CN115232081B - 含突烯片段的三唑磺酰胺类衍生物及其制备方法和应用和一种杀菌剂及其应用 - Google Patents
含突烯片段的三唑磺酰胺类衍生物及其制备方法和应用和一种杀菌剂及其应用 Download PDFInfo
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Abstract
本发明涉及农药领域,公开了一种含突烯片段的三唑磺酰胺类衍生物及其制备方法和应用和一种杀菌剂及其应用,该衍生物具有式(I)所示的结构,本发明提供的化合物在相对较低浓度下针对霜霉病、霜疫霉病、疫病、晚疫病等卵菌纲植物病害具有明显比现有技术更好的效果,如黄瓜霜霉病、大豆疫霉病、番茄晚疫病、马铃薯晚疫病、茄子霜霉病、柑桔脚腐病、南瓜疫病、葡萄霜霉病等;具有潜在的商业化价值。
Description
技术领域
本发明涉及农药领域,具体地,涉及一种含突烯片段的三唑磺酰胺类衍生物及其制备方法,一种含突烯片段的三唑磺酰胺类衍生物作为细胞色素bc1复合物Qi位点抑制剂以及在抗植物真菌病中的应用,一种杀菌剂及其在抗植物真菌病中的应用。
背景技术
复合物Ⅲ(也叫细胞色素bc1复合物)作为当前最具发展前景的农用杀菌剂靶标之一,其作用是催化从辅酶Q到细胞色素C的电子传递过程,同时将质子由线粒体基质泵至膜间隙。而细胞色素bc1复合物抑制剂是通过作用于病原菌线粒体呼吸电子传递链上的复合体Ⅲ,干扰呼吸电子传递链来抑制线粒体功能,阻止其产生能量,抑制病原菌生长,最终导致其死亡,以达到防治病害的目的。根据复合物Ⅲ的功能该靶标可分为Qo位点和Qi位点,基于该靶标的商品化Qo位点杀菌剂数量多达21种,但随着使用时间的延长,这些杀菌剂的抗性问题越来越严重。目前商品化的3个Qi位点杀菌剂(cyazofamid、amisulbrom、fenpicoxamid),很少有抗性问题的报道,其中,氰霜唑和吲唑磺菌胺对卵菌纲病害有着很好的防效。但由于氰霜唑和吲唑磺菌胺合成复杂,成本高昂。
基于此,本发明将胺部分进行取代基优化,设计出具有新颖结构的三唑磺酰胺类衍生物。同时,对于本发明中的中间体酸和重要中间体N-(2-苯基烯丙基)环丙胺、N-(2,2-二氯-1-苯基乙烯基)环丙胺等的合成,原料廉价易得,反应步骤和后处理简单,并且化合物具有安全性高,持续性好的优点,且这类新型化合物在低浓度下仍具有良好的杀菌活性。
发明内容
本发明的目的是为了提供一种新的三唑磺酰胺类衍生物,以期该类三唑磺酰胺类衍生物能够在低浓度下实现明显更高的抗真菌病防效。
为了实现上述目的,本发明第一方面提供一种含突烯片段的三唑磺酰胺类衍生物,该衍生物具有式(I)所示的结构:
其中,式(I)中,R1选自C1-6的烷基、C1-6的烷氧基、C3-6的环烷基;
R2选自H、C1-6的烷基;
R3、R4、R5、R6、R7选自H、卤素、C1-6的烷基、C1-6的烷氧基、氰基、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基;
R8均为H或Cl。
本发明第二方面提供一种制备第一方面所述的含突烯片段的三唑磺酰胺类衍生物的方法,该方法包括将式(II)所示的化合物与式(III)所示的化合物进行接触反应;
其中,R9和R10中一者为卤素,另一者为-NHR1,
R1、R2、R3、R4、R5、R6、R7、R8的定义与第一方面所述的定义对应相同。
本发明的第三方面提供前述含突烯片段的三唑磺酰胺类衍生物作为细胞色素bc1复合物Qi位点抑制剂的应用。
本发明的第四方面提供前述含突烯片段的三唑磺酰胺类衍生物在抗植物真菌病中的应用。
本发明的第五方面提供一种杀菌剂,该杀菌剂的活性成分为前述含突烯片段的三唑磺酰胺类衍生物中的至少一种,以所述杀菌剂的总重量计,所述活性成分的含量为0.1-100重量%。
本发明的第六方面提供一种第五方面所述的杀菌剂在抗植物真菌病中的应用。
本发明提供的化合物在相对较低浓度下针对霜霉病、霜疫霉病、疫病、晚疫病等卵菌纲植物病害具有明显比现有技术更好的效果,如黄瓜霜霉病、大豆疫霉病、番茄晚疫病、马铃薯晚疫病、茄子霜霉病、柑桔脚腐病、南瓜疫病、葡萄霜霉病等,具有潜在的商业化价值。
具体实施方式
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值,这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说,各个范围的端点值之间、各个范围的端点值和单独的点值之间,以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围,这些数值范围应被视为在本文中具体公开。
以下针对本发明的部分基团提供一些示例性的解释,在没有特别说明的情况下,未列举的部分参照如下示例性的解释进行解释。
“C1-6的烷基”表示碳原子总数为1-6的烷基,包括直链烷基、支链烷基,例如可以为碳原子总数为1、2、3、4、5或6的直链烷基、支链烷基,例如可以为正丁基、异丁基、叔丁基、正戊基、异戊基、正己基等;“C1-3的烷基”的定义与“C1-6烷基”的定义相似,不同的是,碳原子总数不同。
“C1-6的烷氧基”的定义与“C1-6烷基”的定义相似,不同的是,“C1-6的烷氧基”通过O原子直接与母核连接;“C1-3的烷氧基”的定义与“C1-6的烷氧基”的定义相似,不同的是,碳原子总数不同。
“由至少一个卤素取代的C1-6的烷基”的定义与“C1-6烷基”的定义相似,不同的是,“由至少一个卤素取代的C1-6的烷基”中的烷基上的至少一个H由选自氟、氯、溴、碘的至少一种卤素原子取代,且该“由至少一个卤素取代的C1-6的烷基”的碳原子总数为1-6。
“由至少一个卤素取代的C1-6的烷氧基”的定义与“C1-6烷氧基”的定义相似,不同的是,“由至少一个卤素取代的C1-6的烷氧基”表示为“C1-6烷氧基”上的至少一个H由选自氟、氯、溴、碘的至少一种卤素原子取代,且该“由至少一个卤素取代的C1-6的烷氧基”的碳原子总数为1-6。
“C3-6的环烷基”表示碳原子总数为3-6的烷基,且成环原子均为C原子,且所述“C3-6的环烷基”上任意能够被取代的位置能够被取代基取代或未取代,当被取代时,包含取代基在内的整体基团的碳原子总数为3-6。
如前所述,本发明的第一方面提供了一种含突烯片段的三唑磺酰胺类衍生物,该衍生物具有式(I)所示的结构:
其中,式(I)中,R1选自C1-6的烷基、C1-6的烷氧基、C3-6的环烷基;R2选自H、C1-6的烷基;
R3、R4、R5、R6、R7选自H、卤素、C1-6的烷基、C1-6的烷氧基、氰基、由至少一个卤素取代的C1-6的烷基、由至少一个卤素取代的C1-6的烷氧基;
R8均为H或Cl。
优选地,在式(I)中,
R1选自C1-3的烷氧基、C3-6的环烷基;
R2选自H、C1-3的烷基;
R3、R4、R5、R6、R7选自H、卤素、C1-6的烷基、C1-3的烷氧基、氰基、由至少一个卤素取代的C1-3的烷基、由至少一个卤素取代的C1-3的烷氧基;
R8均为H或Cl。
特别优选地,在式(I)中,
R1选自甲氧基、环丙基;
R2选自H、甲基;
R3、R4、R5选自H、F、Cl、甲基、乙基、异丙基、叔丁基、甲氧基、-CF3、-OCF3、氰基;
R6选自H、F、Cl;
R7为H;
R8均为H或Cl。
根据一种特别优选的具体实施方式,所述含突烯片段的三唑磺酰胺类衍生物为以下化合物中的任意一种:
化合物I-1:在式(I)中,R1为环丙基,R2、R3、R4、R5、R6、R7、R8均为H;
化合物I-2:在式(I)中,R1为环丙基,R2为H,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-3:在式(I)中,R1为环丙基,R2为H,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-4:在式(I)中,R1为环丙基,R2为H,R3为甲基,R4、R5、R6、R7、R8均为H;
化合物I-5:在式(I)中,R1为环丙基,R2为H,R3为乙基,R4、R5、R6、R7、R8均为H;
化合物I-6:在式(I)中,R1为环丙基,R2为H,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-7:在式(I)中,R1为环丙基,R2为H,R3为-CF3,R4、R5、R6、R7、R8均为H;
化合物I-8:在式(I)中,R1为环丙基,R2为H,R3为氰基,R4、R5、R6、R7、R8均为H;
化合物I-9:在式(I)中,R1为环丙基,R2为H,R4为F,R3、R5、R6、R7、R8均为H;
化合物I-10:在式(I)中,R1为环丙基,R2为H,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-11:在式(I)中,R1为环丙基,R2为H,R4为甲基,R3、R5、R6、R7、R8均为H;
化合物I-12:在式(I)中,R1为环丙基,R2为H,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-13:在式(I)中,R1为环丙基,R2为H,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-14:在式(I)中,R1为环丙基,R2为H,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-15:在式(I)中,R1为环丙基,R2为H,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-16:在式(I)中,R1为环丙基,R2为H,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-17:在式(I)中,R1为环丙基,R2为H,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-18:在式(I)中,R1为环丙基,R2为H,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-19:在式(I)中,R1为环丙基,R2为H,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-20:在式(I)中,R1为环丙基,R2为H,R5为甲基,R3、R4、R6、R7、R8均为H;
化合物I-21:在式(I)中,R1为环丙基,R2为H,R5为氰基,R3、R4、R6、R7、R8均为H;
化合物I-22:在式(I)中,R1为环丙基,R2为H,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-23:在式(I)中,R1为环丙基,R2为H,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-24:在式(I)中,R1为环丙基,R2为H,R5为叔丁基,R3、R4、R6、R7、R8均为H;
化合物I-25:在式(I)中,R1为环丙基,R2为H,R5为-CF3,R3、R4、R6、R7、R8均为H;
化合物I-26:在式(I)中,R1为环丙基,R2为H,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-27:在式(I)中,R1为环丙基,R2为H,R3和R4均为甲基,R5、R6、R7、R8均为H;
化合物I-28:在式(I)中,R1为环丙基,R2为H,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-29:在式(I)中,R1为环丙基,R2为H,R3为F,R4为Cl,R5、R6、R7、R8均为H;
化合物I-30:在式(I)中,R1为环丙基,R2为H,R3为Cl,R4为F,R5、R6、R7、R8均为H;
化合物I-31:在式(I)中,R1为环丙基,R2为H,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-32:在式(I)中,R1为环丙基,R2为H,R3和R5均为甲基,R4、R6、R7、R8均为H;
化合物I-33:在式(I)中,R1为环丙基,R2为H,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-34:在式(I)中,R1为环丙基,R2为H,R3为F,R5为Cl,R4、R6、R7、R8均为H;
化合物I-35:在式(I)中,R1为环丙基,R2为H,R3为Cl,R5为F,R4、R6、R7、R8均为H;
化合物I-36:在式(I)中,R1为环丙基,R2为H,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-37:在式(I)中,R1为环丙基,R2为H,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-38:在式(I)中,R1为环丙基,R2为H,R4和R5均为甲基,R3、R6、R7、R8均为H;
化合物I-39:在式(I)中,R1为环丙基,R2为H,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-40:在式(I)中,R1为环丙基,R2为H,R4为F,R5为Cl、R3、R6、R7、R8均为H;
化合物I-41:在式(I)中,R1为环丙基,R2为H,R4为Cl,R5为F、R3、R6、R7、R8均为H;
化合物I-42:在式(I)中,R1为环丙基,R2为H,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-43:在式(I)中,R1为环丙基,R2为H,R4和R5均为-CF3,R3、R6、R7、R8均为H;
化合物I-44:在式(I)中,R1为环丙基,R2为H,R4和R6均为甲基,R3、R5、R7、R8均为H;
化合物I-45:在式(I)中,R1为环丙基,R2为H,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-46:在式(I)中,R1为环丙基,R2为H,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-47:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为F,R3、R7、R8均为H;
化合物I-48:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物I-49:在式(I)中,R1为甲氧基,R2、R3、R4、R5、R6、R7、R8均为H;
化合物I-50:在式(I)中,R1为甲氧基,R2为H,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-51:在式(I)中,R1为甲氧基,R2为H,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-52:在式(I)中,R1为甲氧基,R2为H,R3为甲基,R4、R5、R6、R7、R8均为H;
化合物I-53:在式(I)中,R1为甲氧基,R2为H,R3为乙基,R4、R5、R6、R7、R8均为H;
化合物I-54:在式(I)中,R1为甲氧基,R2为H,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-55:在式(I)中,R1为甲氧基,R2为H,R3为-CF3,R4、R5、R6、R7、R8均为H;
化合物I-56:在式(I)中,R1为甲氧基,R2为H,R3为-OCF3,R4、R5、R6、R7、R8均为H;
化合物I-57:在式(I)中,R1为甲氧基,R2为H,R4为F,R3、R5、R6、R7、R8均为H;
化合物I-58:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-59:在式(I)中,R1为甲氧基,R2为H,R4为甲基,R3、R5、R6、R7、R8均为H;
化合物I-60:在式(I)中,R1为甲氧基,R2为H,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-61:在式(I)中,R1为甲氧基,R2为H,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-62:在式(I)中,R1为甲氧基,R2为H,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-63:在式(I)中,R1为甲氧基,R2为H,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-64:在式(I)中,R1为甲氧基,R2为H,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-65:在式(I)中,R1为甲氧基,R2为H,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-66:在式(I)中,R1为甲氧基,R2为H,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-67:在式(I)中,R1为甲氧基,R2为H,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-68:在式(I)中,R1为甲氧基,R2为H,R5为甲基,R3、R4、R6、R7、R8均为H;
化合物I-69:在式(I)中,R1为甲氧基,R2为H,R5为乙基,R3、R4、R6、R7、R8均为H;
化合物I-70:在式(I)中,R1为甲氧基,R2为H,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-71:在式(I)中,R1为甲氧基,R2为H,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-72:在式(I)中,R1为甲氧基,R2为H,R5为-CF3,R3、R4、R6、R7、R8均为H;
化合物I-73:在式(I)中,R1为甲氧基,R2为H,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-74:在式(I)中,R1为甲氧基,R2为H,R3和R4均为甲基,R5、R6、R7、R8均为H;
化合物I-75:在式(I)中,R1为甲氧基,R2为H,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-76:在式(I)中,R1为甲氧基,R2为H,R3为F,R4为Cl,R5、R6、R7、R8均为H;
化合物I-77:在式(I)中,R1为甲氧基,R2为H,R3为Cl,R4为F,R5、R6、R7、R8均为H;
化合物I-78:在式(I)中,R1为甲氧基,R2为H,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-79:在式(I)中,R1为甲氧基,R2为H,R3和R5均为甲基,R4、R6、R7、R8均为H;
化合物I-80:在式(I)中,R1为甲氧基,R2为H,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-81:在式(I)中,R1为甲氧基,R2为H,R3为F,R5为Cl,R4、R6、R7、R8均为H;
化合物I-82:在式(I)中,R1为甲氧基,R2为H,R3为Cl,R5为F,R4、R6、R7、R8均为H;
化合物I-83:在式(I)中,R1为甲氧基,R2为H,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-84:在式(I)中,R1为甲氧基,R2为H,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-85:在式(I)中,R1为甲氧基,R2为H,R4和R5均为甲基,R3、R6、R7、R8均为H;
化合物I-86:在式(I)中,R1为甲氧基,R2为H,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-87:在式(I)中,R1为甲氧基,R2为H,R4为F,R5为Cl,R3、R6、R7、R8均为H;
化合物I-88:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R5为F,R3、R6、R7、R8均为H;
化合物I-89:在式(I)中,R1为甲氧基,R2为H,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-90:在式(I)中,R1为甲氧基,R2为H,R4和R5均为-CF3,R3、R6、R7、R8均为H;
化合物I-91:在式(I)中,R1为甲氧基,R2为H,R4和R6均为甲基,R3、R5、R7、R8均为H;
化合物I-92:在式(I)中,R1为甲氧基,R2为H,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-93:在式(I)中,R1为甲氧基,R2为H,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-94:在式(I)中,R1为甲氧基,R2为H,R4、R5和R6均为F,R3、R7、R8均为H;
化合物I-95:在式(I)中,R1为甲氧基,R2为H,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物I-96:在式(I)中,R1为环丙基,R2为甲基,R3、R4、R5、R6、R7、R8均为H;
化合物I-97:在式(I)中,R1为环丙基,R2为甲基,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-98:在式(I)中,R1为环丙基,R2为甲基,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-99:在式(I)中,R1为环丙基,R2、R3均为甲基,R4、R5、R6、R7、R8均为H;
化合物I-100:在式(I)中,R1为环丙基,R2为甲基,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-101:在式(I)中,R1为环丙基,R2为甲基,R4为F,R3、R5、R6、R7、R8均为H;
化合物I-102:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-103:在式(I)中,R1为环丙基,R2、R4均为甲基,R3、R5、R6、R7、R8均为H;
化合物I-104:在式(I)中,R1为环丙基,R2为甲基,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-105:在式(I)中,R1为环丙基,R2为甲基,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-106:在式(I)中,R1为环丙基,R2为甲基,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-107:在式(I)中,R1为环丙基,R2为甲基,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-108:在式(I)中,R1为环丙基,R2为甲基,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-109:在式(I)中,R1为环丙基,R2为甲基,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-110:在式(I)中,R1为环丙基,R2为甲基,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-111:在式(I)中,R1为环丙基,R2为甲基,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-112:在式(I)中,R1为环丙基,R2、R5均为甲基,R3、R4、R6、R7、R8均为H;
化合物I-113:在式(I)中,R1为环丙基,R2为甲基,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-114:在式(I)中,R1为环丙基,R2为甲基,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-115:在式(I)中,R1为环丙基,R2为甲基,R5为叔丁基,R3、R4、R6、R7、R8均为H;
化合物I-116:在式(I)中,R1为环丙基,R2为甲基,R5为-CF3,R3,R4、R6、R7、R8均为H;
化合物I-117:在式(I)中,R1为环丙基,R2为甲基,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-118:在式(I)中,R1为环丙基,R2、R3、R4均为甲基,R5、R6、R7、R8均为H;
化合物I-119:在式(I)中,R1为环丙基,R2为甲基,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-120:在式(I)中,R1为环丙基,R2为甲基,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-121:在式(I)中,R1为环丙基,R2、R3、R5均为甲基,R4、R6、R7、R8均为H;
化合物I-122:在式(I)中,R1为环丙基,R2为甲基,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-123:在式(I)中,R1为环丙基,R2为甲基,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-124:在式(I)中,R1为环丙基,R2为甲基,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-125:在式(I)中,R1为环丙基,R2、R4、R5均为甲基,R3、R6、R7、R8均为H;
化合物I-126:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-127:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-128:在式(I)中,R1为环丙基,R2、R4、R6均为甲基,R3、R5、R7、R8均为H;
化合物I-129:在式(I)中,R1为环丙基,R2为甲基,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-130:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R6为F,R3、R5、R7、R8均为H;
化合物I-131:在式(I)中,R1为环丙基,R2为甲基,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-132:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为F,R3、R7、R8均为H;
化合物I-133:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物I-134:在式(I)中,R1为甲氧基,R2为甲基,R3、R4、R5、R6、R7、R8均为H;
化合物I-135:在式(I)中,R1为甲氧基,R2为甲基,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-136:在式(I)中,R1为甲氧基,R2为甲基,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-137:在式(I)中,R1为甲氧基,R2为甲基,R3为甲基,R4、R5、R6、R7、R8均为H;
化合物I-138:在式(I)中,R1为甲氧基,R2为甲基,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-139:在式(I)中,R1为甲氧基,R2为甲基,R4为F、R3、R5、R6、R7、R8均为H;
化合物I-140:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-141:在式(I)中,R1为甲氧基,R2为甲基,R4为甲基,R3、R5、R6、R7、R8均为H;
化合物I-142:在式(I)中,R1为甲氧基,R2为甲基,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-143:在式(I)中,R1为甲氧基,R2为甲基,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-144:在式(I)中,R1为甲氧基,R2为甲基,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-145:在式(I)中,R1为甲氧基,R2为甲基,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-146:在式(I)中,R1为甲氧基,R2为甲基,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-147:在式(I)中,R1为甲氧基,R2为甲基,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-148:在式(I)中,R1为甲氧基,R2为甲基,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-149:在式(I)中,R1为甲氧基,R2为甲基,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-150:在式(I)中,R1为甲氧基,R2为甲基,R5为甲基,R3、R4、R6、R7、R8均为H;
化合物I-151:在式(I)中,R1为甲氧基,R2为甲基,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-152:在式(I)中,R1为甲氧基,R2为甲基,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-153:在式(I)中,R1为甲氧基,R2为甲基,R5为叔丁基,R3、R4、R6、R7、R8均为H;
化合物I-154:在式(I)中,R1为甲氧基,R2为甲基,R5为-CF3,R3、R4、R6、R7、R8均为H;
化合物I-155:在式(I)中,R1为甲氧基,R2为甲基,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-156:在式(I)中,R1为甲氧基,R2、R3、R4均为甲基,R5、R6、R7、R8均为H;
化合物I-157:在式(I)中,R1为甲氧基,R2为甲基,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-158:在式(I)中,R1为甲氧基,R2为甲基,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-159:在式(I)中,R1为甲氧基,R2、R3、R5均为甲基,R4、R6、R7、R8均为H;
化合物I-160:在式(I)中,R1为甲氧基,R2为甲基,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-161:在式(I)中,R1为甲氧基,R2为甲基,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-162:在式(I)中,R1为甲氧基,R2为甲基,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-163:在式(I)中,R1为甲氧基,R2、R4、R5均为甲基,R3、R6、R7、R8均为H;
化合物I-164:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-165:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-166:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为甲基,R3、R5、R7、R8均为H;
化合物I-167:在式(I)中,R1为甲氧基,R2为甲基,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-168:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R6为F,R3、R5、R7、R8均为H;
化合物I-169:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-170:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为F、R3、R7、R8均为H;
化合物I-171:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物II-1:在式(I)中,R1为环丙基,R2、R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-2:在式(I)中,R1为环丙基,R2为H,R3为F,R4、R5、R6、R7均为H,R8均为Cl;
化合物II-3:在式(I)中,R1为环丙基,R2为H,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-4:在式(I)中,R1为环丙基,R2为H,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-5:在式(I)中,R1为环丙基,R2为H,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-6:在式(I)中,R1为环丙基,R2为H,R4为乙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-7:在式(I)中,R1为环丙基,R2为H,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-8:在式(I)中,R1为环丙基,R2为H,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-9:在式(I)中,R1为环丙基,R2为H,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-10:在式(II)中,R1为环丙基,R2为H,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-11:在式(I)中,R1为环丙基,R2为H,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-12:在式(I)中,R1为环丙基,R2为H,R5为F,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-13:在式(I)中,R1为环丙基,R2为H,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-14:在式(I)中,R1为环丙基,R2为H,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-15:在式(I)中,R1为环丙基,R2为H,R5为乙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-16:在式(I)中,R1为环丙基,R2为H,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-17:在式(I)中,R1为环丙基,R2为H,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-18:在式(I)中,R1为环丙基,R2为H,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-19:在式(I)中,R1为环丙基,R2为H,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-20:在式(I)中,R1为环丙基,R2为H,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-21:在式(I)中,R1为环丙基,R2为H,R4和R5均为甲基,R3、R6、R7均为H,R8均为Cl;
化合物II-22:在式(I)中,R1为环丙基,R2为H,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-23:在式(I)中,R1为环丙基,R2为H,R4为F,R5为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-24:在式(I)中,R1为环丙基,R2为H,R4为Cl,R5为F,R3、R6、R7均为H,R8均为Cl;
化合物II-25:在式(I)中,R1为环丙基,R2为H,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-26:在式(I)中,R1为环丙基,R2为H,R4和R5均为-CF3,R3、R6、R7均为H,R8均为Cl;
化合物II-27:在式(I)中,R1为环丙基,R2为H,R4和R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-28:在式(I)中,R1为环丙基,R2为H,R4为F,R6为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-29:在式(I)中,R1为环丙基,R2为H,R4和R6均为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-30:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-31:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为Cl,R3、R7均为H,R8均为Cl;
化合物II-32:在式(I)中,R1为甲氧基,R2为H,R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-33:在式(I)中,R1为甲氧基,R2为H,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-34:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-35:在式(I)中,R1为甲氧基,R2为H,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-36:在式(I)中,R1为甲氧基,R2为H,R4为氰基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-37:在式(I)中,R1为甲氧基,R2为H,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-38:在式(I)中,R1为甲氧基,R2为H,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-39:在式(I)中,R1为甲氧基,R2为H,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-40:在式(I)中,R1为甲氧基,R2为H,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-41:在式(I)中,R1为甲氧基,R2为H,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-42:在式(I)中,R1为甲氧基,R2为H,R5为F,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-43:在式(I)中,R1为甲氧基,R2为H,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-44:在式(I)中,R1为甲氧基,R2为H,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-45:在式(I)中,R1为甲氧基,R2为H,R5为乙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-46:在式(I)中,R1为甲氧基,R2为H,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-47:在式(I)中,R1为甲氧基,R2为H,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-48:在式(I)中,R1为甲氧基,R2为H,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-49:在式(I)中,R1为甲氧基,R2为H,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-50:在式(I)中,R1为甲氧基,R2为H,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-51:在式(I)中,R1为甲氧基,R2为H,R4和R5均为甲基,R3、R6、R7均为H,R8均为Cl;
化合物II-52:在式(I)中,R1为甲氧基,R2为H,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-53:在式(I)中,R1为甲氧基,R2为H,R4为F,R5为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-54:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R5为F,R3、R6、R7均为H,R8均为Cl;
化合物II-55:在式(I)中,R1为甲氧基,R2为H,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-56:在式(I)中,R1为甲氧基,R2为H,R4和R5均为-CF3,R3、R6、R7均为H,R8均为Cl;
化合物II-57:在式(I)中,R1为甲氧基,R2为H,R4和R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-58:在式(I)中,R1为甲氧基,R2为H,R4为F,R6为Cl,R5、R3、R7均为H,R8均为Cl;
化合物II-59:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R6为F,R5、R3、R7均为H,R8为Cl;
化合物II-60:在式(I)中,R1为甲氧基,R2为H,R4和R6均为Cl,R5、R3、R7均为H,R8均为Cl;
化合物II-61:在式(I)中,R1为甲氧基,R2为H,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-62:在式(I)中,R1为环丙基,R2为甲基,R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-63:在式(I)中,R1为环丙基,R2为甲基,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-64:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-65:在式(II)中,R1为环丙基,R2为甲基,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-66:在式(I)中,R1为环丙基,R2为甲基,R4为氰基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-67:在式(I)中,R1为环丙基,R2为甲基,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-68:在式(I)中,R1为环丙基,R2为甲基,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-69:在式(I)中,R1为环丙基,R2为甲基,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-70:在式(I)中,R1为环丙基,R2为甲基,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-71:在式(I)中,R1为环丙基,R2为甲基,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-72:在式(I)中,R1为环丙基,R2为甲基,R5为F,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-73:在式(I)中,R1为环丙基,R2为甲基,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-74:在式(I)中,R1为环丙基,R2为甲基,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-75:在式(I)中,R1为环丙基,R2为甲基,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-76:在式(I)中,R1为环丙基,R2为甲基,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-77:在式(I)中,R1为环丙基,R2为甲基,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-78:在式(I)中,R1为环丙基,R2为甲基,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-79:在式(I)中,R1为环丙基,R2为甲基,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-80:在式(I)中,R1为环丙基,R2、R4、R5均为甲基、R3、R6、R7均为H,R8均为Cl;
化合物II-81:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-82:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-83:在式(I)中,R1为环丙基,R2、R4、R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-84:在式(I)中,R1为环丙基,R2为甲基,R4为F,R6为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-85:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R6为F,R3、R5、R7均为H,R8均为Cl;
化合物II-86:在式(I)中,R1为环丙基,R2为甲基,R4和R6均为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-87:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-88:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为Cl,R3、R7均为H,R8均为Cl;
化合物II-89:在式(I)中,R1为甲氧基,R2为甲基,R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-90:在式(I)中,R1为甲氧基,R2为甲基,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-91:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-92:在式(I)中,R1为甲氧基,R2为甲基,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-93:在式(I)中,R1为甲氧基,R2为甲基,R4为乙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-94:在式(I)中,R1为甲氧基,R2为甲基,R4为氰基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-95:在式(I)中,R1为甲氧基,R2为甲基,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-96:在式(I)中,R1为甲氧基,R2为甲基,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-97:在式(I)中,R1为甲氧基,R2为甲基,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-98:在式(I)中,R1为甲氧基,R2为甲基,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-99:在式(I)中,R1为甲氧基,R2为甲基,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-100:在式(I)中,R1为甲氧基,R2为甲基,R5为F、R3、R4、R6、R7均为H,R8均为Cl;
化合物II-101:在式(I)中,R1为甲氧基,R2为甲基,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-102:在式(I)中,R1为甲氧基,R2为甲基,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-103:在式(I)中,R1为甲氧基,R2为甲基,R5为氰基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-104:在式(I)中,R1为甲氧基,R2为甲基,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-105:在式(I)中,R1为甲氧基,R2为甲基,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-106:在式(I)中,R1为甲氧基,R2为甲基,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-107:在式(I)中,R1为甲氧基,R2为甲基,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-108:在式(I)中,R1为甲氧基,R2为甲基,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-109:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为甲基,R3、R6、R7均为H,R8均为Cl;
化合物II-110:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-111:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-112:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-113:在式(I)中,R1为甲氧基,R2为甲基,R4为F,R6为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-114:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R6为F,R3、R5、R7均为H,R8均为Cl;
化合物II-115:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-116:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-117:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为Cl,R3、R7均为H,R8均为Cl。
本发明中对所述式(I)所示的化合物的立体结构没有特别限制,所述式(I)所示的化合物可以以不同的立体异构体或光学异构体或互变异构的形式存在,本发明包含所有立体异构体或光学异构体或互变异构及其各种比例的混合物。
本发明公开化合物的任何不对称原子(例如,碳等)均可以以外消旋或对映体富集的形式存在,例如(R)-、(S)-或(R,S)-构型形式存在。
本发明对制备所述含突烯片段的三唑磺酰胺类衍生物的方法没有特别的限制,本领域技术人员可以通过结构式的特征,结合有机合成领域内的已知方法制备获得,但是,为了更高收率地获得本发明所述的含突烯片段的三唑磺酰胺类衍生物,本发明提供如下第二方面所述的方法制备含突烯片段的三唑磺酰胺类衍生物。
具体地,如前所述,本发明的第二方面提供了一种制备第一方面所述的含突烯片段的三唑磺酰胺类衍生物的方法,该方法包括将式(II)所示的化合物与式(III)所示的化合物进行接触反应;
其中,R9和R10中一者为卤素,另一者为-NHR1,
R1、R2、R3、R4、R5、R6、R7、R8的定义与第一方面所述的定义对应相同。
优选地,所述接触的条件至少满足:温度为5-45℃,时间为20-60min。
优选地,所述式(II)所示的化合物与式(III)所示的化合物的用量摩尔比为(0.5-3):1。
如前所述,本发明的第三方面提供了前述含突烯片段的三唑磺酰胺类衍生物作为细胞色素bc1复合物Qi位点抑制剂的应用。
如前所述,本发明的第四方面提供了前述含突烯片段的三唑磺酰胺类衍生物在抗植物真菌病中的应用。
优选地,所述植物包括但不限于黄瓜、大豆、小麦、番茄、马铃薯、茄子、玉米、水稻、南瓜、柑桔、葡萄。
特别优选地,所述植物真菌病包括但不限于霜霉病、霜疫霉病、疫病、晚疫病。
优选地,所述植物真菌病包括但不限于黄瓜霜霉病、大豆疫霉病、番茄晚疫病、马铃薯晚疫病、茄子霜霉病、柑桔脚腐病、南瓜疫病、葡萄霜霉病。
如前所述,本发明的第五方面提供了一种杀菌剂,该杀菌剂的活性成分为前述含突烯片段的三唑磺酰胺类衍生物中的至少一种,以所述杀菌剂的总重量计,所述活性成分的含量为0.1-100重量%。
优选情况下,所述活性成分的含量为1-98重量%。
更优选地,所述活性成分的含量为5-90重量%。
优选地,所述杀菌剂的剂型选自水合剂、粉剂、乳剂、悬浮剂、乳油剂和粒剂。
如前所述,本发明的第六方面提供了第五方面所述的杀菌剂在抗植物真菌病中的应用。
以下将通过实例对本发明进行详细描述。以下实例中,在没有特别说明的情况下,使用的各种原料均为市售品。
在没有特别说明的情况下,以下所述的室温或常温均表示25±1℃。
制备例1:
该制备例用来说明式(II-1)所示的化合物的合成:
步骤a:在冰浴下将式1-3所示的化合物(10mmol),加入到溶有式1-2所示的化合物(10mmol)的超干THF(10mL)溶液中,加完后撤冰浴,于室温下反应5min,再继续在冰浴下加入式1-1所示的化合物(5mmol),加完后撤冰浴,于室温下反应10min,TLC监测反应完全后,加水猝灭,乙酸乙酯萃取,拌样(45℃以下),柱层析(纯石油醚为洗脱剂),旋出洗脱剂(45℃以下),即得式1-4所示的化合物。
步骤b:提前将温度预热到100℃,然后将NBS(6mmol)加入到溶有式1-4所示的化合物(5mmol)的THF(10mL)溶液中,接着加入对甲苯磺酸(1.2mmol),回流25min,TLC监测反应完全后,加水猝灭,然后用乙酸乙酯萃取,无水Na2SO4干燥,旋出溶剂,即得式1-5所示的化合物。
步骤c:冰浴下将环丙胺(11mmol)加入到溶有式1-5所示的化合物(5mmol)的乙腈溶液(10mL)中,再加入碳酸钾(15mmol),室温下反应10min,TLC监测反应完全后直接拌样,柱层析,然后旋出洗脱剂,即得式(II-1)所示的化合物。
制备例2:
该制备例用来说明式(III-1)所示的化合物的合成:
步骤a:将5.05g式2-1所示的化合物溶于25.0mL重蒸的CH2Cl2中,继续加入3.95g重蒸的吡啶,在冰浴的条件下滴加4.4g重蒸的苯磺酰氯,1小时滴加完毕后,移去冰浴,在常温条件下反应16小时,然后蒸去CH2Cl2,接着加入25mL乙醇,反应1小时,过滤得固体,然后依次用10mL水和10mL乙醇清洗,真空干燥(65℃),即得式2-2所示的化合物。
步骤b:将4.68g式2-2所示的化合物溶于50mL重蒸的DMF,与7.8g无水碳酸钾的溶液混合搅拌1小时后,冰浴下加入7.0g的N,N-二甲基磺酰氯,反应完全后,依次加入水、CH2Cl2萃取,脱干,得到无色油状物,加入少量甲醇,即析出大量白色固体,抽滤干燥,即得到式2-3所示的化合物。
步骤c:将829mg的式2-3所示结构的化合物溶于10mL的1,2-二氯乙烷中,加入20mL水,冰浴下加入10mL乙酸,然后连续通入氯气20min,TLC检测反应完全后,用CH2Cl2萃取,无水硫酸钠干燥,旋出溶剂,即得式(III-1)所示的化合物。
制备例3:
该制备例用来说明式(I-1)所示的化合物的合成:
向50mL梨形瓶中加入1.1mmol式(II-1)所示的化合物,然后加入10mL超干四氢呋喃溶解,接着加入三乙胺(0.2mL,1.5mmol),最后加入式(III-1)所示的化合物(1mmol),室温反应30min,TLC监测反应完全后,减压旋出溶剂,柱色谱层析即得式(I-1)所示的化合物。
采用制备例3所述的方法制备表1中所述的化合物,仅仅是原料取代基进行替换。
表1
以下列举前述获得的部分具体化合物的核磁数据:
白色粉末,mp=87.6-88.2℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.47(d,J=7.5Hz,2H),7.37(t,J=7.4Hz,2H),7.33(d,J=7.2Hz,1H),5.54(s,1H),5.34(s,1H),4.39(s,2H),2.99(s,6H),2.49–2.46(m,1H),0.73(s,2H),0.65(d,J=6.7Hz,2H).HRMS(MALDI)理论值C16H21N5O4S2(M+Na)+:434.0927,实测值434.0933.
白色粉末,mp=67.2-68.0℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.36(dt,J=15.9,6.1Hz,2H),7.26–7.11(m,2H),5.53(s,1H),5.38(s,1H),4.31(s,2H),2.98(s,6H),2.09(s,1H),0.84–0.56(m,4H).HRMS(MALDI)理论值C16H20FN5O4S2(M+H)+:430.10135,实测值430.10100.
白色粉末,mp=76.2-77.0℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.52–7.43(m,1H),7.41–7.30(m,2H),7.26(d,J=6.5Hz,1H),5.53(s,1H),5.21(s,1H),4.26(s,2H),2.97(s,6H),2.64–2.55(m,1H),0.77(s,2H),0.68(d,J=6.3Hz,2H).HRMS(MALDI)理论值C16H20ClN5O4S2(M+Na)+:468.05374,实测值468.05359.
白色粉末,mp=85.4-86.2℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.29–7.13(m,3H),7.08(d,J=7.3Hz,1H),5.41(s,1H),5.05(s,1H),4.12(s,2H),2.96(s,6H),2.66–2.58(m,1H),2.27(s,3H),0.85–0.63(m,4H).HRMS(MALDI)理论值C17H23N5O4S2(M+H)+:426.12642,实测值426.12626.
白色粉末,mp=80.4-81.2℃.1H NMR(600MHz,DMSO-d6)δ9.38(s,1H),7.29(t,J=8.0Hz,1H),7.08(d,J=7.2Hz,1H),6.98(d,J=8.3Hz,1H),6.92(q,J=8.4,7.5Hz,1H),5.34(s,1H),5.15(s,1H),4.29(s,2H),3.76(s,3H),2.96(d,J=2.7Hz,6H),2.08(s,1H),0.74(d,J=3.5Hz,2H),0.64(d,J=7.0Hz,2H).HRMS(MALDI)理论值C17H23N5O5S2(M+H)+:442.12134,实测值442.12122.
黄色粉末,mp=99.0-99.9℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.77(d,J=7.9Hz,1H),7.69(t,J=7.6Hz,1H),7.57(t,J=7.8Hz,1H),7.34(d,J=7.6Hz,1H),5.49(s,1H),5.13(s,1H),4.14(s,2H),2.96(s,6H),2.76–2.62(m,1H),0.85–0.66(m,4H).HRMS(MALDI)理论值C17H20F3N5O4S2(M+Na)+:502.08010,实测值502.08085.
白色粉末,mp=78.4-79.3℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.48(t,J=7.6Hz,1H),7.45–7.33(m,3H),5.54(s,1H),5.29(s,1H),4.24(s,2H),2.97(s,6H),2.58(td,J=7.0,3.6Hz,1H),0.77(p,J=4.7Hz,2H),0.71–0.64(m,2H).HRMS(MALDI)理论值C17H20F3N5O5S2(M+Na)+:518.07502,实测值518.07548.
黄色粉末,mp=95.8-96.5℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.41(d,J=7.4Hz,1H),7.32(d,J=9.2Hz,2H)7.16(t,J=8.5Hz,1H),5.63(s,1H),5.41(s,1H),4.38(s,2H),2.99(s,6H),2.47(dt,J=6.6,3.2Hz,1H),0.75–0.61(m,4H).HRMS(MALDI)理论值C16H20FN5O4S2(M+H)+:430.1014,实测值430.1028.
黄色粉末,mp=111.2-112.0℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.54(s,1H),7.42(dd,J=27.0,5.5Hz,3H),5.62(s,1H),5.41(s,1H),4.38(s,2H),2.99(s,6H),2.47(s,1H),0.82–0.59(m,4H).HRMS(MALDI)理论值C16H20ClN5O4S2(M+H)+:446.0718,实测值446.07135.
白色粉末,mp=94.0-94.3℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.26(d,J=19.4Hz,3H),7.14(s,1H),5.51(s,1H),5.31(s,1H),4.36(s,2H),2.99(s,6H),2.31(s,3H),2.09(s,1H),0.73(d,J=3.2Hz,2H),0.65(d,J=5.2Hz,2H).HRMS(MALDI)理论值C17H23N5O4S2(M+H)+:426.1264,实测值426.1272.
白色粉末,mp=102.5-103.0℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.28(t,J=7.8Hz,1H),7.09–6.98(m,2H),6.90(d,J=7.9Hz,1H),5.56(s,1H),5.34(s,1H),4.38(s,2H),3.77(s,3H),2.99(d,J=3.2Hz,6H),2.47(q,J=3.7Hz,1H),0.80–0.57(m,4H).HRMS(MALDI)理论值C17H23N5O5S2(M+H)+:442.12134,实测值442.12114.
黄色粉末,mp=131.3-131.8℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.83–7.78(m,2H),7.70(d,J=7.8Hz,1H),7.62(t,J=7.8Hz,1H),5.68(s,1H),5.47(s,1H),4.45(s,2H),2.99(s,6H),2.48–2.44(m,1H),0.71(s,2H),0.66(d,J=6.8Hz,2H).HRMS(MALDI)理论值C17H20F3N5O4S2(M+H)+:480.0982,实测值480.1008.
白色粉末,mp=85.9-86.5℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.52(d,J=6.3Hz,2H),7.47(s,1H),7.34(d,J=6.6Hz,1H),5.66(s,1H),5.45(s,1H),4.41(s,2H),2.99(s,6H),2.47(s,1H),0.76–0.61(m,4H).HRMS(MALDI)理论值C17H20F3N5O5S2(M+Na)+:518.07502,实测值518.07522.
白色粉末,mp=101.1-101.9℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.59–7.46(m,2H),7.20(t,J=8.6Hz,2H),5.52(s,1H),5.34(s,1H),4.37(s,2H),2.99(s,6H),2.50–2.42(m,1H),0.72(s,2H),0.65(d,J=5.7Hz,2H).HRMS(MALDI)理论值C16H20FN5O4S2(M+H)+:430.10135,实测值430.10136.
白色粉末,mp=128.1-128.7℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.50(d,J=8.1Hz,2H),7.43(d,J=8.2Hz,2H),5.57(s,1H),5.38(s,1H),4.38(s,2H),2.99(s,6H),2.46(s,1H),0.71(s,2H),0.65(d,J=6.1Hz,2H).HRMS(MALDI)理论值C16H20ClN5O4S2(M+H)+:446.0718,实测值446.0733.
白色粉末,mp=106.8-107.5℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),7.35(d,J=7.9Hz,2H),7.16(d,J=7.8Hz,2H),5.48(s,1H),5.28(s,1H),4.36(s,2H),2.98(s,6H),2.46(tt,J=7.1,3.7Hz,1H),2.30(s,3H),0.72(q,J=3.9Hz,2H),0.64(dd,J=7.6,5.3Hz,2H).HRMS(MALDI)理论值C17H23N5O4S2(M+H)+:426.12642,实测值426.12641.
白色粉末,mp=139.5-140.1℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.84(d,J=8.0Hz,2H),7.67(d,J=8.0Hz,2H),5.71(s,1H),5.52(s,1H),4.43(s,2H),2.98(s,6H),2.45(tt,J=7.1,3.7Hz,1H),0.70(d,J=3.8Hz,2H),0.65(d,J=6.7Hz,2H).HRMS(MALDI)理论值C17H20N6O4S2(M+H)+:437.10602,实测值437.10527.
黄色粉末,mp=118.5-119.4℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.41(d,J=7.6Hz,2H),6.92(d,J=7.3Hz,2H),5.44(s,1H),5.23(s,1H),4.35(s,2H),3.77(s,3H),2.99(s,6H),2.46(s,1H),0.77–0.57(m,4H).HRMS(MALDI)理论值C17H23N5O5S2(M+H)+:442.12134,实测值442.12111.
白色粉末,mp=123.7-124.3℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.39(d,J=8.0Hz,2H),7.23(d,J=8.0Hz,2H),5.50(s,1H),5.29(s,1H),4.36(s,2H),2.99(s,6H),2.89(p,J=6.7Hz,1H),2.50–2.45(m,1H),1.20(d,J=6.9Hz,6H),0.77–0.70(m,2H),0.68–0.61(m,2H).HRMS(MALDI)理论值C19H27N5O4S2(M+Na)+:476.13967,实测值476.13960.
白色粉末,mp=155.7-156.3℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.39(q,J=8.2Hz,4H),5.51(s,1H),5.29(s,1H),4.37(s,2H),2.99(s,6H),2.48(s,1H),1.28(s,9H),0.73(s,2H),0.65(q,J=6.6Hz,2H).HRMS(MALDI)理论值C20H29N5O4S2(M+H)+:468.17337,实测值468.17282.
黄色粉末,mp=111.5-112.0℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.76–7.67(m,4H),5.68(s,1H),5.49(s,1H),4.44(s,2H),2.99(s,6H),2.49–2.44(m,1H),0.74–0.64(m,4H).HRMS(MALDI)理论值C17H20F3N5O4S2(M+H)+:480.0972,实测值480.0975.
黄色粉末,mp=106.7-107℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.60(d,J=8.3Hz,2H),7.37(d,J=8.3Hz,2H),5.59(s,1H),5.40(s,1H),4.39(s,2H),2.99(s,6H),2.48(s,1H),0.72(s,2H),0.66(d,J=6.8Hz,2H).HRMS(MALDI)理论值C17H20F3N5O5S2(M+Na)+:518.075,实测值518.0762.
白色粉末,mp=91.8-92.7℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.15–7.02(m,2H),6.90(d,J=7.5Hz,1H),5.39(s,1H),5.00(s,1H),4.08(s,2H),2.96(s,6H),2.71–2.58(m,1H),2.24(s,3H),2.16(s,3H),0.78(s,2H),0.75–0.64(m,2H).HRMS(MALDI)理论值C18H25N5O4S2(M+Na)+:462.12402,实测值462.12404.
白色粉末,mp=76.8-77.6℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.40(q,J=9.4,9.0Hz,1H),7.25–7.14(m,2H),5.61(s,1H),5.45(s,1H),4.32(s,2H),2.98(s,6H),2.48(s,1H),0.76(s,2H),0.68(d,J=6.8Hz,2H).HRMS(MALDI)理论值C16H19F2N5O4S2(M+Na)+:470.07387,实测值470.07381.
白色粉末,mp=100.9-101.7℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.62(d,J=8.0Hz,1H),7.38(t,J=7.7Hz,1H),7.25(d,J=7.5Hz,1H),5.57(s,1H),5.25(s,1H),4.26(s,2H),2.98(s,6H),2.61(s,1H),0.74(d,J=45.1Hz,4H).HRMS(MALDI)理论值C16H19Cl2N5O4S2(M+H)+:480.03283,实测值480.03282.
白色粉末,mp=106.7-107.0℃.1H NMR(600MHz,DMSO-d6)δ9.38(s,1H),7.00(s,1H),6.94(s,2H),5.38(s,1H),4.99(s,1H),4.09(s,2H),2.94(s,6H),2.62–2.56(m,1H),2.23(d,J=17.4Hz,6H),0.76(s,2H),0.70–0.65(m,2H).HRMS(MALDI)理论值C18H25N5O4S2(M+H)+:440.1421,实测值440.1410.
白色粉末,mp=96.7-97.6℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.40(q,J=8.2Hz,1H),7.26(t,J=10.8Hz,1H),7.10(t,J=7.4Hz,1H),5.55(s,1H),5.37(s,1H),4.29(s,2H),2.98(s,6H),2.48(s,1H)0.81–0.62(m,4H).HRMS(MALDI)理论值C16H19F2N5O4S2(M+Na)+:470.07387,实测值470.07338.
白色粉末,mp=112.4-113.2℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.48–7.33(m,2H),7.30(d,J=8.3Hz,1H),5.56(s,1H),5.40(s,1H),4.29(s,2H),2.97(s,6H),2.50(s,1H),0.73(s,2H),0.66(s,2H).HRMS(MALDI)理论值C16H19ClFN5O4S2(M+H)+:464.06238,实测值464.06258.
白色粉末,mp=107.1-108.2℃.1H NMR(400MHz,DMSO-d6)δ9.40(s,1H),7.64(d,J=2.1Hz,1H),7.45–7.42(m,1H),7.29(d,J=8.3Hz,1H),5.57(s,1H),5.24(s,1H),4.24(s,2H),2.97(s,6H),2.59–2.55(m,1H),0.76(d,J=2.9Hz,2H),0.68(d,J=6.2Hz,2H).HRMS(MALDI)理论值C16H19Cl2N5O4S2(M+Na)+:502.0148,实测值502.0154.
白色粉末,mp=80.0-80.7℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.09(d,J=7.7Hz,1H),7.01(d,J=7.8Hz,1H),6.88(s,1H),5.39(s,1H),5.02(s,1H),4.10(s,2H),2.96(s,6H),2.63(s,1H),2.23(d,J=21.3Hz,6H),0.84–0.66(m,4H).HRMS(MALDI)理论值C18H25N5O4S2(M+Na)+:462.12402,实测值462.12472.
白色粉末,mp=108.7-109.3℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.25(d,J=29.1Hz,3H),5.59(s,1H),5.46(s,1H),4.31(s,2H),2.98(s,6H),2.50(s,1H),0.75(s,2H),0.68(s,2H).HRMS(MALDI)理论值C16H19F2N5O4S2(M+H)+:448.09193,实测值448.09135.
黄色粉末,mp=160.1-160.7℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.52(d,J=8.6Hz,1H),7.44(d,J=8.5Hz,1H),7.36–7.30(m,1H),5.58(s,1H),5.28(s,1H),4.26(s,2H),2.97(s,6H),2.59(dt,J=7.0,3.3Hz,1H),0.82–0.66(m,4H).HRMS(MALDI)理论值C16H19Cl2N5O4S2(M+H)+:480.03283,实测值480.03226.
白色粉末,mp=85.2-86.1℃.1H NMR(600MHz,DMSO-d6)δ9.40(s,1H),7.43(q,J=7.0,6.5Hz,1H),7.12(t,J=7.9Hz,2H),5.74(s,1H),5.37(s,1H),4.21(s,2H),2.97(s,6H),2.63–2.54(m,1H),0.80(s,2H),0.69(t,J=6.1Hz,2H).HRMS(MALDI)理论值C16H19F2N5O4S2(M+H)+:448.09193,实测值448.09150.
白色粉末,mp=90.3-91.0℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.45–7.33(m,1H),7.26(t,J=8.4Hz,2H),5.77–5.67(m,2H),4.17(s,2H),2.97(s,6H),2.66(dt,J=6.9,3.5Hz,1H),0.82(s,2H),0.70(d,J=5.7Hz,2H).HRMS(MALDI)理论值C16H19ClFN5O4S2(M+Na)+:486.04432,实测值486.04418.
黄色粉末,mp=110.5-111.2℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.24(s,1H),7.17(d,J=7.8Hz,1H),7.11(d,J=7.8Hz,1H),5.47(s,1H),5.26(s,1H),4.35(s,2H),2.98(s,6H),2.50–2.45(m,1H),2.22(d,J=7.2Hz,6H),0.73(s,2H),0.65(d,J=6.7Hz,2H).HRMS(MALDI)理论值C18H25N5O4S2(M+Na)+:462.12402,实测值462.12431.
白色粉末,mp=113.5-114.0℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.57(t,J=10.2Hz,1H),7.43(q,J=9.1Hz,1H),7.33(s,1H),5.61(s,1H),5.40(s,1H),4.37(s,2H),2.98(s,6H),2.48–2.44(m,1H),0.71(d,J=3.5Hz,2H),0.65(d,J=6.9Hz,2H).HRMS(MALDI)理论值C16H19F2N5O4S2(M+H)+:448.09193,实测值448.09166.
白色粉末,mp=131.9-132.4℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.70(t,J=7.8Hz,1H),7.51(d,J=9.9Hz,1H),7.29(d,J=8.2Hz,1H),5.69(s,1H),5.45(s,1H),4.38(s,2H),2.98(s,6H),2.46(s,1H),0.76–0.58(m,4H).HRMS(MALDI)理论值C16H19BrFN5O4S2(M+Na)+:529.99381,实测值529.99360.
黄色粉末,mp=137.7-138.3℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.37(d,J=13.0Hz,1H),7.27(d,J=8.4Hz,1H),7.15(t,J=8.8Hz,1H),5.54(s,1H),5.30(s,1H),4.35(s,2H),3.85(s,3H),2.99(s,6H),2.46(tt,J=7.0,3.6Hz,1H),0.71(d,J=3.7Hz,2H),0.65(q,J=6.9,6.5Hz,2H).HRMS(MALDI)理论值C14H17Br2N5O5S2(M+Na)+:482.09386,实测值482.09341.
白色粉末,mp=119.6-120.5℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.75(s,1H),7.64(d,J=8.4Hz,1H),7.48(d,J=8.1Hz,1H),5.67(s,1H),5.45(s,1H),4.39(s,2H),2.99(s,6H),2.48–2.44(m,1H),0.71(s,2H),0.65(d,J=6.9Hz,2H).HRMS(MALDI)理论值C16H19Cl2N5O4S2(M+H)+:480.0328,实测值480.0343.
白色粉末,mp=130.1-130.6℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.06(s,2H),6.95(s,1H),5.48(s,1H),5.28(s,1H),4.34(s,2H),2.48(s,1H),2.99(s,6H),2.27(s,6H),0.74(s,2H),0.66(d,J=6.2Hz,2H).HRMS(MALDI)理论值C18H25N5O4S2(M+Na)+:462.12402,实测值462.12390.
黄色粉末,mp=130.1-130.6℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.22(dd,J=21.5,8.7Hz,3H),5.73(s,1H),5.47(s,1H),4.38(s,2H),2.99(s,6H),2.47(d,J=2.9Hz,1H),0.76–0.63(m,4H).HRMS(MALDI)理论值C16H19F2N5O4S2(M+Na)+:470.07387,实测值470.07366.
白色固体,mp=137.8-138.1℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.58–7.56(m,1H),7.54(t,J=1.9Hz,2H),5.72(s,1H),5.47(s,1H),2.99(s,6H),2.46(s,1H),0.71(d,J=3.8Hz,2H),0.68–0.60(m,2H).HRMS(MALDI)理论值C16H19Cl2N5O4S2(M+H)+:480.08283,实测值480.03326.
黄色固体,mp=148.2-149.0℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),8.16(s,2H),8.07(s,1H),5.87(s,1H),5.60(s,1H),4.51(s,2H),2.99(s,6H),2.48–2.43(m,1H),0.75–0.62(m,4H).HRMS(MALDI)理论值C18H19F6N5O4S2(M+H)+:548.08554,实测值548.08530.
黄色固体,mp=153.9-154.5℃.1H NMR(600MHz,DMSO-d6)δ9.48(s,1H),7.81(s,1H),7.71(s,2H),5.70(s,1H),5.46(s,1H),4.37(s,2H),2.99(s,6H),2.46(s,1H),0.78–0.58(m,4H).HRMS(MALDI)理论值C16H19Br2N5O4S2(M+H)+:567.93180,实测值567.93110.
白色固体,mp=90.9-91.6℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.72–7.64(m,1H),7.21–7.10(m,2H),5.56(s,1H),5.25(s,1H),4.26(s,2H),2.97(s,6H),2.66–2.57(m,1H),0.77(d,J=3.8Hz,2H),0.70(d,J=6.7Hz,2H).HRMS(MALDI)理论值C16H19BrFN5O4S2(M+Na)+:529.99381,实测值529.99400.
白色固体,mp=100.4-101.2℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.58(t,J=7.3Hz,1H),7.43–7.34(m,2H),5.52(s,1H),5.15(s,1H),4.13(s,2H),2.96(s,6H),2.72–2.62(m,1H),0.77(q,J=4.1Hz,2H),0.71(q,J=7.3,6.2Hz,2H).HRMS(MALDI)理论值C17H19F4N5O4S2(M+Na)+:529.99381,实测值520.07070.
白色固体,mp=132.9-133.6℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.91(s,1H),7.81(d,J=8.1Hz,1H),7.74(d,J=8.4Hz,1H),5.73(s,1H),5.51(s,1H),4.45(s,2H),2.99(s,6H),2.48–2.40(m,1H),0.74–0.62(m,4H).HRMS(MALDI)理论值C17H19ClF3N5O4S2(M+Na)+:536.04113,实测值536.04125.
黄色固体,mp=83.8-84.5℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.23(t,J=8.7Hz,2H),5.75(s,1H),5.38(s,1H),4.19(s,2H),2.97(s,6H),2.59–2.53(m,1H),0.78(s,2H),0.74–0.61(m,2H).HRMS(MALDI)理论值C16H18F3N5O4S2(M+H)+:466.08251,实测值466.08281.
白色固体,mp=118.6-119.4℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.84(d,J=6.4Hz,1H),7.42(d,J=9.6Hz,1H),5.63(s,1H),5.32(s,1H),4.27(s,2H),2.97(s,6H),2.66–2.57(m,1H),0.79(t,J=3.7Hz,2H),0.70(d,J=6.4Hz,2H).HRMS(MALDI)理论值C16H18Cl2FN5O4S2(M+Na)+:520.00535,实测值520.00575.
黄色固体,mp=114.5-115.3℃.1H NMR(600MHz,DMSO-d6)δ9.47(s,1H),7.56–7.40(m,2H),5.70(s,1H),5.46(s,1H),4.36(s,2H),2.98(s,6H),2.48(s,1H),0.77–0.60(m,4H).HRMS(MALDI)理论值C16H18F3N5O4S2(M+H)+:466.08251,实测值466.08226.
白色粉末,mp=88.4-89.0℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.58(d,J=7.4Hz,2H),7.43(t,J=7.4Hz,2H),7.36(t,J=7.4Hz,1H),5.69(s,1H),5.40(s,1H),4.39(s,2H),3.51(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H19N5O5S2(M+H)+:402.09,实测值402.0909.
白色粉末,mp=75.2-76.1℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.54–7.36(m,2H),7.27(t,J=9.6Hz,2H),5.61(s,1H),5.54(s,1H),4.36(s,2H),3.54(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H18FN5O5S2(M+Na)+:442.06256,实测值442.06213.
白色粉末,mp=92.0-92.8℃.1H NMR(600MHz,DMSO-d6)δ9.54(s,1H),7.52(d,J=7.1Hz,1H),7.42(d,J=13.7Hz,3H),5.66(s,1H),5.39(s,1H),4.36(s,2H),3.66(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H18ClN5O5S2(M+H)+:436.05106,实测值436.05103.
黄色粉末,mp=92.9-93.7℃.1H NMR(600MHz,DMSO-d6)δ9.53(s,1H),7.31–7.17(m,4H),5.58(s,1H),5.22(s,1H),4.25(s,2H),3.61(s,3H),2.98(s,6H),2.31(s,3H).HRMS(MALDI)理论值C15H21N5O5S2(M+H)+:416.10569,实测值416.10556.
白色粉末,mp=71.8-72.6℃.1H NMR(600MHz,DMSO-d6)δ9.51(s,1H),7.79(d,J=7.9Hz,1H),7.71(d,J=7.7Hz,1H),7.60(d,J=7.8Hz,1H),7.49(d,J=7.8Hz,1H),5.69(s,1H),5.28(s,1H),4.19(s,2H),3.76(s,3H),2.97(s,6H).HRMS(MALDI)理论值C15H18F3N5O5S2(M+Na)+:492.05937,实测值492.05913.
油,1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.53(d,J=7.9Hz,2H),7.45(q,J=9.1,8.0Hz,2H),5.65(s,1H),5.46(s,1H),4.33(s,2H),3.58(s,3H),2.99(s,6H).HRMS(MALDI)理论值C15H18F3N5O6S2(M+H)+:486.07234,实测值486.07262.
黄色粉末,mp=67.4-68.2℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.48(q,J=7.9Hz,1H),7.42(d,J=13.4Hz,2H),7.21(t,J=8.2Hz,1H),5.79(s,1H),5.48(s,1H),4.39(s,2H),3.52(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H18FN5O5S2(M+H)+:420.0806,实测值420.0800.
黄色粉末,mp=63.8-64.6℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.64(s,1H),7.55(d,J=7.7Hz,1H),7.50–7.41(m,2H),5.78(s,1H),5.47(s,1H),4.39(s,2H),3.52(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H18ClN5O5S2(M+H)+:436.05106,实测值436.05136.
黄色粉末,mp=57.8-58.6℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.40–7.29(m,3H),7.17(d,J=7.4Hz,1H),5.66(s,1H),5.37(s,1H),4.37(s,2H),3.52(s,3H),3.00(s,6H),2.34(s,3H).HRMS(MALDI)理论值C15H21N5O5S2(M+H)+:416.10569,实测值416.10573.
黄色粉末,mp=82.9-83.6℃.1HNMR(600MHz,DMSO-d6)δ9.57(d,J=3.1Hz,1H),7.34(t,J=7.6Hz,1H),7.22–7.08(m,2H),6.94(d,J=8.3Hz,1H),5.71(s,1H),5.40(s,1H),4.38(s,2H),3.79(s,3H),3.53(s,3H),3.01(s,6H).HRMS(MALDI)理论值C15H21N5O6S2(M+H)+:432.10060,实测值432.10032.
黄色粉末,mp=75.1-75.7℃.1H NMR(600MHz,DMSO-d6)δ8.72(d,J=2.2Hz,1H),7.82–7.74(m,2H),7.60(d,J=7.9Hz,1H),7.53(t,J=7.8Hz,1H),5.72(s,1H),5.48(s,1H),4.46(s,2H),3.10(s,6H).HRMS(MALDI)理论值C15H18F3N5O5S2(M+H)+:470.0774,实测值470.0781.
油,1HNMR(600MHz,DMSO-d6)δ9.57(s,1H),7.68–7.52(m,3H),7.37(d,J=8.2Hz,1H),5.81(s,1H),5.51(s,1H),4.41(s,2H),3.50(s,3H),3.01(s,6H).HRMS(MALDI)理论值C15H18F3N5O6S2(M+H)+:486.07234,实测值486.07225.
白色粉末,mp=125.2-125.7℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.60(d,J=8.5Hz,2H),7.50(d,J=8.5Hz,2H),5.73(s,1H),5.44(s,1H),4.39(s,2H),3.50(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H18ClN5O5S2(M+H)+:436.0511,实测值436.0521.
白色粉末,mp=120.2-120.7℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.46(d,J=7.8Hz,2H),7.23(d,J=7.9Hz,2H),5.64(s,1H),5.33(s,1H),4.36(s,2H),3.50(s,3H),3.00(s,6H),2.32(s,3H).HRMS(MALDI)理论值C15H21N5O5S2(M+H)+:416.10569,实测值416.10601.
黄色粉末,mp=87.1-88.0℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.52(d,J=8.4Hz,2H),6.99(d,J=8.4Hz,2H),5.59(s,1H),5.28(s,1H),4.35(s,2H),3.79(s,3H),3.50(s,3H),3.01(s,6H)HRMS(MALDI)理论值C15H21N5O6S2(M+H)+:432.10060,实测值432.10020.
黄色粉末,mp=99.4-100.3℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.50(d,J=6.8Hz,2H),7.30(d,J=5.9Hz,2H),5.65(s,1H),5.35(s,1H),4.37(s,2H),3.52(s,3H),3.01(s,6H),1.22(d,J=6.8Hz,7H).HRMS(MALDI)理论值C17H25N5O5S2(M+H)+:444.13699,实测值444.13633.
白色粉末,mp=86.2-86.9℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.54–7.48(m,2H),7.44(d,J=8.0Hz,2H),5.65(s,1H),5.35(s,1H),4.37(s,2H),3.53(s,3H),3.01(s,6H),1.30(s,9H).HRMS(MALDI)理论值C18H27N5O5S2(M+H)+:458.15264,实测值458.15205.
白色粉末,mp=108.6-109.7℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.80(s,4H),5.84(s,1H),5.56(s,1H),4.45(s,2H),3.50(s,3H),3.01(s,6H).HRMS(MALDI)理论值C15H18F3N5O5S2(M+H)+:470.0774,实测值470.0784.
白色粉末,mp=60.9-61.6℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.71(d,J=9.2Hz,2H),7.43(d,J=8.5Hz,2H),5.74(s,1H),5.47(s,1H),4.41(s,2H),3.51(s,3H),3.01(s,6H).HRMS(MALDI)理论值C15H18F3N5O6S2(M+H)+:486.0723,实测值486.0717.
白色粉末,mp=145.8-146.9℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.91(d,J=7.9Hz,2H),7.78(d,J=7.9Hz,2H),5.87(s,1H),5.59(s,1H),4.43(s,2H),3.49(d,J=2.0Hz,3H),3.00(d,J=2.0Hz,6H).HRMS(MALDI)理论值C15H18N6O5S2(M+H)+:427.08529,实测值427.08452.
白色粉末,mp=104.1-104.9℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.50–7.40(m,1H),7.38–7.25(m,2H),5.70(s,1H),5.61(s,1H),4.36(s,2H),3.55(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H17F2N5O5S2(M+Na)+:460.05314,实测值460.05319.
白色粉末,mp=74.8-75.6℃.1H NMR(600MHz,DMSO-d6)δ9.54(s,1H),7.67(d,J=4.8Hz,1H),7.43(s,2H),5.70(s,1H),5.42(s,1H),4.35(s,2H),3.68(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H17Cl2N5O5S2(M+H)+:470.01209,实测值470.01195.
白色粉末,mp=80.3-81.0℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.60–7.49(m,2H),7.38(d,J=8.4Hz,1H),5.65(s,1H),5.56(s,1H),4.35(s,2H),3.54(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H17ClFN5O5S2(M+H)+:454.04164,实测值454.04186.
黄色粉末,mp=57.6-58.3℃.1H NMR(600MHz,DMSO-d6)δ9.53(s,1H),7.13(d,J=7.6Hz,1H),7.05(d,J=10.2Hz,2H),5.56(s,1H),5.19(s,1H),4.23(s,2H),3.62(s,3H),2.98(s,6H),2.26(d,J=17.0Hz,6H).HRMS(MALDI)理论值C16H23N5O5S2(M+Na)+:452.10328,实测值452.10342.
白色粉末,84.2%,mp=68.2-69.0℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.43–7.26(m,3H),5.67(s,1H),5.61(s,1H),4.36(s,2H),3.56(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H17F2N5O5S2(M+Na)+:460.05314,实测值460.05324.
白色粉末,mp=140.8-141.4℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.67–7.52(m,2H),7.52–7.42(m,1H),5.72(s,1H),5.46(s,1H),4.36(s,2H),3.67(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H17Cl2N5O5S2(M+H)+:470.01209,实测值470.01228.
黄色粉末,mp=97.7-98.5℃.1H NMR(600MHz,DMSO-d6)δ9.54(s,1H),7.55–7.41(m,1H),7.28–7.13(m,2H),5.83(s,1H),5.51(s,1H),4.27(s,2H),3.63(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H17F2N5O5S2(M+H)+:438.07119,实测值438.07098.
白色粉末,mp=116.6-117.4℃.1H NMR(600MHz,DMSO-d6)δ9.54(s,1H),7.50–7.39(m,2H),7.33(t,J=8.6Hz,1H),5.87(s,1H),5.45(s,1H),4.27(s,2H),3.71(s,3H),2.98(s,6H).HRMS(MALDI)理论值C14H17ClFN5O5S2(M+H)+:454.04164,实测值454.04121.
黄色粉末,mp=112.2-112.8℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.74(t,J=7.1Hz,1H),7.34(d,J=9.2Hz,1H),7.22(t,J=8.7Hz,1H),5.71(s,1H),5.42(s,1H),4.35(s,2H),3.70(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H17BrFN5O5S2(M+Na)+:519.97307,实测值519.97313.
白色粉末,mp=119.1-110.2℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.67(dd,J=12.1,8.4Hz,1H),7.51(q,J=9.2Hz,1H),7.43(s,1H),5.75(s,1H),5.46(s,1H),4.38(s,2H),3.51(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H17F2N5O5S2(M+H)+:438.07199,实测值438.07073.
白色粉末,mp=111.4-112.2℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),8.02(s,1H),7.92(d,J=8.2Hz,2H),7.81(d,J=8.4Hz,1H),5.89(s,1H),5.57(s,1H),4.45(s,2H),3.51(s,3H),3.01(s,6H).HRMS(MALDI)理论值C15H17ClF3N5O5S2(M+H)+:504.03845,实测值504.03888.
黄色粉末,mp=138.6-139.4℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.46(d,J=13.0Hz,1H),7.37(d,J=7.9Hz,1H),7.22(t,J=8.5Hz,1H),5.68(s,1H),5.34(s,1H),4.35(s,2H),3.87(s,3H),3.51(s,3H),3.01(s,6H).HRMS(MALDI)理论值C15H20FN5O6S2(M+Na)+:472.07312,实测值472.07328.
黄色粉末,mp=103.7-104.5℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.78(t,J=8.0Hz,1H),7.61(dd,J=10.6,2.1Hz,1H),7.43–7.36(m,1H),5.83(s,1H),5.51(s,1H),4.39(s,2H),3.51(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H17BrFN5O5S2(M+H)+:497.99113,实测值497.991
黄色粉末,mp=95.0-96.1℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.85(s,1H),7.71(d,J=8.3Hz,1H),7.58(d,J=8.5Hz,1H),5.83(s,1H),5.51(s,1H),4.40(s,2H),3.52(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H17Cl2N5O5S2(M+H)+:470.0721,实测值470.0721.
白色粉末,mp=102.5-103.3℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.38–7.22(m,3H),5.87(s,1H),5.54(s,1H),4.39(s,2H),3.53(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H17F2N5O5S2(M+H)+:438.07119,实测值438.07113.
黄色粉末,mp=104.7-105.6℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.17(s,2H),6.99(s,1H),5.63(s,1H),5.35(s,1H),4.34(s,2H),3.53(s,3H),3.00(s,6H),2.29(s,6H).HRMS(MALDI)理论值C16H23N5O5S2(M+H)+:430.12134,实测值430.12183.
白色粉末,mp=114.9-115.5℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.65(d,J=2.0Hz,2H),7.61(s,1H),5.88(s,1H),5.54(s,1H),4.39(s,2H),3.53(s,3H),3.00(s,1H).HRMS(MALDI)理论值C14H17Cl2N5O5S2(M+H)+:470.01209,实测值470.01055.
黄色粉末,mp=118.1-118.9℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.84(s,1H),7.81(d,J=1.7Hz,2H),5.86(s,1H),5.53(s,1H),4.38(s,2H),3.53(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H17Br2N5O5S2(M+H)+:557.91106,实测值557.911
白色粉末,mp=76.1-76.9℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.32(t,J=8.9Hz,2H),5.84(s,1H),5.52(s,1H),4.24(s,2H),3.63(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H16F3N5O5S2(M+H)+:456.06177,实测值456.06179.
白色粉末,mp=102.9-103.7℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.91(d,J=6.7Hz,1H),7.63(d,J=9.7Hz,1H),5.76(s,1H),5.49(s,1H),4.37(s,2H),3.68(s,3H),3.00(s,6H).HRMS(MALDI)理论值C14H16Cl2FN5O5S2(M+H)+:488.00267,实测值488.00365.
白色粉末,mp=110.7-111.6℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.56(t,J=8.2Hz,2H),5.83(s,1H),5.53(s,1H),4.39(s,2H),3.53(s,3H),3.01(s,6H).HRMS(MALDI)理论值C14H16F3N5O5S2(M+H)+:456.06177,实测值456.06199.
白色粉末,mp=121.5-122.0℃.1H NMR(600MHz,DMSO-d6)δ9.36(s,1H),7.27(p,J=6.6Hz,1H),7.16(t,J=7.3Hz,1H),7.12–7.07(m,2H),5.74(q,J=7.0Hz,1H),4.38(s,2H),2.95(s,6H),2.25(tt,J=7.2,3.5Hz,1H),1.85(d,J=6.7Hz,4H),0.70–0.65(m,3H),0.56(d,J=6.9Hz,3H).HRMS(MALDI)理论值C17H22FN5O4S2(M+H)+:444.117,实测值444.11710.
白色粉末,mp=92.3-93.1℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.35(q,J=7.5Hz,1H),7.19(t,J=9.1Hz,2H),7.09–7.05(m,1H),6.05(q,J=7.0Hz,1H),4.48(s,2H),2.99(s,6H),2.22(dt,J=7.0,3.5Hz,1H),1.87(d,J=7.0Hz,3H),0.65(d,J=3.5Hz,2H),0.60–0.55(m,2H).HRMS(MALDI)理论值C17H22FN5O4S2(M+H)+:444.1170,实测值444.11728.
白色粉末,mp=96.4-97.2℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),7.41(s,1H),7.31(d,J=10.1Hz,3H),6.01(q,J=7.4,3.4Hz,1H),4.47(s,2H),2.99(s,6H),2.27–2.16(m,1H),1.87(d,J=3.5Hz,3H),0.66(s,2H),0.58(s,2H).HRMS(MALDI)理论值C17H22ClN5O4S2(M+H)+:460.08745,实测值460.08739.
白色粉末,mp=94.2-95.0℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.22–7.09(m,3H),7.05(d,J=7.1Hz,1H),5.92(q,J=6.2,5.3Hz,1H),4.47(s,2H),2.99(s,6H),2.29(s,3H),2.24–2.16(m,1H),1.86(d,J=4.9Hz,3H),0.67(s,2H),0.57(d,J=6.8Hz,2H).HRMS(MALDI)理论值C18H25N5O4S2(M+H)+:440.14207,实测值440.14138.
白色粉末,mp=58.4-59.3℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),6.92(t,J=5.2Hz,2H),6.81(dd,J=8.3,2.5Hz,1H),6.76–6.70(m,1H),5.99(q,J=7.0Hz,1H),4.48(s,2H),3.75(s,3H),2.99(s,6H),2.21(dq,J=6.9,3.5Hz,1H),1.86(d,J=7.0Hz,3H),0.66(p,J=5.3,4.4Hz,2H),0.57(dt,J=6.9,3.5Hz,2H).HRMS(MALDI)理论值C18H25N5O5S2(M+Na)+:478.11893,实测值478.11893.
白色粉末,mp=68.0-68.7℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.77–7.58(m,4H),6.06(q,J=7.1Hz,1H),4.53(s,2H),2.99(s,6H),2.28–2.15(m,1H),1.89(d,J=7.7Hz,3H),0.65(s,2H),0.58(s,2H).HRMS(MALDI)理论值C18H22F3N5O4S2(M+H)+:494.11381,实测值494.11405.
白色粉末,mp=109.0-109.5℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.42–7.32(m,2H),7.12(t,J=8.9Hz,2H),5.91(q,J=6.9Hz,1H),4.47(s,2H),2.99(s,6H),2.25–2.18(m,1H),1.86(d,J=7.0Hz,3H),0.65(q,J=4.3,3.8Hz,2H),0.57(q,J=6.3,5.7Hz,2H).HRMS(MALDI)理论值C17H22FN5O4S2(M+H)+:444.11700,实测值444.11739.
白色粉末,mp=109.2-109.9℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.36(s,4H),5.97(q,J=9.3,8.0Hz,1H),4.47(s,2H),2.99(s,6H),2.26–2.15(m,1H),1.95–1.79(m,3H),0.65(s,2H),0.57(s,2H).HRMS(MALDI)理论值C17H22ClN5O4S2(M+Na)+:482.06939,实测值482.07012.
白色粉末,mp=129.8-130.6℃.1H NMR(600MHz,DMSO-d6)δ9.41(s,1H),7.22(d,J=4.0Hz,2H),7.10(d,J=4.1Hz,2H),5.91(dd,J=7.2,3.6Hz,1H),4.47(s,2H),2.98(s,6H),2.23(s,3H),1.86(d,J=10.5Hz,3H),0.66(s,2H),0.62–0.48(m,3H).HRMS(MALDI)理论值C18H25N5O4S2(M+H)+:440.14207,实测值440.14201.
白色粉末,mp=145.6-146.1℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.27(d,J=8.4Hz,2H),6.86(d,J=8.1Hz,2H),5.87(q,J=7.1Hz,1H),4.45(s,2H),3.74(s,3H),2.99(s,6H),2.23–2.16(m,1H),1.84(d,J=7.1Hz,3H),0.66(s,2H),0.56(d,J=6.8Hz,2H).HRMS(MALDI)理论值C18H25N5O5S2(M+H)+:456.13699,实测值456.13682.
白色粉末,mp=115.2-115.8℃.1H NMR(600MHz,DMSO-d6)δ9.38(s,1H),7.23(d,J=8.0Hz,2H),7.10(d,J=7.9Hz,2H),5.90(q,J=7.0Hz,1H),4.45(s,2H),2.96(s,6H),2.56(q,J=7.7Hz,2H),2.18(tt,J=7.2,3.7Hz,1H),1.83(d,J=7.0Hz,3H),1.15(t,J=7.6Hz,3H),0.64(q,J=4.4,3.9Hz,2H),0.54(t,J=6.7Hz,2H).HRMS(MALDI)理论值C19H27N5O4S2(M+H)+:454.15772,实测值454.15753.
白色粉末,mp=87.8-88.4℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.66(d,J=8.2Hz,2H),7.57(d,J=8.0Hz,2H),6.08(q,J=7.0Hz,1H),4.53(s,2H),2.99(s,6H),2.27–2.18(m,1H),1.90(d,J=7.0Hz,2H),0.67–0.63(m,2H),0.59(t,J=5.9Hz,2H).HRMS(MALDI)理论值C18H22F3N5O4S2(M+Na)+:516.09575,实测值516.09533.
白色粉末,mp<50℃.1H NMR(600MHz,DMSO-d6)δ9.39(s,1H),7.24(p,J=8.8,7.6Hz,3H),5.97(q,J=6.9Hz,1H),4.37(s,2H),2.98(s,6H),2.36–2.28(m,1H),1.87(d,J=7.1Hz,3H),0.77–0.67(m,4H).HRMS(MALDI)理论值C17H21F2N5O4S2(M+H)+:462.10758,实测值462.10731.
白色粉末,mp=74.1-74.9℃.1H NMR(600MHz,DMSO-d6)δ9.45(d,J=2.1Hz,1H),7.40(s,1H),7.35(t,J=8.9Hz,1H),7.19(t,J=6.0Hz,1H),6.00(q,J=7.1Hz,1H),4.46(s,2H),2.99(s,6H),2.24(dp,J=7.6,3.6Hz,1H),1.86(d,J=7.1Hz,3H),0.67–0.64(m,2H),0.58(d,J=6.8Hz,2H).HRMS(MALDI)理论值C17H21F2N5O4S2(M+H)+:462.10758,实测值462.10725.
白色粉末,mp=96.1-96.9℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),7.63–7.59(m,1H),7.56(d,J=8.4Hz,1H),7.39–7.32(m,1H),6.05(q,J=7.0Hz,1H),4.47(s,2H),3.33(s,3H),2.99(s,7H),2.28–2.19(m,1H),1.87(d,J=7.1Hz,3H),0.66(s,2H),0.59(d,J=6.6Hz,2H).HRMS(MALDI)理论值C17H21Cl2N5O4S2(M+H)+:494.04848,实测值494.04800.
白色粉末,mp=87.7-88.3℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),8.04(s,6H),7.97(s,3H),6.21(q,J=6.9Hz,3H),4.58(s,6H),2.99(s,8H),2.24(tt,J=7.0,3.7Hz,3H),1.92(d,J=7.0Hz,8H),0.65(d,J=3.8Hz,5H),0.62–0.55(m,5H).HRMS(MALDI)理论值C19H21F6N5O4S2(M+Na)+:584.08314,实测值584.08315.
白色粉末,mp=95.0-96.1℃.1H NMR(600MHz,DMSO-d6)δ9.52(s,1H),7.37(t,J=7.8Hz,1H),7.32(t,J=6.8Hz,1H),7.19(dd,J=9.3,5.0Hz,2H),5.99(q,J=7.1Hz,1H),4.38(s,2H),3.51(s,3H),2.96(s,6H),1.79(d,J=7.0Hz,3H).HRMS(MALDI)理论值C15H20FN5O5S2(M+Na)+:456.07821,实测值456.07845.
白色粉末,mp=136.7-137.2℃.1H NMR(600MHz,DMSO-d6)δ9.48(s,1H),7.79(d,J=7.9Hz,1H),7.73(t,J=7.6Hz,2H),7.57(t,J=7.7Hz,1H),7.36(d,J=7.6Hz,1H),6.02(q,J=6.8Hz,1H),4.38(s,2H),3.50(s,3H),2.94(s,6H),1.36(d,J=6.7Hz,3H).HRMS(MALDI)理论值C16H20F3N5O5S2(M+Na)+:506.07502,实测值506.07499.
白色粉末,mp=63.0-63.8℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.41(q,J=7.4Hz,2H),7.32(t,J=9.9Hz,1H),7.12(t,J=8.7Hz,1H),6.31(q,J=6.9Hz,1H),4.46(s,2H),3.51(s,3H),3.00(s,6H),1.81(d,J=7.0Hz,3H).HRMS(MALDI)理论值C15H20FN5O5S2(M+H)+:434.0963,实测值434.09621.
油状产物,1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.53(s,1H),7.48–7.37(m,2H),7.35(d,J=8.0Hz,1H),6.29(q,J=7.9,7.4Hz,1H),4.46(s,2H),3.52(s,3H),3.00(s,6H),1.81(d,J=6.7Hz,3H).HRMS(MALDI)理论值C15H20ClN5O5S2(M+H)+:450.06671,实测值450.06888.
白色粉末,mp=95.0-96.1℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.27(t,J=8.0Hz,1H),7.04(d,J=7.8Hz,1H),7.01(s,1H),6.85(d,J=8.8Hz,1H),6.23(q,J=7.0Hz,1H),4.43(s,2H),3.75(s,3H),2.99(s,6H),2.07(s,3H),1.79(d,J=6.9Hz,3H).HRMS(MALDI)理论值C16H23N5O6S2(M+Na)+:468.0982,实测值468.09775.
白色粉末,mp=63.8-64.4℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.80(d,J=8.2Hz,2H),7.64(s,2H),6.35(q,J=6.2,5.7Hz,1H),4.51(s,2H),3.51(s,3H),3.01(s,6H),1.84(d,J=6.2Hz,3H).HRMS(MALDI)理论值C16H20F3N5O5S2(M+H)+:484.09307,实测值484.09298.
白色粉末,mp=65.5-66.3℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.55–7.45(m,2H),7.23–7.15(m,2H),6.17(q,J=6.8Hz,1H),4.45(s,2H),3.51(s,3H),3.00(s,6H),1.80(d,J=6.9Hz,3H).HRMS(MALDI)理论值C15H20FN5O5S2(M+H)+:434.09626,实测值434.09586.
白色粉末,mp=72.3-72.8℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.49(s,2H),7.43(d,J=5.0Hz,2H),6.24(q,J=6.4Hz,1H),4.46(s,2H),3.50(s,3H),3.00(s,6H),1.81(d,J=6.4Hz,3H).HRMS(MALDI)理论值C15H20ClN5O5S2(M+H)+:450.06671,实测值450.06901.
白色粉末,mp=100.6-101.4℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.36(d,J=7.9Hz,2H),7.17(d,J=7.8Hz,2H),6.16(q,J=6.9Hz,1H),4.44(s,2H),3.50(s,3H),3.00(s,6H),2.30(s,3H),1.79(d,J=7.0Hz,6H).HRMS(MALDI)理论值C16H23N5O5S2(M+Na)+:452.10328,实测值452.10312.
白色粉末,mp=95.0-96.1℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.40(d,J=8.2Hz,2H),6.93(d,J=8.2Hz,2H),6.11(q,J=7.0Hz,1H),4.43(s,2H),3.76(s,3H),3.50(s,3H),3.00(s,6H),1.78(d,J=6.9Hz,3H).HRMS(MALDI)理论值C16H23N5O6S2(M+H)+:446.11625,实测值446.11593.
白色粉末,mp=127.0-127.6℃.1H NMR(600MHz,DMSO-d6)δ9.56(d,J=1.9Hz,1H),7.43–7.32(m,2H),7.20(d,J=7.8Hz,2H),6.17(q,J=7.0Hz,1H),4.44(s,2H),3.51(d,J=1.7Hz,3H),3.00(d,J=1.7Hz,6H),2.61(dq,J=15.4,7.7Hz,2H),1.79(d,J=7.1Hz,3H),1.28–1.11(m,3H).HRMS(MALDI)理论值C17H25N5O5S2(M+H)+:444.13699,实测值444.13628.
白色粉末,mp=104.3-104.9℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.74(d,J=8.2Hz,2H),7.70(d,J=8.1Hz,2H),6.36(q,J=7.0Hz,1H),4.51(s,2H),3.51(s,3H),3.00(s,6H),1.85(d,J=7.0Hz,3H).HRMS(MALDI)理论值C16H20F3N5O5S2(M+H)+:484.09307,实测值484.09307.
黄色粉末,mp=59.6-60.3℃.1H NMR(600MHz,DMSO-d6)δ9.54(s,1H),7.55–7.39(m,2H),7.37–7.29(m,1H),6.01(t,J=8.1Hz,1H),4.38(s,2H),3.61(s,3H),2.99(s,6H),1.81(d,J=6.9Hz,3H).HRMS(MALDI)理论值C15H19F2N5O5S2(M+H)+:452.08684,实测值452.08717.
黄色粉末,mp=90.1-91.0℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.59–7.52(m,1H),7.44(q,J=9.3Hz,1H),7.32(d,J=8.7Hz,1H),6.26(q,J=7.0Hz,1H),4.45(s,2H),3.51(s,3H),3.00(s,6H),1.80(d,J=7.0Hz,3H).HRMS(MALDI)理论值C15H19F2N5O5S2(M+H)+:452.0868,实测值452.08678.
白色粉末,mp=95.6-96.3℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.76–7.72(m,1H),7.63(d,J=8.4Hz,1H),7.51–7.45(m,1H),6.33(q,J=6.9Hz,1H),4.46(s,2H),3.52(s,3H),3.00(s,6H),1.82(d,J=7.0Hz,3H).HRMS(MALDI)理论值C15H19Cl2N5O5S2(M+H)+:484.02774,实测值484.02804.
白色粉末,mp=145.3-146.0℃.1H NMR(600MHz,DMSO-d6)δ9.54(s,1H),8.13(s,1H),8.04(s,1H),7.98(s,1H),6.50(q,J=6.9Hz,1H),4.54(s,2H),3.48(s,3H),2.98(s,6H),1.84(d,J=7.0Hz,3H).HRMS(MALDI)理论值C17H19F6N5O5S2(M+H)+:552.08046,实测值552.08021
制备例4
该制备例用来说明式(IV-1)所示的化合物的合成:
步骤a:将原料1(30mmol)加入到250mL茄形瓶中,室温条件下,依次加入80mL超干二氯甲烷溶剂和Ph3P(90mmol),反应15min后,再加入CCl3Br(48mmol),室温条件下反应2小时,TCL检测反应完成后,进行柱层析,减压脱去溶剂,得中间体2。
步骤b:提前将温度预热到100℃,然后将NBS(24mmol)加入到溶有中间体2(20mmol)的THF(40mL)溶液中,接着加入对甲苯磺酸(4.8mmol),回流25min,TLC监测反应完全后,加水猝灭,然后用乙酸乙酯萃取,无水Na2SO4干燥,旋出溶剂,即得式(IV-1)所示的中间体。
制备例5
该制备例用来说明式(V-1)所示的化合物的合成:
将式(III-1)(20mmol)所示结构溶于超干THF(30mL)中,然后在冰浴下滴加环丙胺(30mmol),室温条件下反应2小时,TCL检测反应完成后,用乙酸乙酯萃取,无水Na2SO4干燥,旋出溶剂,即得式(V-1)所示化合物。
制备例6
该制备例用来说明如下所示的化合物的合成:
向50mL梨形瓶中加入1.2mmol中间体式(IV-1),加入10mL乙腈溶解,加入碳酸钾(1.5mmol),最后加入中间体式(V-1)(1mmol),室温反应30min,TLC监测反应完全后,减压旋出溶剂,柱层析即可得式(VI-1)所示目标化合物。
采用制备例6所示的方法制备表2中所示的具体化合物,仅仅是原料取代基进行替换。
表2
以下列举前述获得的部分具体化合物的核磁数据:
白色粉末,mp=90.4-91.5℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),7.44–7.34(m,3H),7.31(d,J=7.6Hz,2H),4.57(s,2H),2.98(s,6H),2.38-2.35(m,1H),0.55(d,J=42.5Hz,4H).HRMS(MALDI)理论值C16H19Cl2N5O4S2(M+H)+:480.0328,实测值480.0310.
白色粉末,mp=133.5-134.1℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.46(p,J=6.5,5.6Hz,1H),7.36(td,J=7.6,1.7Hz,1H),7.27(q,J=8.3,7.1Hz,2H),4.53(s,2H),2.98(s,6H),2.40-2.38(m,1H),0.71–0.57(m,4H).HRMS(MALDI)理论值C16H18Cl2FN5O4S2(M+H)+:498.02341,实测值498.02237.
黄色粉末,mp=98.0-98.8℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.50–7.40(m,1H),7.26–7.08(m,3H),4.55(s,2H),2.96(s,6H),2.34–2.28(m,1H),0.61(d,J=5.4Hz,2H),0.53(s,2H).HRMS(MALDI)理论值C16H18Cl2FN5O4S2(M+Na)+:520.0054,实测值520.0060.
白色粉末,mp=117.8-118.2℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.44(d,J=17.4Hz,3H),7.29(s,1H),4.57(s,2H),2.98(d,J=2.3Hz,6H),2.33(s,1H),0.58(d,J=48.2Hz,4H).HRMS(MALDI)理论值C16H18Cl3N5O4S2(M+H)+:513.99386,实测值513.99298.
白色粉末,mp=101.0-101.8℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.43–7.25(m,2H),7.18(d,J=7.5Hz,1H),7.16–7.06(m,1H),4.56(s,2H),2.98(s,6H),2.34(d,J=23.5Hz,3H),2.29–2.24(m,1H),0.56(dd,J=38.6,5.2Hz,4H).HRMS(MALDI)理论值C17H21Cl2N5O4S2(M+Na)+:516.0304,实测值516.0305.
黄色粉末,mp=110.1-110.6℃.1H NMR(600MHz,DMSO-d6)δ9.46(s,1H),7.79–7.73(m,2H),7.71–7.63(m,2H),4.62(s,2H),2.99(s,6H),2.32(dt,J=7.0,3.4Hz,1H),0.61(d,J=5.8Hz,2H),0.50(s,2H).HRMS(MALDI)理论值C17H18Cl2F3N5O4S2(M+H)+:548.0202,实测值548.0199.
白色粉末,mp=119.1-119.6℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.41–7.34(m,2H),7.27(t,J=8.7Hz,2H),4.57(s,2H),2.98(s,6H),2.32(dt,J=6.9,3.4Hz,1H),0.62(d,J=5.6Hz,2H),0.55(s,2H).HRMS(MALDI)理论值C16H18Cl2FN5O4S2(M+H)+:498.0234,实测值498.0265.
白色粉末,mp=112.8-113.5℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),7.50(d,J=7.3Hz,2H),7.36(d,J=7.4Hz,2H),4.57(s,2H),2.98(s,6H),2.37–2.29(m,1H),0.64(d,J=6.3Hz,2H),0.56(s,2H).HRMS(MALDI)理论值C16H18Cl3N5O4S2(M+Na)+:535.9758,实测值535.9758.
黄色粉末,mp=116.3-117.1℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.21(d,J=8.1Hz,2H),7.18(d,J=8.1Hz,1H),4.56(s,2H),2.98(s,6H),2.32(s,3H),2.30–2.25(m,1H),0.67–0.53(m,4H).HRMS(MALDI)理论值C17H21Cl2N5O4S2(M+H)+:494.04848,实测值494.04800.
白色粉末,mp=125.7-126.1℃.1H NMR(600MHz,DMSO-d6)δ9.72–9.11(m,1H),7.53–7.10(m,2H),6.96(d,J=8.2Hz,2H),4.56(s,2H),3.78(d,J=2.4Hz,3H),2.98(d,J=2.3Hz,6H),2.28(s,1H),0.70–0.50(m,4H).HRMS(MALDI)理论值C17H21Cl2N5O5S2(M+H)+:510.04339,实测值510.04409.
白色粉末,mp=137.3-137.8℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.43(d,J=8.2Hz,2H),7.24(d,J=8.1Hz,2H),4.56(s,2H),2.98(s,6H),2.25(dd,J=7.5,2.9Hz,1H),1.40(s,9H),0.58(d,J=6.9Hz,2H),0.52(d,J=3.8Hz,2H).HRMS(MALDI)理论值C20H27Cl2N5O4S2(M+H)+:536.09543,实测值536.09518.
黄色粉末,mp=112.8-113.5℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),7.81(d,J=8.0Hz,2H),7.58(d,J=7.9Hz,2H),4.60(s,2H),2.98(s,6H),2.36–2.31(m,1H),0.66–0.53(m,4H).HRMS(MALDI)理论值C17H18Cl2F3N5O4S2(M+H)+:548.0202,实测值548.0176.
黄色粉末,mp=114.4-115.1℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.47(d,J=8.7Hz,2H),7.43(d,J=8.4Hz,2H),4.57(s,2H),2.98(s,6H),2.36–2.28(m,1H),0.64–0.50(m,4H).HRMS(MALDI)理论值C17H18Cl2F3N5O5S2(M+H)+:564.0151,实测值564.0126.
白色粉末,mp=88.4-89.3℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.51(d,J=10.0Hz,2H),7.20(d,J=8.2Hz,1H),4.56(s,2H),2.98(s,6H),2.38(dt,J=6.9,3.4Hz,1H),0.69–0.58(m,4H).HRMS(MALDI)理论值C16H17Cl2F2N5O4S2(M+H)+:516.0140,实测值516.0148.
黄色粉末,mp=86.5-87.3℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.65(t,J=7.5Hz,1H),7.38(t,J=7.0Hz,1H),7.31(t,J=7.9Hz,1H),4.52(d,J=41.0Hz,2H),2.97(s,6H),2.45–2.40(m,1H),0.71–0.60(m,4H).HRMS(MALDI)理论值C16H17Cl3FN5O4S2(M+Na)+:553.96638,实测值553.96931.
黄色粉末,mp=73.9-74.5℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.45(q,J=8.0Hz,1H),7.35(t,J=9.5Hz,1H),7.18(dd,J=9.3,6.6Hz,1H),4.51(s,2H),2.97(s,6H),2.41(s,1H),0.65(d,J=9.9Hz,4H).HRMS(MALDI)理论值C16H17Cl2F2N5O4S2(M+H)+:516.01398,实测值516.01386.
白色粉末,mp=100.3-100.9℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.55(dd,J=9.9,2.1Hz,1H),7.44(t,J=8.0Hz,1H),7.38(dd,J=8.4,2.1Hz,1H),4.52(s,2H),2.97(d,J=2.0Hz,6H),2.42(d,J=7.0Hz,1H),0.71–0.58(m,4H).HRMS(MALDI)理论值C16H17Cl3FN5O4S2(M+H)+:531.98443,实测值531.98510.
白色粉末,mp=123.7-124.1℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.25–7.17(m,2H),7.10(d,J=8.2Hz,1H),4.55(s,2H),3.87(s,3H),2.98(s,6H),2.40(s,1H),0.64(d,J=6.9Hz,2H),0.59(s,2H).HRMS(MALDI)理论值C17H20Cl2FN5O5S2(M+Na)+:550.01591,实测值550.01606.
黄色粉末,mp=81.0-81.6℃.1H NMR(600MHz,DMSO-d6)δ9.43(t,J=3.3Hz,1H),7.33(s,3H),4.53(s,2H),2.97(s,6H),2.50(s,1H),0.81–0.51(m,4H).HRMS(MALDI)理论值C16H17Cl2F2N5O4S2(M+H)+:516.01398,实测值516.01355.
白色粉末,mp=81.9-82.8℃.1H NMR(600MHz,DMSO-d6)δ9.48(s,1H),7.34(d,J=7.9Hz,1H),7.19–7.09(m,2H),4.52(s,2H),3.00(s,6H),2.30(s,1H),2.17(s,6H),0.62(d,J=6.0Hz,4H).HRMS(MALDI)理论值C18H23Cl2N5O4S2(M+H)+:508.06413,实测值508.06399.
白色粉末,mp=88.4-89.3℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.51(d,J=10.0Hz,2H),7.20(d,J=8.2Hz,1H),4.56(s,2H),2.98(s,6H),2.38(dt,J=6.9,3.4Hz,1H),0.69–0.58(m,4H).HRMS(MALDI)理论值C16H17Cl2F2N5O4S2(M+H)+:516.01398,实测值516.01380.
白色粉末,mp=120.8-121.4℃.1H NMR(600MHz,DMSO-d6)δ9.43(s,1H),7.26–7.16(m,2H),7.10(d,J=8.4Hz,1H),4.55(s,2H),3.87(s,3H),2.98(s,6H),2.32(td,J=7.3,6.9,3.8Hz,1H),0.64(d,J=7.0Hz,2H),0.61–0.57(m,2H).HRMS(MALDI)理论值C17H20Cl2FN5O5S2(M+Na)+:550.01591,实测值550.01554.
白色粉末,mp=109.9-110.8℃.1H NMR(600MHz,DMSO-d6)δ9.44(d,J=1.6Hz,1H),7.61(dd,J=7.0,2.2Hz,1H),7.49(t,J=8.8Hz,1H),7.39–7.33(m,1H),4.56(s,2H),2.98(d,J=1.7Hz,6H),2.37(td,J=6.9,3.6Hz,1H),0.71–0.51(m,4H).HRMS(MALDI)理论值C16H17Cl3FN5O4S2(M+H)+:531.98443,实测值531.98363.
黄色粉末,mp=127.3-128.1℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.74–7.65(m,2H),7.35(d,J=8.2Hz,1H),4.57(s,2H),2.98(s,6H),2.38(td,J=7.5,7.0,3.7Hz,1H),0.66(d,J=5.4Hz,2H),0.60(s,2H).HRMS(MALDI)理论值C16H17Cl4N5O4S2(M+H)+:547.9538,实测值547.9531.
白色粉末,mp=73.8-74.6℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.88(s,1H),7.83(s,1H),7.69(s,1H),4.61(s,2H),2.98(s,6H),2.09(s,1H),0.62(d,J=53.9Hz,4H).HRMS(MALDI)理论值C17H17Cl3F3N5O4S2(M+H)+:581.98124,实测值581.98055.
白色粉末,mp=106.1-106.7℃.1H NMR(600MHz,DMSO-d6)δ9.44(s,1H),6.98(s,1H),6.88(s,2H),4.54(s,2H),2.98(d,J=3.6Hz,6H),2.30(s,1H),2.28(d,J=3.7Hz,6H),0.56(d,J=33.8Hz,4H).HRMS(MALDI)理论值C18H23Cl2N5O4S2(M+H)+:508.06413,实测值508.06446.
白色粉末,mp=112.2-112.7℃.1H NMR(600MHz,DMSO-d6)δ9.42(s,1H),7.27(t,J=9.4Hz,1H),7.10(d,J=7.2Hz,2H),4.53(s,2H),2.95(s,6H),2.38(s,1H),0.77–0.46(m,4H).HRMS(MALDI)理论值C16H17Cl2F2N5O4S2(M+Na)+:537.99593,实测值537.99751.
白色粉末,mp=126.5-127.1℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.49(d,J=8.6Hz,1H),7.31(s,1H),7.26(d,J=9.2Hz,1H),4.56(s,2H),2.98(s,6H),2.40(td,J=7.2,3.6Hz,1H),0.66(d,J=6.7Hz,2H),0.60(d,J=3.8Hz,2H).HRMS(MALDI)理论值C16H17Cl3FN5O4S2(M+H)+:531.98443,实测值531.98366.
白色粉末,mp=109.8-110.4℃.1H NMR(600MHz,DMSO-d6)δ9.45(s,1H),7.65(d,J=2.0Hz,1H),7.44(d,J=2.0Hz,2H),4.56(s,2H),2.98(s,6H),2.40(dd,J=7.3,4.0Hz,1H),0.73–0.48(m,4H).HRMS(MALDI)理论值C16H17Cl4N5O4S2(M+H)+:547.95488,实测值547.95584.
黄色粉末,mp=58.9-59.2℃.1H NMR(400MHz,DMSO-d6)δ9.44(s,1H),8.18(s,1H),8.11(s,2H),4.65(s,2H),2.97(s,6H),2.40(s,1H),0.59(d,J=44.3Hz,4H).HRMS(MALDI)理论值C18H17Cl2F6N5O4S2(M+H)+:616.0076,实测值616.00948.
白色粉末,mp=78.7-79.4℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.44(d,J=39.3Hz,5H),4.61(s,2H),3.58(s,3H),2.98(s,6H).HRMS(MALDI)理论值C14H17Cl2N5O5S2(M+Na)+:491.994,实测值491.9915.
黄色粉末,mp=101.3-102.1℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.56(s,1H),7.54(s,1H),7.50(dd,J=13.4,6.2Hz,1H),7.37–7.29(m,1H),4.57(s,2H),3.60(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H16Cl2FN5O5S2(M+H)+:488.00267,实测值488.00258.
油状物.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.53(d,J=6.9Hz,1H),7.40(d,J=9.9Hz,1H),7.34(d,J=7.3Hz,1H),7.27(t,J=8.1Hz,1H),4.62(s,2H),3.61(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H16Cl2FN5O5S2(M+H)+:488.0037,实测值488.0051.
白色粉末,mp=81.4-82.0℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.60(s,1H),7.49(q,J=7.4Hz,2H),7.46(d,J=7.2Hz,1H),4.61(s,2H),3.61(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H16Cl3N5O5S2(M+H)+:503.97312,实测值503.97415.
油,1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.35(t,J=7.6Hz,1H),7.30–7.19(m,3H),4.58(s,2H),3.60(s,3H),2.99(s,6H),2.35(s,3H).HRMS(MALDI)理论值C15H19Cl2N5O5S2(M+Na)+:506.0097,实测值506.0092.
黄色粉末,mp=84.5-85.4℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.58–7.51(m,2H),7.32(t,J=8.5Hz,2H),4.61(s,2H),3.60(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H16Cl2FN5O5S2(M+Na)+:509.9846,实测值509.9848.
黄色粉末,mp=105.5-106.6℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.59–7.48(m,4H),4.61(s,2H),3.61(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H16Cl3N5O5S2(M+H)+:503.9731,实测值503.9744.
油.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.35(d,J=7.7Hz,2H),7.27(d,J=7.4Hz,2H),4.58(s,2H),3.59(s,3H),2.98(d,J=3.4Hz,6H),2.33(s,3H).HRMS(MALDI)理论值C15H19Cl2N5O5S2(M+H)+:484.02774,实测值484.02784.
油.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.40(d,J=8.1Hz,2H),7.01(d,J=8.4Hz,2H),4.59(s,2H),3.80(s,3H),3.58(s,3H),2.99(d,J=4.0Hz,6H).HRMS(MALDI)理论值C15H19Cl2N5O6S2(M+H)+:500.02266,实测值500.02386.
油.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.50–7.45(m,2H),7.40(dd,J=8.4,1.8Hz,2H),4.58(s,2H),3.59(d,J=1.7Hz,3H),2.98(d,J=1.8Hz,6H),1.30(s,9H).HRMS(MALDI)理论值C18H25Cl2N5O5S2(M+H)+:526.07469,实测值526.07504.
油.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.86(d,J=8.1Hz,2H),7.74(d,J=8.0Hz,2H),4.65(s,2H),3.62(s,3H),2.99(s,6H).HRMS(MALDI)理论值C15H16Cl2F3N5O5S2(M+H)+:537.9995,实测值538.0002.
油.1H NMR(400MHz,DMSO-d6)δ9.59(s,1H),7.58(q,J=9.0Hz,1H),7.48–7.30(m,2H),4.62(s,2H),3.66(s,3H),2.97(s,6H).HRMS(MALDI)理论值C14H15Cl2F2N5O5S2(M+Na)+:527.97519,实测值527.97599.
白色粉末,mp=93.2-94.3℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.65(q,J=8.3Hz,1H),7.43(t,J=9.9Hz,1H),7.25(t,J=8.4Hz,1H),4.56(s,2H),3.61(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H15Cl2F2N5O5S2(M+H)+:505.99325,实测值505.99382.
白色粉末,mp=97.7-98.2℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),δ7.62(dt,J=9.8,3.2Hz,2H),7.45(d,J=8.0Hz,1H),4.56(s,2H),3.72–3.48(m,3H),2.95(s,6H).HRMS(MALDI)理论值C14H15Cl3FN5O5S2(M+H)+:521.9637,实测值521.96469.
黄色粉末,mp=100.5-101.3℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,J=2.3Hz,1H),7.41(d,J=12.3Hz,1H),7.32–7.23(m,2H),4.59(s,2H),3.88(s,3H),3.61(s,3H),2.99(s,6H).HRMS(MALDI)理论值C15H18Cl2FN5O6S2(M+Na)+:539.99518,实测值539.99702.
白色粉末,mp=72.4-72.8℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.57–7.52(m,1H),7.42(td,J=9.1,4.4Hz,1H),7.39–7.35(m,1H),4.57(s,2H),3.63(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H15Cl2F2N5O5S2(M+H)+:505.99325,实测值505.99304.
白色粉末,mp=202.6-203.1℃.1H NMR(600MHz,DMSO-d6)δ9.58(s,1H),7.30(d,J=7.8Hz,1H),7.22(d,J=6.7Hz,1H),7.15(d,J=7.9Hz,1H),4.48(s,2H),3.32(s,3H),3.01(s,6H),2.40(d,J=3.1Hz,6H).HRMS(MALDI)理论值C16H21Cl2N5O5S2(M+H)+:498.04339,实测值498.04323.
油.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.68(t,J=9.3Hz,1H),7.56(q,J=9.2Hz,1H),7.38(d,J=8.1Hz,1H),4.61(s,2H),3.63(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H15Cl2F2N5O5S2(M+Na)+:527.9752,实测值527.9754.
白色粉末,mp=101.9-102.4℃.1H NMR(600MHz,DMSO-d6)δ9.55(s,1H),7.41(d,J=12.3Hz,1H),7.25(dd,J=15.0,6.9Hz,2H),4.59(s,2H),3.88(s,3H),3.69–3.57(m,3H),2.99(s,6H).HRMS(MALDI)理论值C15H18Cl2FN5O6S2(M+H)+:518.01323,实测值518.01318.
白色粉末,mp=88.8-89.5℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.79(d,J=6.9Hz,1H),7.53(d,J=6.9Hz,2H),4.60(s,2H),3.62(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H15Cl3FN5O5S2(M+H)+:521.9637,实测值521.96381.
黄色粉末,mp=131.9-132.8℃.1H NMR(600MHz,DMSO-d6)δ9.57(s,1H),7.85(s,1H),7.76(d,J=8.2Hz,1H),7.52(d,J=8.3Hz,1H),4.61(s,2H),3.63(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H15Cl4N5O5S2(M+H)+:537.9341,实测值537.9349.
白色粉末,mp=85.6-86.8℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),8.02(s,1H),7.85(d,J=5.9Hz,2H),4.65(s,2H),3.62(d,J=4.2Hz,3H),2.98(d,J=4.3Hz,6H).HRMS(MALDI)理论值C15H15Cl3F3N5O5S2(M+H)+:571.9605,实测值571.96096.
白色粉末,mp=92.1-93.2℃.1H NMR(600MHz,DMSO-d6)δ9.52(s,1H),7.02(s,2H),7.00(s,1H),4.53(s,2H),3.58(s,3H),2.96(s,6H),2.27(s,6H).HRMS(MALDI)理论值C16H21Cl2N5O5S2(M+H)+:498.04339,实测值498.04326.
白色粉末,mp=76.9-77.3℃.1H NMR(600MHz,DMSO-d6)δ9.44(d,J=3.8Hz,1H),7.29(t,J=9.5Hz,2H),7.02(s,1H),4.56(d,J=4.4Hz,2H),3.58(s,3H),2.97(s,6H).HRMS(MALDI)理论值C14H15Cl2F2N5O5S2(M+H)+:505.99325,实测值505.99286.
黄色粉末,mp=104.5-105.6℃.1H NMR(600MHz,DMSO-d6)δ9.56(s,1H),7.53(d,J=8.9Hz,1H),7.49(s,1H),7.44(d,J=9.3Hz,1H),4.61(s,2H),3.64(s,3H),2.99(s,6H).HRMS(MALDI)理论值C14H15Cl3FN5O5S2(M+H)+:521.9637,实测值521.96642.
白色粉末,mp=92.1-93.2℃.1H NMR(600MHz,DMSO-d6)δ9.52(s,1H),7.02(s,2H),7.00(s,1H),4.53(s,2H),3.58(s,3H),2.96(s,6H),2.27(s,6H).HRMS(MALDI)理论值C16H21Cl2N5O5S2(M+H)+:498.04339,实测值498.04326.
黄色粉末,mp=84.4-85.3℃.1H NMR(600MHz,DMSO-d6)δ9.02(s,1H),7.60(t,J=7.6Hz,2H),4.60(s,2H),2.91(s,6H),2.08(s,3H).HRMS(MALDI)理论值C14H14Cl2F3N5O5S2(M+H)+:523.9838,实测值523.9815.
白色粉末,mp=150.6-151.3℃.1H NMR(600MHz,DMSO-d6)δ9.50(s,1H),7.55(q,J=7.5Hz,1H),7.32(td,J=8.8,2.6Hz,1H),7.03(s,2H),5.45(q,J=7.4Hz,1H),2.99(s,6H),2.09–1.99(m,1H),1.43(d,J=7.4Hz,3H),0.59(q,J=7.8Hz,2H),0.28(dq,J=13.5,7.5Hz,1H),-0.97(d,J=9.5Hz,1H).HRMS(MALDI)理论值C17H20Cl2FN5O4S2(M+Na)+:534.021,实测值534.02263.
白色粉末,mp=161.1-162.0℃.1H NMR(600MHz,DMSO-d6)δ9.49(s,1H),7.53(d,J=6.2Hz,2H),7.21(s,1H),7.15(s,1H),5.44(q,J=7.2Hz,1H),2.98(s,6H),2.07(td,J=7.0,3.6Hz,1H),1.45(d,J=7.4Hz,3H),0.58(p,J=7.3,6.4Hz,2H),0.27(q,J=7.4Hz,1H),-1.01(s,1H).HRMS(MALDI)理论值C17H20Cl3N5O4S2(M+H)+:547.0079,实测值547.00724.
白色粉末,mp=141.3-142.1℃.1H NMR(600MHz,DMSO-d6)δ9.48(s,1H),7.65(d,J=8.1Hz,1H),7.44(t,J=7.9Hz,1H),7.33(s,1H),7.18(s,1H),5.41(q,J=7.4Hz,1H),2.96(s,6H),1.42(d,J=7.3Hz,3H),0.57(s,2H),0.25(s,1H),-1.05(s,1H).(MALDI)理论值C17H20BrCl2N5O4S2(M+H)+:547.959,实测值571.95923.
白色粉末,mp=120.1-120.8℃.1H NMR(600MHz,DMSO-d6)δ9.50(s,1H),7.85(d,J=7.8Hz,1H),7.76(s,1H),7.52(s,2H),5.48(d,J=9.3Hz,1H),2.98(s,6H),2.08(s,1H),1.47(d,J=7.4Hz,3H),0.55(d,J=26.2Hz,2H),0.24(s,1H),-1.18(s,1H).(MALDI)理论值C18H20Cl2F3N5O4S2(M+H)+:562.0359,实测值562.03576.
白色粉末,mp=161.1-162.0℃.1H NMR(600MHz,DMSO-d6)δ9.49(s,1H),7.34(t,J=8.7Hz,2H),7.20(s,2H),5.44(d,J=7.4Hz,1H),2.98(s,6H),2.05(s,1H),1.44(d,J=7.3Hz,3H),0.58(q,J=7.3,6.2Hz,2H),0.26(t,J=7.2Hz,1H),-1.00(s,1H).(MALDI)理论值C17H20Cl2FN5O4S2(M+H)+:512.0391,实测值512.03932.
白色粉末,mp=185.1-185.9℃.1H NMR(600MHz,DMSO-d6)δ9.50(s,1H),7.58(d,J=8.2Hz,2H),7.20(d,J=7.9Hz,2H),5.45(q,J=7.4Hz,1H),2.99(s,6H),2.07(s,1H),1.45(d,J=7.4Hz,3H),0.60(q,J=8.3Hz,2H),0.29(d,J=7.7Hz,1H),-0.94(s,1H).(MALDI)理论值C17H20Cl3N5O4S2(M+H)+:528.0089,实测值528.00854.
白色粉末,mp=171.0-171.8℃.1H NMR(600MHz,DMSO-d6)δ9.49(s,1H),7.06(d,J=8.8Hz,2H),7.03(d,J=8.0Hz,2H),5.47–5.37(m,1H),3.78(s,3H),2.98(s,6H),2.04(s,1H),1.44(d,J=7.3Hz,3H),0.56(d,J=9.4Hz,2H),0.22(d,J=8.5Hz,1H),-0.93(s,1H).(MALDI)理论值C18H23Cl2N5O5S2(M+H)+:524.059,实测值524.05879.
白色粉末,mp=122.6-123.2℃.1H NMR(600MHz,DMSO-d6)δ9.50(s,1H),7.89(d,J=8.0Hz,2H),7.43(s,2H),5.49(q,J=7.4Hz,1H),2.99(s,6H),2.07(s,1H),1.48(d,J=7.4Hz,3H),0.58(d,J=8.8Hz,2H),0.27(s,1H),-1.07(s,1H).(MALDI)理论值C18H20Cl2F3N5O4S2(M+H)+:562.0359,实测值562.03489.
白色粉末,mp=161.5-162.3℃.1H NMR(600MHz,DMSO-d6)δ9.49(s,1H),7.72(d,J=7.7Hz,2H),7.13(s,2H),5.44(d,J=7.4Hz,1H),2.98(s,6H),2.07(s,1H),1.46(d,J=7.8Hz,3H),0.60(s,2H),0.29(s,1H),-0.93(s,1H).(MALDI)理论值C17H20BrCl2N5O4S2(M+H)+:571.959,实测值571.95879.
白色粉末,mp=102.7-103.4℃.1H NMR(600MHz,DMSO-d6)δ9.48(s,1H),7.79(dd,J=8.4,2.9Hz,1H),7.44(s,1H),7.18(s,1H),5.40(d,J=7.5Hz,1H),2.96(s,6H),2.10(s,1H),1.43(d,J=7.4Hz,3H),0.60(d,J=8.9Hz,2H),0.35(s,1H),-0.89(s,1H).HRMS(MALDI)理论值C17H19Cl2F2N5O4S2(M+H)+:530.02963,实测值530.02951.
白色粉末,mp=175.4-176.1℃.1H NMR(600MHz,DMSO-d6)δ9.50(s,1H),7.60(t,J=9.5Hz,1H),7.31(s,1H),7.04(s,1H),5.43(q,J=7.3Hz,1H),2.99(s,6H),2.09(d,J=10.3Hz,1H),1.46(d,J=7.3Hz,3H),0.62(d,J=9.2Hz,2H),0.37(s,1H),-0.85(s,1H).HRMS(MALDI)理论值C17H19Cl2F2N5O4S2(M+H)+:530.02963,实测值530.02941.
白色粉末,mp=148.2-148.9℃.1H NMR(600MHz,DMSO-d6)δ9.48(s,1H),7.79(dd,J=8.4,2.9Hz,1H),7.44(s,1H),7.18(s,1H),5.40(d,J=7.5Hz,1H),2.96(s,6H),2.10(s,1H),1.43(d,J=7.3Hz,3H),0.60(d,J=8.9Hz,2H),0.35(s,1H),-0.89(s,1H).HRMS(MALDI)理论值C17H19Cl4N5O4S2(M+H)+:561.9705,实测值561.9702.
白色粉末,mp=124.7-125.3℃.1H NMR(400MHz,DMSO-d6)δ9.50(s,1H),7.51–7.35(m,1H),6.96(s,2H),5.43(q,J=7.3Hz,1H),2.99(s,6H),2.13(dt,J=6.9,3.3Hz,1H),1.48(d,J=7.3Hz,3H),0.72–0.54(m,2H),0.41(dq,J=14.3,6.7Hz,1H),-0.76(d,J=9.0Hz,1H).HRMS(MALDI)理论值C17H19Cl2F2N5O4S2(M+H)+:530.02963,实测值530.02961.
白色粉末,mp=155.6-156.4℃.1H NMR(600MHz,DMSO-d6)δ9.49(s,1H),8.28(s,1H),7.95(d,J=47.3Hz,2H),5.44(d,J=7.5Hz,1H),2.97(s,6H),2.13(d,J=7.6Hz,1H),1.45(d,J=7.2Hz,3H),0.59(s,1H),0.49(s,1H),0.32(s,1H),-1.17(s,1H).HRMS(MALDI)理论值C19H19Cl2F6N5O4S2(M+H)+:630.0232,实测值630.0212.
测试例1
本测试例针对表1中所示的如下化合物进行活性测试,结果见表3。
具体测试方法为:
试验采取幼苗盆栽法。
幼苗盆栽试验的处理,实验化合物剂量见表3。另设不施药剂的空白对照。每个处理重复3次。选用2片真叶平展的黄瓜盆栽幼苗,剪去生长点,用喉头喷雾器进行人工手动喷雾。处理后的试验材料均在药液晾干后,第二天接种黄瓜霜霉病孢子悬浮液,然后放置人工气候室中培养。培养温度:昼25℃。夜间20℃;相对湿度:90%~100%。保湿培养7天后调查防治效果。调查方法按农业部药检所《农药室内生物测定试验准则》-杀菌剂防治黄瓜霜霉病试验盆栽法(NY/T 1156.7-2006)的分级标准分级记载,以病情指数计算防治效果。
0级:无病;
1级:病斑面积占整片叶面积的5%以下;
3级:病斑面积占整片叶面积的6%~10%;
5级:病斑面积占整片叶面积的11%~25%;
7级:病斑面积占整片叶面积的26%~50%;
9级:病斑面积占整片叶面积的50%以上。
病情指数及防治效果计算方法如下:
式中:CK0空白对照区施药前病情指数,CK1空白对照区施药后病情指数,PT0药剂处理区施药前病情指数,PT1药剂处理区施药后病情指数。
防效评级列于表3中。
表3
80%≦A≦100%;70%≦B<80%,50%≦C<70%,D<50%
测试例2
本测试例的测试和调查方法同测试例1,不同之处在于,被测试化合物为表4中所示的化合物,测试浓度列于表4中。
防效评级列于表4中。
表4
80%≦A≦100%;70%≦B<80%,50%≦C<70%,D<50%
测试例3
田间活性测试。
以黄瓜霜霉病为试验对象、作物和品种。
试验安排在陕西省兴平市进行(2021年5月至2021年6月,每间隔10天施药一次,共施药2次)。试验地(粘壤土,pH值为5.8,肥力水平及土壤有机质含量较高)黄瓜大棚栽培,各试验小区的土壤类型、栽培条件及水肥管理等均匀一致。采用喷雾器将配制好的各参试药剂的药液均匀喷施到黄瓜茎叶上。
其余调查和评价方法同测试例1。
本试验期间各药剂处理区内,试验作物均生长正常,未发生药害及其它不良影响。
采用农业部针对农药田间药效试验要求的方法进行试验药剂的处理,调查方法按农业部农药检定所《农药田间药效试验准则(一)》-杀菌剂防治黄瓜霜霉病(GB/T17980.26-2000)的分级标准分级记载,以病情指数计算防治效果,本测试例的具体测试结果见表5。
表5
80%≦A≦100%;70%≦B<80%,50%≦C<70%,D<50%
本发明提供的化合物针对黄瓜霜霉病、大豆疫霉病、番茄晚疫病、马铃薯晚疫病、茄子霜霉病、柑桔脚腐病、南瓜疫病、葡萄霜霉病等卵菌纲植物真菌病具有明显比现有技术更好的效果。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于此。在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,包括各个技术特征以任何其它的合适方式进行组合,这些简单变型和组合同样应当视为本发明所公开的内容,均属于本发明的保护范围。
Claims (15)
2.根据权利要求1所述的含突烯片段的三唑磺酰胺类衍生物,其中,在式(I)中,
R1选自C1-3的烷氧基、C3-6的环烷基;
R2选自H、C1-3的烷基;
R3、R4、R5、R6、R7选自H、卤素、C1-6的烷基、C1-3的烷氧基、氰基、由至少一个卤素取代的C1-3的烷基、由至少一个卤素取代的C1-3的烷氧基;
R8均为H或Cl。
3.根据权利要求1或2所述的含突烯片段的三唑磺酰胺类衍生物,其中,在式(I)中,
R1选自甲氧基、环丙基;
R2选自H、甲基;
R3、R4、R5选自H、F、Cl、甲基、乙基、异丙基、叔丁基、甲氧基、-CF3、-OCF3、氰基;
R6选自H、F、Cl;
R7为H;
R8均为H或Cl。
4.根据权利要求1或2所述的含突烯片段的三唑磺酰胺类衍生物,其中,所述含突烯片段的三唑磺酰胺类衍生物为以下化合物中的任意一种:
化合物I-1:在式(I)中,R1为环丙基,R2、R3、R4、R5、R6、R7、R8均为H;
化合物I-2:在式(I)中,R1为环丙基,R2为H,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-3:在式(I)中,R1为环丙基,R2为H,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-4:在式(I)中,R1为环丙基,R2为H,R3为甲基,R4、R5、R6、R7、R8均为H;
化合物I-5:在式(I)中,R1为环丙基,R2为H,R3为乙基,R4、R5、R6、R7、R8均为H;
化合物I-6:在式(I)中,R1为环丙基,R2为H,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-7:在式(I)中,R1为环丙基,R2为H,R3为-CF3,R4、R5、R6、R7、R8均为H;
化合物I-8:在式(I)中,R1为环丙基,R2为H,R3为氰基,R4、R5、R6、R7、R8均为H;
化合物I-9:在式(I)中,R1为环丙基,R2为H,R4为F,R3、R5、R6、R7、R8均为H;
化合物I-10:在式(I)中,R1为环丙基,R2为H,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-11:在式(I)中,R1为环丙基,R2为H,R4为甲基,R3、R5、R6、R7、R8均为H;
化合物I-12:在式(I)中,R1为环丙基,R2为H,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-13:在式(I)中,R1为环丙基,R2为H,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-14:在式(I)中,R1为环丙基,R2为H,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-15:在式(I)中,R1为环丙基,R2为H,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-16:在式(I)中,R1为环丙基,R2为H,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-17:在式(I)中,R1为环丙基,R2为H,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-18:在式(I)中,R1为环丙基,R2为H,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-19:在式(I)中,R1为环丙基,R2为H,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-20:在式(I)中,R1为环丙基,R2为H,R5为甲基,R3、R4、R6、R7、R8均为H;
化合物I-21:在式(I)中,R1为环丙基,R2为H,R5为氰基,R3、R4、R6、R7、R8均为H;
化合物I-22:在式(I)中,R1为环丙基,R2为H,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-23:在式(I)中,R1为环丙基,R2为H,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-24:在式(I)中,R1为环丙基,R2为H,R5为叔丁基,R3、R4、R6、R7、R8均为H;
化合物I-25:在式(I)中,R1为环丙基,R2为H,R5为-CF3,R3、R4、R6、R7、R8均为H;
化合物I-26:在式(I)中,R1为环丙基,R2为H,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-27:在式(I)中,R1为环丙基,R2为H,R3和R4均为甲基,R5、R6、R7、R8均为H;
化合物I-28:在式(I)中,R1为环丙基,R2为H,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-29:在式(I)中,R1为环丙基,R2为H,R3为F,R4为Cl,R5、R6、R7、R8均为H;
化合物I-30:在式(I)中,R1为环丙基,R2为H,R3为Cl,R4为F,R5、R6、R7、R8均为H;
化合物I-31:在式(I)中,R1为环丙基,R2为H,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-32:在式(I)中,R1为环丙基,R2为H,R3和R5均为甲基,R4、R6、R7、R8均为H;
化合物I-33:在式(I)中,R1为环丙基,R2为H,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-34:在式(I)中,R1为环丙基,R2为H,R3为F,R5为Cl,R4、R6、R7、R8均为H;
化合物I-35:在式(I)中,R1为环丙基,R2为H,R3为Cl,R5为F,R4、R6、R7、R8均为H;
化合物I-36:在式(I)中,R1为环丙基,R2为H,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-37:在式(I)中,R1为环丙基,R2为H,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-38:在式(I)中,R1为环丙基,R2为H,R4和R5均为甲基,R3、R6、R7、R8均为H;
化合物I-39:在式(I)中,R1为环丙基,R2为H,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-40:在式(I)中,R1为环丙基,R2为H,R4为F,R5为Cl、R3、R6、R7、R8均为H;
化合物I-41:在式(I)中,R1为环丙基,R2为H,R4为Cl,R5为F、R3、R6、R7、R8均为H;
化合物I-42:在式(I)中,R1为环丙基,R2为H,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-43:在式(I)中,R1为环丙基,R2为H,R4和R5均为-CF3,R3、R6、R7、R8均为H;
化合物I-44:在式(I)中,R1为环丙基,R2为H,R4和R6均为甲基,R3、R5、R7、R8均为H;
化合物I-45:在式(I)中,R1为环丙基,R2为H,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-46:在式(I)中,R1为环丙基,R2为H,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-47:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为F,R3、R7、R8均为H;
化合物I-48:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物I-49:在式(I)中,R1为甲氧基,R2、R3、R4、R5、R6、R7、R8均为H;
化合物I-50:在式(I)中,R1为甲氧基,R2为H,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-51:在式(I)中,R1为甲氧基,R2为H,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-52:在式(I)中,R1为甲氧基,R2为H,R3为甲基,R4、R5、R6、R7、R8均为H;
化合物I-53:在式(I)中,R1为甲氧基,R2为H,R3为乙基,R4、R5、R6、R7、R8均为H;
化合物I-54:在式(I)中,R1为甲氧基,R2为H,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-55:在式(I)中,R1为甲氧基,R2为H,R3为-CF3,R4、R5、R6、R7、R8均为H;
化合物I-56:在式(I)中,R1为甲氧基,R2为H,R3为-OCF3,R4、R5、R6、R7、R8均为H;
化合物I-57:在式(I)中,R1为甲氧基,R2为H,R4为F,R3、R5、R6、R7、R8均为H;
化合物I-58:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-59:在式(I)中,R1为甲氧基,R2为H,R4为甲基,R3、R5、R6、R7、R8均为H;
化合物I-60:在式(I)中,R1为甲氧基,R2为H,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-61:在式(I)中,R1为甲氧基,R2为H,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-62:在式(I)中,R1为甲氧基,R2为H,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-63:在式(I)中,R1为甲氧基,R2为H,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-64:在式(I)中,R1为甲氧基,R2为H,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-65:在式(I)中,R1为甲氧基,R2为H,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-66:在式(I)中,R1为甲氧基,R2为H,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-67:在式(I)中,R1为甲氧基,R2为H,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-68:在式(I)中,R1为甲氧基,R2为H,R5为甲基,R3、R4、R6、R7、R8均为H;
化合物I-69:在式(I)中,R1为甲氧基,R2为H,R5为乙基,R3、R4、R6、R7、R8均为H;
化合物I-70:在式(I)中,R1为甲氧基,R2为H,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-71:在式(I)中,R1为甲氧基,R2为H,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-72:在式(I)中,R1为甲氧基,R2为H,R5为-CF3,R3、R4、R6、R7、R8均为H;
化合物I-73:在式(I)中,R1为甲氧基,R2为H,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-74:在式(I)中,R1为甲氧基,R2为H,R3和R4均为甲基,R5、R6、R7、R8均为H;
化合物I-75:在式(I)中,R1为甲氧基,R2为H,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-76:在式(I)中,R1为甲氧基,R2为H,R3为F,R4为Cl,R5、R6、R7、R8均为H;
化合物I-77:在式(I)中,R1为甲氧基,R2为H,R3为Cl,R4为F,R5、R6、R7、R8均为H;
化合物I-78:在式(I)中,R1为甲氧基,R2为H,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-79:在式(I)中,R1为甲氧基,R2为H,R3和R5均为甲基,R4、R6、R7、R8均为H;
化合物I-80:在式(I)中,R1为甲氧基,R2为H,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-81:在式(I)中,R1为甲氧基,R2为H,R3为F,R5为Cl,R4、R6、R7、R8均为H;
化合物I-82:在式(I)中,R1为甲氧基,R2为H,R3为Cl,R5为F,R4、R6、R7、R8均为H;
化合物I-83:在式(I)中,R1为甲氧基,R2为H,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-84:在式(I)中,R1为甲氧基,R2为H,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-85:在式(I)中,R1为甲氧基,R2为H,R4和R5均为甲基,R3、R6、R7、R8均为H;
化合物I-86:在式(I)中,R1为甲氧基,R2为H,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-87:在式(I)中,R1为甲氧基,R2为H,R4为F,R5为Cl,R3、R6、R7、R8均为H;
化合物I-88:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R5为F,R3、R6、R7、R8均为H;
化合物I-89:在式(I)中,R1为甲氧基,R2为H,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-90:在式(I)中,R1为甲氧基,R2为H,R4和R5均为-CF3,R3、R6、R7、R8均为H;
化合物I-91:在式(I)中,R1为甲氧基,R2为H,R4和R6均为甲基,R3、R5、R7、R8均为H;
化合物I-92:在式(I)中,R1为甲氧基,R2为H,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-93:在式(I)中,R1为甲氧基,R2为H,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-94:在式(I)中,R1为甲氧基,R2为H,R4、R5和R6均为F,R3、R7、R8均为H;
化合物I-95:在式(I)中,R1为甲氧基,R2为H,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物I-96:在式(I)中,R1为环丙基,R2为甲基,R3、R4、R5、R6、R7、R8均为H;
化合物I-97:在式(I)中,R1为环丙基,R2为甲基,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-98:在式(I)中,R1为环丙基,R2为甲基,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-99:在式(I)中,R1为环丙基,R2、R3均为甲基,R4、R5、R6、R7、R8均为H;
化合物I-100:在式(I)中,R1为环丙基,R2为甲基,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-101:在式(I)中,R1为环丙基,R2为甲基,R4为F,R3、R5、R6、R7、R8均为H;
化合物I-102:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-103:在式(I)中,R1为环丙基,R2、R4均为甲基,R3、R5、R6、R7、R8均为H;
化合物I-104:在式(I)中,R1为环丙基,R2为甲基,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-105:在式(I)中,R1为环丙基,R2为甲基,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-106:在式(I)中,R1为环丙基,R2为甲基,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-107:在式(I)中,R1为环丙基,R2为甲基,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-108:在式(I)中,R1为环丙基,R2为甲基,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-109:在式(I)中,R1为环丙基,R2为甲基,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-110:在式(I)中,R1为环丙基,R2为甲基,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-111:在式(I)中,R1为环丙基,R2为甲基,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-112:在式(I)中,R1为环丙基,R2、R5均为甲基,R3、R4、R6、R7、R8均为H;
化合物I-113:在式(I)中,R1为环丙基,R2为甲基,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-114:在式(I)中,R1为环丙基,R2为甲基,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-115:在式(I)中,R1为环丙基,R2为甲基,R5为叔丁基,R3、R4、R6、R7、R8均为H;
化合物I-116:在式(I)中,R1为环丙基,R2为甲基,R5为-CF3,R3,R4、R6、R7、R8均为H;
化合物I-117:在式(I)中,R1为环丙基,R2为甲基,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-118:在式(I)中,R1为环丙基,R2、R3、R4均为甲基,R5、R6、R7、R8均为H;
化合物I-119:在式(I)中,R1为环丙基,R2为甲基,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-120:在式(I)中,R1为环丙基,R2为甲基,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-121:在式(I)中,R1为环丙基,R2、R3、R5均为甲基,R4、R6、R7、R8均为H;
化合物I-122:在式(I)中,R1为环丙基,R2为甲基,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-123:在式(I)中,R1为环丙基,R2为甲基,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-124:在式(I)中,R1为环丙基,R2为甲基,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-125:在式(I)中,R1为环丙基,R2、R4、R5均为甲基,R3、R6、R7、R8均为H;
化合物I-126:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-127:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-128:在式(I)中,R1为环丙基,R2、R4、R6均为甲基,R3、R5、R7、R8均为H;
化合物I-129:在式(I)中,R1为环丙基,R2为甲基,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-130:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R6为F,R3、R5、R7、R8均为H;
化合物I-131:在式(I)中,R1为环丙基,R2为甲基,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-132:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为F,R3、R7、R8均为H;
化合物I-133:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物I-134:在式(I)中,R1为甲氧基,R2为甲基,R3、R4、R5、R6、R7、R8均为H;
化合物I-135:在式(I)中,R1为甲氧基,R2为甲基,R3为F,R4、R5、R6、R7、R8均为H;
化合物I-136:在式(I)中,R1为甲氧基,R2为甲基,R3为Cl,R4、R5、R6、R7、R8均为H;
化合物I-137:在式(I)中,R1为甲氧基,R2为甲基,R3为甲基,R4、R5、R6、R7、R8均为H;
化合物I-138:在式(I)中,R1为甲氧基,R2为甲基,R3为甲氧基,R4、R5、R6、R7、R8均为H;
化合物I-139:在式(I)中,R1为甲氧基,R2为甲基,R4为F、R3、R5、R6、R7、R8均为H;
化合物I-140:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R3、R5、R6、R7、R8均为H;
化合物I-141:在式(I)中,R1为甲氧基,R2为甲基,R4为甲基,R3、R5、R6、R7、R8均为H;
化合物I-142:在式(I)中,R1为甲氧基,R2为甲基,R4为乙基,R3、R5、R6、R7、R8均为H;
化合物I-143:在式(I)中,R1为甲氧基,R2为甲基,R4为甲氧基,R3、R5、R6、R7、R8均为H;
化合物I-144:在式(I)中,R1为甲氧基,R2为甲基,R4为异丙基,R3、R5、R6、R7、R8均为H;
化合物I-145:在式(I)中,R1为甲氧基,R2为甲基,R4为叔丁基,R3、R5、R6、R7、R8均为H;
化合物I-146:在式(I)中,R1为甲氧基,R2为甲基,R4为-CF3,R3、R5、R6、R7、R8均为H;
化合物I-147:在式(I)中,R1为甲氧基,R2为甲基,R4为-OCF3,R3、R5、R6、R7、R8均为H;
化合物I-148:在式(I)中,R1为甲氧基,R2为甲基,R5为F,R3、R4、R6、R7、R8均为H;
化合物I-149:在式(I)中,R1为甲氧基,R2为甲基,R5为Cl,R3、R4、R6、R7、R8均为H;
化合物I-150:在式(I)中,R1为甲氧基,R2为甲基,R5为甲基,R3、R4、R6、R7、R8均为H;
化合物I-151:在式(I)中,R1为甲氧基,R2为甲基,R5为甲氧基,R3、R4、R6、R7、R8均为H;
化合物I-152:在式(I)中,R1为甲氧基,R2为甲基,R5为异丙基,R3、R4、R6、R7、R8均为H;
化合物I-153:在式(I)中,R1为甲氧基,R2为甲基,R5为叔丁基,R3、R4、R6、R7、R8均为H;
化合物I-154:在式(I)中,R1为甲氧基,R2为甲基,R5为-CF3,R3、R4、R6、R7、R8均为H;
化合物I-155:在式(I)中,R1为甲氧基,R2为甲基,R5为-OCF3,R3、R4、R6、R7、R8均为H;
化合物I-156:在式(I)中,R1为甲氧基,R2、R3、R4均为甲基,R5、R6、R7、R8均为H;
化合物I-157:在式(I)中,R1为甲氧基,R2为甲基,R3和R4均为F,R5、R6、R7、R8均为H;
化合物I-158:在式(I)中,R1为甲氧基,R2为甲基,R3和R4均为Cl,R5、R6、R7、R8均为H;
化合物I-159:在式(I)中,R1为甲氧基,R2、R3、R5均为甲基,R4、R6、R7、R8均为H;
化合物I-160:在式(I)中,R1为甲氧基,R2为甲基,R3和R5均为F,R4、R6、R7、R8均为H;
化合物I-161:在式(I)中,R1为甲氧基,R2为甲基,R3和R5均为Cl,R4、R6、R7、R8均为H;
化合物I-162:在式(I)中,R1为甲氧基,R2为甲基,R3和R5均为-CF3,R4、R6、R7、R8均为H;
化合物I-163:在式(I)中,R1为甲氧基,R2、R4、R5均为甲基,R3、R6、R7、R8均为H;
化合物I-164:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为F,R3、R6、R7、R8均为H;
化合物I-165:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为Cl,R3、R6、R7、R8均为H;
化合物I-166:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为甲基,R3、R5、R7、R8均为H;
化合物I-167:在式(I)中,R1为甲氧基,R2为甲基,R4为F,R6为Cl,R3、R5、R7、R8均为H;
化合物I-168:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R6为F,R3、R5、R7、R8均为H;
化合物I-169:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为Cl,R3、R5、R7、R8均为H;
化合物I-170:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为F、R3、R7、R8均为H;
化合物I-171:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为Cl,R3、R7、R8均为H;
化合物II-1:在式(I)中,R1为环丙基,R2、R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-2:在式(I)中,R1为环丙基,R2为H,R3为F,R4、R5、R6、R7均为H,R8均为Cl;
化合物II-3:在式(I)中,R1为环丙基,R2为H,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-4:在式(I)中,R1为环丙基,R2为H,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-5:在式(I)中,R1为环丙基,R2为H,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-6:在式(I)中,R1为环丙基,R2为H,R4为乙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-7:在式(I)中,R1为环丙基,R2为H,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-8:在式(I)中,R1为环丙基,R2为H,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-9:在式(I)中,R1为环丙基,R2为H,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-10:在式(II)中,R1为环丙基,R2为H,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-11:在式(I)中,R1为环丙基,R2为H,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-12:在式(I)中,R1为环丙基,R2为H,R5为F,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-13:在式(I)中,R1为环丙基,R2为H,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-14:在式(I)中,R1为环丙基,R2为H,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-15:在式(I)中,R1为环丙基,R2为H,R5为乙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-16:在式(I)中,R1为环丙基,R2为H,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-17:在式(I)中,R1为环丙基,R2为H,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-18:在式(I)中,R1为环丙基,R2为H,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-19:在式(I)中,R1为环丙基,R2为H,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-20:在式(I)中,R1为环丙基,R2为H,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-21:在式(I)中,R1为环丙基,R2为H,R4和R5均为甲基,R3、R6、R7均为H,R8均为Cl;
化合物II-22:在式(I)中,R1为环丙基,R2为H,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-23:在式(I)中,R1为环丙基,R2为H,R4为F,R5为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-24:在式(I)中,R1为环丙基,R2为H,R4为Cl,R5为F,R3、R6、R7均为H,R8均为Cl;
化合物II-25:在式(I)中,R1为环丙基,R2为H,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-26:在式(I)中,R1为环丙基,R2为H,R4和R5均为-CF3,R3、R6、R7均为H,R8均为Cl;
化合物II-27:在式(I)中,R1为环丙基,R2为H,R4和R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-28:在式(I)中,R1为环丙基,R2为H,R4为F,R6为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-29:在式(I)中,R1为环丙基,R2为H,R4和R6均为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-30:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-31:在式(I)中,R1为环丙基,R2为H,R4、R5和R6均为Cl,R3、R7均为H,R8均为Cl;
化合物II-32:在式(I)中,R1为甲氧基,R2为H,R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-33:在式(I)中,R1为甲氧基,R2为H,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-34:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-35:在式(I)中,R1为甲氧基,R2为H,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-36:在式(I)中,R1为甲氧基,R2为H,R4为氰基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-37:在式(I)中,R1为甲氧基,R2为H,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-38:在式(I)中,R1为甲氧基,R2为H,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-39:在式(I)中,R1为甲氧基,R2为H,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-40:在式(I)中,R1为甲氧基,R2为H,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-41:在式(I)中,R1为甲氧基,R2为H,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-42:在式(I)中,R1为甲氧基,R2为H,R5为F,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-43:在式(I)中,R1为甲氧基,R2为H,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-44:在式(I)中,R1为甲氧基,R2为H,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-45:在式(I)中,R1为甲氧基,R2为H,R5为乙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-46:在式(I)中,R1为甲氧基,R2为H,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-47:在式(I)中,R1为甲氧基,R2为H,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-48:在式(I)中,R1为甲氧基,R2为H,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-49:在式(I)中,R1为甲氧基,R2为H,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-50:在式(I)中,R1为甲氧基,R2为H,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-51:在式(I)中,R1为甲氧基,R2为H,R4和R5均为甲基,R3、R6、R7均为H,R8均为Cl;
化合物II-52:在式(I)中,R1为甲氧基,R2为H,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-53:在式(I)中,R1为甲氧基,R2为H,R4为F,R5为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-54:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R5为F,R3、R6、R7均为H,R8均为Cl;
化合物II-55:在式(I)中,R1为甲氧基,R2为H,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-56:在式(I)中,R1为甲氧基,R2为H,R4和R5均为-CF3,R3、R6、R7均为H,R8均为Cl;
化合物II-57:在式(I)中,R1为甲氧基,R2为H,R4和R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-58:在式(I)中,R1为甲氧基,R2为H,R4为F,R6为Cl,R5、R3、R7均为H,R8均为Cl;
化合物II-59:在式(I)中,R1为甲氧基,R2为H,R4为Cl,R6为F,R5、R3、R7均为H,R8为Cl;
化合物II-60:在式(I)中,R1为甲氧基,R2为H,R4和R6均为Cl,R5、R3、R7均为H,R8均为Cl;
化合物II-61:在式(I)中,R1为甲氧基,R2为H,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-62:在式(I)中,R1为环丙基,R2为甲基,R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-63:在式(I)中,R1为环丙基,R2为甲基,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-64:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-65:在式(II)中,R1为环丙基,R2为甲基,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-66:在式(I)中,R1为环丙基,R2为甲基,R4为氰基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-67:在式(I)中,R1为环丙基,R2为甲基,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-68:在式(I)中,R1为环丙基,R2为甲基,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-69:在式(I)中,R1为环丙基,R2为甲基,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-70:在式(I)中,R1为环丙基,R2为甲基,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-71:在式(I)中,R1为环丙基,R2为甲基,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-72:在式(I)中,R1为环丙基,R2为甲基,R5为F,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-73:在式(I)中,R1为环丙基,R2为甲基,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-74:在式(I)中,R1为环丙基,R2为甲基,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-75:在式(I)中,R1为环丙基,R2为甲基,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-76:在式(I)中,R1为环丙基,R2为甲基,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-77:在式(I)中,R1为环丙基,R2为甲基,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-78:在式(I)中,R1为环丙基,R2为甲基,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-79:在式(I)中,R1为环丙基,R2为甲基,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-80:在式(I)中,R1为环丙基,R2、R4、R5均为甲基、R3、R6、R7均为H,R8均为Cl;
化合物II-81:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-82:在式(I)中,R1为环丙基,R2为甲基,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-83:在式(I)中,R1为环丙基,R2、R4、R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-84:在式(I)中,R1为环丙基,R2为甲基,R4为F,R6为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-85:在式(I)中,R1为环丙基,R2为甲基,R4为Cl,R6为F,R3、R5、R7均为H,R8均为Cl;
化合物II-86:在式(I)中,R1为环丙基,R2为甲基,R4和R6均为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-87:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-88:在式(I)中,R1为环丙基,R2为甲基,R4、R5和R6均为Cl,R3、R7均为H,R8均为Cl;
化合物II-89:在式(I)中,R1为甲氧基,R2为甲基,R3、R4、R5、R6、R7均为H,R8均为Cl;
化合物II-90:在式(I)中,R1为甲氧基,R2为甲基,R4为F,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-91:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-92:在式(I)中,R1为甲氧基,R2为甲基,R4为甲基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-93:在式(I)中,R1为甲氧基,R2为甲基,R4为乙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-94:在式(I)中,R1为甲氧基,R2为甲基,R4为氰基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-95:在式(I)中,R1为甲氧基,R2为甲基,R4为甲氧基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-96:在式(I)中,R1为甲氧基,R2为甲基,R4为异丙基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-97:在式(I)中,R1为甲氧基,R2为甲基,R4为叔丁基,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-98:在式(I)中,R1为甲氧基,R2为甲基,R4为-CF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-99:在式(I)中,R1为甲氧基,R2为甲基,R4为-OCF3,R3、R5、R6、R7均为H,R8均为Cl;
化合物II-100:在式(I)中,R1为甲氧基,R2为甲基,R5为F、R3、R4、R6、R7均为H,R8均为Cl;
化合物II-101:在式(I)中,R1为甲氧基,R2为甲基,R5为Cl,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-102:在式(I)中,R1为甲氧基,R2为甲基,R5为甲基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-103:在式(I)中,R1为甲氧基,R2为甲基,R5为氰基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-104:在式(I)中,R1为甲氧基,R2为甲基,R5为甲氧基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-105:在式(I)中,R1为甲氧基,R2为甲基,R5为异丙基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-106:在式(I)中,R1为甲氧基,R2为甲基,R5为叔丁基,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-107:在式(I)中,R1为甲氧基,R2为甲基,R5为-CF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-108:在式(I)中,R1为甲氧基,R2为甲基,R5为-OCF3,R3、R4、R6、R7均为H,R8均为Cl;
化合物II-109:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为甲基,R3、R6、R7均为H,R8均为Cl;
化合物II-110:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为F,R3、R6、R7均为H,R8均为Cl;
化合物II-111:在式(I)中,R1为甲氧基,R2为甲基,R4和R5均为Cl,R3、R6、R7均为H,R8均为Cl;
化合物II-112:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为甲基,R3、R5、R7均为H,R8均为Cl;
化合物II-113:在式(I)中,R1为甲氧基,R2为甲基,R4为F,R6为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-114:在式(I)中,R1为甲氧基,R2为甲基,R4为Cl,R6为F,R3、R5、R7均为H,R8均为Cl;
化合物II-115:在式(I)中,R1为甲氧基,R2为甲基,R4和R6均为Cl,R3、R5、R7均为H,R8均为Cl;
化合物II-116:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为F,R3、R7均为H,R8均为Cl;
化合物II-117:在式(I)中,R1为甲氧基,R2为甲基,R4、R5和R6均为Cl,R3、R7均为H,R8均为Cl。
6.根据权利要求5所述的方法,其中,所述接触反应至少满足以下条件:温度为5-45℃,时间为20-60min。
7.根据权利要求5所述的方法,其中,所述式(II)所示的化合物与式(III)所示的化合物的用量摩尔比为(0.5-3):1。
8.权利要求1-4中任意一项所述的含突烯片段的三唑磺酰胺类衍生物在抗植物真菌病中的应用。
9.根据权利要求8所述的应用,其中,所述植物真菌病为霜霉病、疫病中的至少一种。
10.根据权利要求8所述的应用,其中,所述植物真菌病为黄瓜霜霉病、大豆疫霉病、番茄晚疫病、马铃薯晚疫病、茄子霜霉病、柑桔脚腐病、南瓜疫病、葡萄霜霉病中的至少一种。
11.一种杀菌剂,其特征在于,该杀菌剂的活性成分为权利要求1-4中任意一项所述的含突烯片段的三唑磺酰胺类衍生物中的至少一种,以所述杀菌剂的总重量计,所述活性成分的含量为0.1-100重量%。
12.根据权利要求11所述的杀菌剂,其中,所述活性成分的含量为1-98重量%。
13.根据权利要求11或12所述的杀菌剂,其中,所述活性成分的含量为5-90重量%。
14.根据权利要求11或12所述的杀菌剂,其中,所述杀菌剂的剂型选自水合剂、粉剂、乳剂、悬浮剂和粒剂中的至少一种。
15.权利要求11-14中任意一项所述的杀菌剂在抗植物真菌病中的应用。
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