CN1195734C - 邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法 - Google Patents
邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法 Download PDFInfo
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- CN1195734C CN1195734C CNB008100071A CN00810007A CN1195734C CN 1195734 C CN1195734 C CN 1195734C CN B008100071 A CNB008100071 A CN B008100071A CN 00810007 A CN00810007 A CN 00810007A CN 1195734 C CN1195734 C CN 1195734C
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Abstract
由通式(I)代表的杂环胺衍生物,其中R1、R2和R3各自代表H、任选被卤化的C3-C6环烷基等;Q代表任选被取代的含O、S或N的杂环;X代表卤素、氰基、卤代C1-C6烷基等;n是1至4;Z1和Z4各自代表O或S;及其由下列通式(IV’)代表的中间体:Q’-NH2,其中Q’代表一定的杂环,选自由Q代表的那些。农业/园艺杀虫剂,具有显著的防治农作物害虫的作用,例如稻、果树和蔬菜以及各种农业、林业、园艺和储存谷物害虫。
Description
发明背景
发明领域
本发明涉及邻苯二甲酰胺衍生物、其中间体的制备、含有所述化合物作为活性成分的农艺杀虫剂和使用所述杀虫剂的方法。
相关技术
一部分本发明的邻苯二甲酰胺衍生物公开在JP-A-59-163353、JP-A-61-180753、《英国化学会志(J.C.S.)柏尔金汇刊I》1338-1350(1978)等中。不过,关于这些化合物作为农艺杀虫剂的有用性其中完全没有说明和提示。另一方面,由通式(IV)代表的杂环胺衍生物作为制备所述邻苯二甲酰胺衍生物的中间体化合物,是文献中没有记载的新化合物。
发明概述
本发明人为研制新颖的农艺药物而进行了反复研究。结果发现,由通式(I)代表的本发明的邻苯二甲酰胺衍生物是新颖的化合物,有些是现有技术公开的已知化合物,它们可用作新颖的农艺杀虫剂。进一步发现,由通式(IV’)代表的杂环胺衍生物是文献中没有记载的新化合物,它们可用作各种生理活性化合物制备的中间体,这些生理活性物质可用作药物、农药等。基于这些发现,完成了本发明。
发明的详细说明
本发明涉及由通式(I)代表的邻苯二甲酰胺衍生物:
{其中R1、R2和R3可以是相同或不同的,代表氢原子、C3-C6环烷基、卤代C3-C6环烷基或-A1-(G)r(该式中,A1代表C1-C8亚烷基、C3-C6亚烯基或C3-C6亚炔基;G可以是相同或不同的,代表氢原子,卤原子,氰基,硝基,卤代C1-C6烷基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基羰基,二(C1-C6)烷氧基磷酰基、其中(C1-C6)烷氧基可以是相同或不同的,二(C1-C6)烷氧基硫代磷酰基、其中(C1-C6)烷氧基可以是相同或不同的,二苯基膦基,二苯基膦酰基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(此处所用的术语“杂环基”表示吡啶基、吡啶-N-氧化物、嘧啶基、呋喃基、四氢呋喃基、噻吩基、四氢噻吩基、四氢吡喃基、噁唑基、异噁唑基、噁二唑基、噻唑基、异噻唑基、噻二唑基、咪唑基、三唑基或吡唑基),取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-Z3-R4(该式中,Z3代表-O-、-S-、-SO-、-SO2-、-N(R5)-(该式中,R5代表氢原子,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧基羰基,苯基羰基,取代的苯基羰基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯基C1-C4烷氧基羰基,取代的苯基C1-C4烷氧基羰基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,C1-C6烷基磺酰基,或卤代C1-C6烷基磺酰基)、-C(=O)-或-C(=NOR6)-(该式中,R6代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6烯基,卤代C3-C6烯基,C3-C6炔基,C3-C6环烷基,苯基C1-C4烷基,或取代的苯基C1-C4烷基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组),和R4代表氢原子,C1-C6烷基、卤代C1-C6烷基,C3-C6烯基,卤代C3-C6烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基C1-C6烷基,C1-C6烷硫基C1-C6烷基,甲酰基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧基羰基,一(C1-C6)烷基氨基羰基,二(C1-C6)烷基氨基羰基、其中(C1-C6)烷基可以是相同或不同的,一(C1-C6)烷基氨基硫代羰基,二(C1-C6)烷基氨基硫代羰基、其中(C1-C6)烷基可以是相同或不同的,二(C1-C6)烷氧基磷酰基、其中(C1-C6)烷氧基可以是相同或不同的,二(C1-C6)烷氧基硫代磷酰基、其中(C1-C6)烷氧基可以是相同或不同的,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯基C1-C4烷基,取代的苯基C1-C4烷基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组);r代表1至4的整数);进一步,R1和R2可以结合一起形成可以被1至3个相同或不同的氧原子、硫原子或氮原子间断的4-至7-元环;
X可以是相同或不同的,代表卤原子,氰基,硝基,C3-C6环烷基,卤代C3-C6环烷基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-A2-R7[该式中,A2代表-O-、-S-、-SO-、-SO2-、-NR8-(该式中,R8代表氢原子,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧基羰基,苯基羰基,取代的苯基羰基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯基C1-C4烷氧基羰基,或取代的苯基C1-C4烷氧基羰基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组)、-C(=O)-、-C(=NOR6)-(该式中,R6定义同上)、C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚烯基、卤代C2-C6亚烯基、C2-C6亚炔基或卤代C3-C6亚炔基;和
(1)在A2代表-O-、-S-、-SO-、-SO2-或-NR8-(该式中,R8定义同上)的情况下,R7代表氢原子,卤代C3-C6环烷基,卤代C3-C6环烯基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-A3-R9(该式中,A3代表C1-C6亚烷基、卤代C1-C6亚烷基、C3-C6亚烯基、卤代C3-C6亚烯基、C3-C6亚炔基或卤代C3-C6亚炔基;R9代表氢原子,卤原子,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基羰基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-A4-R10(该式中,A4代表-O-、-S-、-SO-、-SO2-或-C(=O)-;R10代表C1-C6烷基,卤代C1-C6烷基,C3-C6烯基,卤代C3-C6烯基,C3-C6环烷基,卤代C3-C6环烷基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组));
(2)在A2代表-C(=O)-或-C(=NOR6)-(该式中,R6定义同上)的情况下,R7代表氢原子,C1-C6烷基,卤代C1-C6烷基,C2-C6烯基,卤代C2-C6烯基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基,C1-C6烷硫基,一(C1-C6)烷基氨基,二(C1-C6)烷基氨基、其中(C1-C6)烷基可以是相同或不同的,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯基氨基,取代的苯基氨基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组;和
(3)在A2代表C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚烯基、卤代C2-C6亚烯基、C2-C6亚炔基或卤代C3-C6亚炔基的情况下,R7代表氢原子,卤原子,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基羰基,三(C1-C6)烷基甲硅烷基、其中(C1-C6)烷基可以是相同或不同的,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-A5-R11(该式中,A5代表-O-、-S-、-SO-、或-SO2-;R11代表C3-C6环烷基,卤代C3-C6环烷基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-A6-R12(该式中,A6代表C1-C6亚烷基、卤代C1-C6亚烷基、C2-C6亚烯基、卤代C2-C6亚烯基、C2-C6亚炔基或卤代C3-C6亚炔基;R12代表氢原子,卤原子,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯氧基,取代的苯氧基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯硫基,取代的苯硫基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),或取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组))];
n代表0至4的整数;进一步,X可以与苯环上相邻的碳原子结合一起形成稠合的环(此处所用的术语稠合的环表示萘、四氢化萘、茚、二氢化茚、喹啉、喹唑啉、苯并二氢吡喃、异苯并二氢吡喃、吲哚、二氢吲哚、苯并二噁烷、苯并间二氧杂环戊烯、苯并呋喃、二氢苯并呋喃、苯并噻吩、二氢苯并噻吩、苯并噁唑、苯并噻唑、苯并咪唑或吲唑),所述稠合的环可以具有至少一个相同或不同的取代基,选自卤原子,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),和取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组;
Q代表含N-、S-或O-的、任选被取代的杂环基或稠合的杂环基,选自由下式Q1至Q60组成的组:
(这些式中,Y可以是相同或不同的,代表卤原子,氰基,硝基,卤代C3-C6环烷基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,或-A2-R7(该式中,A2和R7定义同上);m代表0至6的整数;式Q22和Q23中的R13代表氢原子,C1-C6烷基,卤代C1-C6烷基,C3-C6烯基,卤代C3-C6烯基,C3-C6炔基,卤代C3-C6炔基,C3-C6环烷基,卤代C3-C6环烷基,C1-C6烷氧基C1-C6烷基,卤代C1-C6烷氧基C1-C6烷基,C1-C6烷硫基C1-C6烷基,卤代C1-C6烷硫基C1-C6烷基,C1-C6烷基亚磺酰基C1-C6烷基,卤代C1-C6烷基亚磺酰基C1-C6烷基,C1-C6烷基磺酰基C1-C6烷基,卤代C1-C6烷基磺酰基C1-C6烷基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧基羰基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯基C1-C4烷基,取代的苯基C1-C4烷基、在其环上具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,苯基羰基,或取代的苯基羰基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组);
或者,Y可以与环上相邻的碳原子结合一起形成稠合的环(稠合的环定义同上),所述稠合的环可以具有至少一个相同或不同的取代基,选自卤原子,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,苯基,取代的苯基、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组,杂环基(术语杂环基定义同上),和取代的杂环基(术语杂环基定义同上)、具有至少一个相同或不同的取代基、选自由卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基组成的组;
W代表O、S或N-R13(该式中,R13定义同上);Z1和Z2代表氧原子或硫原子;
其条件是若X、R1和R3同时代表氢原子,Z1和Z2同时代表氧原子,Q代表Q27,Y是2-位的氯原子,则R2不是1,2,2-三甲基丙基};
还涉及农艺杀虫剂及其使用方法。
本发明进一步涉及由下列通式(IV’)代表的杂环胺衍生物:
Q’-NH2 (IV’)
其中:
(1)在Q’代表下式Q26、Q28-Q31和Q33-Q39的情况下,
Y可以是相同或不同的,代表氢原子、卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基,m代表1至4的整数,总数为m的Y至少有一个是全氟C2-C6烷基;
(2)在Q’代表Q27和Q32的情况下,
Y可以是相同或不同的,代表氢原子、卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基或卤代C1-C6烷基磺酰基,m代表1至4的整数,总数为m的Y至少有一个是全氟C2-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷氧基卤代C1-C6烷氧基或卤代C1-C6烷硫基。
式(IV’)的杂环胺衍生物可用作制备式(I)的邻苯二甲酰胺衍生物的中间体化合物。
在本发明邻苯二甲酰胺衍生物通式(I)的定义中,“卤原子”表示氯原子、溴原子、碘原子或氟原子;“C1-C6烷基”表示具有1至6个碳原子的直链或支链烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基等;“卤代C1-C6烷基”表示被至少一个相同或不同的卤原子取代的、具有1至6个碳原子的直链或支链烷基;“C1-C8亚烷基”表示具有1至8个碳原子的直链或支链亚烷基,例如亚甲基、亚乙基、1,2-亚丙基、1,3-亚丙基、二甲基亚甲基、亚丁基、异亚丁基、二甲基亚乙基、亚辛基等。
关于“R1和R2结合一起形成可以被1至3个相同或不同的氧原子、硫原子或氮原子间断的4-至7-元环”的实例,可以提及氮杂环丁烷环、吡咯烷环、吡咯啉环、哌啶环、咪唑烷环、咪唑啉环、噁唑烷环、噻唑烷环、异噁唑烷环、异噻唑烷环、四氢吡啶环、哌嗪环、吗啉环、硫代吗啉环、二噁嗪环、二噻嗪环等。
有些由通式(I)代表的本发明的邻苯二甲酰胺衍生物在其结构式中具有不对称碳原子或不对称中心,有时可以存在两种旋光异构体。本发明包括所有这样的旋光异构体和它们的任意比例混合物,有时包括它们的盐和水合物。
在由通式(I)代表的本发明的邻苯二甲酰胺衍生物中,优选的取代基如下。因而,本发明的邻苯二甲酰胺衍生物优选为这样的通式(I)的邻苯二甲酰胺衍生物,其中R1、R2和R3可以是相同或不同的,代表氢原子或-A1-G(该式中,A1代表C1-C8亚烷基,G代表氢原子、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷基羰基氨基或C1-C6烷氧基羰基氨基);X可以是相同或不同的,代表卤原子、硝基、卤代C1-C6烷基、卤代C1-C6烷氧基或卤代C1-C6烷硫基;n代表0至4的整数;Q代表Q27;Y可以是相同或不同的,代表卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、卤代C1-C6烷氧基卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、卤代C1-C6烷氧基卤代C1-C6烷硫基、卤代C1-C6烷基亚磺酰基或卤代C1-C6烷基磺酰基;m代表0至4的整数;Z1和Z2代表氧原子。进一步优选地,本发明的邻苯二甲酰胺衍生物是这样的通式(I)的邻苯二甲酰胺衍生物,其中R1和R3代表氢原子;R2代表C1-C6烷硫基C1-C6烷基;X代表卤原子;n代表1至2的整数;Q代表Q27;Y可以是相同或不同的,代表卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基;m代表1至2的整数;Z1和Z2代表氧原子。
本发明化合物可以按照下述流程1和2加以制备,不过本发明化合物也可以通过JP-A-11-240857所述方法加以制备。
制备方法1
其中R1、R2、Z1、Z2、X、Q和n定义同上。
在惰性溶剂的存在下,由通式(V)代表的邻苯二甲酸酐衍生物与由通式(IV)代表的杂环胺衍生物反应,生成由通式(III)代表的邻苯二甲酰亚胺衍生物。分离或者不分离邻苯二甲酰亚胺衍生物(III)后,(III)与由通式(II)代表的胺反应。因而,可以制备由通式(I-1)代表的邻苯二甲酰亚胺衍生物。
(1)通式(V)→通式(III)
关于用在该反应中的惰性溶剂,可以使用任意溶剂,只要它不明显妨碍反应进行即可。可以使用的惰性溶剂实例包括芳族烃,例如苯、甲苯、二甲苯等,卤代烃,例如二氯甲烷、氯仿、四氯化碳等,氯代芳族烃,例如氯苯、二氯苯等,无环族与环族醚,例如乙醚、二噁烷、四氢呋喃等,酯,例如乙酸乙酯等,酰胺,例如二甲基甲酰胺、二甲基乙酰胺等,酸,例如乙酸等,二甲基亚砜,1,3-二甲基-2-咪唑烷酮等。这些惰性溶剂既可以单独使用,也可以两种或多种溶剂结合使用。
由于该反应是等摩尔反应,可以使用等摩尔量的反应物。不过如果需要的话,也可以使用过量的任意一种反应物。根据需要,该反应可以在脱水条件下进行。
反应可以在室温至所用惰性溶剂的回流温度之间的温度下进行。尽管反应时间可以因反应的规模和温度而异,不过可以在若干分钟至48小时的范围内加以适当选择。
反应完全后,按常规方式从反应系统中分离目标产物,根据需要通过重结晶、柱色谱等方法纯化,由此可以得到目标产物。不经分离而将目标产物送入随后的步骤也是可能的。
由通式(V)代表的邻苯二甲酸酐衍生物可以按照《有机化学杂志》
52,129(1987)、《美国化学会志》
51,1865(1929)、出处同上
63,1542(1941)等所述方法加以制备。由通式(IV)代表的杂环胺衍生物可以按照《有机化学杂志》
18,138(1953)、《有机化学杂志》28,1877(1963)、《化学报告》
89,2742(1956)、《印度科学院院报》
37A,758(1953)、《杂环化学杂志》
17,143(1980)、JP-A-62-96479、JP-A-10-340345、JP-A-11-302233等所述方法加以制备。
(2)通式(III)→通式(I-1)
关于可用在该反应中的惰性溶剂,可以与可用在上述反应(1)中的那些相同。由于该反应是等摩尔反应,可以使用等摩尔量的反应物,不过如果需要的话,也可以使用过量的通式(II)的胺。反应可以在室温至所用惰性溶剂的回流温度之间的温度下进行。尽管反应时间可以因反应的规模和温度而异,不过可以在若干分钟至48小时的范围内加以适当选择。
反应完全后,按常规方式从含有产物的反应系统中分离目标产物。根据需要通过重结晶、柱色谱等方法纯化产物,由此可以得到目标产物。
制备方法2
其中R1、R2、R3、X、Q和n定义同上。
在惰性溶剂的存在下,由通式(V)代表的邻苯二甲酸酐衍生物与由通式(II)代表的胺反应,生成由通式(III-2)代表的邻苯二甲酰胺。在(III-2)中的R1是氢原子的情况下,分离或者不分离邻苯二甲酰胺(III-2),然后在缩合剂的存在下进行缩合反应,生成由通式(VI-1)代表的化合物,分离或者不分离(VI-1)后,在惰性溶剂的存在下,化合物(VI-1)与由通式(IV)代表的杂环胺衍生物反应。在邻苯二甲酰胺(III-2)中的R1不是氢原子的情况下,在缩合剂的存在下,已经分离或者末分离的(III-2)与由通式(IV)代表的杂环胺进行缩合反应。按这些方式,可以制备由通式(I-2)代表的邻苯二甲酰胺衍生物。
或者,在惰性溶剂的存在下,由通式(V)代表的邻苯二甲酸酐衍生物与由通式(IV)代表的杂环胺衍生物反应,生成由通式(III-1)代表的邻苯二甲酰胺。在(III-1)中的R3是氢原子的情况下,分离或者不分离邻苯二甲酰胺(III-1),然后在缩合剂的存在下进行缩合反应,生成由通式(VI)代表的化合物,分离或者不分离(VI)后,在惰性溶剂的存在下,(VI)与由通式(II)代表的胺进行反应。在(III-1)中的R3不是氢原子的情况下,在缩合剂的存在下,已经分离或者未分离的(III-1)与由通式(II)代表的胺进行缩合反应。按这些方式,可以制备由通式(I-2)代表的邻苯二甲酰胺衍生物。
(1)通式(V)→(III-2)或通式(VI-1)→通式(I-2)
该反应可以按与制备方法1-(2)相同的方式进行,由此可以得到目标产物。
(2)通式(III-1)→(VI)或通式(III-2)→通式(VI-1)
该反应可以按照《药物化学杂志》
10,982(1967)的说明进行,由此可以得到目标产物。
(3)通式(VI)→(I-2)或通式(V)→通式(III-2)
该反应可以按与制备方法1-(2)相同的方式进行,由此可以得到目标产物。
(4)通式(III-1)或通式(III-2)→通式(I-2)
该反应可以这样进行,即,在缩合剂和惰性溶剂的存在下,由通式(III-1)或(III-2)代表的邻苯二甲酰胺衍生物与由通式(II)或(IV)代表的胺反应。如果必要的话,该反应可以在碱的存在下进行。
关于用在该反应中的惰性溶剂实例,可以提及四氢呋喃、乙醚、二噁烷、氯仿、二氯甲烷等。关于用在该反应中的缩合剂,可以使用用在常规酰胺制备中的那些,其实例包括Mukaiyama试剂(2-氯-N-甲基吡啶输碘化物)、DCC(1,3-二环己基碳二亚胺)、CDI(羰基二咪唑)、DEPC(氰基膦酸二乙酯)等。基于由通式(III-1)或(III-2)代表的邻苯二甲酰胺衍生物而言,缩合剂的量可以在等摩尔量至过量摩尔量的范围内加以适当选择。
关于可以用在该反应中的碱实例,可以提及有机碱,例如三乙胺、吡啶等,和无机碱,例如碳酸钾等。基于由通式(III-1)或(III-2)代表的邻苯二甲酰胺衍生物而言,碱的量可以在等摩尔量至过量摩尔量的范围内加以适当选择。
反应可以在0℃至所用惰性溶剂的沸点之间的温度下进行。尽管反应时间可以因反应的规模和温度而异,不过在若干分钟至48小时的范围内。
反应完全后,通过常规方法从反应系统中分离目标产物,根据需要可以通过重结晶、柱色谱等方法纯化产物,由此可以得到目标产物。
下面,由通式(IV’)代表的杂环胺衍生物的典型实例列在表1中,由通式(I)代表的邻苯二甲酰胺衍生物的典型实例列在表2至12中。本发明决不限于这里所示的化合物。下表中,“Me”表示甲基,“Et”表示乙基,“Pr”表示丙基,“Bu”表示丁基,“Ac”表示乙酰基,“Ph”表示苯基,“c-”表示脂环族烃,“mp”表示熔点,“nD”表示折光指数。
通式(IV’)
Q′-NH2 (IV′)
表1
No. Q′ Ym mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-1 Q26 3-Me-5-C2F5 2.17(s.3H),4.82(br.2H),7.42(d.
1H),8.16(s.1H).
IV′-2 Q26 3-Me-5-n-C3F7 2.18(s.3H),4.94(br.2H),7.41(d.
1H),8.19(s.1H).
IV′-3 Q26 3-Me-5-i-C3F7 2.18(s.3H),4.80(br.2H),7.42(d.
1H),8.15(s.1H).
表1(续)
No. Q′ Ym mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-4 Q27 2-n-C3F7 4.08(br.2H),7.04(dd.1H),7.43(d.
1H),8.16(d.1H).
IV′-5 Q27 6-Cl-2-n-C3F7 4.65(br.2H),7.17(d.1H),7.57(d.
1H).
IV′-6 Q27 2-C2F5 3.72(br.2H),7.04(dd.1H),7.46(d.
1H),8.16(d.1H).
IV′-7 Q27 2-i-C3F7 4.12(br.2H),7.06(dd.1H),7.44(dd.
1H),8.13(d.1H).
IV′-8 Q27 4-Me-2-i-C3F7 2.22(s.3H),4.12(br.2H),7.34(d.
1H),8.07(s.1H).
IV′-9 Q27 4-Me-6-i-C3F7 2.21(s.3H),4.26(br.2H),7.09(dd.
1H),7.98(d.1H).
IV′-10 Q27 6-Me-2-i-C3F7 2.42(s.3H),4.12(br.2H),6.98(d.
1H),7.31(dd.1H).
IV′-11 Q27 6-Cl-2-i-C3F7 4.40(br.2H),7.12(d.1H),7.41(dd.
1H).
IV′-12 Q27 6-F-2-i-C3F7
IV′-13 Q27 6-i-C3F7 4.28(br.2H),7.04(dd.1H),7.18(m.
1H),8.07(d.1H).
IV′-14 Q27 4,6-Cl2-2-i-C3F7 4.80(br.2H),7.53(d.1H).
IV′-15 Q27 6-MeO-2-i-C3F7 3.96(s.3H),4.03(br.2H),6.91(d.
1H),7.10(dd.1H).
IV′-16 Q27 6-MeS-2-i-C3F7 2.58(s.3H),4.00(br.2H),6.91(d.
1H),7.22(dd.1H).
IV′-17 Q27 6-MeSO-2-i-C3F7
表1(续)
No. Q′ Ym mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-18 Q27 6-MeSO2-2-I-C3F7
IV′-19 Q32 4-Me-2-i-C3F7 2.46(s.3H),3.94(br.2H),8.15(s.1H).
IV′-20 Q32 4-Me-6-i-C3F7 2.49(s.3H),4.35(br.2H),8.55(s.1H).
IV′-21 Q34 5-i-C3F7 5.0(br.2H),8.01(s.1H),8.31(s.1H).
IV′-22 Q27 2-OCF2CHF2 3.43(br.2H),6.13(tt.1H),6.88(d.
1H),7.08(dd.1H),7.74(d.1H).
IV′-23 Q27 2-OCHF2 3.60(br.2H),6.72(d.1H),7.07(dd.
1H),7.26(dd.1H),7.63(d.1H).
IV′-24 Q27 6-Me-2-OCHF2 1.30(s.3H),3.45(br.2H),6.58(d.1H),
6.98(d.1H),7.30(t.1H).
IV′-25 Q27 2-SCHF2 3.81(br.2H),6.94(dd.1H),7.24(t.
1H),7.25(d.1H),8.06(d.1H).
IV′-26 Q27 6-Me-2-SCHF2 44-46℃
IV′-27 Q27 2-OCH(CF3)2 3.70(br.2H),6.40(m.1H),6.76(d.1H),
7.08(dd.1H),7.59(d.1H).
IV′-28 Q27 6-Me-2-OCH(CF3)2 2.33(s.3H),3.45(br.2H),6.49(m.1H),
6.64(d.1H),7.03(d.1H).
IV′-29 Q27 6-Cl-2-OCH(CF3)2 3.89(br.2H),6.24(m.1H),6.76(d.1H),
7.16(d.1H).
IV′-30 Q27 6-F-2-OCH(CF3)2
IV′-31 Q27 6-OMe-2-OCH(CF3)2 3.15-3.60(br.2H),3.95(s.3H),6.15(m.
1H),6.38(d.1H),6.99(d.1H).
IV′-32 Q27 6-Cl-2-SCH(CF3)2
IV′-33 Q27 6-Me-2-SCH(CF3)2
表1(续)
No. Q′ Ym mp(℃)或1H-NMR[δ(ppm/CDCl3)]
IV′-34 Q27 6-F-2-SCH(CF3)2
IV′-35 Q27 6-OMe-2-SCH(CF3)2
IV′-36 Q27 2-OCF2CHFOCF3
IV′-37 Q27 6-Me-2-OCF2CHFOCF3 2.35(s.3H),3.50(br.2H),6.31(dt.
1H),6.77(d.1H),7.01(d.1H).
IV′-38 Q27 6-Cl-2-OCF2CHFOCF3
IV′-39 Q27 2-OCF2CHFO-n-C3F7 3.20(br.2H),6.43(dt.1H),6.84(d.
1H),7.08(dd.1H),7.73(d.1H).
IV′-40 Q27 6-Me-2-OCF2CHFO- 2.35(s.3H),3.60(br.2H),6.50(dt.
n-C3F7 1H),6.74(d.1H),7.02(d.1H).
IV′-41 Q27 6-Cl-2-OCF2CHFO- 3.40(br.2H),6.37(dt.1H),6.85(d.
n-C3F7 1H),7.14(d.1H).
IV′-42 Q27 6-Me-2-OCF2CHFCF3 2.36(s.3H),3.30(br.2H),5.35(m.
1H),6.76(d.1H),7.01(d.1H).
IV′-43 Q27 6-Me-2-OCF=CFCF3 2.04(s.3H),3.10(br.2H),6.65(d.
0.5H),6.69(d.0.5H),7.03(d.1H).
(E,Z混合物)
IV′-44 Q27 6-Me-2-OCH(CF3)2 2.20(s.3H),3.20-3.60(br.2H),
6.41(m.1H),6.67(s.1H),7.55(s.1H).
IV′-45 Q27 6-Me-2-OCF2CHF2 2.37(s.3H),3.40(br.2H),6.16(tt.
1H),6.79(d.1H),7.06(d.1H).
IV′-46 Q27 6-Cl-2-OCF2CHF3 3.50(br.2H),6.11(tt.1H),6.88(d.
1H),7.15(d.1H).
IV′-47 Q27 6-Me-2-OCH2C2F5 2.31(s.3H),3.33(br.2H),4.75(t.
2H),6.55(d.1H),6.98(d.1H).
通式(I):
表2(Z1=Z2=O)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q1 1-1 3-Cl H i-Pr H O H
Q1 1-2 3-Cl H i-Pr H O 3-Me-5-C2F5
Q1 1-3 3-Cl H i-Pr H S 4,5-Br2 143
Q1 1-4 3-Br H i-Pr H O 3-Me-5-n-C3F7
Q1 1-5 3-NO2 H i-Pr H O 3-Me-5-i-C3F7
Q1 1-6 3-I H i-Pr H S H
Q1 1-7 3-I H i-Pr H S 3-Me 207
Q1 1-8 3-I H i-Pr H S 5-Cl
Q1 1-9 3-I H i-Pr H S 5-C2F5
Q1 1-10 3-I H i-Pr H S 5-n-C3F7
Q1 1-11 3-I H i-Pr H S 5-i-C3F7
Q1 1-12 3-I H i-Pr H S 3-Me-5-t-Bu 160
Q1 1-13 3-I H i-Pr H S 3-Me-5-Br
Q1 1-14 3-I H i-Pr H S 3-Me-5-C2F5
Q1 1-15 3-I H i-Pr H S 3-Me-5-n-C3F7
Q1 1-16 3-I H i-Pr H S 3-Me-5-i-C3F7
Q1 1-17 3-I H i-Pr H S 3-Me-4-C2F5
Q1 1-18 3-I H i-Pr H S 3-Me-4-n-C3F7
Q1 1-19 3-I H i-Pr H S 3-Me-4-i-C3F7
Q1 1-20 3-I H t-Bu H NMe 5-i-C3F7
Q1 1-21 3-I H t-Bu H NMe 5-C2F5
Q1 1-22 3-I H t-Bu H NMe 5-n-C3F7
Q1 1-23 3-I H t-Bu H NMe 3-Me-5-i-C3F7
表2(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q1 1-24 3-I H CH(CH3)CH2SCH3 H S 3-Me-5-i-C3F7
Q1 1-25 3-I H CH(CH3)CH2SOCH3 H S 3-Me-5-i-C3F7
Q1 1-26 3-I H CH(CH3)CH2SO2CH3 H S 3-Me-5-i-C3F7
Q1 1-27 3-I H C(CH3)2CH2SCH3 H S 3-Me-5-i-C3F7
Q1 1-28 3-I H C(CH3)2CH2SOCH3 H S 3-Me-5-i-C3F7
Q1 1-29 3-I H C(CH3)2CH2SO2CH3 H S 3-Me-5-i-C3F7
Q1 1-30 3-I H CH(CH3)CH2NHAc H S 3-Me-5-i-C3F7
Q1 1-31 3-I H C(CH3)2CH2NHAc H S 3-Me-5-i-C3F7
Q1 1-32 3-I H CH(CH3)CH2CH2OCH3 H S 3-Me-5-i-C3F7
Q1 1-33 3-I H C(CH3)2CH2CH2OCH3 H S 3-Me-5-i-C3F7
Q1 1-34 3-I Et Et H O H
Q1 1-35 3-I Et Et H O 3-Me-5-C2F5
Q1 1-36 3-I Et Et H O 3-Me-5-n-C3F7
Q1 1-37 3-I Et Et H O 3-Me-5-i-C3F7
Q1 1-38 3-I Et Et H O 5-Cl
Q1 1-39 3-I Et Et H O 5-Br
Q1 1-40 3-I Et Et H O 5-n-C3F7
Q1 1-41 6-I H i-Pr H S 3-Me-5-t-Bu 97
Q1 1-42 6-I H i-Pr H S 3-Me 168
Q1 1-43 3-CF3 H i-Pr H NMe 3-Me-5-C2F5
Q1 1-44 3-Ph H i-Pr H NMe 3-Me-5-n-C3F7
Q1 1-45 3-SOCF3 H i-Pr H NMe 3-Me-5-i-C3F7
Q1 1-46 3-C2F5 H i-Pr H NMe 3-Me-5-C2F5
表2(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q1 1-47 3-I-4-Cl H i-Pr H NMe 3-Me-5-n-C3F7
Q1 1-48 3-I-4-CF3 H i-Pr H S 3-Me-5-i-C3F7
Q1 1-49 3-CF3-4-Cl H i-Pr H S 3-Me-5-C2F5
Q1 1-50 3-OCF2O-4 H i-Pr H S 3-Me-5-n-C3F7
Q1 1-51 3-OCF2CF2O-4 H i-Pr H S 3-Me-5-i-C3F7
Q2 2-1 3-I H i-Pr H S 2-Me-5-C2F5
Q2 2-2 3-I H i-Pr H S 2-Me-5-n-C3F7
Q2 2-3 3-I H i-Pr H S 2-Me-5-i-C3F7
Q2 2-4 3-I H i-Pr H S 4-Me-5-C2F5
Q2 2-5 3-I H i-Pr H S 4-Me-5-n-C3F7
Q2 2-6 3-I H i-Pr H S 4-Me-5-i-C3F7
Q2 2-7 3-I H t-Bu H NMe 5-i-C3F7
Q2 2-8 3-I H t-Bu H NMe 5-C2F5
Q2 2-9 3-I H t-Bu H NMe 5-n-C3F7
Q2 2-10 3-I H t-Bu H NMe 4-Me-5-i-C3F7
Q2 2-11 3-I H CH(CH3)CH2SCH3 H S 4-Me-5-i-C3F7
Q2 2-12 3-I H CH(CH3)CH2SOCH3 H S 4-Me-5-i-C3F7
Q2 2-13 3-I H CH(CH3)CH2SO2CH3 H S 4-Me-5-i-C3F7
Q2 2-14 3-I H C(CH3)2CH2SCH3 H S 4-Me-5-i-C3F7
Q2 2-15 3-I H C(CH3)2CH2SOCH3 H S 2-Me-5-i-C3F7
Q2 2-16 3-I H C(CH3)2CH2SO2CH3 H S 2-Me-5-i-C3F7
Q2 2-17 3-I H CH(CH3)CH2NHAc H S 2-Me-5-i-C3F7
Q2 2-18 3-I H C(CH3)2CH2NHAc H S 2-Me-5-i-C3F7
表2(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q2 2-19 3-I H CH(CH3)CH2CH2OCH3 H S 2-Me-5-i-C3F7
Q2 2-20 3-I H C(CH3)2CH2CH2OCH3 H S 4-Me-5-i-C3F7
Q2 2-21 3-I Et Et H O H
Q2 2-22 3-I Et Et H O 2-Me-5-C2F5
Q2 2-23 3-I Et Et H O 2-Me-5-n-C3F7
Q2 2-24 3-I Et Et H O 4-Me-5-i-C3F7
表3(Z2=Z2=O)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q4 4-1 H H i-Pr H O 5-Me 185
Q4 4-2 3-Cl H i-Pr H O H
Q4 4-3 3-Cl H i-Pr H O 4-Me-5-C2F5
Q4 4-4 3-Cl H i-Pr H O 4,5-Br2
Q4 4-5 3-Cl H i-Pr H O 5-Me 136
Q4 4-6 3-Cl H i-Pr H O 5-(4-Br-Ph) 158
Q4 4-7 3-Cl H i-Pr H O 4-Me-5-(4-Cl-Ph) 184
Q4 4-8 6-Cl H i-Pr H O 4-Me-5-(4-Cl-Ph) 101
Q4 4-9 3-Br H i-Pr H O 4-Me-5-n-C3F7
Q4 4-10 3-NO2 H i-Pr H O 4-Me-5-i-C3F7
Q4 4-11 3-I H i-Pr H O 4-Me 144
Q4 4-12 3-I H i-Pr H O 4-Me-5-CF3 151
Q4 4-13 3-I H i-Pr H S H
Q4 4-14 3-I H i-Pr H S 4-Me
Q4 4-15 3-I H i-Pr H S 5-Cl
Q4 4-16 3-I H i-Pr H S 5-C2F5
Q4 4-17 3-I H i-Pr H S 5-n-C3F7
Q4 4-18 3-I H i-Pr H S 5-i-C3F7
Q4 4-19 3-I H i-Pr H S 4-Me-5-t-Bu
Q4 4-20 3-I H i-Pr H S 4-Me-5-Br
Q4 4-21 3-I H i-Pr H S 4-Me-5-C2F5
Q4 4-22 3-I H i-Pr H S 4-Me-5-n-C3F7
Q4 4-23 3-I H i-Pr H S 4-Me-5-i-C3F7
表3(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q4 4-24 3-I H t-Bu H NMe 5-i-C3F7
Q4 4-25 3-I H t-Bu H NMe 5-C2F5
Q4 4-26 3-I H t-Bu H NMe 5-n-C3F7
Q4 4-27 3-I H t-Bu H NMe 4-Me-5-i-C3F7
Q4 4-28 3-I H CH(CH3)CH2SCH H S 4-Me-5-i-C3F7
Q4 4-29 3-I H CH(CH3)CH2SOCH3 H S 4-Me-5-i-C3F7
Q4 4-30 3-I H CH(CH3)CH2SO2CH3 H S 4-Me-5-i-C3F7
Q4 4-31 3-I H C(CH3)2CH2SCH3 H S 4-Me-5-i-C3F7
Q4 4-32 3-I H C(CH3)2CH2SOCH3 H S 4-Me-5-i-C3F7
Q4 4-33 3-I H C(CH3)2CH2SO2CH3 H S 4-Me-5-i-C3F7
Q4 4-34 3-I H CH(CH3)CH2NHAc H S 4-Me-5-i-C3F7
Q4 4-35 3-I H C(CH3)2CH2NHAc H S 4-Me-5-i-C3F7
Q4 4-36 3-I H CH(CH3)CH2CH2OCH3 H S 4-Me-5-i-C3F7
Q4 4-37 3-I H C(CH3)2CH2CH2OCH3 H S 4-Me-5-i-C3F7
Q4 4-38 3-I Et Et H O H
Q4 4-39 3-I Et Et H O 4-Me-5-C2F5
Q4 4-40 3-I Et Et H O 4-Me-5-n-C3F7
Q4 4-41 3-I Et Et H O 4-Me-5-i-C3F7
Q4 4-42 3-I Et Et H O 5-Cl
Q4 4-43 3-I Et Et H O 5-Br
Q4 4-44 3-I Et Et H O 5-n-C3F7
Q4 4-45 6-I H i-Pr H O 4-Me-5-CF3 143
Q4 4-46 3-CF3 H i-Pr H NMe 4-Me-5-C2F5
表3(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q4 4-47 3-Ph H i-Pr H NMe 4-Me-5-n-C3F7
Q4 4-48 3-SOCF3 H i-Pr H NMe 4-Me-5-i-C3F7
Q4 4-49 3-C2F5 H i-Pr H NMe 4-Me-5-C2F5
Q4 4-50 3-I-4-Cl H i-Pr H NMe 4-Me-5-n-C3F7
Q4 4-51 3-I-4-CF3 H i-Pr H S 4-Me-5-i-C3F7
Q4 4-52 3-CF3-4-Cl H i-Pr H S 4-Me-5-C2F5
Q4 4-53 3-OCF2O-4 H i-Pr H S 4-Me-5-n-C3F7
Q4 4-54 3-OCF2CF2O-4 H i-Pr H S 4-Me-5-i-C3F7
Q5 5-1 3-Cl H i-Pr H O H
Q5 5-2 3-Cl H i-Pr H O 3-Me-5-Cl
Q5 5-3 3-Cl H i-Pr H O 3,5-Br2
Q5 5-4 3-Cl H i-Pr H NMe 3-Me 180
Q5 5-5 3-Cl H i-Pr H NMe 3-Me-5-OMe 220
Q5 5-6 3-Cl H n-Pr H NMe 3-Me-5-OMe 90
Q5 5-7 3-Cl H n-Pr H NMe 3-Me-5-OPh 190
Q5 5-8 6-Cl H i-Pr H NMe 3-Me-5-OPh 245
Q5 5-9 6-Cl H i-Pr H NMe 3-Me-5-OMe 175
Q5 5-10 3-Br H i-Pr H O 3,5-Me2
Q5 5-11 3-NO2 H i-Pr H O 3,5-Me2
Q5 5-12 3-I H i-Pr H O 3-CF3
Q5 5-13 3-I H i-Pr H O 5-CF3
Q5 5-14 3-I H i-Pr H S H
Q5 5-15 3-I H i-Pr H S 3-Me
表3(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q5 5-16 3-I H i-Pr H S 5-Cl
Q5 5-17 3-I H i-Pr H S 5-C2F5
Q5 5-18 3-I H i-Pr H S 5-n-C3F7
Q5 5-19 3-I H i-Pr H S 5-i-C3F7
Q5 5-20 3-I H i-Pr H S 3-C2F5
Q5 5-21 3-I H i-Pr H S 3-n-C3F7
Q5 5-22 3-I H i-Pr H S 3-i-C3F7
Q5 5-23 3-I H i-Pr H S 3-Me-5-Br
Q5 5-24 3-I H i-Pr H S 3-Me-5-C2F5
Q5 5-25 3-I H i-Pr H S 3-Me-5-n-C3F7
Q5 5-26 3-I H i-Pr H S 3-Me-5-i-C3F7
Q5 5-27 3-I H t-Bu H NMe 5-i-C3F7
Q5 5-28 3-I H t-Bu H NMe 5-C2F5
Q5 5-29 3-I H t-Bu H NMe 5-n-C3F7
Q5 5-30 3-I H CH(CH3)CH2SCH3 H NMe 3,5-Me2
Q5 5-31 3-I H CH(CH3)CH2SOCH3 H NMe 3,5-Me2
Q5 5-32 3-I H CH(CH3)CH2SO2CH3 H NMe 3,5-Me2
Q5 5-33 3-I H C(CH3)2CH2SCH3 H NMe 3,5-Me2
Q5 5-34 3-I H C(CH3)2CH2SOCH3 H NMe 3,5-Me2
Q5 5-35 3-I H C(CH3)2CH2SO2CH3 H NMe 3,5-Me2
Q5 5-36 3-I H CH(CH3)CH2NHAc H NMe 3,5-Me2
Q5 5-37 3-I H C(CH3)2CH2NHAc H NMe 3,5-Me2
Q5 5-38 3-I H CH(CH3)CH2CH2OCH3 H NMe 3,5-Me2
表3(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q5 5-39 3-I H C(CH3)2CH2CH2OCH3 H NMe 3,5-Me2
Q5 5-40 3-I Et Et H O H
Q5 5-41 3-I Et Et H O 3-Me-5-C2F5
Q5 5-42 3-I Et Et H O 3-Me-5-n-C3F7
Q5 5-43 3-I Et Et H O 3-Me-5-i-C3F7
Q5 5-44 3-I Et Et H O 5-Cl
Q5 5-45 3-I Et Et H O 5-Br
Q5 5-46 3-I Et Et H O 5-n-C3F7
Q5 5-47 3-I Et Et H O 5-n-C3F7
Q5 5-48 3-CF3 H i-Pr H NMe 3-Me-5-C2F5
Q5 5-49 3-Ph H i-Pr H NMe 3-Me-5-n-C3F7
Q5 5-50 3-SOCF3 H i-Pr H NMe 3-Me-5-i-C3F7
Q5 5-51 3-C2F5 H i-Pr H NMe 3-Me-5-C2F5
Q5 5-52 3-I-4-Cl H i-Pr H NMe 3-Me-5-n-C3F7
Q5 5-53 3-I-4-CF3 H i-Pr H S 3-Me-5-i-C3F7
Q5 5-54 3-CF3-4-Cl H i-Pr H S 3-Me-5-C2F5
Q5 5-55 3-OCF2O-4 H i-Pr H S 3-Me-5-n-C3F7
Q5 5-56 3-OCF2CF2O-4 H i-Pr H S 3-Me-5-i-C3F7
Q6 6-1 3-Cl H i-Pr H O H
Q6 6-2 3-Cl H i-Pr H O 4-Me-3-C2F5
Q6 6-3 3-Cl H i-Pr H O 3,4-Br2
Q6 6-4 3-Br H i-Pr H O 4-Me-3-n-C3F7
Q6 6-5 3-NO2 H i-Pr H O 4-Me-3-i-C3F7
表3(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q6 6-6 3-NO2 H i-Pr H NMe 3-Me 176
Q6 6-7 3-I H i-Pr H O 4-Me-3-Et 85
Q6 6-8 3-I H i-Pr H O 4-Me-3-CF3 103
Q6 6-9 3-I H i-Pr H S H
Q6 6-10 3-I H i-Pr H S 4-Me
Q6 6-11 3-I H i-Pr H S 3-Cl
Q6 6-12 3-I H i-Pr H S 3-C2F5
Q6 6-13 3-I H i-Pr H S 3-n-C3F7
Q6 6-14 3-I H i-Pr H S 3-i-C3F7
Q6 6-15 3-I H i-Pr H S 4-Me-3-t-Bu
Q6 6-16 3-I H i-Pr H S 4-Me-3-Br
Q6 6-17 3-I H i-Pr H S 4-Me-3-C2F5
Q6 6-18 3-I H i-Pr H S 4-Me-3-n-C3F7
Q6 6-19 3-I H i-Pr H S 4-Me-3-i-C3F7
Q6 6-20 3-I H t-Bu H NMe 3-i-C3F7
Q6 6-21 3-I H t-Bu H NMe 3-C2F5
Q6 6-22 3-I H t-Bu H NMe 3-n-C3F7
Q6 6-23 3-I H t-Bu H NMe 4-Me-3-i-C3F7
Q6 6-24 3-I H CH(CH3)CH2SCH3 H S 4-Me-3-i-C3F7
Q6 6-25 3-I H CH(CH3)CH2SOCH3 H S 4-Me-3-i-C3F7
Q6 6-26 3-I H CH(CH3)CH2SO2CH3 H S 4-Me-3-i-C3F7
Q6 6-27 3-I H C(CH3)2CH2SCH3 H S 4-Me-3-i-C3F7
Q6 6-28 3-I H C(CH3)2CH2SOCH3 H S 4-Me-3-i-C3F7
表3(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q6 6-29 3-I H C(CH3)2CH2SO2CH3 H S 4-Me-3-i-C3F7
Q6 6-30 3-I H CH(CH3)CH2NHAc H S 4-Me-3-i-C3F7
Q6 6-31 3-I H C(CH3)2CH2NHAc H S 4-Me-3-i-C3F7
Q6 6-32 3-I H CH(CH3)CH2CH2OCH3 H S 4-Me-3-i-C3F7
Q6 6-33 3-I H C(CH3)2CH2CH2OCH3 H S 4-Me-3-i-C3F7
Q6 6-34 3-I Et Et H O H
Q6 6-35 3-I Et Et H O 4-Me-3-C2F5
Q6 6-36 3-I Et Et H O 4-Me-3-n-C3F7
Q6 6-37 3-I Et Et H O 4-Me-3-i-C3F7
Q6 6-38 3-I Et Et H O 3-Cl
Q6 6-39 3-I Et Et H O 3-Br
Q6 6-40 3-I Et Et H O 3-n-C3F7
Q6 6-41 3-CF3 H i-Pr H NMe 4-Me-3-C2F5
Q6 6-42 3-Ph H i-Pr H NMe 4-Me-3-n-C3F7
Q6 6-43 3-SOCF3 H i-Pr H NMe 4-Me-3-i-C3F7
Q6 6-44 3-C2F5 H i-Pr H NMe 4-Me-3-C2F5
Q6 6-45 3-I-4-Cl H i-Pr H NMe 4-Me-3-n-C3F7
Q6 6-46 3-I-4-CF3 H i-Pr H S 4-Me-3-i-C3F7
Q6 6-47 3-CF3-4-Cl H i-Pr H S 4-Me-3-C2F5
Q6 6-48 3-OCF2O-4 H i-Pr H S 4-Me-3-n-C3F7
Q6 6-49 3-OCF2CF2O-4 H i-Pr H S 4-Me-3-i-C3F7
表4(Z1=Z2=O)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q8 8-1 3-Cl H i-Pr H S H 137
Q8 8-2 3-Cl H i-Pr H S 4-Me 175
Q8 8-3 3-Cl H i-Pr H S 4-CF3 185
Q8 8-4 3-Cl H i-Pr H S 4-Ph 175
Q8 8-5 3-Cl H i-Pr H S 4-Ph-5-Cl 205
Q8 8-6 3-Cl H i-Pr H O 4-Me-5-Cl
Q8 8-7 3-Cl H i-Pr H O 4,5-Br2
Q8 8-8 3-Cl H i-Pr H NMe 4-Me
Q8 8-9 3-Cl H i-Pr H NMe 4-Me-5-OMe
Q8 8-10 3-Cl H n-Pr H NMe 4-Me-5-OMe
Q8 8-11 3-Cl H n-Pr H NMe 4-Me-5-OPh
Q8 8-12 6-Cl H i-Pr H S 4-CH3 155
Q8 8-13 6-Cl H i-Pr H S 4-CF3 165
Q8 8-14 6-Cl H i-Pr H S 4-Ph 155
Q8 8-15 6-Cl H i-Pr H S 4-Ph-5-Cl 155
Q8 8-16 3-Br H i-Pr H O 4,5-Me2
Q8 8-17 3-NO2 H i-Pr H O 4,5-Me2
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q8 8-18 3-I H i-Pr H O 4-CF3
Q8 8-19 3-I H i-Pr H O 5-CF3
Q8 8-20 3-I H i-Pr H S H
Q8 8-21 3-I H i-Pr H S 4-Me
Q8 8-22 3-I H i-Pr H S 5-Cl
Q8 8-23 3-I H i-Pr H S 5-C2F5
Q8 8-24 3-I H i-Pr H S 5-n-C3F7
Q8 8-25 3-I H i-Pr H S 5-i-C3F7
Q8 8-26 3-I H i-Pr H S 4-C2F5
Q8 8-27 3-I H i-Pr H S 4-n-C3F7
Q8 8-28 3-I H i-Pr H S 4-i-C3F7
Q8 8-29 3-I H i-Pr H S 4-Me-5-Br
Q8 8-30 3-I H i-Pr H S 4-Me-5-C2F5
Q8 8-31 3-I H i-Pr H S 4-Me-5-n-C3F7
Q8 8-32 3-I H i-Pr H S 4-Me-5-i-C3F7
Q8 8-33 3-I H t-Bu H NMe 5-i-C3F7
Q8 8-34 3-I H t-Bu H NMe 5-C2F5
Q8 8-35 3-I H t-Bu H NMe 5-n-C3F7
Q8 8-36 3-I H CH(CH3)CH2SCH3 H NMe 4,5-Me2
Q8 8-37 3-I H CH(CH3)CH2SO2CH3 H NMe 4,5-Me2
Q8 8-38 3-I H CH(CH3)CH2SOCH3 H NMe 4,5-Me2
Q8 8-39 3-I H C(CH3)2CH2SCH3 H NMe 4,5-Me2
Q8 8-40 3-I H C(CH3)2CH2SOCH3 H NMe 4,5-Me2
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q8 8-41 3-I H C(CH3)2CH2SO2CH3 H NMe 4,5-Me2
Q8 8-42 3-I H CH(CH3)CH2NHAc H NMe 4,5-Me2
Q8 8-43 3-I H C(CH3)2CH2NHAc H NMe 4,5-Me2
Q8 8-44 3-I H CH(CH3)CH2CH2OCH3 H NMe 4,5-Me2
Q8 8-45 3-I H C(CH3)2CH2CH2OCH3 H NMe 4,5-Me2
Q8 8-46 3-I Et Et H O H
Q8 8-47 3-I Et Et H O 5-C2F5
Q8 8-48 3-I Et Et H O 4-n-C3F7
Q8 8-49 3-I Et Et H O 4-i-C3F7
Q8 8-50 3-I Et Et H O 5-Cl
Q8 8-51 3-I Et Et H O 5-Br
Q8 8-52 3-I Et Et H O 5-n-C3F7
Q8 8-53 3-I Et Et H S 4-(4-Cl-Ph) 139
Q8 8-54 3-CF3 H i-Pr H NMe 5-C2F5
Q8 8-55 3-Ph H i-Pr H NMe 4-n-C3F7
Q8 8-56 3-SOCF3 H i-Pr H NMe 4-i-C3F7
Q8 8-57 3-C2F5 H i-Pr H NMe 5-C2F5
Q8 8-58 3-I-4-Cl H i-Pr H NMe 4-n-C3F7
Q8 8-59 3-I-4-CF3 H i-Pr H S 4-i-C3F7
Q8 8-60 3-CF3-4-Cl H i-Pr H S 5-C2F5
Q8 8-61 3-OCF2O-4 H i-Pr H S 4-n-C3F7
Q8 8-62 3-OCF2CF2O-4 H i-Pr H S 4-i-C3F7
Q8 8-63 3-I H i-Pr H S 4-S-Et 86
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q8 8-64 6-I H i-Pr H S 4-S-Et 135
Q8 8-65 3-I H i-Pr H S 4-Me-5-CO2-Et
无定形固体
Q9 9-1 3-Cl H i-Pr H O H
Q9 9-2 3-Cl H i-Pr H O 5-Me-2-C2F5
Q9 9-3 3-Cl H i-Pr H O 2,5-Br2
Q9 9-4 3-Cl H i-Pr H S 2-Ph 131
Q9 9-5 3-Br H i-Pr H O 5-Me-2-n-C3F7
Q9 9-6 3-NO2 H i-Pr H O 5-Me-2-i-C3F7
Q9 9-7 3-I H i-Pr H O 5-Me-2-CF3
Q9 9-8 3-I H i-Pr H S H
Q9 9-9 3-I H i-Pr H S 2-Me
Q9 9-10 3-I H i-Pr H S 2-Cl
Q9 9-11 3-I H i-Pr H S 2-C2F5
Q9 9-12 3-I H i-Pr H S 2-n-C3F7
Q9 9-13 3-I H i-Pr H S 2-i-C3F7
Q9 9-14 3-I H i-Pr H S 5-Me-2-t-Bu
Q9 9-15 3-I H i-Pr H S 5-Me-2-I 135
Q9 9-16 3-I H i-Pr H S 5-Me-2-C2F5
Q9 9-17 3-I H i-Pr H S 5-Me-2-n-C3F7
Q9 9-18 3-I H i-Pr H S 5-Me-2-i-C3F7
Q9 9-19 3-I H i-Pr H S 5-Me-2-I 191
Q9 9-20 3-I H t-Bu H NMe 2-i-C3F7
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q9 9-21 3-I H t-Bu H NMe 2-C2F5
Q9 9-22 3-I H t-Bu H NMe 2-n-C3F7
Q9 9-23 3-I H t-Bu H NMe 5-Me-2-i-C3F7
Q9 9-24 3-I H CH(CH3)CH2SCH3 H S 5-Me-2-i-C3F7
Q9 9-25 3-I H CH(CH3)CH2SOCH3 H S 5-Me-2-i-C3F7
Q9 9-26 3-I H CH(CH3)CH2SO2CH3 H S 5-Me-2-i-C3F7
Q9 9-27 3-I H C(CH3)2CH2SCH3 H S 5-Me-2-i-C3F7
Q9 9-28 3-I H C(CH3)2CH2SOCH3 H S 5-Me-2-i-C3F7
Q9 9-29 3-I H C(CH3)2CH2SO2CH3 H S 5-Me-2-i-C3F7
Q9 9-30 3-I H CH(CH3)CH2NHAc H S 5-Me-2-i-C3F7
Q9 9-31 3-I H C(CH3)2CH2NHAc H S 5-Me-2-i-C3F7
Q9 9-32 3-I Et Et H O H
Q9 9-33 3-I Et Et H O 5-Me-2-C2F5
Q9 9-34 3-I Et Et H O 5-Me-2-n-C3F7
Q9 9-35 3-I Et Et H O 5-Me-2-i-C3F7
Q9 9-36 3-I Et Et H O 2-Cl
Q9 9-37 3-I Et Et H O 2-Br
Q9 9-38 3-I Et Et H O 2-n-C3F7
Q9 9-39 3-CF3 H i-Pr H NMe 5-Me-2-C2F5
Q9 9-40 3-Ph H i-Pr H NMe 5-Me-2-n-C3F7
Q9 9-41 3-SOCF3 H i-Pr H NMe 5-Me-2-i-C3F7
Q9 9-42 3-C2F5 H i-Pr H NMe 5-Me-2-C2F5
Q9 9-43 3-I-4-Cl H i-Pr H NMe 5-Me-2-n-C3F7
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q9 9-44 3-I-4-CF3 H i-Pr H S 5-Me-2-i-C3F7
Q9 9-45 3-CF3-4-Cl H i-Pr H S 5-Me-2-C2F5
Q9 9-46 3-OCF2O-4 H i-Pr H S 5-Me-2-n-C3F7
Q9 9-47 3-OCF2CF2O-4 H i-Pr H S 5-Me-2-i-C3F7
Q10 10-1 3-Cl H i-Pr H O H
Q10 10-2 3-Cl H i-Pr H O 4-Me-2-C2F5
Q10 10-3 3-Cl H i-Pr H O 2,4-Br2
Q10 10-4 3-Cl H i-Pr H O 2-Ph
Q10 10-5 3-Br H i-Pr H O 4-Me-2-n-C3F7
Q10 10-6 3-NO2 H i-Pr H O 4-Me-2-i-C3F7
Q10 10-7 3-I H i-Pr H S 4-Me 230
Q10 10-8 3-I H i-Pr H O 4-Me-2-CF3
Q10 10-9 3-I H i-Pr H S H
Q10 10-10 3-I H i-Pr H S 4-Me
Q10 10-11 3-I H i-Pr H S 2-Cl
Q10 10-12 3-I H i-Pr H S 2-C2F5
Q10 10-13 3-I H i-Pr H S 2-n-C3F7
Q10 10-14 3-I H i-Pr H S 2-i-C3F7
Q10 10-15 3-I H i-Pr H S 4-Me-2-t-Bu
Q10 10-16 3-I H i-Pr H S 4-Me-2-I
Q10 10-17 3-I H i-Pr H S 4-Me-2-C2F5
Q10 10-18 3-I H i-Pr H S 4-Me-2-n-C3F7
Q10 10-19 3-I H i-Pr H S 4-Me-2-i-C3F7
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q10 10-20 6-I H i-Pr H S 4-Me 198
Q10 10-21 3-I H t-Bu H NMe 2-i-C3F7
Q10 10-22 3-I H t-Bu H NMe 2-C2F5
Q10 10-23 3-I H t-Bu H NMe 2-n-C3F7
Q10 10-24 3-I H t-Bu H NMe 4-Me-2-i-C3F7
Q10 10-25 3-I H CH(CH3)CH2SCH3 H S 4-Me-2-i-C3F7
Q10 10-26 3-I H CH(CH3)CH2SOCH3 H S 4-Me-2-i-C3F7
Q10 10-27 3-I H CH(CH3)CH2SO2CH3 H S 4-Me-2-i-C3F7
Q10 10-28 3-I H C(CH3)2CH2SCH3 H S 4-Me-2-i-C3F7
Q10 10-29 3-I H C(CH3)2CH2SOCH3 H S 4-Me-2-i-C3F7
Q10 10-30 3-I H C(CH3)2CH2SO2CH3 H S 4-Me-2-i-C3F7
Q10 10-31 3-I H CH(CH3)CH2MHAc H S 4-Me-2-i-C3F7
Q10 10-32 3-I H C(CH3)2CH2NHAc H S 4-Me-2-i-C3F7
Q10 10-33 3-I Et Et H O H
Q10 10-34 3-I Et Et H O 4-Me-2-C2F5
Q10 10-35 3-I Et Et H O 4-Me-2-n-C3F7
Q10 10-36 3-I Et Et H O 4-Me-2-i-C3F7
Q10 10-37 3-I Et Et H O 2-Cl
Q10 10-38 3-I Et Et H O 2-Br
Q10 10-39 3-I Et Et H O 2-n-C3F7
Q10 10-40 3-CF3 H i-Pr H NMe 4-Me-2-C2F5
Q10 10-41 3-Ph H i-Pr H NMe 4-Me-2-n-C3F7
Q10 10-42 3-SOCF3 H i-Pr H NMe 4-Me-2-i-C3F7
表4(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q10 10-43 3-C2F5 H i-Pr H NMe 4-Me-2-C2F5
Q10 10-44 3-I-4-Cl H i-Pr H NMe 4-Me-2-n-C3F7
Q10 10-45 3-I-4-CF3 H i-Pr H S 4-Me-2-i-C3F7
Q10 10-46 3-CF3-4-Cl H i-Pr H S 4-Me-2-C2F5
Q10 10-47 3-OCF2O-4 H i-Pr H S 4-Me-2-n-C3F7
Q10 10-48 3-OCF2CF2O-4 H i-Pr H S 4-Me-2-i-C3F7
表5(Z1=Z2=O)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q13 13-1 3-Cl H i-Pr H S 4-Me
Q13 13-2 3-Cl H i-Pr H O 4-Me
Q13 13-3 3-Cl H i-Pr H NMe 4-Me
Q13 13-4 3-I H i-Pr H S H
Q13 13-5 3-I H i-Pr H S 4-Me 60
Q13 13-6 3-I H i-Pr H S 4-Cl
Q13 13-7 3-I H i-Pr H S 4-CF3
Q13 13-8 3-I H i-Pr H S 4-C2F5
Q13 13-9 3-I H i-Pr H S 4-n-C3F7
Q13 13-10 3-I H i-Pr H S 4-i-C3F7
Q13 13-11 3-I H i-Pr H S 4-t-Bu
Q13 13-12 6-I H i-Pr H S 4-Me 73
Q13 13-13 3-I H CH(CH3)CH2SCH3 H S 4-CF3
Q13 13-14 3-I H CH(CH3)CH2SOCH3 H S 4-CF3
Q13 13-15 3-I H CH(CH3)CH2SO2CH3 H S 4-CF3
Q13 13-16 3-I H C(CH3)2CH2SCH3 H S 4-CF3
Q13 13-17 3-I H C(CH3)2CH2SOCH3 H S 4-CF3
Q13 13-18 3-I H C(CH3)2CH2SO2CH3 H S 4-CF3
Q13 13-19 3-I H CH(CH3)CH2NHAc H S 4-CF3
Q13 13-20 3-I H C(CH3)2CH2NHAc H S 4-CF3
Q13 13-21 3-I H CH(CH3)CH2CH2OCH3 H S 4-CF3
Q13 13-22 3-I H C(CH3)2CH2CH2OCH3 H S 4-CF3
Q13 13-23 3-I Et Et H S H
表5(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q13 13-24 3-I Et Et H S 4-CF3
Q13 13-25 3-I Et Et H S 4-CF3
Q13 13-26 3-I Et Et H S 4-CF3
Q13 13-27 3-I Et Et H S 4-CF3
Q13 13-28 3-CF3 H i-Pr H S 3-C2F5
Q13 13-29 3-Ph H i-Pr H S 3-n-C3F7
Q13 13-30 3-SOCF3 H i-Pr H S 3-i-C3F7
Q13 13-31 3-C2F5 H i-Pr H S 3-C2F5
Q13 13-32 3-I-4-Cl H i-Pr H S 3-n-C3F7
Q13 13-33 3-I-4-CF3 H i-Pr H S 3-i-C3F7
Q13 13-34 3-CF3-4-Cl H i-Pr H S 3-C2F5
Q13 13-35 3-OCF2O-4 H i-Pr H S 3-n-C3F7
Q13 13-36 3-OCF2CF2O-4 H i-Pr H S 3-i-C3F7
表6(Z1=Z2=O)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q19 19-1 3-Cl H i-Pr H O H
Q19 19-2 3-Cl H i-Pr H O 5-C2F5
Q19 19-3 3-Cl H i-Pr H S 5-Me 166
Q19 19-4 3-Br H i-Pr H O 5-n-C3R7
Q19 19-5 3-NO2 H i-Pr H O 5-i-C3R7
Q19 19-6 3-I H i-Pr H S H
Q19 19-7 3-I H i-Pr H S 5-Me
Q19 19-8 3-I H i-Pr H S 5-Cl
Q19 19-9 3-I H i-Pr H S 5-CF3 104
Q19 19-10 3-I H i-Pr H S 5-C2R5
Q19 19-11 3-I H i-Pr H S 5-n-C3F7
Q19 19-12 3-I H i-Pr H S 5-i-C3F7
Q19 19-13 3-I H i-Pr H S 5-t-Bu
Q19 19-14 3-I H i-Pr H S 5-CF3 176
Q19 19-15 3-I H t-Bu H NMe 5-i-C3F7
Q19 19-16 3-I H t-Bu H NMe 5-C2F5
Q19 19-17 3-I H t-Bu H NMe 5-n-C3F7
Q19 19-18 3-I H t-Bu H NMe 5-CF3
Q19 19-19 3-I H CH(CH3)CH2SCH3 H S 5-i-C3F7
Q19 19-20 3-I H CH(CH3)CH2SOCH3 H S 5-i-C3F7
Q19 19-21 3-I H CH(CH3)CH2SO2CH3 H S 5-i-C3F7
Q19 19-22 3-I H C(CH3)2CH2SCH3 H S 5-i-C3F7
Q19 19-23 3-I H C(CH3)2CH2SOCH3 H S 5-i-C3F7
表6(续)
Q No. Xn R1 R2 R3 W Ym mp(℃)
Q19 19-24 3-I H C(CH3)2CH2SO2CH3 H S 5-i-C3F7
Q19 19-25 3-I H CH(CH3)CH2NHAc H S 5-i-C3F7
Q19 19-26 3-I H C(CH3)2CH2NHAc H S 5-i-C3F7
Q19 19-27 3-I H CH(CH3)CH2CH2OCH3 H S 5-i-C3F7
Q19 19-28 3-I H C(CH3)2CH2CH2OCH3 H S 5-i-C3F7
Q19 19-29 3-I Et Et H O H
Q19 19-30 3-I Et Et H O 5-C2F5
Q19 19-31 3-I Et Et H O 5-n-C3F7
Q19 19-32 3-I Et Et H O 5-i-C3F7
Q19 19-33 3-I Et Et H O 5-Cl
Q19 19-34 3-I Et Et H S 5-t-Bu 59
Q19 19-35 3-CF3 H i-Pr H NMe 5-C2F5
Q19 19-36 3-Ph H i-Pr H NMe 5-n-C3F7
Q19 19-37 3-SOCF3 H i-Pr H NMe 5-i-C3F7
Q19 19-38 3-C2F5 H i-Pr H NMe 5-C2F5
Q19 19-39 3-I-4-Cl H i-Pr H NMe 5-n-C3F7
Q19 19-40 3-I-4-CF3 H i-Pr H S 5-i-C3F7
Q19 19-41 3-CF3-4-Cl H i-Pr H S 5-C2F5
Q19 19-42 3-OCF2O-4 H i-Pr H S 5-n-C3F7
Q19 19-43 3-OCF2CF2O-4 H i-Pr H S 5-i-C3F7
表7(Z1=Z2=O)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q26 26-1 H H i-Pr H 3-Cl-5-CF3 85
Q26 26-2 3-Cl H i-Pr H H
Q26 26-3 3-Cl H i-Pr H 3-Me-5-C2F5
Q26 26-4 3-Br H i-Pr H 3-Me-5-n-C3F7
Q26 26-5 3-NO2 H i-Pr H 3-Me-5-i-C3F7
Q26 26-6 3-I H i-Pr H 5-C2F5
Q26 26-7 3-I H i-Pr H 5-n-C3F7
Q26 26-8 3-I H i-Pr H 5-i-C3F7
Q26 26-9 3-I H i-Pr H 3-Me-5-C2F5
Q26 26-10 3-I H i-Pr H 3-Me-5-n-C3F7
Q26 26-11 3-I H i-Pr H 3-Me-5-i-C3F7 140
Q26 26-12 3-I H i-Pr H 3-Me-4-C2F5
Q26 26-13 3-I H i-Pr H 3-Me-4-n-C3F7
Q26 26-14 3-I H i-Pr H 3-Me-4-i-C3F7
Q26 26-15 3-I H t-Bu H 5-i-C3F7
Q26 26-16 3-I H t-Bu H 5-C2F5
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q26 26-17 3-I H t-Bu H 5-n-C3F7
Q26 26-18 3-I H t-Bu H 3-Me-5-i-C3F7
Q26 26-19 3-I H CH(CH3)CH2SCH3 H 3-Me-5-i-C3F7
Q26 26-20 3-I H CH(CH3)CH2SOCH3 H 3-Me-5-i-C3F7
Q26 26-21 3-I H CH(CH3)CH2SO2CH3 H 3-Me-5-i-C3F7
Q26 26-22 3-I H C(CH3)2CH2SCH3 H 3-Me-5-i-C3F7
Q26 26-23 3-I H C(CH3)2CH2SOCH3 H 3-Me-5-i-C3F7
Q26 26-24 3-I H C(CH3)2CH2SO2CH3 H 3-Me-5-i-C3F7
Q26 26-25 3-I H CH(CH3)CH2SEt H 3-Me-5-i-C3F7
Q26 26-26 3-I H C(CH3)CH2SEt H 3-Me-5-i-C3F7
Q26 26-27 3-I H CH(CH3)CH2CH2SCH3 H 3-Me-5-i-C3F7
Q26 26-28 3-I H CH(CH3)2CH2CH2SCH3 H 3-Me-5-i-C3F7
Q26 26-29 3-I Et Et H 3-Me-5-C2F5 糊状
Q26 26-30 3-I Et Et H 3-Me-5-n-C3F7 糊状
Q26 26-31 3-I Et Et H 3-Me-5-i-C3F7 159
Q26 26-32 3-I Et Et H 5-Cl 127
Q26 26-33 3-I Et Et H 5-Br 154
Q26 26-34 3-CF3 H i-Pr H 3-Me-5-C2F5
Q26 26-35 3-Ph H i-Pr H 3-Me-5-n-C3F7
Q26 26-36 3-SOCF3 H i-Pr H 3-Me-5-i-C3F7
Q26 26-37 3-C2F5 H i-Pr H 3-Me-5-C2F5
Q26 26-38 3-I-4-Cl H i-Pr H 3-Me-5-n-C3F7
Q26 26-39 3-I-4-CF3 H i-Pr H 3-Me-5-i-C3F7
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q26 26-40 3-CF3-4-Cl H i-Pr H 3-Me-5-C2F5
Q26 26-41 3-OCF2O-4 H i-Pr H 3-Me-5-n-C3F7
Q26 26-42 3-OCF2CF2O-4 H i-Pr H 3-Me-5-i-C3F7
Q26 26-43 3-I H i-Pr H 3-Me-5-i-C3F7 140
Q27 27-1 H H i-Pr H H 139
Q27 27-2 H H i-Pr H 2-Me
Q27 27-3 H H i-Pr H 3-Me
Q27 27-4 H H i-Pr H 4-Me
Q27 27-5 H H i-Pr H 6-Me
Q27 27-6 H H i-Pr H 2-Cl
Q27 27-7 H H i-Pr H 3-Cl
Q27 27-8 H H i-Pr H 4-Cl
Q27 27-9 H H i-Pr H 6-Cl
Q27 27-10 3-Cl H i-Pr H 2-CF3
Q27 27-11 3-Cl H i-Pr H 3-CF3
Q27 27-12 3-Cl H i-Pr H 4-CF3
Q27 27-13 3-Cl H i-Pr H 6-CF3
Q27 27-14 3-Cl H i-Pr H 2-NO2
Q27 27-15 3-Cl H i-Pr H 3-NO2
Q27 27-16 3-Cl H i-Pr H 4-NO2
Q27 27-17 3-Cl H i-Pr H 6-NO2
Q27 27-18 3-Cl H i-Pr H 2-Et
Q27 27-19 3-Cl H i-Pr H 2-i-Pr
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-20 3-Cl H i-Pr H 2-t-Bu
Q27 27-21 3-Cl H i-Pr H 2-SCH3
Q27 27-22 3-Cl H i-Pr H 2-SOCH3
Q27 27-23 3-Cl H i-Pr H 2-SO2CH3
Q27 27-24 3-Cl H i-Pr H 2-SCF3
Q27 27-25 3-Cl H i-Pr H 2-SCHF2
Q27 27-26 3-Cl H i-Pr H 2-COCH3
Q27 27-27 3-Cl H i-Pr H 2-CN
Q27 27-28 3-Cl H i-Pr H 2-OCH3
Q27 27-29 3-Cl H i-Pr H 2-O-(4-Br-Ph) 101
Q27 27-30 3-Cl H i-Pr H 2-O-(2,4-Cl2-Ph) 97
Q27 27-31 3-Cl H i-Pr H 4-S-i-Pr 193
Q27 27-32 3-Cl H i-Pr H 4-S-i-Bu 183
Q27 27-33 3-Cl H i-Pr H 2-OCF2CCl2F
Q27 27-34 3-Cl H i-Pr H 2-OCH2CF3
Q27 27-35 3-Cl H i-Pr H 2-OCH2CF2CHF2
Q27 27-36 3-Cl H i-Pr H 2-CF2CF3
Q27 27-37 3-Cl H i-Pr H 2-COOCH(CF3)2
Q27 27-38 3-Cl H i-Pr H 2-Ph
Q27 27-39 3-Cl H n-Bu H 2-Cl
Q27 27-40 3-Cl H i-Bu H 2-Cl
Q27 27-41 3-Cl H s-Bu H 2-Cl
Q27 27-42 3-Cl H t-Bu H 2-Cl
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-43 3-Cl H c-C3H5 H 2-Cl
Q27 27-44 3-Cl H c-C4H7 H 2-Cl
Q27 27-45 3-Cl H c-C5H9 H 2-Cl
Q27 27-46 3-Cl H c-C6H11 H 2-Cl
Q27 27-47 3-Cl H CH2CH=CH2 H 2-Cl
Q27 27-48 3-Cl H CH2C≡CH H 2-Cl
Q27 27-49 3-Cl H CH2Ph H 2-Cl
Q27 27-50 3-Cl H C(CH3)2C≡CH H 2-Cl
Q27 27-51 3-Cl H C(CH3)2C≡CPh H 2-Cl
Q27 27-52 3-Cl H CH2CH2SCH3 H 2-Cl
Q27 27-53 3-Cl H CH2CH2SPh H 2-Cl
Q27 27-54 3-Cl H CH2CH2SO2Ph H 2-Cl
Q27 27-55 3-Cl H CH2CH2SO2CH3 H 2-Cl
Q27 27-56 3-Cl H CH2CH2CO2CH3 H 2-Cl
Q27 27-57 3-Cl H CH2CH2CONHCH3 H 2-Cl
Q27 27-58 3-Cl Et Et H 2-Cl
Q27 27-59 3-Cl n-Pr n-Pr H 2-Cl
Q27 27-60 3-Cl i-Pr i-Pr H 2-Cl
Q27 27-61 3-Cl i-Pr Me H 2-Cl
Q27 27-62 3-Cl i-Bu Me H 2-Cl
Q27 27-63 3-Cl CH2CH=CH2 CH2CH=CH2 H 2-Cl
Q27 27-64 3-Cl Et Et Me 2-Cl
Q27 27-65 3-Cl n-Pr i-Pr Me 2-Cl
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-66 3-Cl i-Pr i-Pr Me 2-Cl
Q27 27-67 3-Cl Et Et Ac 2-Cl
Q27 27-68 3-Cl n-Pr i-Pr Ac 2-Cl
Q27 27-69 3-Cl i-Pr i-Pr Ac 2-Cl
Q27 27-70 3-Cl -(CH2)4- H 2-Cl
Q27 27-71 3-Cl -(CH2)2O(CH2)2- H 2-Cl
Q27 27-72 3-Cl i-Pr SO2CH3 H 2-Cl
Q27 27-73 3-Cl i-Pr CN H 2-Cl
Q27 27-74 3-Cl i-Pr CO2CH3 H 2-Cl
Q27 27-75 3-Cl i-Pr COCH3 H 2-Cl
Q27 27-76 3-Cl i-Pr COPh H 2-Cl
Q27 27-77 3-Cl i-Pr NHCOCH3 H 2-Cl
Q27 27-78 3-Cl H i-Pr H 2,4-Me2
Q27 27-79 3-Cl H i-Pr H 2,4-Cl2
Q27 27-80 3-Cl H i-Pr H 4,6-Me2
Q27 27-81 3-Cl H i-Pr H 4-Me-2-Cl 211
Q27 27-82 3-Cl H i-Pr H 4-Me-2-F
Q27 27-83 3-Cl H i-Pr H 4-Me-2-Br
Q27 27-84 3-Cl H i-Pr H 4-Me-2-I
Q27 27-85 3-Cl H i-Pr H 4-Me-2-OCHF2
Q27 27-86 3-Cl H i-Pr H 4-Me-2-OCF3
Q27 27-87 3-Cl H i-Pr H 4-Me-2-NO2
Q27 27-88 3-Cl H i-Pr H 4-Me-2-NMe2
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-89 3-Cl H i-Pr H 4-Me-2-C≡CH
Q27 27-90 3-Cl H i-Pr H 4-Me-2-C≡C-t-Bu
Q27 27-91 3-Cl H i-Pr H 4-Me-2-C≡CPh
Q27 27-92 3-Cl H i-Pr H 4-Me-2-CF2CF3
Q27 27-93 3-Cl H i-Pr H 4-Me-2-i-C3F7
Q27 27-94 3-Cl H i-Pr H 4-Me-2-n-C3F7
Q27 27-95 3-Cl H i-Pr H 4-Me-2-OCH2OCH3
Q27 27-96 3-Cl H i-Pr H 4-Me-2-OCF2CHF2
Q27 27-97 3-Cl H i-Pr H 4-Me-2-OPh
Q27 27-98 3-Cl H i-Pr H 4-Me-2-O-(4-Br-Ph) 79
Q27 27-99 3-Cl H i-Pr H 4-Me-2-OSO2Ph
Q27 27-100 3-Cl H i-Pr H 4-Me-2-OCH2CO2CH3
Q27 27-101 3-Cl H i-Pr H 4-Me-2-CO2CH3
Q27 27-102 3-Cl H i-Pr H 4-Me-2-S-i-Pr
Q27 27-103 3-Cl H i-Pr H 4-Me-2-SCHF2
Q27 27-104 3-Cl H i-Pr H 4-Me-2-SOCHF2
Q27 27-105 3-Cl H i-Pr H 4-Me-2-SO2CHF2
Q27 27-106 3-Cl H i-Pr H 4-Cl-2-CF3
Q27 27-107 3-Cl H i-Pr H 4-Cl-2-OCF3
Q27 27-108 3-Cl H i-Pr H 4-Cl-2-i-C3F7
Q27 27-109 3-Cl H i-Pr H 4-Cl-2-C2F5
Q27 27-110 3-Cl H i-Pr H 4-Cl-2-OCHF2
Q27 27-111 3-Cl H i-Pr H 4-Cl-2-OSO2Ph
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-112 3-Cl H i-Pr H 4-OCH3-2-Ph
Q27 27-113 3-Cl H i-Pr H 4-CF3-2-Cl
Q27 27-114 3-Cl H i-Pr H 4-Me-3-CF3
Q27 27-115 3-Cl H i-Pr H 4-Me-3-Cl
Q27 27-116 3-Cl H i-Pr H 4-Me-3-OCF3
Q27 27-117 3-Cl H i-Pr H 4-Me-3-CF2CF3
Q27 27-118 3-Cl H i-Pr H 4-Me-3-n-C3F7
Q27 27-119 3-Cl H i-Pr H 4-Me-3-i-C3F7
Q27 27-120 3-Cl H i-Pr H 3,4-Me2-2-Cl
Q27 27-121 3-Cl H i-Pr H 3,4-Me2-2-OMe
Q27 27-122 3-Cl H i-Pr H 3,4-Me2-2-SMe
Q27 27-123 3-Cl H i-Pr H 4-Me-2,3-Cl2
Q27 27-124 6-Cl H i-Pr H 2-O-(4-Br-Ph) 170
Q27 27-125 6-Cl H i-Pr H 2-O-(2,4-Cl2-Ph) 189
Q27 27-126 6-Cl H i-Pr H 2-S-i-Pr 120
Q27 27-127 6-Cl H i-Pr H 2-S-i-Bu 187
Q27 27-128 6-Cl H i-Pr H 4-Me-2-Cl 230
Q27 27-129 3-I Et Et H 6-Cl-2-n-C3F7 122
Q27 27-130 3-I Et Et H 2-Cl 203
Q27 27-131 3-I Et Et H 2-n-C3F7 200
Q27 27-132 3-I Et Et H 2-O-(4-Br-Ph) 247
Q27 27-133 3-I H i-Pr H 2-Cl 215
Q27 27-134 3-I H i-Pr H 2-C2F5 无定形固体
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-135 3-I H i-Pr H 2-n-C3F7 200
Q27 27-136 3-I H i-Pr H 2-i-C3R7 270
Q27 27-137 3-I H i-Pr H 4-Me-2-i-C3F7 257
Q27 27-138 3-I H i-Pr H 6-Me-2-i-C3F7 234
Q27 27-139 3-I H t-Bu H 2-i-C3F7 275
Q27 27-140 3-I H t-Bu H 2-C2F5 260
Q27 27-141 3-I H t-Bu H 2-n-C3F7 245
Q27 27-142 3-I H t-Bu H 4-Me-2-i-C3F7 250
Q27 27-143 3-I H t-Bu H 6-Me-2-i-C3F7 246
Q27 27-144 3-I H CH(CH3)CH2SCH3 H 4-Me-2-i-C3F7 225
Q27 27-145 3-I H CH(CH3)CH2SCH3 H 6-Me-2-i-C3F7 229
Q27 27-146 3-I H CH(CH3)CH2SOCH3 H 4-Me-2-i-C3F7
Q27 27-147 3-I H CH(CH3)CH2SOCH3 H 6-Me-2-i-C3F7
Q27 27-148 3-I H CH(CH3)CH2SO2CH3 H 4-Me-2-i-C3F7
Q27 27-149 3-I H CH(CH3)CH2SO2CH3 H 6-Me-2-i-C3F7
Q27 27-150 3-I H C(CH3)2CH2SCH3 H 4-Me-2-i-C3F7 173
Q27 27-151 3-I H C(CH3)2CH2SCH3 H 6-Me-2-i-C3F7 213
Q27 27-152 3-I H C(CH3)2CH2SOCH3 H 4-Me-2-i-C3F7
Q27 27-153 3-I H C(CH3)2CH2SOCH3 H 6-Me-2-i-C3F7 无定形
Q27 27-154 3-I H C(CH3)2CH2SO2CH3 H 4-Me-2-i-C3F7
Q27 27-155 3-I H C(CH3)2CH2SO2CH3 H 6-Me-2-i-C3F7
Q27 27-156 3-I H i-Pr H 4-Me-2-i-C3F7
Q27 27-157 3-I H t-Bu H 6-Me-2-i-C3F7
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-158 3-F H C(CH3)2CH2SCH3 H 4-Me-2-i-C3F7
Q27 27-159 3-F H C(CH3)2CH2SCH3 H 6-Me-2-i-C3F7
Q27 27-160 3-Br H i-Pr H 4-Me-2-i-C3F7
Q27 27-161 3-Br H t-Bu H 6-Me-2-i-C3F7
Q27 27-162 3-Br H CH(CH3)CH2SCH3 H 4-Me-2-i-C3F7
Q27 27-163 3-Br H C(CH3)2CH2SCH3 H 6-Me-2-i-C3F7
Q27 27-164 3-NO2 H i-Pr H H 209
Q27 27-165 3-NO2 H i-Pr H 4-Me-2-CF2CF3
Q27 27-166 3-NO2 H i-Pr H 4-Me-2-n-C3F7
Q27 27-167 3-NO2 H i-Pr H 4-Me-2-i-C3F7
Q27 27-168 3-NO2 H i-Pr H 6-Me-2-CF2CF3
Q27 27-169 3-NO2 H i-Pr H 6-Me-2-n-C3F7
Q27 27-170 3-NO2 H i-Pr H 6-Me-2-i-C3F7
Q27 27-171 3-NO2 H i-Pr H 4-Me-2-Cl
Q27 27-172 3-CN Et Et H 4-Me-2-CF2CF3
Q27 27-173 3-CN Et Et H 4-Me-2-n-C3F7
Q27 27-174 3-CN Et Et H 4-Me-2-i-C3F7
Q27 27-175 3-CN Et Et H 6-Me-2-CF2CF3
Q27 27-176 3-CN Et Et H 6-Me-2-n-C3F7
Q27 27-177 3-CN Et Et H 6-Me-2-i-C3F7
Q27 27-178 3-CN Et Et H 4-Me-2-Cl
Q27 27-179 3-CF3 H i-Pr H 4-Me-2-CF2CF3
Q27 27-180 3-CF3 H i-Pr H 6-Me-2-n-C3F7
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-181 3-OCH3 H i-Pr H 4-Me-2-i-C3F7
Q27 27-182 3-OCH3 H i-Pr H 6-Me-2-CF2CF3
Q27 27-183 3-OCH3 H i-Pr H 4-Me-2-n-C3F7
Q27 27-184 3-OCH3 H i-Pr H 6-Me-2-i-C3F7
Q27 27-185 3-SCH3 H i-Pr H 4-Me-2-CF2CF3
Q27 27-186 3-SCH3 H i-Pr H 6-Me-2-n-C3F7
Q27 27-187 3-S-i-Pr H i-Pr H 4-Me-2-i-C3F7
Q27 27-188 3-S-i-Pr H i-Pr H 6-Me-2-CF2CF3
Q27 27-189 3-SOCH3 H i-Pr H 4-Me-2-n-C3F7
Q27 27-190 3-SOCH3 H i-Pr H 6-Me-2-i-C3F7
Q27 27-191 3-SO2CH3 H i-Pr H 4-Me-2-CF2CF3
Q27 27-192 3-SO2CH3 H i-Pr H 6-Me-2-n-C3F7
Q27 27-193 3-SCH2CF3 H i-Pr H 4-Me-2-i-C3F7
Q27 27-194 3-SCF3 H i-Pr H 4-Me-2-CF2CF3
Q27 27-195 3-SOCF3 H i-Pr H 4-Me-2-n-C3F7
Q27 27-196 3-SO2CF3 H i-Pr H 4-Me-2-i-C3F7
Q27 27-197 3-SPh H i-Pr H 6-Me-2-CF2CF3
Q27 27-198 3-SOPh H i-Pr H 6-Me-2-n-C3F7
Q27 27-199 3-SO2Ph H i-Pr H 6-Me-2-i-C3F7
Q27 27-200 3-OPh H i-Pr H 4-Me-2-CF2CF3
Q27 27-201 3-Ph H i-Pr H 4-Me-2-i-C3F7
Q27 27-202 3-C≡CH H i-Pr H 4-Me-2-i-C3F7
Q27 27-203 3-C≡C-t-Bu H i-Pr H 4-Me-2-i-C3F7
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-204 3-C≡CPh H i-Pr H 4-Me-2-i-C3F7
Q27 27-205 3-C2F5 H i-Pr H 4-Me-2-i-C3F7
Q27 27-206 3-CO2CH3 H i-Pr H 6-Me-2-i-C3F7
Q27 27-207 3-CONHCH3 H i-Pr H 6-Me-2-i-C3F7
Q27 27-208 3-COCH3 H i-Pr H 6-Me-2-i-C3F7
Q27 27-209 3-CCH3(=NOCH3) H i-Pr H 6-Me-2-i-C3F7
Q27 27-210 3,4-Cl2 H i-Pr H 4-Me-2-i-C3F7
Q27 27-211 3,6-Cl2 H i-Pr H 4-Me-2-n-C3F7
Q27 27-212 3,5-Cl2 H i-Pr H 4-Me-2-i-C3F7
Q27 27-213 3,5-Cl2 H i-Pr H 6-Me-2-CF2CF3
Q27 27-214 4,5-Cl2 H i-Pr H 4-Me-2-n-C3F7
Q27 27-215 4,5-Cl2 H i-Pr H 6-Me-2-i-C3F7
Q27 27-216 3-I-4-Cl H i-Pr H 4-Me-2-CF2CF3
Q27 27-217 3-I-4-F H i-Pr H 4-Me-2-n-C3F7
Q27 27-218 3-I-4CF3 H i-Pr H 4-Me-2-i-C3F7
Q27 27-219 3-I-4-OCH3 H i-Pr H 4-Me-2-CF2CF3
Q27 27-220 3-CF3-4-Cl H i-Pr H 4-Me-2-n-C3F7
Q27 27-221 3-CF3-4-OCH3 H i-Pr H 6-Me-2-i-C3F7
Q27 27-222 3-OCH2O-4 H i-Pr H 6-Me-2-i-C3F7
Q27 27-223 3-OCF2O-4 H i-Pr H 6-Me-2-CF2CF3
Q27 27-224 3-OCH2CH2O-4 H i-Pr H 6-Me-2-n-C3F7
Q27 27-225 3-OCF2CF2O-4 H i-Pr H 6-Me-2-i-C3F7
Q27 27-226 3-CH=CH-CH=CH-4 H i-Pr H 6-Me-2-i-C3F7
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-227 3-I H i-Pr H 4-Me-3-CF2CF3
Q27 27-228 3-I H i-Pr H 4-Me-3-i-C3F7
Q27 27-229 3-I H i-Pr H 4-Me-3-n-C3F7
Q27 27-230 3-I H i-Pr H 6-Cl-2-i-C3F7 188
Q27 27-231 3-I Et Et H 6-Cl-2-i-C3F7 164
Q27 27-232 3-I H CH(Me)CH2SMe H 6-Cl-2-i-C3F7 177
Q27 27-233 3-I H C(Me)2CH2SMe H 2-i-C3F7 229
Q27 27-234 3-I H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 175
Q27 27-235 3-I H C(Me)2CH2SOMe H 6-Cl-2-i-C3F7 糊状
Q27 27-236 3-I H C(Me)2CH2SO2Me H 6-Cl-2-i-C3F7 无定形
Q27 27-237 3-I H C(Me)2CH2SMe H 6-i-C3F7 183
Q27 27-238 3-I H C(Me)2CH2SOMe H 6-i-C3F7 无定形
Q27 27-239 3-I H C(Me)2CH2SO2Me H 6-i-C3F7 无定形
Q27 27-240 3-I H C(Me)2CH2SMe H 4,6-Cl2-2-i-C3F7 120
Q27 27-241 3-I H CH(Me)CH2SMe H 6-MeO-2-i-C3F7 134
Q27 27-242 3-I H i-Pr H 6-MeO-2-i-C3F7 158
Q27 27-243 3-I H C(Me)2CH2SMe H 6-MeO-2-i-C3F7 134
Q27 27-244 3-I H C(Me)2CH2SOMe H 6-MeO-2-i-C3F7 无定形
Q27 27-245 3-I H C(Me)2CH2SMe H 6-MeS-2-i-C3F7 179
Q27 27-246 3-I H i-Pr H 6-MeS-2-i-C3F7 219
Q27 27-247 3-I H i-Pr H 6-MeSO-2-i-C3F7 无定形
Q27 27-248 3-I H C(Me)2CH2SMe H 2-OCHF2 198
Q27 27-249 3-I H C(Me)2CH2SO2Me H 2-OCHF2 207
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-250 3-I H i-Pr H 2-OCHF2 205
Q27 27-251 3-I H C(Me)2CH2SMe H 2-SCHF2 174
Q27 27-252 3-I H i-Pr H 2-SCHF2 226
Q27 27-253 3-I H i-Pr H 2-SO2CHF2 230
Q27 27-254 3-I H i-Pr H 6-Me-2-OCHF2 252
Q27 27-255 3-I H C(Me)2CH2SMe H 6-Me-2-OCHF 124
Q27 27-256 3-I H C(Me)2CH2SOMe H 6-Me-2-OCHF2 185
Q27 27-257 3-I H C(Me)2CH2SO2Me H 6-Me-2-OCHF2 102
Q27 27-258 3-I H i-Pr H 6-Me-2-SCHF2 226
Q27 27-259 3-I H C(Me)2CH2SMe H 6-Me-2-SCHF2 198
Q27 27-260 3-I H i-Pr H 6-Me-2-OCH(CF3)2 266
Q27 27-261 3-I H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2 223
Q27 27-262 3-I H i-Pr H 6-Cl-2-OCH(CF3)2 216
Q27 27-263 3-I H C(Me)2CH2SMe H 6-Cl-2-OCH(CF3)2 100
Q27 27-264 3-I H C(Me)2CH2SOMe H 6-Me-2-OCH(CF3)2 168
Q27 27-265 3-I H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2 134
Q27 27-266 3-I H C(Me)2CH2SOMe H 6-Cl-2-OCH(CF3)2
Q27 27-267 3-I H C(Me)2CH2SO2Me H 6-Cl-2-OCH(CF3)2 121
Q27 27-268 3-I H C(Me)2CH2SMe H 6-OMe-2-OCH(CF3)2 159
Q27 27-269 3-I H C(Me)2CH2SMe H 6-F-2-OCH(CF3)2
Q27 27-270 3-I H i-Pr H OCH(CF3)2 240
Q27 27-271 3-I H t-Bu H OCH(CF3)2
Q27 27-272 3-I H CH(Me)CH2SMe H OCH(CF3)2
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-273 3-I H C(Me)2CH2SMe H OCH(CF3)2 237
Q27 27-274 3-I H i-Pr H 2-Me-6-OCH(CF3)2 232
Q27 27-275 3-I H C(Me)2CH2SMe H 2-Me-6-OCH(CF3)2 171
Q27 27-276 3-Cl H i-Pr H 4-Me-2-OCH(CF3)2 226
Q27 27-277 3-I H i-Pr H 4-Me-2-OCH(CF3)2 248
Q27 27-278 3-I H C(Me)2CH2SMe H 4-Me-2-OCH(CF3)2 200
Q27 27-279 3-I H C(Me)2CH2SOMe H 4-Me-2-OCH(CF3)2 118
Q27 27-280 3-I H C(Me)2CH2SO2Me H 4-Me-2-OCH(CF3)2 112
Q27 27-281 3-I H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-282 3-I H CH(Me)CH2SEt H 6-Me-2-OCH(CF3)2 256
Q27 27-283 H H i-Pr H 6-Me-2-OCH(CF3)2 235
Q27 27-284 H H t-Bu H 6-Me-2-OCH(CF3)2 255
Q27 27-285 H H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-286 H H CH(Me)CH2SOMe H 6-Me-2-OCH(CF3)2
Q27 27-287 H H CH(Me)CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-288 H H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-289 H H C(Me)2CH2SOMe H 6-Me-2-OCH(CF3)2 108
Q27 27-290 H H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-291 3-F H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-292 3-F H t-Bu H 6-Me-2-OCH(CF3)2
Q27 27-293 3-F H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-294 3-F H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-295 3-F H C(Me)2CH2SOMe H 6-Me-2-OCH(CF3)2
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-296 3-F H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-297 3-Cl H i-Pr H 6-Me-2-OCH(CF3)2 257
Q27 27-298 3-Cl H t-Bu H 6-Me-2-OCH(CF3)2 255
Q27 27-299 3-Cl Et Et H 6-Me-2-OCH(CF3)2
Q27 27-300 3-Cl H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-301 3-Cl H CH(Me)CH2SOMe H 6-Me-2-OCH(CF3)2
Q27 27-302 3-Cl H CH(Me)CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-303 3-Cl H CH(Me)CH2SEt H 6-Me-2-OCH(CF3)2
Q27 27-304 3-Cl H CH(Me)CH2SO2Et H 6-Me-2-OCH(CF3)2
Q27 27-305 3-Cl H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2 236
Q27 27-306 3-Cl H C(Me)2CH2SOMe H 6-Me-2-OCH(CF3)2 115
Q27 27-307 3-Cl H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2 221
Q27 27-308 3-Br H i-Pr H 6-Me-2-OCH(CF3)2 252
Q27 27-309 3-Br H t-Bu H 6-Me-2-OCH(CF3)2 255
Q27 27-310 3-Br Et Et H 6-Me-2-OCH(CF3)2
Q27 27-311 3-Br H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-312 3-Br H CH(Me)CH2SOMe H 6-Me-2-OCH(CF3)2
Q27 27-313 3-Br H CH(Me)CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-314 3-Br H CH(Me)CH2SEt H 6-Me-2-OCH(CF3)2
Q27 27-315 3-Br H CH(Me)CH2SO2Et H 6-Me-2-OCH(CF3)2
Q27 27-316 3-Br H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2 228
Q27 27-317 3-Br H C(Me)2CH2SOMe H 6-Me-2-OCH(CF3)2 115
Q27 27-318 3-Br H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2 225
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-319 3-I H Me H 6-Me-2-OCH(CF3)2
Q27 27-320 3-I H Et H 6-Me-2-OCH(CF3)2
Q27 27-321 3-I H n-Pr H 6-Me-2-OCH(CF3)2
Q27 27-322 3-I H c-C3H5 H 6-Me-2-OCH(CF3)2
Q27 27-323 3-I H n-Bu H 6-Me-2-OCH(CF3)2 261
Q27 27-324 3-I H s-Bu H 6-Me-2-OCH(CF3)2 274
Q27 27-325 3-I H t-Bu H 6-Me-2-OCH(CF3)2 241
Q27 27-326 3-I H i-Bu H 6-Me-2-OCH(CF3)2 264
Q27 27-327 3-I Et Et H 6-Me-2-OCH(CF3)2 165
Q27 27-328 3-I Me i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-329 3-Cl-4-F H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-330 3-Cl-4-F H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-331 3-Cl-4-F H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-332 3,4-Cl2 H i-Pr H 6-Me-2-OCH(CF3)2 267
Q27 27-333 3,4-Cl2 H t-Bu H 6-Me-2-OCH(CF3)2
Q27 27-334 3,4-Cl2 H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2 210
Q27 27-335 3,4-Cl2 H CH(Me)CH2SOMe H 6-Me-2-OCH(CF3)2
Q27 27-336 3,4-Cl2 H CH(Me)CH2SO2Me H 6-Me-2-OCH(CF3)2 126
Q27 27-337 3,4-Cl2 H CH(Me)CH2SEt H 6-Me-2-OCH(CF3)2 205
Q27 27-338 3,4-Cl2 H CH(Me)CH2SOEt H 6-Me-2-OCH(CF3)2 119
Q27 27-339 3,4-Cl2 H CH(Me)CH2SO2Et H 6-Me-2-OCH(CF3)2 111
Q27 27-340 3,4-Cl2 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-341 3-Br-4-Cl H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-342 3,4-Br2 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-343 3-I-4-F H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-344 3-I-4-Cl H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-345 3-I-4-Br H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-346 3,4-I2 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-347 3-NO2 H i-Pr H 6-Me-2-OCH(CF3)2 207
Q27 27-348 3-NO2 H t-Bu H 6-Me-2-OCH(CF3)2
Q27 27-349 3-NO2 Et Et H 6-Me-2-OCH(CF3)2
Q27 27-350 3-NO2 H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-351 3-NO2 H CH(Me)CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-352 3-NO2 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2 244
Q27 27-353 3-NO2 H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2 230
Q27 27-354 3-CF3 H i-Pr H 6-Me-2-OCH(CF3)2 211
Q27 27-355 3-CF3 H t-Bu H 6-Me-2-OCH(CF3)2 246
Q27 27-356 3-CF3 Et Et H 6-Me-2-OCH(CF3)2
Q27 27-357 3-CF3 H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-358 3-CF3 H CH(Me)CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-359 3-CF3 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2 226
Q27 27-360 3-CF3 H C(Me)2CH2SOMe H 6-Me-2-OCH(CF3)2 112
Q27 27-361 3-CF3 H C(Me)2CH2SO2Me H 6-Me-2-OCH(CF3)2
Q27 27-362 3-OCF3 H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-363 3-OCF3 H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-364 3-OCF3 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-365 3-SCF3 H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-366 3-SCF3 H CH(Me)CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-367 3-SCF3 H C(Me)2CH2SMe H 6-Me-2-OCH(CF3)2
Q27 27-368 3-SOCF3 H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-369 3-SO2CF3 H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-370 3-Me H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-371 3-Et H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-372 5-t-Bu H i-Pr H 6-Me-2-OCH(CF3)2 280
Q27 27-373 3-C≡CH H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-374 3-C≡CCF3 H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-375 3-C≡C-t-Bu H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-376 3-C≡C-SiMe3 H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-377 3-C≡C-Ph H i-Pr H 6-Me-2-OCH(CF3)2
Q27 27-378 3-I H i-Pr H 6-Me-2-OCF2CHF2 217
Q27 27-379 3-I H t-Bu H 6-Me-2-OCF2CHF2
Q27 27-380 3-I Et Et H 6-Me-2-OCF2CHF2
Q27 27-381 3-I H CH(Me)CH2SMe H 6-Me-2-OCF2CHF2
Q27 27-382 3-I H CH(Me)CH2SOMe H 6-Me-2-OCF2CHF2
Q27 27-383 3-I H CH(Me)CH2SO2Me H 6-Me-2-OCF2CHF2
Q27 27-384 3-I H C(Me)2CH2SMe H 6-Me-2-OCF2CHF2 99
Q27 27-385 3-I H C(Me)2CH2SOMe H 6-Me-2-OCF2CHF2
Q27 27-386 3-I H C(Me)2CH2SO2Me H 6-Me-2-OCF2CHF2
Q27 27-387 3-I H i-Pr H 6-Cl-2-OCF2CHF2 200
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-388 3-I H C(Me)2CH2SMe H 6-Cl-2-OCF2CHF2 142
Q27 27-389 3-I H C(Me)2CH2SOMe H 6-Cl-2-OCF2CHF2
Q27 27-390 3-I H C(Me)2CH2SO2Me H 6-Cl-2-OCF2CHF2
Q27 27-391 3-I H i-Pr H 6-Me-2-OCF2CHFCF3 205
Q27 27-392 3-I H CH(Me)CH2SMe H 6-Me-2-OCF2CHFCF3
Q27 27-393 3-I H C(Me)2CH2SMe H 6-Me-2-OCF2CHFCF3 158
Q27 27-394 3-I H i-Pr H 6-Me-2-OCF2CHFCF3
Q27 27-395 3-I H CH(Me)CH2SMe H 6-Me-2-OCF2CHFCF3
Q27 27-396 3-I H C(Me)2CH2SMe H 6-Me-2-OCF2CHFCF3 126
Q27 27-397 3-I H i-Pr H 6-Me-2-OCF2CHFOC3F7-n 194
Q27 27-398 3-I H t-Bu H 6-Me-2-OCF2CHFOC3F7-n
Q27 27-399 3-I H CH(Me)CH2SMe H 6-Me-2-OCF2CHFOC3F7-n
Q27 27-400 3-I H CH(Me)CH2SOMe H 6-Me-2-OCF2CHFOC3F7-n
Q27 27-401 3-I H CH(Me)CH2SO2Me H 6-Me-2-OCF2CHFOC3F7-n
Q27 27-402 3-I H C(Me)2CH2SMe H 6-Me-2-OCF2CHFOC3F7-n 91
Q27 27-403 3-I H C(Me)2CH2SOMe H 6-Me-2-OCF2CHFOC3F7-n 81
Q27 27-404 3-I H C(Me)2CH2SO2Me H 6-Me-2-OCF2CHFOC3F7-n 157
Q27 27-405 3-I H i-Pr H 6-Cl-2-OCF2CHFOC3F7-n 205
Q27 27-406 3-I H t-Bu H 6-Cl-2-OCF2CHFOC3F7-n
Q27 27-407 3-I H CH(Me)CH2SMe H 6-Cl-2-OCF2CHFOC3F7-n 106
Q27 27-408 3-I H CH(Me)CH2SOMe H 6-Cl-2-OCF2CHFOC3F7-n
Q27 27-409 3-I H CH(Me)CH2SO2Me H 6-Cl-2-OCF2CHFOC3F7-n
Q27 27-410 3-I H C(Me)2CH2SMe H 6-Cl-2-OCF2CHFOC3F7-n
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-411 3-I H C(Me)2CH2SOMe H 6-Cl-2-OCF2CHFOC3F7-n
Q27 27-412 3-I H C(Me)2CH2SO2Me H 6-Cl-2-OCF2CHFOC3F7-n
Q27 27-413 3-I H i-Pr H 6-Me-2-OCH2C2F5 259
Q27 27-414 3-I H CH(Me)CH2SMe H 6-Me-2-OCH2C2F5 208
Q27 27-415 3-I H C(Me)2CH2SMe H 6-Me-2-OCH2C2F5
Q27 27-416 3-I H i-Pr H 6-Me-2-OCH2-n-C3F7
Q27 27-417 3-I H CH(Me)CH2SMe H 6-Me-2-OCH2-n-C3F7
Q27 27-418 3-I H C(Me)2CH2SMe H 6-Me-2-OCH2-n-C3F7
Q27 27-419 3-I H i-Pr H 6-Me-2-O-(2,4-Cl2-Ph)
Q27 27-420 3-I H C(Me)2CH2SMe H 6-Me-2-O-(2,4-Cl2-Ph)
Q27 27-421 3-I H i-Pr H 6-Me-2-O-(2-Cl-4-CF3-Ph)
Q27 27-422 3-I H C(Me)2CH2SMe H 6-Me-2-O-(2-Cl-4-CF3-Ph)
Q27 27-423 3-I H i-Pr H 6-Me-2-SCF3
Q27 27-424 3-I H CH(Me)CH2SMe H 6-Me-2-SCF3
Q27 27-425 3-I H C(Me)2CH2SMe H 6-Me-2-SCF3
Q27 27-426 3-I H C(Me)2CH2SOMe H 6-Me-2-SCF3
Q27 27-427 3-I H C(Me)2CH2SO2Me H 6-Me-2-SCF3
Q27 27-428 3-I H C(Me)2CH2SO2Me H 6-Me-2-SOCF3
Q27 27-429 3-I H C(Me)2CH2SO2Me H 6-Me-2-SO2CF3
Q27 27-430 3-I H i-Pr H 6-Me-2-SC2F5
Q27 27-431 3-I H C(Me)2CH2SMe H 6-Me-2-SC2F5
Q27 27-432 3-I H i-Pr H 6-Me-2-S-n-C3F7
Q27 27-433 3-I H C(Me)2CH2SMe H 6-Me-2-S-n-C3F7
Q27 27-436 3-I H C(Me)2CH2SMe H 6-Me-2-S-CH(CF3)2
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-434 3-I H i-Pr H 6-Me-2-SCF2CHF2
Q27 27-435 3-I H CH(Me)CH2SMe H 6-Me-2-SCF2CHFCF3
Q27 27-437 3-I H i-Pr H 6-Me-2-NHCOCF3
Q27 27-438 3-I H i-Pr H 6-Me-2-NHCOC2F5 192
Q27 27-439 3-I H C(Me)2CH2SMe H 6-Me-2-NHCOC2F5 205
Q27 27-440 3-I H i-Pr H 6-Me-2-NHCOC3F7-n
Q27 27-441 3-I H C(Me)2CH2SMe H 6-Me-2-NHCOC3F7-n
Q27 27-442 3-I H C(Me)2CH2SMe H 6-Me-2-NHCO-(2,4-Cl2-Ph)
Q27 27-443 3-I H i-Pr H 6-Me-2-NHCO-(4-CF3-Ph)
Q27 27-444 3-I H C(Me)2CH2SMe H 6-Me-2-N(COC2F5)2
Q27 27-445 3-I H C(Me)2CH2SMe H 6-Me-2-NHCH2CF3
Q27 27-446 3-I H C(Me)2CH2SMe H 6-Me-2-NHCH2CF3
Q27 27-447 3-I H C(Me)2CH2SMe H 6-Me-2-NHCH2C2F5
Q27 27-448 3-I H C(Me)2CH2SMe H 6-Me-2-Cl 173
Q27 27-449 3-CF3 H C(Me)2CH2SMe H 6-Me-2-i-C3F7 214
Q27 27-450 H H C(Me)2CH2SMe H 6-Me-2-i-C3F7 155
Q27 27-451 3-F H C(Me)2CH2SMe H 6-Me-2-i-C3F7 202
Q27 27-452 3-F H C(Me)2CH2SO2Me H 6-Me-2-i-C3F7 197
Q27 27-453 3-Br H C(Me)2CH2SMe H 6-Me-2-i-C3F7 206
Q27 27-454 3-Br H C(Me)2CH2SO2Me H 6-Me-2-i-C3F7 225
Q27 27-455 3,4-Cl2 H C(Me)2CH2SMe H 6-Me-2-i-C3F7 259
Q27 27-456 3-CF3 H i-Pr H 6-Me-2-i-C3F7 221
表7(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q27 27-457 H H i-Pr H 6-Cl-2-i-C3F7 200
Q27 27-458 H H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 110
Q27 27-459 3-Cl H i-Pr H 6-Cl-2-i-C3F7 181
Q27 27-460 3-I H t-Eu H 6-Cl-2-i-C3F7 191
Q27 27-461 3-F H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 182
Q27 27-462 3-Cl H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 161
Q27 27-463 3,4-Cl2 H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 153
Q27 27-464 3-CF3 H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 165
Q27 27-465 3-NO2 H C(Me)2CH2SMe H 6-Cl-2-i-C3F7 235
Q27 27-466 3-I H i-Pr H 6-Me-2-O(4-CF3-Ph) 238
Q27 27-467 3-I H C(Me)2CH2SMe H 6-Me-2-O(4-CF3-Ph) 111
Q27 27-468 3-I H C(Me)2CH2SOMe H 6-Me-2-O(4-CF3-Ph) 106
Q27 27-469 3-I H C(Me)2CH2SO2Me H 6-Me-2-O(4-CF3-Ph) 97
Q27 27-470 3-CF3 H C(Me)2CH2SMe H 6-Me-2-OCF2CHFOCF3
无定形
Q27 27-471 3-I H i-Pr H 6-Me-2-OCF=CFCF3 165
Q27 27-472 3-I H i-Pr H 6-Me-2-OCF2CHFOCF3 185
表7中,有些化合物是无定形或糊状的。这样的化合物的1H-NMR数据如下所示。
No 1H-NMR[δ(ppm/CDCl3)]
27-153 1.59(s.3H),1.64(s.3H),2.26(s.3H),2.62(s.3H),
2.88(d.1H),3.02(d.1H),6.83(br.1H),7.23(t.1H),
7.58(dd.1H),7.78(d.1H),8.00(dd.1H),8.58(br.
1H),8.81(d.1H).
27-235 1.64(s.3H),1.66(s.3H),2.40(s.3H),2.88(d.1H),
3.24(d.1H),6.72(br.1H),7.24(t.1H),7.70(dd.1H),
7.74(d.1H),8.03(dd.1H),8.85(br.1H),9.12(d.1H).
27-236 1.71(s.6H),2.71(s.3H),3.63(s.2H),6.25(br.1H),
7.25(t.1H),7.70(dd.1H),7.75(dd.1H),8.05(dd.
1H),8.81(br.1H),9.11(d.1H).
27-238 1.68(s.3H),1.72(s.3H),2.49(s.3H),2.99(d.1H),
3.21(d.1H),6.76(br.1H),7.21(t.1H),7.50(dd.1H),
7.66(dd.1H),7.84(dd.1H),8.37(dd.1H),8.68(d.
1H),9.75(br.1H).
27-239 1.80(s.6H),2.87(s.3H),3.73(s.2H),6.23(br.1H),
7.23(t.1H),7.43(dd.1H),7.65(dd.1H),7.82(dd.
1H),8.35(dd.1H),8.64(d.1H),9.88(br.1H).
27-244 1.60(s.3H),1.63(s.3H),2.41(s.3H),2.84(d.1H),
3.31(d.1H),4.02(s.1H),6.59(br.1H),7.21(t.1H),
7.34(dd.1H),7.69(dd.1H),7.99(dd.1H),8.65(br.
1H),8.88(d.1H).
27-247 1.31(dd.6H),3.50(s.3H),4.33(m.1H),5.60(d.1H),
7.19(t.1H),7.68(d.1H),7.74(dd.1H),8.00(d.1H),
9.26(d.1H),11.8(br.1H).
27-470 1.42(s.6H),1.96(s.3H),2.53(s.3H),2.81(s.2H),
6.17(s.1H),6.62(dt.1H),6.90(d.1H),7.66(t.1H),
7.85(d.1H),8.03(d.1H),8.63(d.1H),8.71(s.1H).
表8(Z1=Z2=O)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q29 29-1 3-Cl H i-Pr H H
Q29 29-2 3-Cl H i-Pr H 4-Me-6-C2F5
Q29 29-3 3-Br H i-Pr H 4-Me-6-n-C3F7
Q29 29-4 3-NO2 H i-Pr H 4-Me-6-i-C3F7
Q29 29-5 3-I H i-Pr H H
Q29 29-6 3-I H i-Pr H 6-Cl 136
Q29 29-7 3-I H i-Pr H 6-C2F5
Q29 29-8 3-I H i-Pr H 6-n-C3F7
Q29 29-9 3-I H i-Pr H 6-i-C3F7
Q29 29-10 3-I H i-Pr H 4-Me-6-C2F5
Q29 29-11 3-I H i-Pr H 4-Me-6-n-C3F7
Q29 29-12 3-I H i-Pr H 4-Me-6-i-C3F7
Q29 29-13 3-I H i-Pr H 4-Me-5-C2F5
Q29 29-14 3-I H i-Pr H 4-Me-5-n-C3F7
Q29 29-15 3-I H i-Pr H 4-Me-5-i-C3F7
表8(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q29 29-16 3-I H t-Bu H 6-i-C3F7
Q29 29-17 3-I H t-Bu H 6-C2F5
Q29 29-18 3-I H t-Bu H 6-n-C3F7
Q29 29-19 3-I H t-Bu H 4-Me-6-i-C3F7
Q29 29-20 3-I H CH(CH3)CH2SCH3 H 4-Me-6-i-C3F7
Q29 29-21 3-I H CH(CH3)CH2SOCH3 H 4-Me-6-i-C3F7
Q29 29-22 3-I H CH(CH3)CH2SO2CH3 H 4-Me-6-i-C3F7
Q29 29-23 3-I H C(CH3)2CH2SCH3 H 4-Me-6-i-C3F7
Q29 29-24 3-I H C(CH3)2CH2SOCH3 H 4-Me-6-i-C3F7
Q29 29-25 3-I H C(CH3)2CH2SO2CH3 H 4-Me-6-i-C3F7
Q29 29-26 3-I H CH(CH3)CH2NHAc H 4-Me-6-i-C3F7
Q29 29-27 3-I H C(CH3)2CH2NHAc H 4-Me-6-i-C3F7
Q29 29-28 3-I H CH(CH3)CH2CH2OCH3 H 4-Me-6-i-C3F7
Q29 29-29 3-I H C(CH3)2CH2CH2OCH3 H 4-Me-6-i-C3F7
Q29 29-30 3-I Et Et H H
Q29 29-31 3-I Et Et H 4-Me-6-C2F5
Q29 29-32 3-I Et Et H 4-Me-6-n-C3F7
Q29 29-33 3-I Et Et H 4-Me-6-i-C3F7
Q29 29-34 3-I Et Et H 6-Cl
Q29 29-35 3-I Et Et H 6-Br
Q29 29-36 3-I Et Et H 6-n-C3F7
Q29 29-37 3-CF3 H i-Pr H 4-Me-6-C2F5
Q29 29-38 3-Ph H i-Pr H 4-Me-6-n-C3F7
表8(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q29 29-39 3-SOCF3 H i-Pr H 4-Me-6-i-C3F7
Q29 29-40 3-C2F5 H i-Pr H 4-Me-6-C2F5
Q29 29-41 3-I-4-Cl H i-Pr H 4-Me-6-n-C3F7
Q29 29-42 3-I-4-CF3 H i-Pr H 4-Me-6-i-C3F7
Q29 29-43 3-CF3-4-Cl H i-Pr H 4-Me-6-C2F5
Q29 29-44 3-OCF2O-4 H i-Pr H 4-Me-6-n-C3F7
Q29 29-45 3-OCF2CF2O-4 H i-Pr H 4-Me-6-i-C3F7
表9(Z1=Z2=O)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q32 32-1 3-Cl H i-Pr H H
Q32 32-2 3-Cl H i-Pr H 4-Me-2-C2F5
Q32 32-3 3-Br H i-Pr H 4-Me-2-n-C3F7
Q32 32-4 3-NO2 H i-Pr H 4-Me-2-i-C3F7
Q32 32-5 3-I H i-Pr H 2-C2F5
Q32 32-6 3-I H i-Pr H 2-n-C3F7
Q32 32-7 3-I H i-Pr H 2-i-C3F7
Q32 32-8 3-I H i-Pr H 4-Me-2-C2F5
Q32 32-9 3-I H i-Pr H 4-Me-2-n-C3F7
Q32 32-10 3-I H i-Pr H 4-Me-2-i-C3F7
Q32 32-11 3-I H i-Pr H 4,6-Cl2 257
Q32 32-12 3-I H t-Bu H 2-i-C3F7
Q32 32-13 3-I H t-Bu H 2-C2F5
Q32 32-14 3-I H t-Bu H 2-n-C3F7
Q32 32-15 3-I H t-Bu H 4-Me-2-i-C3F7
Q32 32-16 3-I H CH(CH3)CH2SCH3 H 4-Me-2-i-C3F7
Q32 32-17 3-I H CH(CH3)CH2SOCH3 H 4-Me-2-i-C3F7
Q32 32-18 3-I H CH(CH3)CH2SO2CH3 H 4-Me-2-i-C3F7
Q32 32-19 3-I H C(CH3)2CH2SCH3 H 4-Me-2-i-C3F7 202
Q32 32-20 3-I H C(CH3)2CH2SOCH3 H 4-Me-2-i-C3F7
Q32 32-21 3-I H C(CH3)2CH2SO2CH3 H 4-Me-2-i-C3F7
Q32 32-22 3-I H CH(CH3)CH2SEt H 4-Me-2-i-C3F7
Q32 32-23 3-I H C(CH3)2CH2SEt H 4-Me-2-i-C3F7
表9(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q32 32-24 3-I H CH(CH3)CH2CH2SCH3 H 4-Me-2-i-C3F7
Q32 32-25 3-I H C(CH3)2CH2CH2SCH3 H 4-Me-2-i-C3F7
Q32 32-26 3-I Et Et H 4-Me-2-C2F5
Q32 32-27 3-I Et Et H 4-Me-2-n-C3F7
Q32 32-28 3-I Et Et H 4-Me-2-i-C3F7
Q32 32-29 3-I Et Et H 2-Cl
Q32 32-30 3-I Et Et H 2-Br
Q32 32-31 3-I Et Et H 2-n-C3F7
Q32 32-32 3-CF3 H i-Pr H 4-Me-2-C2F5
Q32 32-33 3-Ph H i-Pr H 4-Me-2-n-C3F7
Q32 32-34 3-SOCF3 H i-Pr H 4-Me-2-i-C3F7
Q32 32-35 3-C2F5 H i-Pr H 4-Me-2-C2F5
Q32 32-36 3-I-4-Cl H i-Pr H 4-Me-2-n-C3F7
Q32 32-37 3-I-4-CF3 H i-Pr H 4-Me-2-i-C3F7
Q32 32-38 3-CF3-4-Cl H i-Pr H 4-Me-2-C2F5
Q32 32-39 3-OCF2O-4 H i-Pr H 4-Me-2-n-C3F7
Q32 32-40 3-OCF2CF2O-4 H i-Pr H 4-Me-2-i-C3F7
Q32 32-41 3-I H CH(Me)CH2SMe H 4-Me-2-Cl 210
Q32 32-42 3-I Et Et H 4,6-(OCH2CF3)2
无定形
表9中,无定形化合物的1H-NMR数据如下所示。
No 1H-NMR[δ(ppm/CDCl3)]
32-42 1.04(s.3H),1.31(t.3H),3.10(m.3H),3.42(m.1H),
3.80(m.1H),4.96-4.74(m.4H),7.22(t.1H),7.87(d.
1H),8.04(dd.1H),8.39(s.1H).
表10(Z1=Z2=O)
Q No. Xn R1 R2 R3 Ym mp(℃),nD(℃)
Q33 33-1 H H i-Pr H 4,6-(OMe)2 61
Q33 33-2 3-Cl H i-Pr H H
Q33 33-3 3-Cl H i-Pr H 5-C2F5
Q33 33-4 3-Br H i-Pr H 5-n-C3F7
Q33 33-5 3-NO2 H i-Pr H 5-i-C3F7
Q33 33-6 3-I H i-Pr H 5-C2F5
Q33 33-7 3-I H i-Pr H 5-n-C3F7
Q33 33-8 3-I H i-Pr H 5-i-C3F7
Q33 33-9 3-I H i-Pr H 4,6-OMe2
nD 1.5672(20.9)
Q33 33-10 3-I H i-Pr H 4,6-OMe2-5-i-C3F7
nD 1.5045(21.9)
Q33 33-11 3-I H t-Bu H 5-i-C3F7
Q33 33-12 3-I H t-Bu H 5-C2F5
Q33 33-13 3-I H t-Bu H 5-n-C3F7
Q33 33-14 3-I H CH(CH3)CH2SCH3 H 5-i-C3F7
Q33 33-15 3-I H CH(CH3)CH2SOCH3 H 5-i-C3F7
表10(续)
Q No. Xn R1 R2 R3 Ym mp(℃),nD(℃)
Q33 33-16 3-I H CH(CH3)CH2SO2CH3 H 5-i-C3F7
Q33 33-17 3-I H C(CH3)2CH2SCH3 H 5-i-C3F
Q33 33-18 3-I H C(CH3)2CH2SOCH3 H 5-i-C3F7
Q33 33-19 3-I H C(CH3)2CH2SO2CH3 H 5-i-C3F7
Q33 33-20 3-I H CH(CH3)CH2SEt H 5-i-C3F7
Q33 33-21 3-I H C(CH3)2CH2SEt H 5-i-C3F7
Q33 33-22 3-I H CH(CH3)CH2CH2SCH3 H 5-i-C3F7
Q33 33-23 3-I H C(CH3)2CH2CH2SCH3 H 5-i-C3F7
Q33 33-24 3-I Et Et H 5-C2F5
Q33 33-25 3-I Et Et H 5-n-C3F7
Q33 33-26 3-I Et Et H 5-i-C3F7
Q33 33-27 3-I Et Et H 5-Cl
Q33 33-28 3-I Et Et H 5-Br
Q33 33-29 3-I Et Et H 5-n-C3F7
表11(Z1=Z2=O)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q34 34-1 3-Cl H i-Pr H H
Q34 34-2 3-Cl H i-Pr H 3-Me-5-C2F5
Q34 34-3 3-Br H i-Pr H 3-Me-5-n-C3F7
Q34 34-4 3-NO2 H i-Pr H 3-Me-5-i-C3F7
Q34 34-5 3-I H i-Pr H H 185
Q34 34-6 3-I H i-Pr H 5-I 198
Q34 34-7 3-I H i-Pr H 5-C2F5
Q34 34-8 3-I H i-Pr H 5-n-C3F7
Q34 34-9 3-I H i-Pr H 5-i-C3F7
Q34 34-10 3-I H i-Pr H 3-Me-5-C2F5
Q34 34-11 3-I H i-Pr H 3-Me-5-n-C3F7
Q34 34-12 3-I H i-Pr H 3-Me-5-i-C3F7
Q34 34-13 3-I H i-Pr H 6-Me-5-C2F5
Q34 34-14 3-I H i-Pr H 6-Me-5-n-C3F7
Q34 34-15 3-I H i-Pr H 6-Me-5-i-C3F7
Q34 34-16 3-I H t-Bu H 5-i-C3F7
Q34 34-17 3-I H t-Bu H 5-C2F5
Q34 34-18 3-I H t-Bu H 5-n-C3F7
Q34 34-19 3-I H t-Bu H 3-Me-5-i-C3F7
Q34 34-20 3-I H CH(CH3)CH2SCH3 H 3-Me-5-i-C3F7
Q34 34-21 3-I H CH(CH3)CH2SOCH3 H 3-Me-5-i-C3F7
Q34 34-22 3-I H CH(CH3)CH2SO2CH3 H 3-Me-5-i-C3F7
Q34 34-23 3-I H C(CH3)2CH2SCH3 H 3-Me-5-i-C3F7
表11(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q34 34-24 3-I H C(CH3)2CH2SOCH3 H 3-Me-5-i-C3F7
Q34 34-25 3-I H C(CH3)2CH2SO2CH3 H 3-Me-5-i-C3F7
Q34 34-26 3-I H CH(CH3)CH2NHAc H 3-Me-5-i-C3F7
Q34 34-27 3-I H C(CH3)2CH2NHAc H 3-Me-5-i-C3F7
Q34 34-28 3-I H CH(CH3)CH2CH2OCH3 H 3-Me-5-i-C3F7
Q34 34-29 3-I H C(CH3)2CH2CH2OCH3 H 3-Me-5-i-C3F7
Q34 34-30 3-I Et Et H H 144
Q34 34-31 3-I Et Et H 3-Me-5-C2F5
Q34 34-32 3-I Et Et H 3-Me-5-n-C3F7
Q34 34-33 3-I Et Et H 3-Me-5-i-C3F7
Q34 34-34 3-I Et Et H 5-Cl
Q34 34-35 3-I Et Et H 5-Br
Q34 34-36 3-I Et Et H 5-n-C3F7
Q34 34-37 3-CF3 H i-Pr H 3-Me-5-C2F5
Q34 34-38 3-Ph H i-Pr H 3-Me-5-n-C3F7
Q34 34-39 3-SOCF3 H i-Pr H 3-Me-5-i-C3F7
Q34 34-40 3-C2F5 H i-Pr H 3-Me-5-C2F5
Q34 34-41 3-I-4-Cl H i-Pr H 3-Me-5-n-C3F7
Q34 34-42 3-I-4-CF3 H i-Pr H 3-Me-5-i-C3F7
Q34 34-43 3-CF3-4-Cl H i-Pr H 3-Me-5-C2F5
Q34 34-44 3-OCF2O-4 H i-Pr H 3-Me-5-n-C3F7
Q34 34-45 3-OCF2CF2O-4 H i-Pr H 3-Me-5-i-C3F7
Q34 34-46 3-I H Et H 5-i-C3F7 175
表11(续)
Q No. Xn R1 R2 R3 Ym mp(℃)
Q3 3-1 3-I H i-Pr H H
Q7 7-1 3-I H i-Pr H H
Q11 11-1 3-I H i-Pr H H
Q14 14-1 3-I H i-Pr H H
Q15 15-1 3-I H i-Pr H H 185
Q18 18-1 3-I H i-Pr H H
Q20 20-1 3-I H i-Pr H H
表12 (Z1=Z2=O)
Q No. Xn R1 R2 R3 W Ym 性质,Mp(℃)
Q16 16-1 3-Cl H i-Pr H N-i-Pr SMe 糊状
Q16 16-2 3-Cl H i-Pr H N-n-Pr SMe 糊状
Q44 43-1 H H i-Pr H S 6-Cl 47
实施例
下面,本发明的典型实施例如下所示。本发明决不限于这些实施例。
制备例1
(1-1)N-(4-甲基-3-三氟甲基异噁唑-5-基)-3-碘邻苯二甲酰亚胺的制备
在20ml乙酸中,溶解0.6g 3-碘邻苯二甲酸酐和0.44g 5-氨基-4-甲基-3-三氟甲基异噁唑,在加热回流下反应9小时。反应完全后,在减压下蒸馏除去溶剂,将残余物溶于乙酸乙酯,用稀盐酸、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤,然后在硫酸钠上干燥。在减压下蒸馏除去溶剂后,残余物经过硅胶柱色谱纯化,用己烷与乙酸乙酯的3/1混合物作为洗脱剂,得到0.71g目标产物。
性质:m.p.105℃;收率:69%
(1-2)N1-(4-甲基-3-三氟甲基异噁唑-5-基)-N2-异丙基-3-碘邻苯二甲酰胺(化合物No.Q6-8)的制备
在50ml二噁烷中溶解1.06g N-(4-甲基-3-三氟甲基异噁唑-5-基)-3-碘邻苯二甲酰亚胺。然后,向上述所得溶液中加入0.4g异丙胺,在室温下搅拌3小时。反应完全后,在减压下蒸馏除去溶剂,残余物经过硅胶柱色谱纯化,用己烷与乙酸乙酯的2/1混合物作为洗脱剂,得到0.32g目标产物。
性质:m.p.103℃;收率:26%
制备例2
(2-1)N1-[2-(1,1-二甲基乙基)-1,3,4-噻二唑-4-基]-N2,N2-二乙基-3-碘邻苯二甲酰胺(化合物No.Q19-34)的制备
在20ml四氢呋喃中溶解0.5g N,N-二乙基-3-碘邻苯二甲酸2-酰胺和0.27g 5-氨基-2-(1,1-二甲基乙基)-1,3,4-噻二唑。加入0.28g二乙基磷酰氰和0.18g三乙胺后,在加热回流下进行反应7小时。反应完全后,向反应混合物中加入乙酸乙酯,将所得乙酸乙酯溶液用稀盐酸、饱和碳酸氢钠水溶液和饱和氯化钠水溶液洗涤,在硫酸钠上干燥。蒸馏除去溶剂后,残余物经过硅胶柱色谱纯化,用己烷与乙酸乙酯的3/1混合物洗脱,得到0.11g目标产物。
性质:m.p.59℃;收率:16%
制备例3
(3-1)N1-(4-甲基-2-七氟异丙基吡啶-5-基)-N2-(1-甲基-2-甲硫基乙基)-3-碘邻苯二甲酰胺(化合物No.Q27-144)的制备
在4ml乙腈中溶解0.37g N-(1-甲基-2-甲硫基乙基)-3-碘邻苯二甲酸异酰亚胺(isoimide)和0.28g 5-氨基-4-甲基-2-七氟异丙基吡啶。加入催化量的三氟乙酸后,将所得混合物在室温下搅拌30分钟。过滤收集所得晶体,得到0.28g目标产物。
性质:m.p.225℃;收率:44%
制备例4:2-氨基-3-甲基-6-五氟乙基吡啶(化合物No.IV-1)的制备
向20ml二甲基亚砜中加入2.34g(0.01mol)2-氨基-5-碘-3-甲基吡啶、2.5g金属铜粉和3.7g(0.015mol)碘代五氟乙烷。将混合物保持在110℃下,剧烈搅拌6小时。将反应混合物冷却至室温后,将混合物倒在500ml冰水中,充分搅拌。过滤除去不溶物,用300ml乙酸乙酯从滤液中萃取目标产物。将萃取溶液用水洗涤,在无水硫酸钠上干燥,在减压下浓缩。残余物经过柱色谱纯化,用乙酸乙酯与己烷的3/7混合物作为洗脱剂,得到1.1g目标产物(收率20%)。
1H-NMR[δ(CDCl3)]:2.17(s,3H),4.82(br,2H),7.42(d,1H),8.16(s,1H),
制备例5:3-氨基-2-甲氧基-6-(七氟丙-2-基)吡啶(化合物No.IV-15)的制备
向20ml甲基叔丁基醚中加入3.2g(0.026mol)3-氨基-2-甲氧基吡啶、0.6g氯化三乙基苄基铵、2.0g碳酸钠和10.0g(0.031mol)2-碘七氟丙烷。在30℃下搅拌混合物的同时,向其中滴加2.8g亚硫酸氢钠(sodium hydrosulfite)的10ml水溶液。滴加后,所得混合物在室温下反应20小时,然后分离有机层,用水洗涤,在无水硫酸钠上干燥,在减压下蒸馏除去溶剂。残余物经过柱色谱纯化,用乙酸乙酯与己烷的3/7混合物作为洗脱剂,得到2.0g目标产物(收率26%)。
1H-NMR[δ(CDCl3)]:3.96(s,3H),4.03(br,2H),6.91(d,1H),7.10(dd,1H)
制备例6:3-氨基-6-(1,1,1,3,3,3-六氟异丙氧基)吡啶(化合物No.IV-27)的制备
在不超过5℃的温度下,将氢化钠(2.6g)分批加入到11.3g1,1,1,3,3,3-六氟-2-丙醇的50ml四氢呋喃溶液中,在上述相同温度下搅拌30分钟。然后,加入4.7g 2-氯-5-硝基吡啶,在室温下搅拌12小时。将反应混合物倒在200ml冰水中,用300ml乙酸乙酯萃取。将萃取溶液用水洗涤,在无水硫酸钠上干燥,浓缩。残余物经过柱色谱纯化,用乙酸乙酯与己烷的1/10混合物作为洗脱剂,得到6.2g 2-(1,1,1,3,3,3-六氟异丙氧基)-5-硝基苯(收率64%)。
向20ml乙酸中加入4.4g如上得到的2-(1,1,1,3,3,3-六氟异丙氧基)-5-硝基苯和4.2g电解铁。将所得混合物在60-65℃下搅拌30分钟。将反应混合物冷却,用6N氢氧化钠水溶液中和,过滤除去不溶物,将滤液用300ml叔丁基甲基醚萃取。将萃取溶液用氯化钠水溶液洗涤,在无水硫酸钠上干燥,浓缩。残余物经过柱色谱纯化,用乙酸乙酯与己烷的2/3混合物作为洗脱剂,得到3.6g 3-氨基-6-(1,1,1,3,3,3-六氟异丙氧基)吡啶(收率92%)。
含有本发明的式(I)的邻苯二甲酰胺衍生物作为活性成分的农艺杀虫剂适合于防治各种害虫,例如农业园艺害虫、储存谷物的害虫、卫生害虫、线虫等,它们对水稻、果树、蔬菜、其他作物、花卉、观赏植物等是有害的。它们具有显著的杀虫作用,例如鳞翅目,包括棉褐带卷蛾(
Adoxophyes
orana
fasciata)、smaller teatortrix(
Adoxophyes
sp.)、苹小食心虫(
Grapholita inopinata)、梨小食心虫(
Grapholita
molesta)、大豆食心虫(
Leguminovora
glycinivorella)、桑小卷蛾(
Olethreutes mori)、苯细蛾(
Caloptilla
theivora)、猛花细蛾(
Caloptilia zachrysa)、金纹小潜细蛾(
Phyllonorycter
ringoniella)、梨潜皮细蛾(
Spulerina
astaurota)、菜粉蝶日本亚种(
Pieris
rapae crucivora)、烟芽夜蛾(
Heliothis
sp.)、苹果皮小卷蛾(
Laspey resia
pomonella)、小菜蛾(
Plutella
xylostella)、苹果银蛾(
Argyresthia
conjugella)、桃柱果蛾(
Carposina
niponensis)、二化螟(
Chilo
suppressalis)、稻纵卷叶野螟(
Cnaphalocrocis medinalis)、烟草粉斑螟(
Ephestia
elutella)、桑绢野螟(
Glyphodes
pyloalis)、三化螟(
Scirpophaga
incertulas)、直纹稻弄蝶(
Parnara
guttata)、粘虫(
Pseudaletia
separata)、稻蛀茎夜蛾(
Sesamia
inferens)、斜纹贪夜蛾(
Spodoptera
litura)、贪夜蛾(
Spodoptera
exigua)等;半翅目,包括二点夜蝉(
Macrosteles
fascifrons)、黑尾夜蝉(
Nephotettix cincticepts)、褐飞虱(
Nilaparvata
lugens)、白背飞虱(
Sogatella
furcifera)、橘木虱(
Diaphorina
citri)、日本葡萄粉虱(
Aleurolobus
taonabae)、甘薯粉虱(
Bemisia
tabaci)、温室粉虱(
Trialeurodes
vaporariorum)、萝卜蚜(
Lipaphis erysimi)、桃蚜(
Myzus
persicae)、角蜡蚧(
Ceroplastes ceriferus)、橘绵蚧(
Pulvinaria
aurantii)、樟网盾蚧(
Pseudaonidia
duplex)、圣琼斯康顿蚧(
Comstockaspis perniciosa)、矢尖盾蚧(
Unapsis
yanonensis)等;垫刃线虫科,包括多色异丽金龟(
Anomala
rufocuprea)、日本弧丽金龟(
Popillia
japonica)、烟草窃蠹(
Lasioderma
serricorne)、褐粉蠹(
Lyctus
brunneus)、马铃薯瓢虫(
Epilachna vigintiotopunctata)、绿豆象(
Callosobruchus
chinensis)、番茄象(
Listroderes
costirostris)、玉米象(
Sitophilus zeamais)、棉铃象(
Anthonomus
gradis
gradis)、稻水象(
Lissorhoptrus
oryzophilus)、黄守瓜(
Aulacophora femoralis)、水稻负泥虫(
Oulema
oryzae)、黄曲条菜跳甲(
Phyllotreta
striolata)、纵坑切梢小蠹(
Tomicus
piniperda)、马铃薯叶甲(
Leptinotarsa
decemlineata)、Mexican bean beetle(
Epilachna
varivestis)、corn rootworm(
Diabrotica
sp.)等;双翅目,包括瓜寡鬃实蝇(
Dacus(Zeugodacus)
cucurbitae)、橘果实蝇(
Dacus(Bactrocera)
dorsalis)、大麦毛眼水蝇(
Agnomyza oryzae)、葱地种蝇(
Delia
antiqua)、灰地种蝇(
Delia
platura)、soybean pod gall midge(
Asphondylia
sp.)、家蝇(
Musca domestica)、尖音库蚊(
Culex
pipiens
pipiens)等;和垫刃线虫科,包括短体线虫(
Pratylenchus
sp.)、咖啡短体线虫(
Pratylenchus
coffeae)、马铃薯金线虫(
Globodera rostochiensis)、根结线虫(
Meloidogyne
sp.)、半穿刺线虫(
Tylenchulus
semipenetrans)、Aphelenchus sp.(
Aphelenchus avenae)、菊叶芽滑刃线虫(
Aphelenchoides
ritzemabosi)等。
含有本发明的由式(I)代表的邻苯二甲酰胺衍生物的农业园艺药剂、特别是农业园艺杀虫剂对上述例举的昆虫害虫、卫生害虫和/或线虫具有显著的防治作用,它们对稻田作物、旱田作物、果树、蔬菜和其他作物、花卉和观赏植物等是有害的。因此,在昆虫害虫、卫生害虫或线虫预期出现的季节、在它们出现之前或者在确认它们出现之时,将杀虫剂施用于稻田水、茎和叶或稻田土壤、旱田、果树、蔬菜、其他作物或花卉和观赏植物,可以表现出本发明的农业园艺杀虫剂的所需效果。
一般来说,在按照普通的农用化学品制备方法制成常用剂型之后,使用本发明的农业园艺药剂。
也就是说,将式(I)的邻苯二甲酰胺衍生物和适当载体以及可选的助剂按适当比例混合,通过溶解、分离、悬浮、混合、浸渍、吸附或附着作用,制成适合的剂型,例如悬浮液、乳油、可溶性浓缩物、可湿性粉剂、颗粒剂、粉剂或片剂。
用在本发明中的惰性载体既可以是固体也可以是液体。关于固体载体,可以提及大豆粉、谷物粉、木粉、树皮粉、锯屑、烟草茎粉、胡桃壳粉、糠、纤维素粉、植物提取残余物、合成聚合物或树脂粉、粘土(例如高岭土、膨润土和酸性粘土)、滑石(例如滑石和叶蜡石)、二氧化硅材料(例如硅藻土、硅沙、云母、白炭,即合成的高分散性硅酸,也称微细粉碎的水合二氧化硅或水合硅酸,有些商业上可得到的产品含有硅酸钙作为主要组分)、活性炭、硫粉、浮石、煅烧硅藻土、磨碎的砖、飞灰、沙子、碳酸钙、磷酸钙和其他无机或矿物粉末,化学肥料,例如硫酸铵、磷酸铵、硝酸铵、尿素、氯化铵等,和堆肥。这些载体既可以单独使用,也可以使用两种或多种载体的混合物。
液体载体本身具有溶解性,或者虽然没有溶解性但是能够借助助剂分散活性成分。下面是液体载体的典型实例,它们既可以单独使用,也可以使用其混合物:水;醇,例如甲醇、乙醇、异丙醇、丁醇和乙二醇;酮,例如丙酮、甲乙酮、甲基异丁基酮、二异丁酮和环己酮;醚,例如乙醚、二噁烷、溶纤剂、二丙醚和四氢呋喃;脂族烃,例如煤油和矿物油;芳族烃,例如苯、甲苯、二甲苯、溶剂石脑油和烷基萘;卤代烃,例如二氯乙烷、氯仿、四氯化碳和氯苯;酯,例如乙酸乙酯、邻苯二甲酸二异丙基酯、邻苯二甲酸二丁基酯和邻苯二甲酸二辛基酯;酰胺,例如二甲基甲酰胺、二乙基甲酰胺和二甲基乙酰胺;腈,例如乙腈;和二甲基亚砜。
下面是助剂的典型实例,它们是根据目的而使用的,单独使用或者在有些情况下两种或多种助剂结合使用,或者根本不必使用。
为了乳化、分散、溶解和/或湿润活性成分,使用表面活性剂。关于表面活性剂,可以例举聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨醇单月桂酸酯、聚氧乙烯脱水山梨醇单油酸酯、烷基芳基磺酸盐、萘磺酸缩合产物、木素磺酸盐和高级醇硫酸酯盐。
进而,为了稳定活性成分的分散液,增粘之和/或粘合之,可以使用的助剂例如酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、阿拉伯胶、聚乙烯醇、松节油、米糠油、膨润土和木素磺酸盐。
为了提高固体产品的可流动性,可以使用的助剂例如蜡、硬脂酸酯和烷基磷酸酯。
诸如萘磺酸缩合产物和磷酸盐的缩聚物等助剂可以用作可分散产品的胶溶剂。
诸如硅酮油等助剂也可以用作消泡剂。
活性成分的含量可以因需要而异,每100重量份制剂含0.01至80重量份。在粉剂或颗粒剂中,其适合的含量为0.01至50重量%。在乳油和可流动的可湿性粉剂中,适合的含量也是0.01至50重量%。
本发明的农艺杀虫剂用于以下列方式防治各种害虫。也就是说,将其直接或者用水等适当稀释或悬浮后,施用于预期出现害虫的作物或者不希望出现害虫的场所,用量对抑制害虫来说是有效的。
本发明的农艺杀虫剂的施用剂量因各种因素而异,例如目的、所要防治的害虫、植物的生长状态、害虫出现的趋势、天气、环境条件、剂型、施药方法、施药场所和施药时间。根据目的,可以在每10公亩0.1g至10kg(以活性成分化合物计)的范围内加以适当选择。
本发明的农艺杀虫剂可以与其他农业和园艺病害或害虫防治剂混合使用,目的是扩大可防治病害和害虫种类的范围,延长有效施药时间或者减少剂量。
下面,介绍本发明的典型制剂例和试验例。本发明决不限于这些
实施例。
在制剂例中,术语“份”表示“重量份”。
制剂例1
表2至12所列各化合物 50份
二甲苯 40份
聚氧乙烯壬基苯基醚与烷基苯磺酸钙的混合物 10份
将上述成分均匀混合进行溶解,制得乳油。
制剂例2
表2至12所列各化合物 3份
粘土粉 82份
硅藻土粉 15份
将上述成分均匀混合并研磨,制得粉剂。
制剂例3
表2至12所列各化合物 5份
膨润土与粘土的混合粉末 90份
木素磺酸钙 5份
将上述成分均匀混合,将所得混合物与适量水一起捏和,然后造粒并干燥,制得颗粒剂。
制剂例4
表2至12所列各化合物 20份
高岭土与合成高分散性硅酸的混合物 75份
聚氧乙烯壬基苯基醚与烷基苯磺酸钙的混合物 5份
将上述成分均匀混合并研磨,制成可湿性粉剂。
试验例1:对小菜蛾(
Plutella
xylostella)的杀虫作用
释放成年小菜蛾,使其在中国卷心菜幼苗上产卵。释放后两天,将沉积有卵的幼苗浸入液体化学品达约30秒钟,所述液体化学品是这样制备的,即,稀释含有表2至12所列各化合物作为活性成分的制剂,调节浓度至1,000ppm。风干后,放置在恒温25℃的房间内。浸入后六天,统计孵化的昆虫。根据下列等式计算死亡率,根据如下所示标准判断杀虫作用。试验重复进行三组,每组10只昆虫。
标准:
A---死亡率100%
B---死亡率99-90%
C---死亡率89-80%
D---死亡率79-50%
在上述试验中,表现B级或以上活性的化合物如下:
Q1-12,Q1-41,Q1-42,Q4-6,Q4-8,Q4-12,Q4-45,Q6-6,
Q6-8,Q8-1,Q8-2,Q8-3,Q8-5,Q8-11,Q8-13,Q8-14,Q8-
15,Q8-53,Q9-15,Q10-7,Q15-1,Q26-1,Q26-11,Q26-29,
Q26-30,Q26-31,Q26-32,Q26-33,Q26-43,Q27-29,Q27-30,
Q27-31,Q27-32,Q27-81,Q27-98,Q27-124,Q27-125,Q27-
126,Q27-127,Q27-128,Q27-129,Q27-130,Q27-131,Q27-
132,Q27-133,Q27-134,Q27-135,Q27-136,Q27-137,Q27-
138,Q27-139,Q27-140,Q27-141,Q27-142,Q27-143,Q27-
144,Q27-145,Q27-150,Q27-151,Q27-153,Q27-155,Q27-
164,Q27-230, Q27-231,Q27-232,Q27-233,Q27-234,Q27-
235,Q27-236,Q27-238,Q27-239,Q27-240,Q27-241,Q27-
242,Q27-243,Q27-244,Q27-245,Q27-246,Q27-247,Q27-
248至Q27-265,Q27-267,Q27-268,Q27-270,Q27-273至
Q27-280,Q27-282至Q27-284,Q27-289,Q27-297,Q27-298,
Q27-305至Q27-309,Q27-316至Q27-318,Q27-323至Q27-
327,Q27-332,Q27-334,Q27-335,Q27-336至Q27-339,
Q27-347,Q27-352,Q27-353,Q27-354,Q27-355,Q27-359,
Q27-360,Q27-378,Q27-384,Q27-387,Q27-388,Q27-391,
Q27-393,Q27-396,Q27-397,Q27-402至Q27-405,Q27-407,
Q27-413,Q27-414,Q27-439,Q27-449至Q27-457,Q27-459
至Q27-469,Q32-11,Q32-19,Q33-1,Q33-10,Q34-30,Q34-
46和Q42-1。
试验例2:对斜纹贪夜蛾(
Spodoptera
litura)的杀虫作用
将一片卷心菜叶(栽培品种;Shikidori)浸入液体化学品达约30秒钟,所述液体化学品是这样制备的,即,稀释含有表2至12所列各化合物作为活性成分的制剂,调节浓度至500ppm。风干后,将其放置在直径9cm的塑料陪替氏培养皿中,接种斜纹贪夜蛾的二龄幼虫,然后密封培养皿,放置在恒温25℃的房间内。接种后八天,统计死亡的和存活的数量。根据下列等式计算死亡率,根据试验例1所示标准判断杀虫作用。试验重复进行三组,每组10只昆虫。
在上述试验中,表现B级或以上活性的化合物如下:
Q26-1,Q26-11,Q2 6-29,Q26-30,Q26-31,Q26-32,Q26-33,
Q26-43,Q27-29,Q27-30,Q27-31,Q27-32,Q27-81,Q27-98,
Q27-124,Q27-125,Q27-126,Q27-127,Q27-128,Q27-129,
Q27-130,Q27-131,Q27-132,Q27-133,Q27-134,Q27-135,
Q27-136,Q27-137,Q27-138,Q27-139,Q27-140,Q27-141,
Q27-142,Q27-143,Q27-144,Q27-145,Q27-150,Q27-151,
Q27-152,Q27-153,Q27-155,Q27-164,Q27-230,Q27-231,
Q27-232,Q27-233,Q27-234,Q27-235,Q27-236,Q27-238,
Q27-239,Q27-240,Q27-241,Q27-242,Q27-243,Q27-244,
Q27-245,Q27-24 6,Q27-247,Q27-248至Q27-265,Q27-267,
Q27-268,Q27-270,Q27-273至Q27-280,Q27-282至Q27-
284,Q27-289, Q27-297,Q27-298,Q27-305至Q27-309,
Q27-316至Q27-318,Q27-323至Q27-327,Q27-332,Q27-
334,Q27-335, Q27-336至Q27-339,Q27-347,Q27-352,
Q27-353,Q27-354,Q27-355,Q27-359,Q27-360,Q27-378,
Q27-384,Q27-387,Q27-388,Q27-397,Q27-402至Q27-405,
Q27-407,Q27-413,Q27-414,Q27-439,Q27-459,Q27-466,
Q32-19和Q34-46。
试验例3:对稻纵卷叶野螟(
Cnaphalocrosis
medinalis)的杀虫作用
将处于6至8叶期的稻植株叶片浸入液体化学品达约30秒钟,所述液体化学品是这样制备的,即,稀释含有表2至12所列各化合物作为活性成分的制剂,调节浓度至500ppm。风干后,将叶片放置在直径9cm的塑料陪替氏培养皿中,培养皿底部覆盖有湿润的滤纸。在叶片上接种稻纵卷叶野螟的三龄幼虫,然后将培养皿放置在恒温在25℃和湿度为70%的房间内。接种后四天,统计死亡的和存活的数量,根据试验例1所示标准判断杀虫作用。试验重复进行三组,每组10只昆虫。
在上述试验中,表现B级或以上活性的化合物如下:
Q26-1,Q26-29,Q26-30,Q26-31,Q26-32,Q26-33,Q27-29,
Q27-30,Q27-31,Q27-32,Q27-81,Q27-98,Q27-124,Q27-
125,Q27-126,Q27-127,Q27-128,Q27-129,Q27-130,Q27-
131,Q27-132,Q27-133,Q27-134,Q27-135,Q27-136,Q27-
137,Q27-138, Q27-139,Q27-140,Q27-141,Q27-142,Q27-
143,Q27-144,Q27-145和Q27-164。
Claims (4)
1.由下述通式(I)代表的邻苯二甲酰胺衍生物:
其中R1、R2和R3可以是相同或不同的,各自代表氢原子、C1-6烷基、C1-6烷硫基C1-6烷基、C1-6烷基亚磺酰基C1-6烷基、C1-6烷基磺酰基C1-6烷基,
X代表氢原子、卤原子、硝基、CF3、C1-6烷基,
n代表0-4的整数,
Z1和Z2代表氧原子,
Q代表选自由下式Q1、Q2、Q4、Q5、Q6、Q8、Q9、Q10、Q13、Q15、Q16、Q19、Q26、Q27、Q29、Q32、Q33、Q34、Q43组成的组的杂环基:
Y代表氢原子、卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷氧基羰基、苯基、苯氧基、卤代苯氧基、C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷硫基、卤代C1-6烷基磺酰基、卤代C1-6烷氧基卤代C1-6烷氧基、卤代C1-6烷酰基氨基,
m代表0-4的整数,
W代表O、S或N-R13,其中R13代表氢原子、C1-6烷基或卤代C1-6烷基;
条件是(1)若X、R1和R3同时代表氢原子,Z1和Z2同时代表氧原子,Q代表Q27,Y是2-位的氯原子,则R2不是1,2,2-三甲基丙基;
(2)若X、R1和R3同时代表氢原子,Z1和Z2同时代表氧原子,Q代表Q27,且m是0,则R2不是1,2,2-三甲基丙基;和
(3)若X、R1和R3同时代表氢原子,Z1和Z2同时代表氧原子,Q代表Q16,且Y代表甲硫基,则R2不是氢原子和甲基。
2.农业园艺杀虫剂,含有由下述通式(I)代表的邻苯二甲酰胺衍生物作为其活性成分:
其中R1、R2和R3可以是相同或不同的,各自代表氢原子、C1-6烷基、C1-6烷硫基C1-6烷基、C1-6烷基亚磺酰基C1-6烷基、C1-6烷基磺酰基C1-6烷基,
X代表氢原子、卤原子、硝基、CF3、C1-6烷基,
n代表0-4的整数,
Z1和Z2代表氧原子,
Q代表选自由下式Q1、Q2、Q4、Q5、Q6、Q8、Q9、Q10、Q13、Q15、Q16、Q19、Q26、Q27、Q29、Q32、Q33、Q34、Q43组成的组的杂环基:
Y代表氢原子、卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷氧基羰基、苯基、苯氧基、卤代苯氧基、C1-6烷硫基、C1-6烷基亚磺酰基、卤代C1-6烷硫基、卤代C1-6烷基磺酰基、卤代C1-6烷氧基卤代C1-6烷氧基、卤代C1-6烷酰基氨基,
m代表0-4的整数,
W代表O、S或N-R13,其中R13代表氢原子、C1-6烷基或卤代C1-6烷基;
条件是若X、R1和R3同时代表氢原子,Z1和Z2同时代表氧原子,Q代表Q27,Y是2-位的氯原子,则R2不是1,2,2-三甲基丙基。
3.使用农业园艺杀虫剂的方法,其特征在于为了防治对有用作物有害的生物,用有效量的根据权利要求2的农业园艺杀虫剂处理目标农作物或施用于土壤。
4.由下述通式(IV,)代表的杂环胺衍生物:
Q’-NH2 (IV’)
其中:
(1)在Q’代表Q26、Q32和Q34之一的情况下,
Y可以是相同或不同的,代表卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基或卤代C1-6烷硫基,m代表1-4的整数,总数为m的Y中至少有一个是全氟C2-6烷基;和
(2)在Q,代表Q27的情况下,
Y可以是相同或不同的,代表卤原子、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、C1-6烷硫基、卤代C1-6烷硫基,m代表1-4的整数,总数为m的Y中至少有一个是全氟C2-6烷基、卤代C1-6烷氧基或卤代C1-6烷硫基,
其条件是Y不是2,2,2-三氟乙氧基。
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP190746/99 | 1999-07-05 | ||
JP19074699 | 1999-07-05 | ||
JP190746/1999 | 1999-07-05 | ||
JP2000080991 | 2000-03-22 | ||
JP080991/2000 | 2000-03-22 | ||
JP080991/00 | 2000-03-22 |
Publications (2)
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CN1360573A CN1360573A (zh) | 2002-07-24 |
CN1195734C true CN1195734C (zh) | 2005-04-06 |
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CNB008100071A Expired - Fee Related CN1195734C (zh) | 1999-07-05 | 2000-07-04 | 邻苯二甲酰胺衍生物、其制备中的中间体和农业/园艺杀虫剂及其使用方法 |
Country Status (16)
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US (1) | US6875768B1 (zh) |
EP (1) | EP1193254A4 (zh) |
JP (1) | JP5311072B2 (zh) |
KR (1) | KR100429276B1 (zh) |
CN (1) | CN1195734C (zh) |
AR (1) | AR030154A1 (zh) |
AU (1) | AU773377B2 (zh) |
BR (1) | BR0012224B1 (zh) |
CO (1) | CO5221024A1 (zh) |
CZ (1) | CZ200239A3 (zh) |
EG (1) | EG22172A (zh) |
HU (1) | HUP0202190A3 (zh) |
IL (1) | IL147228A0 (zh) |
PL (1) | PL353389A1 (zh) |
TR (1) | TR200200210T2 (zh) |
WO (1) | WO2001002354A1 (zh) |
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JP2004515547A (ja) * | 2000-12-11 | 2004-05-27 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 置換複素環式フタル酸ジアミド殺節足動物剤 |
DE10133665A1 (de) * | 2001-07-11 | 2003-01-30 | Boehringer Ingelheim Pharma | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
TWI312274B (en) | 2001-08-13 | 2009-07-21 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
AR036872A1 (es) | 2001-08-13 | 2004-10-13 | Du Pont | Compuesto de antranilamida, composicion que lo comprende y metodo para controlar una plaga de invertebrados |
KR20040022246A (ko) | 2001-08-15 | 2004-03-11 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무척추 해충 방제용 오르토-헤테로시클릭 치환 아릴 아미드 |
EP1423379B1 (en) | 2001-08-15 | 2008-05-28 | E.I. du Pont de Nemours and Company | Ortho-substituted aryl amides for controlling invertebrate pests |
ATE417829T1 (de) | 2001-08-16 | 2009-01-15 | Du Pont | Substituierte anthranilamide und ihre verwendung als pesticide |
WO2003027099A1 (en) | 2001-09-21 | 2003-04-03 | E. I. Du Pont De Nemours And Company | Arthropodicidal anthranilamides |
TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
KR100840083B1 (ko) | 2001-10-15 | 2008-06-19 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 무척추 해충 방제를 위한 이미노벤족사진,이미노벤즈티아진 및 이미노퀴나졸린 |
US7205307B2 (en) * | 2002-02-14 | 2007-04-17 | Icagen, Inc. | Pyrimidines as novel openers of potassium ion channels |
CN100354260C (zh) * | 2002-05-02 | 2007-12-12 | 拜尔农作物科学股份公司 | 邻苯二酰胺衍生物、农业或园艺业杀虫剂及其使用方法 |
JP2004018506A (ja) * | 2002-06-20 | 2004-01-22 | Bayer Ag | 殺虫性フタラミド誘導体 |
DE10330723A1 (de) * | 2003-07-08 | 2005-02-03 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10330724A1 (de) | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
JP2006076990A (ja) | 2004-03-12 | 2006-03-23 | Bayer Cropscience Ag | 殺虫性ベンゼンジカルボキサミド類 |
DE102004035134A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von Halogenalkylnicotinsäurederivaten, Anthranilsäureamiden oder Phthalsäurediamiden und Safenern |
WO2006022225A1 (ja) * | 2004-08-23 | 2006-03-02 | Nihon Nohyaku Co., Ltd. | 光学活性フタルアミド誘導体及び農園芸用殺虫剤並びにその使用方法 |
CA2577942A1 (en) * | 2004-08-31 | 2006-03-09 | Bayer Cropscience Ag | Chiral 3-halophthalic acid derivatives |
DE102004055582A1 (de) | 2004-11-18 | 2006-05-24 | Bayer Cropscience Ag | N-Heterocyclyl-phthalsäurediamide |
WO2006127426A2 (en) * | 2005-05-19 | 2006-11-30 | Bayer Cropscience Ag | Insecticidal substituted benzylamino heterocyclic and heteroaryl derivatives |
US7574570B2 (en) * | 2005-09-30 | 2009-08-11 | Cleversafe Inc | Billing system for information dispersal system |
DE102005059466A1 (de) * | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
DE102006016641A1 (de) * | 2006-04-08 | 2007-10-11 | Bayer Cropscience Ag | Verwendung von 3-(2,4,6-Trimethylphenyl)-4-neopentylcarbonyloxy-5,5-tetramethylen-Δ3-dihydrofuran-2-on zur Bekämpfung von Dipteren aus der Familie der Cecidomyiidae |
KR20090060446A (ko) * | 2006-09-30 | 2009-06-12 | 바이엘 크롭사이언스 아게 | 재배 기재에 적용시 농약 조성물의 생물학적 작용 개선, 적합한 제제 및 그의 용도 |
JP5238172B2 (ja) * | 2007-03-22 | 2013-07-17 | 公益財団法人相模中央化学研究所 | パーフルオロアルキル基を有する含窒素六員環化合物およびその製造方法 |
SG194107A1 (en) * | 2011-05-23 | 2013-11-29 | Merck Patent Gmbh | Thiazole derivatives |
JP2015027951A (ja) * | 2011-11-02 | 2015-02-12 | 日本農薬株式会社 | フタルアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法 |
WO2014007228A1 (ja) | 2012-07-03 | 2014-01-09 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
WO2017144402A1 (de) * | 2016-02-24 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | N-(5-halogen-1,3,4-oxadiazol-2-yl)arylcarbonsäureamide und ihre verwendung als herbizide |
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CA1128044A (en) * | 1978-08-31 | 1982-07-20 | Robert G. Suhr | 1-benzoyl-3-(aryloxy-or arylthiopyridinyl) ureas compounds |
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PH21918A (en) * | 1983-07-25 | 1988-04-08 | Ciba Geigy Ag | N-(2-nitrophenyl)-5-aminopyrimidine derivatives,the preparation and use thereof |
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CZ299375B6 (cs) | 1998-11-30 | 2008-07-09 | Nihon Nohyaku Co., Ltd. | Ftalamidové deriváty nebo jejich soli, zemedelsko-zahradnický insekticid je obsahující a jeho použití |
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- 2000-06-30 AR ARP000103364A patent/AR030154A1/es not_active Application Discontinuation
- 2000-07-04 US US10/018,464 patent/US6875768B1/en not_active Expired - Fee Related
- 2000-07-04 BR BRPI0012224-6A patent/BR0012224B1/pt not_active IP Right Cessation
- 2000-07-04 KR KR10-2002-7000068A patent/KR100429276B1/ko not_active IP Right Cessation
- 2000-07-04 EG EG20000874A patent/EG22172A/xx active
- 2000-07-04 WO PCT/JP2000/004444 patent/WO2001002354A1/ja active IP Right Grant
- 2000-07-04 TR TR2002/00210T patent/TR200200210T2/xx unknown
- 2000-07-04 CO CO00049445A patent/CO5221024A1/es not_active Application Discontinuation
- 2000-07-04 IL IL14722800A patent/IL147228A0/xx unknown
- 2000-07-04 EP EP00942473A patent/EP1193254A4/en not_active Withdrawn
- 2000-07-04 AU AU57093/00A patent/AU773377B2/en not_active Ceased
- 2000-07-04 CZ CZ200239A patent/CZ200239A3/cs unknown
- 2000-07-04 HU HU0202190A patent/HUP0202190A3/hu unknown
- 2000-07-04 PL PL00353389A patent/PL353389A1/xx not_active Application Discontinuation
- 2000-07-04 CN CNB008100071A patent/CN1195734C/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
KR100429276B1 (ko) | 2004-04-29 |
IL147228A0 (en) | 2002-08-14 |
EP1193254A1 (en) | 2002-04-03 |
PL353389A1 (en) | 2003-11-17 |
BR0012224A (pt) | 2002-05-28 |
CZ200239A3 (cs) | 2002-05-15 |
BR0012224B1 (pt) | 2010-12-28 |
AR030154A1 (es) | 2003-08-13 |
AU5709300A (en) | 2001-01-22 |
EP1193254A4 (en) | 2007-09-19 |
CO5221024A1 (es) | 2002-11-28 |
JP5311072B2 (ja) | 2013-10-09 |
KR20020063154A (ko) | 2002-08-01 |
WO2001002354A1 (fr) | 2001-01-11 |
CN1360573A (zh) | 2002-07-24 |
HUP0202190A3 (en) | 2003-01-28 |
US6875768B1 (en) | 2005-04-05 |
TR200200210T2 (tr) | 2002-06-21 |
EG22172A (en) | 2002-10-31 |
AU773377B2 (en) | 2004-05-20 |
JP2011074077A (ja) | 2011-04-14 |
HUP0202190A2 (en) | 2002-09-28 |
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