H),7.45(t,J＝8.0Hz,2H),7.27(t,JH-F＝54.2Hz,1H),7.22(t,J＝7.4Hz,1H),6.02(d,J＝2.6Hz,1H),4.84(dd,J＝13.0,7.1Hz,1H),4.40(dd,J＝10.5,9.1Hz,1H),4.27(dd,J＝10.7,4.8Hz,1H),3.91(s,3H),3.72(s,3H),1.32(d,J＝6.9Hz,3H).
化合物56：1H NMR(400MHz,DMSO-d6)δ8.34(d,J＝2.6Hz,1H),8.28(s,1H),7.72(d,J＝7.8Hz,2H),7.50–7.39(m,2H),7.22(t,J＝7.4Hz,1H),6.02(d,J＝2.6Hz,1H),4.74(s,1H),4.36(t,J＝9.8Hz,1H),4.23(dd,J＝10.7,4.6Hz,1H),3.91(s,3H),3.64(s,3H),1.30(d,J＝6.9Hz,3H).
化合物61：1H NMR(400MHz,DMSO-d6)δ8.83(d,J＝8.2Hz,1H),8.35(s,1H),8.17(d,J＝1.7Hz,1H),7.83(t,J＝7.8Hz,1H),7.63(dd,J＝8.8,4.7Hz,2H),7.33–7.19(m,2H),5.84(s,1H),4.93(s,1H),4.42(t,J＝10.1Hz,1H),4.23(d,J＝7.2Hz,1H),3.77(s,3H),1.43(d,J＝6.9Hz,3H).
化合物62：1H NMR(400MHz,DMSO-d6)δ8.30(d,J＝2.6Hz,1H),7.76–7.71(m,2H),7.67(d,J＝5.0Hz,1H),7.35–7.23(m,2H),6.97(d,J＝5.0Hz,1H),6.00(d,J＝2.6Hz,1H),4.84–4.69(m,1H),4.38(t,J＝10.5Hz,1H),4.22(dd,J＝10.6,4.6Hz,1H),3.68(s,3H),2.39(s,3H),1.31(d,J＝6.9Hz,3H).
化合物63：1H NMR(400MHz,DMSO-d6)δ8.33–8.26(m,2H),7.78–7.71(m,2H),7.34–7.27(m,2H),7.25(t,JH-F＝54.1Hz,1H),6.02(d,J＝2.6Hz,1H),4.83(dd,J＝12.4,7.5Hz,1H),4.39(t,J＝10.6Hz,1H),4.26(dd,J＝10.7,4.8Hz,1H),3.92(s,3H),3.72(s,3H),1.31(d,J＝6.9Hz,3H).
化合物68：1H NMR(400MHz,DMSO-d6)δ8.31(d,J＝2.6Hz,1H),8.28(s,1H),7.77–7.71(m,2H),7.35–7.25(m,2H),6.02(d,J＝2.6Hz,1H),4.74(s,1H),4.35(t,J＝10.6Hz,1H),4.22(dd,J＝10.7,4.6Hz,1H),3.92(s,3H),3.64(s,3H),1.29(d,J＝6.9Hz,3H).
化合物73：1H NMR(500MHz,DMSO-d6)δ8.30(s,1H),7.26(t,JH-F＝54.1Hz,1H),6.78(t,JH-F＝54.6Hz,1H),6.05(s,1H),4.83(s,1H),4.31(t,J＝10.3Hz,1H),4.22(dd,J＝10.5,4.6Hz,1H),3.94(s,3H),3.73(s,3H),3.42(s,3H),1.31(d,J＝7.0Hz,3H).
化合物79：1H NMR(500MHz,DMSO-d6)δ7.71(dd,J＝5.0,1.6Hz,1H),7.00(dd,J＝5.0,1.6Hz,1H),6.78(t,JH-F＝54.6Hz,1H),6.04(s,1H),4.75(s,1H),4.30(t,J＝10.0Hz,1H),4.20(dd,J＝10.4,3.0Hz,1H),3.68(d,J＝1.7Hz,3H),3.44(s,3H),2.40(s,3H),1.32(d,J＝6.8Hz,3H).
化合物80：1H NMR(400MHz,DMSO-d6)δ8.28(s,1H),6.77(t,JH-F＝54.7Hz,1H),6.04(s,1H),4.76(s,1H),4.29(t,J＝10.3Hz,1H),4.20(dd,J＝10.5,4.5Hz,1H),3.95(s,3H),3.63(s,3H),3.47(s,3H),1.29(d,J＝6.9Hz,3H).
化合物85：1H NMR(400MHz,DMSO-d6)δ6.76(t,JH-F＝54.6Hz,1H),6.06(s,1H),4.87(s,1H),4.38(t,J＝10.6Hz,1H),4.28(dd,J＝10.7,4.6Hz,1H),3.75(s,3H),3.40(s,3H),2.86(s,3H),1.38(d,J＝7.0Hz,3H).
化合物86：1H NMR(400MHz,DMSO-d6)δ7.69(d,J＝5.0Hz,1H),6.99(d,J＝5.0Hz,1H),5.47(s,1H),4.76–4.66(m,1H),4.18(t,J＝9.8Hz,1H),4.05(dd,J＝10.3,4.6Hz,1H),3.66(s,3H),3.31(s,3H),2.39(s,3H),2.02(s,3H),1.29(d,J＝6.9Hz,3H).
化合物87：1H NMR(400MHz,DMSO-d6)δ7.69(d,J＝5.0Hz,1H),7.05–6.95(m,2H),6.78(s,1H),6.69(d,J＝7.7Hz,1H),4.81(s,J＝11.5,1H),4.14(t,J＝9.6Hz,1H),4.02(dd,J＝9.9,4.7Hz,1H),3.66(s,3H),3.17–3.06(m,1H),2.41(s,3H),2.25(s,3H),1.34(d,J＝6.9Hz,3H),1.03(d,J＝6.9Hz,3H),0.96(d,J＝6.9Hz,3H).
化合物88：1H NMR(400MHz,DMSO-d6)δ8.29(s,1H),7.29(t,JH-F＝54.2Hz,1H),7.00(d,J＝7.7Hz,1H),6.77(s,1H),6.68(d,J＝7.6Hz,1H),4.93–4.83(m,1H),4.12(t,J＝9.5Hz,1H),4.04(dd,J＝9.8,4.8Hz,1H),3.92(s,3H),3.72(s,3H),3.03(dt,J＝13.8,6.8Hz,1H),2.25(s,3H),1.34(d,J＝6.9Hz,3H),1.00(d,J＝6.9Hz,3H),0.90(d,J＝6.9Hz,3H).
化合物93：1H NMR(400MHz,DMSO-d6)δ8.26(s,1H),7.02(d,J＝7.7Hz,1H),6.78(s,1H),6.70(d,J＝7.7Hz,1H),4.80(s,1H),4.13(t,J＝9.5Hz,1H),4.03(dd,J＝10.0,4.8Hz,1H),3.93(s,3H),3.62(s,3H),3.10(dt,J＝13.8,6.9Hz,1H),2.25(s,3H),1.32(d,J＝6.9Hz,3H),1.04(d,J＝6.9Hz,3H),0.98(d,J＝6.9Hz,3H).
化合物98：1H NMR(400MHz,DMSO-d6)δ7.57–7.48(m,1H),7.40(td,J＝7.4,1.7Hz,1H),7.34–7.25(m,2H),7.06(d,J＝7.7Hz,1H),6.77(s,1H),6.72(d,J＝7.7Hz,1H),4.88(s,1H),4.15(s,1H),3.99(s,1H),3.51(s,3H),3.27–3.17(m,1H),2.24(s,3H),1.33(d,J＝5.7Hz,3H),1.13(d,J＝6.9Hz,6H).
化合物99：1H NMR(400MHz,DMSO-d6)δ7.53(d,J＝5.7Hz,1H),7.47(t,J＝7.5Hz,1H),7.43–7.27(m,2H),7.07(d,J＝7.7Hz,1H),6.82(s,1H),6.73(d,J＝7.6Hz,1H),4.88(s,1H),4.22(s,1H),4.10(s,1H),3.85(s,3H),3.31–3.21(m,1H),2.26(s,3H),1.37(s,3H),1.15(d,J＝6.8Hz,6H).
化合物100：1H NMR(400MHz,DMSO-d6)δ8.94(dd,J＝8.2,0.6Hz,1H),8.50(d,J＝7.4Hz,1H),7.95–7.87(m,1H),6.93(d,J＝7.7Hz,1H),6.77(s,1H),6.66(d,J＝7.7Hz,1H),5.01(s,1H),4.23(t,J＝9.8Hz,1H),4.06(dd,J＝9.9,4.3Hz,1H),3.77(s,3H),2.93–2.79(m,1H),2.23(s,3H),1.46(d,J＝6.9Hz,3H),0.80(d,J＝6.8Hz,3H),0.73(d,J＝6.9Hz,3H).
化合物101：1H NMR(400MHz,DMSO-d6)δ6.98(d,J＝7.7Hz,1H),6.78(s,1H),6.69(d,J＝7.6Hz,1H),4.94(s,1H),4.19(t,J＝9.7Hz,1H),4.09(dd,J＝10.0,4.6Hz,1H),3.77(s,3H),3.00–2.90(m,1H),2.89(s,3H),2.25(s,3H),1.42(d,J＝7.0Hz,3H),0.97(d,J＝6.9Hz,3H),0.81(d,J＝6.9Hz,3H).
化合物102：1H NMR(400MHz,DMSO-d6)δ8.51(dd,J＝4.8,1.8Hz,1H),7.89(d,J＝7.1Hz,1H),7.60–7.49(m,1H),7.08(d,J＝7.7Hz,1H),6.83(s,1H),6.73(d,J＝7.6Hz,1H),4.86(s,1H),4.24(t,J＝9.0Hz,1H),4.11(dd,J＝9.4,4.5Hz,1H),3.41(s,3H),3.30–3.21(m,1H),2.27(s,3H),1.40(d,J＝6.5Hz,3H),1.14(d,J＝6.9Hz,6H).
化合物103：1H NMR(400MHz,DMSO-d6)δ7.59–7.53(m,2H),7.51–7.45(m,1H),7.07(d,J＝7.7Hz,1H),6.83(s,1H),6.75–6.69(m,1H),4.92–4.82(m,1H),4.22(t,J＝10.3Hz,1H),4.13(dd,J＝10.3,4.7Hz,1H),3.45(s,3H),3.32–3.16(m,1H),2.27(s,3H),1.38(d,J＝6.8Hz,3H),1.13(dd,J＝6.9,2.3Hz,6H)。
本发明目的之二在于提供一种上述化合物的应用，所述化合物用于制备控制农业、林业或非治疗目的植物病害的药物。
其中，所述农业、林业或非治疗目的植物病害包括以防治卵菌纲(Oomycetes)、子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)或半知菌纲(Deuteromycetes)病害。
本发明中，由上述列出的纲名下的细菌引发的病害的实例包括但不限于：小麦锈病、小麦白粉病、小麦赤霉病、小麦根腐病、小麦纹枯病、小麦全蚀病、小麦颖枯病、黄瓜霜霉病、黄瓜白粉病、黄瓜炭疽病、黄瓜枯萎病、黄瓜灰霉病、葡萄霜霉病、番茄早疫病、番茄晚疫病、水稻纹枯病、水稻稻瘟病、西瓜蔓枯病、花生疮痂病、花生黑斑病、柑橘疮痂病、辣椒根腐病、棉花黄萎病、棉花枯萎病、油菜黑茎病、油菜菌核病、梨黑星病、人参锈腐病、玉米锈病、玉米弯孢病、玉米大斑病、芒果蒂腐病、苹果轮纹病、苹果腐菌烂病、香蕉叶斑病或大豆锈病等。
本发明目的之三在于提供一种杀菌剂组合物，所述杀菌剂组合物含有上述的化合物作为活性组分和载体，所述杀菌剂组合物中活性组分的重量百分含量为1～99％。
其中，所述杀菌剂组合物中活性组分的重量百分含量可以是1％、2％、5％、8％、10％、15％、20％、25％、30％、40％、50％、60％、70％、80％、90％或99％等，但并不仅限于所列举的数值，该数值范围内其他未列举的数值同样适用。
本发明目的之四在于提供一种控制植物病害的方法，所述方法为将上述杀菌剂组合物以每公顷10～1000g的有效剂量施于需要控制的病害或其生长介质上。
其中，所述有效剂量可以是每公顷10g、20g、50g、100g、200g、300g、400g、500g、600g、700g、800g、900g或1000g等，但并不仅限于所列举的数值，该数值范围内其他未列举的数值同样适用。
与现有技术相比，本发明至少具有以下有益效果：
本发明提供一种酰胺类化合物，所述化合物对控制农业、林业或非治疗目的植物病害具有显著效果，对由卵菌纲(Oomycetes)、子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)或半知菌纲(Deuteromycetes)等引起的病害的防效可达80％以上，对某些病害的防效最高可达98％。
具体实施方式
为便于理解本发明，本发明列举实施例如下。本领域技术人员应该明了，所述实施例仅仅是帮助理解本发明，不应视为对本发明的具体限制。
合成实施例
实施例1
化合物21的制备：
步骤1：1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮的合成：
Figure BDA0001637890800000301
取一反应瓶，将化合物1-(4-氯苯基)-1H-吡唑-3-醇(来自商业购买，51.38mmol，1.0eq)、碳酸钾(51.38mmol,1.0eq)、碘化钾(0.5138mmol,0.01eq)溶于60mL DMF，室温下搅拌5min，将氯丙酮(56.52mmol,1.1eq)缓慢滴加到上述体系中，60℃反应5h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到浅褐色油状粗产物1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮(11.6g，收率90％)。
步骤2：1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮-O-甲基肟的合成：
Figure BDA0001637890800000302
将1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮(46.27mmol,1.0eq)、碳酸钾(92.55mmol,2.0eq)溶于乙醇/水(体积比1:1)中，85℃温度下分次加入甲氧胺盐酸盐(92.55mmol,2.0eq)，保持温度为85℃反应2～3h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到淡黄色油状粗产物1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮-O-甲基肟(9.84g，收率76％)。
步骤3：N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺的合成：
Figure BDA0001637890800000311
将1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮-O-甲基肟(35.18mmol,1.0eq)用适量甲醇溶解，加入30mL乙酸，室温下分次加入氰基硼氢化钠(70.36mmol,2.0eq)，待反应完毕后，向体系中加入10％氢氧化钠水溶液，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝4:1)，得黄色固体产物N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺(4.76g，收率48％)。
步骤4：N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-N-甲氧基庚酰胺的合成(化合物21)：
Figure BDA0001637890800000312
向反应瓶中依次加入N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺(1.77mmol,1.0eq)、二氯甲烷(20mL)，室温搅拌至固体完全溶解后，加入三乙胺(1.88mmol,1.06eq)，缓慢滴加庚酰氯(1.86mmol,1.05eq)。室温下反应2h，向反应液中加水淬灭反应，用二氯甲烷萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝4:1)，得淡黄色油状液体产物N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-N-甲氧基庚酰胺(672mg，收率96％)。
实施例2
化合物26的制备：
Figure BDA0001637890800000321
向反应瓶中依次加入N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺(1.77mmol,1.0eq)、二氯甲烷(20mL)，室温搅拌至固体完全溶解后，加入三乙胺(1.88mmol,1.06eq)，缓慢滴加苯甲酰氯(1.86mmol,1.05eq)。室温下反应2h，向反应液中加入水淬灭反应，用二氯甲烷萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE：EA＝4:1)，得淡黄色固体产物N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-N-甲氧基苯甲酰胺(451mg，收率66％)。
实施例3
化合物33的制备：
步骤1：1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮-O-乙基肟的合成：
Figure BDA0001637890800000322
将1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮(46.27mmol,1.0eq)、碳酸钾(92.55mmol,2.0eq)溶于乙醇/水(体积比1:1)中，85℃温度下分次加入乙氧胺盐酸盐(92.55mmol,2.0eq)，保持温度为85℃反应2～3h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到褐色油状粗产物1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮-O-乙基肟(12.64g，收率93％)。
步骤2：N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-乙基羟胺的合成：
Figure BDA0001637890800000331
将1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-酮-O-乙基肟(43.03mmol,1.0eq)用适量甲醇溶解，加入30mL乙酸，室温下分次加入氰基硼氢化钠(86.06mmol,2.0eq)，待反应完毕后，向体系中加入10％氢氧化钠水溶液，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝10:1)，得橙黄色油状产物N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-乙基羟胺(9.55g，收率75％)。
步骤3：N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-N-乙氧基-3-甲基噻吩-2-甲酰胺的合成(化合物33)：
Figure BDA0001637890800000332
向反应瓶中依次加入N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-O-乙基羟胺(1.69mmol,1.0eq)、二氯甲烷(20mL)，三乙胺(1.79mmol,1.06eq)，缓慢滴加3-甲基噻吩-2-碳酰氯(1.78mmol,1.05eq)。室温下反应2h，向反应液中加水淬灭反应，用二氯甲烷萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝10：1)，得淡黄色油状液体产物N-(1-((1-(4-氯苯基)-1H-吡唑-3-基)氧基)丙-2-基)-N-乙氧基-3-甲基噻吩-2-甲酰胺(490mg，收率69％)。
实施例4
化合物50的制备：
步骤1：1-苯基吡咯烷-3-酮的合成：
Figure BDA0001637890800000341
将苯肼盐酸盐(138.31mmol，1.0eq)用适量乙醇溶解，40℃下加入甲醇钠(414.93mmol,3.0eq)，体系搅拌30min后，缓慢滴加丙烯酸甲酯(207.47mmol,1.5eq)，反应回流4～5h，待反应完毕后，向反应液中加水淬灭反应，用乙酸调节pH＝5-6，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝2:1)，得淡黄色固体粗产物1-苯基吡咯烷-3-酮(13.46g，收率60％)。
步骤2：1-苯基-1H-吡唑-3-醇的合成：
Figure BDA0001637890800000342
将1-苯基吡咯烷-3-酮(82.99mmol,1.0eq)用5％的氢氧化钠水溶液溶解，加入六水合三氯化铁(16.60mmol,0.2eq)，体系通入氧气并保持温度为80℃，待反应完毕后，向反应液中加水淬灭反应，用盐酸调节PH＝1～2，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝2:1)，得淡黄色固体产物1-苯基-1H-吡唑-3-醇(1.46g，收率11％)。
步骤3：1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-酮的合成：
Figure BDA0001637890800000351
取一反应瓶，将化合物1-苯基-1H-吡唑-3-醇(9.12mmol,1.0eq)、碳酸钾(9.12mmol,1.0eq)、碘化钾(0.0912mmol,0.01eq)溶于60mL DMF，室温下搅拌5min，将氯丙酮(10.03mmol，1.1eq)缓慢滴加到上述体系中，60℃反应5h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到淡黄色油状粗产物1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-酮(1.78g，收率90％)。
步骤4：1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-酮-O-甲基肟的合成：
Figure BDA0001637890800000352
将1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-酮(8.23mmol,1.0eq)、碳酸钾(16.46mmol,2.0eq)溶于乙醇/水(体积比1:1)中，85℃温度下分次加入甲氧胺盐酸盐(16.46mmol,2.0eq)，保持温度为85℃反应2～3h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到淡黄色油状粗产物1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-酮-O-甲基肟(1.62g，收率80％)。
步骤5：N-(1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺的合成：
Figure BDA0001637890800000361
将1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-酮-O-甲基肟(6.60mmol,1.0eq)用适量甲醇溶解，加入30mL乙酸，室温下分次加入氰基硼氢化钠(13.21mmol,2.0eq)，待反应完毕后，向体系中加入10％氢氧化钠水溶液，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝4:1)，得淡黄色油状产物N-(1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺(1.34g，收率82％)。
步骤6：N-甲氧基-3-甲基-N-(1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-基)噻吩-2-甲酰胺的合成(化合物50)：
Figure BDA0001637890800000362
向反应瓶中依次加入N-(1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-基)-O-甲基羟胺(1.21mmol,1.0eq)、二氯甲烷(20mL)，三乙胺(1.29mmol,1.06eq)，缓慢滴加3-甲基噻吩-2-碳酰氯(1.27mmol,1.05eq)。室温下反应2h，向反应液中加水淬灭反应，用二氯甲烷萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝10:1)，得淡黄色油状液体产物N-甲氧基-3-甲基-N-(1-((1-苯基-1H-吡唑-3-基)氧基)丙-2-基)噻吩-2-甲酰胺(374mg，收率83％)。
实施例5
化合物73的制备：
步骤1：3-(二氟甲基)-1-甲基-1H-吡唑-5-醇的合成：
Figure BDA0001637890800000371
将化合物二氟甲基乙酰乙酸乙酯(60.20mmol,1.0eq)用适量甲醇溶解，室温下滴加甲基肼(72.24mmol,1.2eq)，滴加完毕后，体系升温回流2～3h，待原料反应完全后，减压下浓缩，得到橙红色油状粗产物3-(二氟甲基)-1-甲基-1H-吡唑-5-醇(8.03g，收率90％)。
步骤2：1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-酮的合成：
Figure BDA0001637890800000372
取一反应瓶，将3-(二氟甲基)-1-甲基-1H-吡唑-5-醇(54.22mmol,1.0eq)、碳酸钾(54.22mmol,1.0eq)、碘化钾(0.0542mmol,0.01eq)溶于60mL DMF，室温下搅拌5min，将氯丙酮(70.48mmol,1.3eq)缓慢滴加到上述体系中，60℃反应5h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到褐色油状粗产物1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-酮(7.86g，收率71％)。
步骤3：1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-酮-O-甲基肟的合成：
Figure BDA0001637890800000381
将1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-酮(38.50mmol,1.0eq)、碳酸钾(76.99mmol,2.0eq)溶于乙醇/水(体积比1:1)中，85℃温度下分次加入甲氧胺盐酸盐(76.99mmol,2.0eq)，保持温度为85℃反应2～3h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到褐色油状粗产物1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-酮-O-甲基肟(8.08g，收率90％)。
步骤4：N-(1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-基)-O-甲基羟胺的合成：
Figure BDA0001637890800000382
将1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-酮-O-甲基肟(34.65mmol,1.0eq)用适量甲醇溶解，加入30mL乙酸，室温下分次加入氰基硼氢化钠(69.29mmol,2.0eq)，待反应完毕后，向体系中加入10％氢氧化钠水溶液，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝4:1)，得淡黄色油状产物N-(1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-基)-O-甲基羟胺(1.39g，收率17％)。
步骤5：3-(二氟甲基)-N-(1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-基)-N-甲氧基-1-甲基-1H-吡唑-4-甲酰胺的合成(化合物73)：
Figure BDA0001637890800000391
向反应瓶中依次加入N-(1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-基)-O-甲基羟胺(1.28mmol,1.0eq)、二氯甲烷(20mL)，三乙胺(1.35mmol,1.06eq)，缓慢滴加3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰氯(1.34mmol,1.05eq)。室温下反应2h，向反应液中加水淬灭反应，用二氯甲烷萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝2:1)，得淡黄色油状液体产物3-(二氟甲基)-N-(1-((3-(二氟甲基)-1-甲基-1H-吡唑-5-基)氧基)丙-2-基)-N-甲氧基-1-甲基-1H-吡唑-4-甲酰胺(216mg，收率43％)。
实施例6
化合物98的制备：
步骤1：1-(2-异丙基-5-甲基苯氧基)丙-2-酮的合成：
Figure BDA0001637890800000392
取一反应瓶，将百里酚(来自商业购买，66.57mmol,1.0eq)、碳酸钾(66.57mmol,1.0eq)、碘化钾(0.0665mmol,0.01eq)溶于60mL DMF，室温下搅拌5min，将氯丙酮(73.23mmol,1.1eq)缓慢滴加到上述体系中，60℃反应5h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到褐色油状粗产物1-(2-异丙基-5-甲基苯氧基)丙-2-酮(12.22g，收率89％)。
步骤2：1-(2-异丙基-5-甲基苯氧基)丙-2-酮-O-甲基肟的合成：
Figure BDA0001637890800000401
将1-(2-异丙基-5-甲基苯氧基)丙-2-酮(59.24mmol，1.0eq)、碳酸钾(118.48mmol,2.0eq)溶于乙醇/水(体积比1:1)中，85℃温度下分次加入甲氧胺盐酸盐(118.48mmol,2.0eq)，保持温度为85℃反应2～3h，待反应完毕后，用水淬灭反应，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，得到淡黄色油状粗产物1-(2-异丙基-5-甲基苯氧基)丙-2-酮-O-甲基肟(12.55g，收率90％)。
步骤3：N-(1-(2-异丙基-5-甲基苯氧基)丙-2-基)-O-甲基羟胺的合成：
Figure BDA0001637890800000402
将1-(2-异丙基-5-甲基苯氧基)丙-2-酮-O-甲基肟(53.33mmol,1.0eq)用适量甲醇溶解，加入30mL乙酸，室温下分次加入氰基硼氢化钠(106.66mmol,2.0eq)，待反应完毕后，向体系中加入10％氢氧化钠水溶液，乙酸乙酯萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝25:1)，得淡黄色油状产物N-(1-(2-异丙基-5-甲基苯氧基)丙-2-基)-O-甲基羟胺(7.47g，收率59％)。
步骤4：2-氟-N-(1-(2-异丙基-5-甲基苯氧基)丙-2-基)-N-甲氧基苯甲酰胺的合成(化合物98)：
Figure BDA0001637890800000411
向反应瓶中依次加入N-(1-(2-异丙基-5-甲基苯氧基)丙-2-基)-O-甲基羟胺(1.69mmol,1.0eq)、二氯甲烷(20mL)，三乙胺(1.79mmol,1.06eq)，缓慢滴加2-氟苯甲酰氯(1.77mmol,1.05eq)。室温下反应2h，向反应液中加水淬灭反应，用二氯甲烷萃取，有机层经饱和食盐水洗涤、无水硫酸钠干燥后，减压下浓缩，残余物经柱色谱提纯(淋洗液为PE:EA＝10:1)，得淡黄色油状液体产物2-氟-N-(1-(2-异丙基-5-甲基苯氧基)丙-2-基)-N-甲氧基苯甲酰胺(394mg，收率65％)。
其他化合物可以通过选择不同的原料，用类似方法制备。
生物活性测定实施例
实施例7
杀菌活性的测定
用本发明化合物对植物的多种病害进行了试验。试验的方法如下：
采用活体盆栽测定方法，即将待测化合物样品用少量溶剂(溶剂的种类如丙酮、甲醇、DMF等，依据其对样品的溶解能力而选择，溶剂量与喷液量的体积比等于或小于0.05。)溶解，用含有0.1％吐温80的水稀释，配制成所需浓度待测液。用本发明化合物按照设计浓度进行叶面喷雾处理。另设喷清水的空白对照，3次重复，处理后第二天进行病害接种。接种后，将植物放在人工气候室中保湿培养(温度：昼25℃、夜20℃，相对湿度：95～99％)。试验材料培养24h后，移置温室培养，将不需要保湿培养的植物直接在温室内接种并培养。待对照充分发病后(通常为一周时间)进行化合物防病效果评估。结果调查参照美国植病学会编写的《A Manual of Assessment Keys for Plant Diseases》，用100～0来表示，以“100”级代表无病和“0”级代表最严重的发病程度。
部分测试结果如下：
黄瓜霜霉病(Pseudoperonospora cubensis)：
按照以上测试方法，部分供试的化合物中，下列化合物在浓度为400ppm时对黄瓜霜霉病的防治效果较好，防效≥80％的为化合物28、34、85、87、99、102和106。
按照以上测试方法，选取本发明化合物28、85、87、102与已知化合物KC1和KC2进行防治黄瓜霜霉病活性的平行测定(对照化合物均为自制，结构经核磁共振氢谱确认与现有公开文献描述的一致)，试验结果见表2。
表2
Figure BDA0001637890800000421
Figure BDA0001637890800000431
对黄瓜白粉病(Erysiphe cichoracearum)的防效：
按照以上测试方法，部分供试的化合物中，下列化合物在浓度为400ppm时对黄瓜白粉病的防治效果较好，防效≥80％的为化合物32、34、39和88。
对大豆锈病(Phakopsora pachyrhizi)的防效：
按照以上测试方法，部分供试的化合物中，下列化合物在浓度为100ppm时对大豆锈病的防治效果较好，防效≥80％的为化合物73、80、85、88和93。
申请人声明，本发明通过上述实施例来说明本发明的酰胺类化合物及其制备方法和应用，但本发明并不局限于上述实施例，即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了，对本发明的任何改进，对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等，均落在本发明的保护范围和公开范围之内。

Claims (5)

1.一种酰胺类化合物，其特征在于，所述化合物为如下化合物或如下化合物的盐中的任意一种：
Figure FDF0000016224860000011
2.根据权利要求1所述的化合物，其特征在于，所述化合物的盐为化合物的盐酸盐、硫酸盐、硝酸盐、碳酸氢盐、碳酸盐、磷酸盐、甲酸盐、醋酸盐、三氟乙酸盐、苯磺酸盐、对甲苯磺酸盐、甲基磺酸盐、苯甲酸盐、柠檬酸盐、苹果酸盐、酒石酸盐、马来酸盐、琥珀酸盐、抗坏血酸盐或草酸盐中的任意一种。
3.一种权利要求1或2所述化合物的应用，其特征在于，所述化合物用于制备控制农业、林业或非治疗目的植物病害的药物。
4.一种杀菌剂组合物，其特征在于，所述杀菌剂组合物含有权利要求1或2任一项所述的化合物作为活性组分和载体，所述杀菌剂组合物中活性组分的重量百分含量为1～99％。
5.一种控制植物病害的方法，其特征在于，所述方法为将权利要求4所述的杀菌剂组合物以每公顷10～1000g的有效剂量施于需要控制的病害或其生长介质上。
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3840596A (en) * 1970-12-23 1974-10-08 Velsicol Chemical Corp Compositions of matter
US4678798A (en) * 1984-04-21 1987-07-07 Basf Aktiengesellschaft N-(azolylcarbamyl)-hydroxylamines and fungicides containing these compounds
WO1990001929A1 (en) * 1988-08-25 1990-03-08 The Wellcome Foundation Limited New medical use
CN1043496A (zh) * 1988-12-14 1990-07-04 山道士有限公司 苯氧肟酸衍生物的制备方法
CS276077B6 (cs) * 1990-09-12 1992-03-18 Vysoka Skola Chem Tech H-(substituované fenoxy)alkyl-hydroxamové kyseliny
WO2010106071A1 (en) * 2009-03-18 2010-09-23 Syngenta Participations Ag N-hydroxy-l-methyl-lh-pyrazole-4-carboxamide derivatives and their use as microbiocides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3840596A (en) * 1970-12-23 1974-10-08 Velsicol Chemical Corp Compositions of matter
US4678798A (en) * 1984-04-21 1987-07-07 Basf Aktiengesellschaft N-(azolylcarbamyl)-hydroxylamines and fungicides containing these compounds
WO1990001929A1 (en) * 1988-08-25 1990-03-08 The Wellcome Foundation Limited New medical use
CN1043496A (zh) * 1988-12-14 1990-07-04 山道士有限公司 苯氧肟酸衍生物的制备方法
CS276077B6 (cs) * 1990-09-12 1992-03-18 Vysoka Skola Chem Tech H-(substituované fenoxy)alkyl-hydroxamové kyseliny
WO2010106071A1 (en) * 2009-03-18 2010-09-23 Syngenta Participations Ag N-hydroxy-l-methyl-lh-pyrazole-4-carboxamide derivatives and their use as microbiocides

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