CN1316418A - 苯磺酸衍生物 - Google Patents

苯磺酸衍生物 Download PDF

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CN1316418A
CN1316418A CN01101527A CN01101527A CN1316418A CN 1316418 A CN1316418 A CN 1316418A CN 01101527 A CN01101527 A CN 01101527A CN 01101527 A CN01101527 A CN 01101527A CN 1316418 A CN1316418 A CN 1316418A
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K·-H·米勒尔
R·基尔斯滕
E·R·格星
J·克卢思
M·W·雷维斯
K·芬德森
J·R·雅森
K·科尼
H·J·里贝尔
O·查尔纳
M·多林格尔
H·J·桑特尔
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Abstract

本发明涉及下式的苯磺酸衍生物：

Description

苯磺酸衍生物
本申请系1996年6月28日提交的96196753的分案申请。
本发明涉及新的苯磺酸衍生物。
已知一些磺酰基氨基羰基化合物，例如化合物4，5-二甲氧基-2-(2-甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺具有除草性能(参见EP-341489、EP-422469、EP-425948、EP-431291、EP-507171、EP-534266、DE-4029753)。但是这些化合物的作用并不是在各方面都令人满意。
现在发现通式(I)新的磺酰基氨基(硫代)羰基化合物，其中A代表一个单键，氧原子，硫原子或N-R基团，其中R代表氢、烷基、链烯基、炔烃基或环烷基，Q代表氧原子或硫原子，R1代表氢或甲酰基或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基、烷基磺酰基、环烷基、环烷基羰基或环烷基磺酰基，R2代表氰基或卤原子或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷氧基、链烯基氧基或炔烃基氧基，和R3代表在各种情况下可有可无地被取代的五元杂环基，五元杂环五个原子中至少有一个原子是氧、硫或氮，而且其它成环原子中还可以有1至3个原子可以是氮，和式(I)化合物的盐，排除先前已知的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
如果进行下面的反应，则会得到通式(I)新的磺酰基氨基(硫代)羰基化合物：(a)在可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(II)氨基磺酰基化合物
Figure A0110152700061
其中A、R1和R2具有上面给出的定义，与通式(III)(硫代)羧酸衍生物反应其中Q和R3具有上面给出的定义，Z代表卤原子、烷氧基、芳基氧基或芳基烷氧基，或者(b)可有可无地存在一种反应助剂和可有可无地存在一种稀释剂下，通式(IV)磺酰基异(硫代)氰酸盐
Figure A0110152700071
其中A、Q、R1和R2具有上面给出的定义，与通式(V)杂环反应，
           H-R3         (V)其中R3具有上面给出的定义，或者(c)可有可无地存在一种反应助剂和可有可无地存在一种稀释剂下，通式(VI)氯代磺酰基化合物
Figure A0110152700072
其中A、R1和R2具有上文给出的定义，与通式(V)杂环
           H-R3         (V)其中R3具有上文给出的定义和通式(VII)金属(硫代)氰酸盐反应
           MQCN         (VII)其中Q具有上文给出的定义，和M代表碱金属或碱土金属等同物，或者(d)可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(VI)氯代磺酰基化合物其中A、R1和R2具有上面给出的定义，与通式(VIII)(硫代)甲酰胺反应其中Q和R3具有上面给出的定义，或者(e)可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(IX)磺酰基氨基(硫代)羰基化合物，其中A、Q、R1和R2具有上面给出的定义，和Z代表卤原子、烷氧基、芳基氧基或芳基烷氧基，与通式(V)杂环反应
            H-R3            (V)其中R3具有上面给出的定义，或者(f)可有可无地存在一种稀释剂，通式(V)杂环
            H-R3            (V)其中R3具有上面给出的定义，与氯代磺酰基异(硫代)氰酸盐反应，而且该反应生成的加成物在可有可无地存在一种酸受体和可有可无地存在一种稀释剂下就地与通式(X)苯衍生物反应
Figure A0110152700091
其中A、R1和R2具有上面给出的定义，而且，如果需要，可以通过常规方法将通过方法(a)、(b)、(c)、(d)、(e)或(f)得到的式(I)化合物转化成盐。
通式(I)新的磺酰基氨基(硫代)羰基化合物具有强的除草活性。
本发明优选涉及式(I)化合物，其中A代表一个单键、氧原子、硫原子或N-R基团，其中R代表氢原子、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔烃基或C3-C6-环烷基，Q代表氧原子或硫原子，R1代表氢或甲酰基或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-、苯基-或C1-C4-烷氧基取代的各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基或烷基磺酰基，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷基取代的C3-C6-环烷基、C3-C6-环烷基羰基或C3-C6-环烷基磺酰基，R2代表氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷氧基取代的各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷氧基，链烯基氧基或炔烃基氧基，和R3代表各种情况下可有可无地被取代的下式杂环基，
Figure A0110152700101
其中：Q1、Q2和Q3各自代表氧原子或硫原子，和R4代表氢、羟基、氨基或氰基，或者代表C2-C10-亚烷基氨基，或代表可有可无地被氟-、氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基-羰基-，或C1-C4-烷氧基羰基取代的C1-C6-烷基，或者代表在各种情况下可有可无地被氟-、氯-、和/或溴取代的C2-C6-链烯基或C2-C6-炔烃基，或代表各种情况下可有可无地被氟-、氯-、溴-、氰基-、C1-C4-烷氧基或C1-C4-烷氧基羰基取代的C1-C6-烷氧基、C1-C6-烷基氨基或C1-C6-烷基羰基氨基，或者代表C3-C6-链烯氧基，或者代表二(C1-C4-烷基)-氨基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-和/或C1-C4-烷基取代的C3-C6-环烷基、C3-C6-环烷基氨基或C3-C6-环烷基-C1-C4-烷基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-和/或C1-C4-烷氧基取代的苯基，苯基氨基或苯基-C1-C4-烷基，R5代表氢、羟基、巯基、氨基、氰基、氟、氯、溴或碘，或者代表可有可无地被氟-、氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基羰基-或C1-C4-烷氧基-羰基取代的C1-C6-烷基，或者代表在各种情况下可有可无地被氟-、氯-、和/或溴-取代的C2-C6-链烯基或C2-C6-炔烃基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、C1-C4-烷氧基-或C1-C4-烷氧基羰基-取代的C1-C6-烷氧基、C1-C6-烷基硫基、C1-C6-烷基氨基或C1-C6-烷基羰基氨基，或者代表C3-C6-链烯基氧基、C3-C6-炔烃基氧基、C3-C6-链烯基硫基、C3-C6-炔烃基硫基、C3-C6-链烯基氨基或C3-C6-炔烃基氨基，或者代表二(C1-C4-烷基)-氨基，或者代表在各种情况下可有可无地被甲基-和/或乙基取代的氮丙啶子基、吡咯烷子基、哌啶子基或吗啉代，或者代表各种情况下可有可无地被氟-、氯-、溴-、氰基-和/或C1-C4-烷基取代的C3-C6-环烷基、C5-C6-环烯基、C3-C6-环烷基氧基、C3-C6-环烷基硫代、C3-C6-环烷基氨基、C3-C6-环烷基-C1-C4-烷基、C3-C6-环烷基-C1-C4-烷氧基、C3-C6-环烷基-C1-C4-烷基硫代或C3-C6-环烷基-C1-C4-烷基氨基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-和/或C1-C4-烷氧基羰基取代的苯基、苯基-C1-C4-烷基、苯氧基、苯基C1-C4-烷氧基、苯基硫基、苯基-C1-C4-烷基硫基、苯基氨基或苯基-C1-C4-烷基氨基，或者R4和R5一起代表可有可无地支链化的具有3至11个碳原子的链烷烃双基，还有R6、R7和R8是相同的或不同的，并且代表氢、氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、溴-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷氧基、链烯基氧基、炔烃基氧基、烷基硫基、链烯基硫基、炔硫基、烷基亚磺酰基和烷基磺酰基，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷基取代的具有3至6个碳原子的环烷基，排除先前已知的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
本发明还优选涉及其中A、Q、R1、R2和R3具有作为优选的给定定义的式(I)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4-烷基铵盐、二(C1-C4-烷基)-铵盐、三(C1-C4-烷基)-铵盐、四(C1-C4-烷基)-铵盐、三(C1-C4-烷基)-锍、C5-或C6-环烷基-铵盐和二(C1-C2-烷基)-苄基铵盐。
本发明特别涉及式(I)化合物，其中A代表一个单键、氧原子或N-R基团，其中R代表氢、甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、环丙基、环丁基、环戊基或环己基，Q代表氧或硫，R1代表氢或甲酰基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、甲氧基-或乙氧基-取代的甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、乙酰基、丙酰基、丁酰基、甲氧基羰基、乙氧基羰基、正-或异-丙氧基羰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、正-、异-、仲-或叔丁基磺酰基，或者代表在各种情况下被氟-、氯-或甲基任选取代的环丙基、环丙基羰基或环丙基磺酰基，R2代表氰基、氟、氯或溴，或代表各种情况下可有可无地被氟-、氯-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-或仲丁氧基、丙烯基氧基、丁烯基氧基、丙炔基氧基或丁炔基氧基，和R3代表在各种情况下可有可无地被取代的下式的杂环基，
Figure A0110152700121
其中Q1、Q2和Q3各自代表氧原子或硫原子，和R4代表氢、羟基或氨基，或者代表C3-C8亚烷基氨基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基，或者代表在各种情况下可有可无地被氟-、氯-或溴取代的丙烯基、丁烯基、丙炔基或丁炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基氨基、乙基氨基、正-或异-丙基氨基、正-、异-、仲-或叔丁基氨基，或者代表丙烯基氧基或丁烯基氧基，或者代表二甲基氨基或二乙基氨基，或者代表在各种情况下可有可无地被氟-、氯-、甲基-和/或乙基取代的环丙基、环丁基、环戊基、环己基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基或者代表在各种情况下可有可无地被氟-、氯-、甲基-、三氟甲基和/或甲氧基取代的苯基或苄基，R5代表氢、羟基、巯基、氨基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基，或者代表在各种情况下可有可无地被氟-、氯-或溴取代的乙烯基、丙烯基、丁烯基、丙炔基或丁炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基硫基、乙基硫基、正-或异丙基硫基、正-、异-、仲-或叔丁基硫基、甲基氨基、乙基氨基、正-或异-丙基氨基、正-、异-、仲-或叔丁基氨基，或者代表丙烯基氧基、丁烯基氧基、丙炔基氧基、丁炔基氧基、丙烯基硫基、丙二烯基硫基、丁烯基硫基、丙炔基硫基、丁炔基硫基、丙烯基氨基、丁烯基氨基、丙炔基氨基或丁炔基氨基，或者代表二甲基氨基、二乙基氨基或二丙基氨基，或者代表在各种情况下可有可无地被氟-、氯-、甲基-和/或乙基取代的环丙基、环丁基、环戊基、环己基、环戊烯基、环己烯基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基硫基、环丁基硫基、环戊基硫基、环己基硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲基硫基、环丁基甲基硫基、环戊基甲基硫基、环己基甲基硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基或环己基甲基氨基，或者代表各种情况下可有可无地被氟-、氯-、甲基-、三氟甲基-、甲氧基-和/或甲氧基羰基取代的苯基、苄基、苯氧基、苄基氧基、苯基硫基、苄基硫基、苯基氨基或苄基氨基，或者R4和R5一起代表可有可无地支化的有3至11个碳原子的链烷烃双基，以及R6、R7和R8是相同的或不同的，并且代表氢、氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、丙烯基氧基、丁烯基氧基、丙炔基氧基、丁炔基氧基、甲基硫基、乙基硫基、正-或异-丙基硫基、正-、异-、仲-或叔丁基硫基、丙烯基硫基、丁烯基硫基、丙炔基硫基、丁炔基硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基，或者代表环丙基，排除先前已在的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
本发明化合物特别优选的组是下面式(I)化合物，其中A代表一个单键，Q代表氧原子或硫原子，R1代表甲基、乙基、正-或异丙基，R2代表在各种情况下在5或6-位上的氯或甲基，和R3代表下式可有可无地被取代的三唑啉基其中：Q1代表氧或硫，和R4代表各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异丙基，或代表丙烯基或丙炔基，或代表甲氧基、乙氧基、正-或异-丙氧基，或代表环丙基，和R5代表氢、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基，或者代表在各种情况下可有可无地被氟和/或氯取代的丙烯基或丙炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、甲基硫基、乙基硫基、正-或异丙基硫基，或者代表丙烯基氧或环丙基。
上述列出的基团的定义，不管是一般定义还是优选范围中列出的定义，都不仅适用于式(I)终产物，也相应地适用于各制备中所需要的起始物和/或中间体。这些基团定义可以根据需要相互组合，因此包括所指出的优选范围之间的相互组合。
例如，使用2-氟-6-甲氧基-苯磺酰胺和5-乙氧基-4-甲基-2-苯氧羰基-2，4-二氢-3H-1，2，4-三唑-3-硫酮为起始物，本发明(a)反应过程可以通过下面的反应式详细说明：
Figure A0110152700152
例如，使用2-乙氧基-6-甲基-苯基磺酰基-异硫氰酸盐和5-乙基-4-甲氧基-2，4-二氢-3H-1，2，4-三唑-3-酮为起始物，本发明方法(b)的反应过程可以通过下面的反应式详细说明：
Figure A0110152700161
例如，使用2-甲氧基-3-甲基-苯磺酰氯、5-乙基硫基-4-甲氧基-2，4-二氢-3H-1，2，4-三唑-3-酮和氰酸钾为起始物，则本发明方法(c)的反应过程可以通过下面的反应式详细说明：
Figure A0110152700162
例如，使用2-乙氧基-4-氟-苯磺酰氯和5-甲基-1，2，4-噁二唑-3-甲酰胺为起始物，则本发明方法(d)反应过程可以通过下面反应式来详细说明：
例如，使用N-(2-氯-6-丙氧基-苯基磺酰基)-O-甲基-尿烷和4-甲基-5-甲基硫基-2，4-二氢-3H-1，2，4-三唑-3-酮为起始物，则本发明方法(e)的反应过程可以通过下面反应式来详细说明：
Figure A0110152700171
例如，使用5-氯-4-乙基-2，4-二氢-3H-1，2，4-三唑-3-酮和氯代磺酰基异氰酸盐和之后2-乙氧基-6-甲基苯胺为起始物，则本发明方法(f)的反应过程可以通过下面反应式来详细说明：
式(II)给出了在本发明制备式(I)化合物的方法(a)中要用作起始物的氨基磺酰基化合物的通式定义。在式(II)中，A、R1和R2优选或特别具有上文中已经指出的，与描述本发明制备的式(I)化合物相关的，分别作为优选或特别优选的A、R1和R2的那些定义。
式(II)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 21 6504、DE 3208189、EP44807、EP 23422)。
文献中还未公开的，也是本发明目的的新的物质是通式(IIa)的磺酰胺，
Figure A0110152700181
其中A1代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟代乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2代表甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基。
如果式(VIa)磺酰氯其中A1和A2具有上面给出的定义，可有可无地在一种稀释剂例如在水的存在下，在0℃和50℃之间的温度下与氨反应，则得到式(IIa)新的磺酰胺(参见制备各实施例)。
式(II)的起始原料一般也可以通过式(IIb)苯酚衍生物
Figure A0110152700183
其中A和R2具有上面给出的定义与式(XI)烷基化试剂反应而获得，
           X-R1              (XI)其中R1具有上面给出的定义，X代表卤原子或R1-O-SO2-O-基团，反应条件是可有可无地存在一种酸受体，例如碳酸钾，和可有可无地存在一种稀释剂，例如甲苯，反应温度在10℃和150℃之间(参见制备实施例)。
需要作为母体的式(IIb)苯酚衍生物是已知的和/或可以用实质上已知的方法制备(参见EP 44807，Metallober flache〔MetalSurface〕-Angew。Elektrochemie 27(1973)，217-227，化学文摘79：86733；制备实施例)。
也需要用作母体的式(XI)烷基化试剂是已知的合成化学品。
式(III)给出了本发明制备式(I)化合物的方法(a)中也要被用作起始物的(硫代)羧酸衍生物的通式定义。在式(III)中。Q和R3优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的分别作为优选或特别优选的Q和R3的定义；Z优选代表氟、氯、溴、C1-C4-烷氧基、苯氧基或苄基氧基，特别是代表氯、甲氧基、乙氧基或苯氧基。
式(III)的起始原料是已知的和/或可以由实质上已知的方法制备(参见EP 459244、EP341489、EP 422469、EP 425948、EP431291、EP 507171、EP 534266)。
式(IV)给出在本发明制备式(I)化合物的方法(b)中要被用作起始原料的磺酰基异(硫代)氰酸盐通式定义。在式(IV)中、A、Q、R1和R2优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的，作为优选的或特别优选的A、Q、R1和R2的定义。
式(IV)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 23422、EP 216504)。
文献中未公开过的，也是本发明目的的新的物质是通式(IVa)磺酰基异(硫代)氰酸盐
Figure A0110152700201
其中Q代表氧或硫，A1代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
如果上面的式(IIa)磺酰胺与碳酰氯或硫代碳酰氯在可有可无地存在异氰酸烷基酯例如异氰酸丁酯，可有可无地存在一种反应助剂，例如二氮杂双环[2.2.2]辛烷，并存在一种稀释剂例如甲苯、二甲苯或氯苯下，在80℃和150℃的温度下反应，反应完全后减压蒸馏掉挥发成份，则得到式(IVa)新的磺酰基异(硫代)氰酸盐。
式(V)给出了本发明制备式(I)化合物的方法(b)、(c)、(e)和(f)中也被用作起始物的杂环的通式定义。在式(V)中，R3优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的作为优选或特别优选的R3的定义。
式V的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 341489、EP 422469、EP 425948、EP 431291、EP 507171、EP 534266)。
式(VI)给出了本发明制备式(I)化合物的方法(c)和(d)中用作起始物的氯代磺酰基化合物的通式定义。在式(VI)中，A、R1和R2优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的作为优选或特别优选的A、R1和R2的定义。
式(VI)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 511826、DE 32081 89、EP 23422)。
文献中未公开的，也是本发明一个目的的新的物质是式(VIa)磺酰氯，
Figure A0110152700211
其中A1代表乙基、正-或异丙基、正-、异-、仲或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，A2代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
如果式(XII)苯胺衍生物
Figure A0110152700212
其中A1和A2具有上面给出的定义，在存在盐酸条件下，在-10℃和+10℃之间的温度下，与碱金属亚硝酸盐例如亚硝酸钠反应，这样得到的重氮盐溶液在存在一种稀释剂，例如二氯甲烷或1，2-二氯乙烷，和存在一种催化剂，例如氯化亚铜(I)，且可有可无地存在另一种催化剂，例如十二烷基三甲基铵溴化物，在-10℃和+50℃之间的温度下，与二氧化硫反应，可得到式(VIa)新的磺酰氯化合物(参见制备实施例)。
需要用作母体的式(XII)苯胺衍生物是已知的和/或可以通过实质上已知的方法制备(参见EP 511826、US 4992091、EP 185128、DE2405479，制备实施例)。
上述新的式(IIa)、(IVa)和(VIa)苯磺酸衍生物可以用下面的式(XIII)综合定义：
Figure A0110152700221
E代表-NH2，-N＝C＝Q或-Cl，其中Q代表O或S，以及A1代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2代表甲基、乙基、正-或异丙基，正-、异-、仲-或叔丁基。
式(VIII)给出了本发明制备式(I)化合物的方法(d)中用作起始物的(硫代)甲酰胺的通式定义。在式(VIII)中，Q和R3优选或特别优选具有上面已经指明的，与描述本发明制备的式(I)化合物相关的，作为优选或特别优选的Q和R3的定义。
式(VIII)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 459244)。
式(IX)给出了本发明制备式(I)化合物的方法(e)中用作起始物的磺酰基氨基(硫代)羰基化合物的通式定义。在式(IX)中，A、Q、R1和R2优选或特别具有上文中已经指明的，与描述本发明制备的式(I)化合物相关的作为优选的或特别优选的A、Q、R1和R2的定义；Z优选代表氟、氯、溴、C1-C4-烷氧基、苯氧基或苄基氧基，特别是代表氯、甲氧基、乙氧基或苯氧基。
式(X)给出了本发明制备式(I)化合物的方法(f)中用作起始物的苯的衍生物的通式定义。在式(X)中，A、R1和R2优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的，作为优选或特别优选的A、R1和R2的定义。
式(X)的起始原料是已知的和/或可以通过实质上已知的方法制备(参见EP 511826、US 4992091、EP 185128、DE 2405479，制备实施例)。
制备本发明式(I)新的化合物的本发明方法(a)、(b)、(c)、(d)、(e)和(f)优选使用稀释剂进行。本说明书中合适的稀释剂实际上是所有惰性有机溶剂。优选包括脂肪族和芳香族的，可有可无地被卤化的烃，例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯甲烷、氯苯和邻二氯苯；醚，例如二乙醚和二丁醚、乙二醇二甲基醚和二乙二醇二甲基醚、四氢呋喃和二噁烷；酮，例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮；酯，例如乙酸甲酯和乙酸乙酯；腈，例如乙腈和丙腈；酰胺，例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮，以及二甲亚砜、四氢噻吩砜，和六甲基磷酸三酰胺。
作为本发明方法(a)、(b)、(c)、(d)、(e)和(f)中的反应助剂和/或作为酸受体，可以使用所有通常用于该类反应的酸结合剂。合适的实施例中优选的是碱金属氢氧化物，例如氢氧化钠和氢氧化钾，碱土金属氢氧化物，例如氢氧化钙，碱金属碳酸盐和醇酸盐，例如碳酸钠和碳酸钾、叔丁醇钠和叔丁醇钾，以及碱性氮化合物，例如三甲胺、三乙胺、三丙胺、三丁胺、二异丁基胺、二环己基胺、乙基二异丙基胺、乙基二环己基胺、N，N-二甲基苄基胺、N，N-二甲苯胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2，4-二甲基-、2，6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基吡啶、1，5-二氮杂双环[4.3.0]-壬-5-烯(DBN)、1，8-二氮杂双环[5.4.0]-十一-7-烯(DBU)和1，4-二氮杂双环-[2.2.2]-辛烷(DABCO)。
本发明方法(a)、(b)、(c)、(d)、(e)和(f)中的反应温度可以在相当宽的范围内变化。一般在-20℃和+150℃之间的温度下进行，优选在0℃和+100℃之间的温度下进行。
本发明方法(a)、(b)、(c)、(d)、(e)和(f)一般在大气压下进行。但是也可以在高压或低压下进行。
为了进行本发明(a)、(b)、(c)、(d)、(e)和(f)，各种情况下需要的起始物一般以大约等摩尔量使用，但是也可以在各种情况下以相当大的过量使用其中之一反应物，反应一般在一种合适的稀释剂中在存在一种酸受体下进行，反应混合物在具体所要求的温度下搅拌数小时。用常规方法在各种情况下在本发明方法(a)、(b)、(c)、(d)、(e)和(f)中进行后处理(参见制备实施例)。
如果需要，可以制备本发明通式(I)化合物的盐，这样的盐通过成盐的常规方法以简单方式获得，例如将式(I)化合物溶解或分散于合适的溶剂中，例如二氯甲烷、丙酮、叔丁基甲基醚或甲苯，并加入一种合适的碱。然后，如果需要，在长时间搅拌后，通过浓缩或抽滤而分离到盐。
本发明活性化合物可以用作脱叶剂，干燥剂，破坏阔叶植物的药剂，特别是作为除草剂。广义上来说，所谓杂草应该理解为在不期望其生长的地点生长的所有植物。本发明物质是以全除草剂还是以选择性除草剂作用主要取决于所使用的量。
例如，与下面的植物相关，可以使用本发明活性化合物：
双子叶杂草种类：芥属(Sinapis)、独行菜属(Lepidium)、猪殃殃属(Galium)、繁缕属(Stellaria)、母菊属(Matricaria)、春黄菊属(Anthemis)、辣子草(Galinsoga)、藜属(Chenopodium)、荨麻属(Urtica)、千里光属(Senecio)、苋属(Amaranthus)、马齿苋属(Portulaca)、苍耳属(Xanthium)、旋花属(Convolvulus)、甘薯属(Ipomoea)、蓼属(Polygonum)、田菁属(Sesbania)、豚草属(Ambrosia)、蓟属(Cirsium)、飞廉属(Carduus)、苦苣菜属(Sonchus)、茄属(Solanum)、蔊菜属(Rorippa)、水松叶属(Rotala)、母草属(Lindemia)、野芝麻属(Lamium)、婆婆纳属(Veronica)、苘麻属(Abutilon)、刺果(Emex)、曼陀罗属(Datura)、堇菜属(Viola)、鼬瓣花属(Galeopsis)、罂粟属(Papaver)、矢车菊属(Centaurea)、车轴草属(Trifolium)、毛茛属(Ranunculus)和蒲公英属(Taraxacum)。
双子叶作物种类：棉属(Gossypium)、Glycine、Beta、胡萝卜属(Daucus)、菜豆属(Phaseolus)、Pisum、茄属(Solanum)、亚麻属(Linum)、甘薯属(Ipomoea)、巢菜属(Vicia)、烟草属(Nicotiana)、番茄属(Lycopersicon)、花生属(Arachis)、芥属(Brassica)、莴苣属(Lactuca)、Cucumis和臭瓜属(Cucurbita)。
单子叶杂草种类：稗属(Echinochloa)、狗毛草属(Setaria)、黍属(Panicum)、马唐属(Digitaria)、梯牧草属(Phleum)、早熟禾属(Poa)、羊茅属(Festuca)、蟋蟀草属(Eleusine)、臂形草属(Brachiaria)、黑麦属(Lolium)、雀麦属(Bromus)、燕麦属(Avena)、莎草属(Cyperus)、蜀黍属(Sorghum)、冰草属(Agropyron)、Cynodon、雨久花属(Monochoria)、飘拂草属(Fimbristylis)、慈姑属(Sagittaria)、荸荠属(Eleocharis)、藨草属(Scirpus)、雀稗属(Paspalum)、Ischaemum、尖瓣花属(Sphenoclea)、龙爪茅属(Dactyloctenium)、翦股颖属(Agrostis)、看麦娘属(Alopecurus)和Apera。
单子叶作物种类：稻属(Oryza)、Zea、Triticum、大麦属(Hordeum)、燕麦属(Avena)、黑麦属(Scale)、蜀黍属(Sorghum)、黍属(Panicum)、甘蔗属(Saccharum)、波罗属(Ananas)、Asparagus和葱属(Allium)。
但是，本发明活性化合物的用途无论如何不受这些种类的限制，也以相同方式扩展到其它植物。
根据浓度，本发明化合物适于例如在工业领域和铁路枕木，轨道和有或没有种植树的广场全部杀死杂草。也就是说，本发明化合物可以用来杀灭长年生作物中的杂草，例如造林、装饰树种植、果园、葡萄园、柑桔园、坚果园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油棕种植园、可可种植园、软果种植园和蛇麻草田、草场和牧场，并用来选择性除灭年生作物中的杂草。
本发明式(I)化合物优选适于除单子叶和双子叶阔叶杂草，可以在出苗前或出苗后除草。当在土壤上和在植物地上部分使用时，这些化合物显示出强的除草活性和广谱作用。
活性化合物可以转化成常规制剂，例如溶液、乳剂、可湿粉剂、混悬剂、粉剂、粗粉剂、糊剂、可溶粉剂、颗粒剂、混悬-乳油，浸有活性化合物的天然和合成材料，非常细的聚合物质中的胶囊。
用已知方法制备这些制剂，例如将活性化合物与增充剂混合，所述增充剂是液体溶剂和/或固体载体，可有可无地使用表面活性剂，所述表面活性剂是乳化剂和/或分散剂和/或成泡剂。
在使用水作为增充剂的情况下，有机溶剂，例如，可以用作辅助溶剂。作为液体溶剂，合适的主要有：芳烃，如二甲苯、甲苯或烷基萘，氯化的芳烃和氯化的脂肪烃，例如氯苯、氯乙烯或二氯甲烷、脂肪烃，例如环己烷或石蜡，例如石油级分、矿物油和植物油，醇，例如丁醇或乙二醇，以及它们的醚类和酯类，酮，例如丙酮、甲乙酮、甲基异丁基酮或环己酮、强极性溶剂，例如二甲基甲酰胺和二甲亚砜，以及水。
作为固体载体合适的有：
例如铵盐和研细的天然矿物，例如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土，和研细的合成矿物，例如高度分散的硅石、矾土，和硅酸盐，作为适于颗粒剂的固体载体，合适的有：例如磨细的和筛分的天然岩石，例如方解石、大理石、浮石、海泡石和白云石，以及合成的无机粉和有机粉的颗粒，和有机材料的颗粒，例如木屑、椰子壳、玉米芯和烟草梗；作为乳化剂和/或起炮剂，合适的有：例如非离子和阴离子乳化剂，例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚，例如烷基芳基聚乙二醇醚、磺酸烷基酯、硫酸烷基酯、磺酸芳基酯以及白蛋白水解产物；作为分散剂，合适的有：例如木素一亚磺酸废液和甲基纤维素。
制剂中可以使用粘合剂，例如羧甲基纤维素、粉末、颗粒或乳胶形式的天然的和合成的聚合物，例如阿拉伯树胶、聚乙烯醇，聚乙酸乙烯酯、以及天然磷脂，例如脑磷脂或卵磷脂，和合成的磷脂。其它的添加剂有矿物油和植物油。
可以使用着色剂，例如无机颜料，例如氧化铁、氧化钛和普鲁士蓝、和有机染料，例如茜素染料，偶氮染料和金属酞菁染料，和痕量营养成分，例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂中一般含有0.1至95％重量比的活性化合物，优选含有0.5至90％。
为了控制杂草，本发明活性化合物或者其制剂形式，也可以作为与已知的除草剂的混合物，完成制剂或可能的罐混制剂而被使用。
混合物中可能的成分是已知的除草剂，例如酰苯胺类，例如吡氟草胺和敌稗；芳基羧酸，例如二氯吡啶酸、dicamba和毒莠定；芳基氧基链烷酸，例如2，4-D、2，4-DB、2，4-DP、氟草烟、MCPA、MCPP和绿草定；芳基氧基-苯氧基-链烷酸酯，例如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵；吖嗪酮(azinonea)，例如杀草敏和达草伏；氨基甲酸酯，例如氯苯胺灵、甜菜安、甜菜宁和苯胺灵；乙酰氯苯胺；例如甲草胺、乙草胺、丁草胺、吡草胺、丙草安、丙草胺和毒草胺；二硝基苯胺，例如安磺灵、二甲戊乐灵和氟乐灵；二苯醚类，例如三氟羧甲醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚；脲，例如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆；羟胺类，如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮；咪唑啉酮类，例如咪草烟、咪草酯、灭草烟和灭草喹；腈类，例如溴苯腈、敌草腈，碘苯腈；氧化乙酰胺类，例如苯噻草胺；磺酰脲类，例如amidosulphuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆；氨基甲酸硫羟酯类，例如丁草特、灭草特、野燕畏、EPTC、禾草畏、草达灭、苄草丹、杀草丹和野燕畏；三嗪类，例如莠去津、氰草津、西玛津、西玛通、特丁净和terbutylazine；三嗪酮类，例如环嗪酮、苯嗪草酮，嗪草酮；其它，例如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草胺膦、草甘膦、isoxaben、哒草特、二氯喹啉酸、喹草酸、草硫磷和灭草环。
也可能是与其它活性化合物的混合物，所述其它已知活性化合物是例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂和改善土壤结构的试剂。
活性化合物可以以其制剂的形式或以由其进一步稀释而制备的使用形式来使用，例如即用型溶液、混悬剂、乳剂、粉剂、糊剂和颗粒剂，以常规方式使用，例如通过灌溉、撒播、雾化、喷施。
本发明活性化合物可以在植物出苗前或出苗后施用。也可以在耕种前加到土壤中。
使用的活性化合物的量可以在一个基本范围内变化。主要取决于所期望作用的性质。一般情况下，使用的量是每公顷土壤表面施用1至10kg活性化合物，优选为5g-5kg/ha。
本发明活性化合物的制备和应用可以由下面的实施例看出。制备实施例：实施例1(方法(a))
2.5g(10mmol)5-乙氧基-4-甲基-2-苯氧基羰基-2，4-二氢-3H-1，2，4-三唑-3-酮，2.3g(10mmol)2-异丙氧基-6-甲基-苯磺酰胺，1.5g(10mmol)二氮杂双环[5.4.0]-十一碳-7-烯(DBU)和50ml乙腈的混合物在20℃搅拌5小时。然后在水泵抽真空下浓缩，残余物与50ml 1N盐酸搅拌，将混合物抽滤，滤出的产物与二乙醚搅拌，再次吸滤混合物。
得到2.4g(理论值60％)5-乙氧基-4-甲基-2-(2-异丙氧基-6-甲基-苯基磺酰基-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点155℃。实施例2(方法(c))
1.7g(10mmol)4-甲基-5-炔丙基硫基-2，4-二氢-3H-1，2，4-三唑-3-酮，1.3g(20mmol)氰酸钠，2.5g(10mmol)2-甲基-6-正丙氧基-苯磺酰氯和50ml乙腈混合物回流下加热3小时。之后，水泵抽真空浓缩，残余物与1N盐酸搅拌，每次用50ml二氯甲烷将混合物萃取三次。浓缩合并的有机萃取液，残余物溶解于异丙醇，抽滤离析结晶产物。
得到2.2g(理论值52％)4-甲基-5-炔丙基硫基-2-(2-甲基-6-正丙氧基-苯基磺酰基-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点151℃。实施例3
Figure A0110152700291
(方法(d))
3.2g(25mmol)5-甲基-1，2，4-噁二唑-3-甲酰胺，4.2g(75mmol)氢氧化钾(粉末)和200ml二噁烷混合物在60℃下搅拌30分钟。然后在水泵抽真空下将其浓缩至大约其一半体积，在大约20℃滴加7g(30mmol)2-乙氧基-6-甲基-苯磺酰氯的10ml二噁烷溶液。然后将反应混合物在20℃搅拌大约15小时以上。之后，水泵抽真空浓缩，残余物与50ml 1N盐酸搅拌，吸滤离析结晶产物。得到4.0g(理论值49％)N-(2-乙氧基-6-甲基-苯基磺酰基)-5-甲基-1，2，4-噁二唑-3-甲酰胺，熔点168℃。实施例4
Figure A0110152700292
(方法(f))
向冷却到5℃的50ml二氯甲烷中1.4g(10mmol)5-乙氧基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的溶液中加入1.7g(12mmol)氯代磺酰基异氰酸盐，然后同样在5℃下滴加10ml二氯甲烷中1.5g(10mmol)2-乙氧基-6-甲基-苯胺和1.0g(10mmol)三乙胺的溶液。之后，反应混合物在大约20℃下搅拌15小时。接着加入100ml 1N盐酸，充分搅拌后，分离有机相，用硫酸钠干燥并过滤。水泵真空浓缩滤液，残余物溶解于异丙醇中，抽滤离析结晶产物。
得到1.8g(理论值45％)5-乙氧基-4-甲基-2-(2-乙氧基-6-甲基-苯基氨基磺酰基-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点147℃。
类似于实施例1至4，并根据本发明制备方法概括性描述，也可以，例如，制备下面表1中列出的式(I)化合物。
Figure A0110152700301
表1：式(I)化合物的实施例实施例号  A    Q       R1         (位置)       R3
                               R2                     熔点(℃)5         -    O    n-C3H7    (6-)CH3        1176         -    O    C2H5      (6-)Cl          1567         -    O    C2H5      (6-)CH3  
Figure A0110152700313
  1108         -    O    C2H5      (6-)CH3     1419         -    O    C2H5      (6-)CH3  
Figure A0110152700315
  162
表1-续实施例号  A    Q        R1        (位置)         R3No.                                R2                      熔点(℃)10        -    O    n-C3H7    (6-)CH3  
Figure A0110152700321
  12611        -    O    n-C3H7    (6-)CH3     15012        -    O    n-C3H7    (6-)CH3  
Figure A0110152700323
  12913        -    O    CH3        (6-)CH3  
Figure A0110152700324
  15314        -    O    CH3        (6-)CH3     167
表1-续实施例号  A    Q     R1           (位置)        R3
                               R2                    熔点(℃)15        -    O    CH3        (6-)CH3     16716        -    O    i-C3H7    (6-)CH3     12517        -    O    i-C3H7    (6-)CH3   13118        -    O    C2H5      (5-)CH3     22219        -    O    C2H5      (5-)CH3 
Figure A0110152700335
   139
表1-续实施例号  A        Q          R1             (位置)          R3
                                     R2                            熔点(℃)20      -        O       C2H5       (4-)CH3    
Figure A0110152700341
    18921      -        O       C2H5       (5-)CH3    
Figure A0110152700342
    13123      -        O       -CH2CH2Cl  (6-)CH3    
Figure A0110152700344
    13724      -        O       -CH2CH2Cl  (6-)CH3         149
表1-续实施例号  A    Q      R1        (位置)      R3
                                R2                  熔点(℃)25        -    O    i-C3H7    (5-)CH3   12526        -    O    i-C3H7    (5-)CH3
Figure A0110152700352
  14027        -    O    n-C3H7    (5-)CH3   11928        -    O    n-C3H7    (5-)CH3   13429        -    O    n-C3H7    (5-)CH3
Figure A0110152700355
  110
表1-续实施例号  A    Q        R1      (位置)      R3
                            R2                     熔点(℃)30        -    O    C2H5    (6-)CH3
Figure A0110152700361
   10831        -    O    C2H5    (6-)CH3    17332        -    O    C2H5    (6-)CH3   11933        -    O    C2H5    (6-)CH3
Figure A0110152700364
   12134        -    O    C2H5    (6-)CH3
Figure A0110152700365
 109
表1-续实施例号  A    Q        R1        (位置)       R3
                             R2                       熔点(℃)35        -    O    C2H5      (6-)CH3     11136        -    O    n-C3H7    (6-)CH3
Figure A0110152700372
    9137        -    O    n-C3H7    (6-)CH3   13038        -    O    n-C3H7    (6-)CH3   12639        -    O    n-C3H7    (6-)CH3   101
表1-续实施例号  A    Q        R1        (位置)      R3
                               R2                    熔点(℃)40        -    O    n-C3H7    (6-)CH3    15241        -    O    n-C3H7    (6-)CH3
Figure A0110152700382
   10042        -    O    n-C3H7    (6-)CH3    12043        -    O    n-C3H7    (6-)CH3   11744        -    O    n-C3H7    (6-)CH3  126
表1-续实施例号  A    Q       R1        (位置)     R3
                             R2                      熔点(℃)45        -    O    n-C3H7    (6-)CH3
Figure A0110152700391
  11346        -    O    i-C3H7    (6-)CH3   13047        -    O    i-C3H7    (6-)CH3
Figure A0110152700393
  13948        -    O    i-C3H7    (6-)CH3
Figure A0110152700394
  12149        -    O    i-C3H7    (6-)CH3
Figure A0110152700395
  119
表1-续实施例号  A    Q       R1        (位置)     R3
                             R2                     熔点(℃)50        -    O    i-C3H7    (6-)CH3   12851        -    O    i-C3H7    (6-)CH3   13452        -    O    i-C3H7    (6-)CH3
Figure A0110152700403
   13053        -    O    i-C3H7    (6-)CH3   11754        -    O    i-C3H7    (6-)CH3
Figure A0110152700405
  134
表1-续实施例号  A    Q       R1        (位置)      R3
                                  R2                 熔点(℃)55        -    O    i-C3H7    (6-)CH3    14156        -    O    i-C3H7    (6-)CH3
Figure A0110152700412
  13257        -    O    i-C3H7    (6-)CH3
Figure A0110152700413
  16658        -    O    i-C3H7    (6-)CH3
Figure A0110152700414
  11859        -    O    i-C3H7    (6-)CH3
Figure A0110152700415
  150
表1-续实施例号  A    Q       R1        (位置)      R3
                             R2                        熔点(℃)60        -    O    i-C3H7    (6-)CH3
Figure A0110152700421
   14461        -    O    i-C3H7    (6-)CH3    17062        -    O    i-C3H7    (6-)CH3   12063        -    O    n-C3H7    (6-)CH3   12464        -    O    n-C3H7    (6-)CH3   12565        -    O    n-C3H7    (6-)CH3
Figure A0110152700426
  116实施例号  A    Q      R1        (位置)      R3
                                R2                     熔点(℃)66        -    O    n-C3H7    (6-)CH3
Figure A0110152700431
   15267        -    O    n-C3H7    (6-)CH    14368        -    O    C2H5      (6-)CH3   16069        -    O    C2H5      (6-)CH3
Figure A0110152700434
  13370        -    O    C2H5      (6-)CH3
Figure A0110152700435
  97
表1-续实施例号  A    Q       R1      (位置)     R3
                              R2                  熔点(℃)71        -    O    C2H5    (6-)CH3
Figure A0110152700441
   9672        -    O    C2H5    (6-)CH3
Figure A0110152700442
  15673        -    O    C2H5    (6-)CH3
Figure A0110152700443
  14574        -    O    C2H5    (6-)CH3
Figure A0110152700444
  12075        -    O    C2H5    (6-)CH3   125
表1-续实施例号  A    Q        R1        (位置)    R3
                              R2                      熔点(℃)76        -    O    C2H5      (6-)CH3    14077        -    O    H           (6-)CH3
Figure A0110152700452
     8878        -    O    C2H5      (5-)CH3   13079        -    O    n-C3H7    (6-)CH3   14180        -    O    n-C3H7    (6-)CH3
Figure A0110152700455
   98
表1-续实施例号  A    Q      R1          (位置)        R3
                                R2                  熔点(℃)81        -    O    n-C3H7    (6-)CH3
Figure A0110152700461
  14182        -    O    n-C3H7    (6-)CH3   10183        -    O    n-C3H7    (6-)CH3
Figure A0110152700463
  13684        -    O    n-C3H7    (6-)CH3
Figure A0110152700464
  9685        -    O    n-C3H7    (6-)CH3
Figure A0110152700465
  9086        -    O    n-C3H7    (6-)CH3
Figure A0110152700466
  136
表1-续实施例号  A    Q        R1        (位置)     R3
                              R2                     熔点(℃)87        -    O    C2H5      (6-)CH3   12288        -    O    C2H5      (6-)CH3
Figure A0110152700472
  15489        -    O    i-C3H7    (6-)CH3
Figure A0110152700473
  13990        -    O    C2H5      (6-)CH3    14291        -    O    C2H5      (6-)CH3   153
表1-续实施例号  A    Q       R1      (位置)     R3
                             R2                     熔点(℃)92        -    O    C2H5    (6-)CH3
Figure A0110152700481
  14593        -    O    C2H5    (6-)CH3
Figure A0110152700482
  13294        -    O    C2H5    (6-)CH3   14195        -    O    C2H5    (6-)CH3
Figure A0110152700484
  13096        -    O    CH3      (5-)CH3
Figure A0110152700485
   15697        -    O    CH3      (5-)CH3
Figure A0110152700486
   177
表1-续实施例号  A    Q      R1     (位置)     R3
                           R2                  熔点(℃)98        -    O    CH3    (4-)CH3  11599        -    O    CH3    (4-)CH3
Figure A0110152700492
 166100       -    O    CH3    (3-)CH3
Figure A0110152700493
 162101       -    O    CH3    (3-)CH3
Figure A0110152700494
 143102       -    O    CH3    (3-)CH3  165
表1-续实施例号  A    Q      R1    (位置)        R3
                          R2                      熔点(℃)103       -    O    CHF2    (5-)CH3
Figure A0110152700501
   176104       -    O    CHF2    (5-)CH3   119105       -    O    CHF2    (5-)CH3
Figure A0110152700503
   126106       -    O    CHF2    (5-)CH3
Figure A0110152700504
   151107       -    O    CHF2    (5-)CH3
Figure A0110152700505
   188
表1-续实施例号  A    Q      R1      (位置)      R3
                           R2                   熔点(℃)108       -    O    CHF2    (5-)CH3
Figure A0110152700511
  137109       -    O    CHF2    (5-)CH3
Figure A0110152700512
 117110       -    O    CHF2    (5-)CH3   155111       -    O    CHF2    (4-)CH3
Figure A0110152700514
  152112       -    O    CHF2    (4-)CH3
Figure A0110152700515
  176113       -    O    CHF2    (4-)CH3   108
表1-续实施例号  A    Q       R1    (位置)     R3
                          R2                        熔点(℃)114       -    O    CHF2    (6-)CH3   163115       -    O    CHF2    (6-)CH
Figure A0110152700522
  136116       -    O    CHF2    (6-)CH3
Figure A0110152700523
  118117       -    O    CHF2    (6-)CH3
Figure A0110152700524
 104118       -    O    CHF2    (5-)CH3
Figure A0110152700525
 98119       -    O    CHF2    (6-)CH3
Figure A0110152700526
 128
表1-续实施例号  A    Q      R1      (位置)     R3
                           R2                   熔点(℃)120       -    O    CHF2    (6-)CH3
Figure A0110152700532
  155122       -    O    CHF2    (6-)CH3
Figure A0110152700533
  105123       -    O    CHF2    (6-)CH3  81124       -    O    CHF2    (6-)CH3   174
表1-续实施例号  A    Q      R1        (位置)      R3
                             R2                     熔点(℃)125       -    O    CHF2       (5-)CH3   150126       -    O    CHF2       (6-)CH3   124127       -    O    CHF2       (6-)CH3
Figure A0110152700543
  200128       -    S    n-C3H7    (6-)CH3   160129       -    S    n-C3H7    (6-)CH3   148130       -    S    C2H5      (6-)CH3
Figure A0110152700546
  141
表1-续实施例号  A    Q      R1        (位置)       R3
                               R2                  熔点(℃)131       -    S    C2H5      (6-)CH3
Figure A0110152700551
  125132       -    S    C2H5      (6-)CH3   158133       -    S    i-C3H7    (6-)CH3
Figure A0110152700553
  155134       -    S    n-C3H7    (6-)CH3
Figure A0110152700554
  153135       -    S    n-C3H7    (6-)CH3   131
表1-续实施例号  A    Q       R1        (位置)       R3
                              R2                     熔点(℃)136       -    S    n-C3H7    (6-)CH3
Figure A0110152700561
  120137       -    O    C2H5      (6-)Cl   149138       -    O    C2H5      (6-)Cl 
Figure A0110152700563
  99139       -    O    CH3        (6-)Cl 
Figure A0110152700564
   176140       -    O    CH3        (6-)Cl 
Figure A0110152700565
  192
表1-续实施例号  A    Q      R1      (位置)        R3
                           R2                         熔点(℃)141       -    O    C2H5    (6-)Cl
Figure A0110152700571
      144142       -    O    CH3      (6-)Cl
Figure A0110152700572
  114143       -    O    C2H5    (6-)Cl       144144       -    O    CH3      (6-)Cl
Figure A0110152700574
      157145       -    O    C2H5    (6-)Cl       142
表1-续实施例号  A    Q      R1      (位置)    R3
                           R2                   熔点(℃)146       -    O    CH3     (6-)Cl
Figure A0110152700581
   191147       -    O    C2H5   (6-)Cl
Figure A0110152700582
  116148       -    O    CH3     (6-)Cl
Figure A0110152700583
  205149       -    O    CH3     (6-)Cl   147150       -    O    C2H5   (6-)Cl
Figure A0110152700585
 117
表1-续实施例号  A    Q      R1     (位置)    R3
                          R2                   熔点(℃)151       -    O    CH3    (6-)Cl
Figure A0110152700591
  149152       -    O    CH3    (6-)Cl
Figure A0110152700592
 176153       -    O    CH3    (6-)Cl
Figure A0110152700593
  150154       -    O    CH3    (6-)Cl  146155       -    O    CH3    (6-)Cl
Figure A0110152700595
  191156       -    O    CH3    (6-)Cl  127
表1-续实施例号  A    Q      R1        (位置)      R3
                               R2                   熔点(℃)157       -    O    CH3        (6-)Cl
Figure A0110152700601
  174158       -    O    n-C3H7    (6-)Cl
Figure A0110152700602
  117159       -    O    n-C3H7    (6-)Cl
Figure A0110152700603
  134160       -    O    n-C3H7    (6-)Cl
Figure A0110152700604
  115161       -    O    n-C3H7    (6-)Cl
Figure A0110152700605
  137
表1-续实施例号  A    Q       R1        (位置)    R3
                              R2                   熔点(℃)162       -    O    n-C3H7    (6-)Cl
Figure A0110152700611
  125163       -    O    n-C3H7    (6-)Cl
Figure A0110152700612
  119164       -    O    H           (6-)Cl     147165       -    O    n-C3H7    (6-)Cl
Figure A0110152700614
   148166       -    O    i-C3H7    (6-)Cl    143
表1-续实施例号  A    Q       R1        (位置)     R3
                             R2                    熔点(℃)167       -    O    i-C3H7    (6-)Cl  122168       -    O    CH3        (6-)Cl   165169       -    O    n-C3H7    (5-)Cl   154170       -    O    n-C3H7    (5-)Cl
Figure A0110152700624
  136171       -    O    n-C3H7    (5-)Cl
Figure A0110152700625
  128
表1-续实施例号  A    Q       R1        (位置)    R3
                             R2                     熔点(℃)172       -    O    CH3        (6-)Cl
Figure A0110152700631
   143173       -    O    i-C3H7    (6-)Cl
Figure A0110152700632
   136174       -    O    i-C3H7    (6-)Cl
Figure A0110152700633
   121175       -    O    i-C3H7    (6-)Cl
Figure A0110152700634
  158176       -    O    i-C3H7    (6-)Cl
Figure A0110152700635
  141
表1-续实施例号  A    Q       R1        (位置)     R3
                             R2                       熔点(℃)177       -    O    i-C3H7    (6-)Cl      127178       -    O    i-C3H7    (6-)Cl  
Figure A0110152700642
  143179       -    O    i-C3H7    (6-)Cl     129180       -    O    i-C3H7    (6-)Cl     95181       -    O    n-C3H7    (6-)CH3 
Figure A0110152700645
 74182       -    O    n-C3H7    (6-)CH3   114
表1-续实施例号  A    Q       R1        (位置)      R3
                              R2                       熔点(℃)183       -    O    n-C3H7    (6-)CH3
Figure A0110152700651
   140184       -    O    n-C3H7    (6-)CH3    159185       -    O    n-C3H7    (6-)CH3
Figure A0110152700653
  107186       -    O    n-C3H7    (6-)CH3
Figure A0110152700654
  132187       -    O    n-C3H7    (6-)CH3   132
表1-续实施例号  A    Q      R1        (位置)      R3
                            R2                       熔点(℃)188       -    O    n-C3H7    (6-)CH3
Figure A0110152700661
   110189       -    O    CH3        (6-)CH3
Figure A0110152700662
   159190       -    O    n-C3H7    (6-)CH3   138191       -    O    n-C3H7    (6-)CH3
Figure A0110152700664
   147192       -    O    n-C3H7    (6-)CH3
Figure A0110152700665
  114193       -    O    n-C3H7    (6-)CH3
Figure A0110152700666
  125
表1-续实施例号  A    Q      R1        (位置)      R3
                            R2                      熔点(℃)194       -    O    n-C3H7    (6-)CH3
Figure A0110152700671
  126195       -    O    n-C3H7    (6-)CH3
Figure A0110152700672
  151196       -    O    n-C3H7    (6-)CH3    121197       -    O    n-C3H7    (6-)CH3
Figure A0110152700674
 147198       NH   O    C2H5      (6-)CH3   135199       -    O    i-C3H7    (6-)CH3
Figure A0110152700676
表1-续实施例号  A    Q       R1      (位置)      R3
                             R2                     熔点(℃)200       -    O    C2H5    (6-)CH3
Figure A0110152700681
   119201       -    O    C2H5    (6-)CH3   146202       -    O    C2H5    (6-)CH3    128203       -    O    C2H5    (6-)CH3    186204       -    O    C2H5    (6-)CH3   239
表1-续实施例号  A    Q      R1        (位置)     R3
                            R2                       熔点(℃)205       -    O    C2H5      (6-)CH3
Figure A0110152700691
  152206       -    O    C2H5      (6-)CH3
Figure A0110152700692
 155207       -    O    C2H5      (6-)CH3
Figure A0110152700693
208       -    O    i-C3H7    (6-)CH3
Figure A0110152700694
209       -    O    C2H5      (6-)CH3
Figure A0110152700695
表1-续实施例号  A    Q       R1        (位置)      R3
                             R2                       熔点(℃)210       -    O    C2H5      (6-)CH3    140211       -    O    C2H5      (6-)CH3
Figure A0110152700702
  118212       -    O    C2H5      (6-)CH3
Figure A0110152700703
   156213       -    O    C2H5      (6-)CH3
Figure A0110152700704
  110214       -    O    C2H5      (6-)CH3
Figure A0110152700705
  133215       -    O    i-C3H7    (6-)CH3
Figure A0110152700706
   138
表1-续实施例号  A    Q       R1        (位置)      R3
                               R2                    熔点(℃)216       -    O    i-C3H7    (6-)CH3
Figure A0110152700711
  154217       -    O    i-C3H7    (6-)CH3
Figure A0110152700712
  149218       -    O    i-C3H7    (6-)CH3
Figure A0110152700713
  112219       -    O    i-C3H7    (6-)CH3
Figure A0110152700714
  162220       -    O    i-C3H7    (6-)CH3    99221       -    O    i-C3H7    (6-)CH3
Figure A0110152700716
  146
表1-续实施例号  A    Q      R1        (位置)      R3
                              R2                   熔点(℃)222       -    O    C2H5     (6-)CH3
Figure A0110152700721
  134223       -    O    CH3       (6-)CH3
Figure A0110152700722
  199224       -    O    CH3       (6-)CH3   176225       -    O    CH3       (6-)CH3
Figure A0110152700724
 145226       -    O    i-C3H7   (6-)CH3
Figure A0110152700725
 133
表1-续实施例号  A    Q      R1        (位置)        R3
                               R2                    熔点(℃)227       NH   O    n-C3H7    (5-)CH3
Figure A0110152700731
  127228       -    O    i-C3H7    (6-)CH3
Figure A0110152700732
 144229       -    O    i-C3H7    (6-)CH3
Figure A0110152700733
  141230       -    O    i-C3H7    (6-)CH3
Figure A0110152700734
  152231       -    O    i-C3H7    (6-)CH3  132232       -    O    i-C3H7    (6-)CH3   147
表1-续实施例号  A    Q       R1        (位置)      R3
                               R2                    熔点(℃)233       -    O    i-C3H7    (6-)CH3   163234       -    O    i-C3H7    (6-)CH3    102235       -    O    C2H5      (6-)CH3   121236       -    O    C2H5      (6-)CH3    113237       -    O    C2H5      (6-)CH3
Figure A0110152700745
  145238       -    O    C2H5      (6-)CH3   137
表1-续实施例号  A    Q      R1      (位置)     R3No.                            R2                       熔点(℃)239       -    O    C2H5    (6-)CH3     172240       -    O    C2H5    (6-)CH3
Figure A0110152700752
  148241       -    O    C2H5    (6-)CH3   157242       -    O    C2H5    (6-)CH3
Figure A0110152700754
  186243       NH   O    CH3     (6-)OCH3    170244       -    O    CHF2    (5-)CH3
Figure A0110152700756
表1-续实施例号  A    Q       R1        (位置)     R3
                             R2                   熔点(℃)245       -    S    i-C3H7   (6-)CH3   160246       -    O    CH3       (6-)CF3      205247       -    S    CH3       (6-)CF3
Figure A0110152700763
    92248       -    S    CH3       (6-)CF3
Figure A0110152700764
   154249       -    S    CH3       (6-)CF3
Figure A0110152700765
   157250       -    O    C2H5     (6-)CF3      176
表1-续实施例号  A    Q      R1          (位置)      R3
                               R2                   熔点(℃)251       -    O    n-C3H7-n   (6-)CF3
Figure A0110152700771
    166252       -    O    i-C3H7     (6-)CF3
Figure A0110152700772
    190253       -    O    CH3         (6-)CF3
Figure A0110152700773
   203254       -    O    CH3         (6-)CF3   156255       -    O    CH3         (6-)CF3
Figure A0110152700775
   170256       -    O    CH3         (6-)CF3
Figure A0110152700776
  198
表1-续实施例号  A    Q     R1     (位置)      R3
                          R2                    熔点(℃)257       -    O    CH3    (6-)CF3
Figure A0110152700781
  213258       -    O    CH3    (6-)CF3  152259       -    O    CH3    (6-)CF3
Figure A0110152700783
  187260       -    O    CH3    (6-)CF3
Figure A0110152700784
   210261       -    O    CH3    (6-)CF3
Figure A0110152700785
   172
表1-续实施例号  A    Q      R1     (位置)      R3
                            R2                    熔点(℃)262       -    O    CH3    (6-)CF3
Figure A0110152700791
   145263       -    O    CH3    (6-)CF3    136264       -    O    CH3    (6-)CF3   153265       -    O    CH3    (6-)CF3
Figure A0110152700794
  136266       -    O    CH3    (6-)CF3
Figure A0110152700795
  210
表1-续实施例号  A    Q    R1      (位置)      R3
                            R2                     熔点(℃)267       -    O    CH3     (6-)CF3
Figure A0110152700801
  147268       -    O    CH3     (6-)CF3    169269       -    O    CH3     (6-)CF3
Figure A0110152700803
 215270       -    O    CH3     (6-)CF3  138271       -    O    CH3     (6-)CF3
Figure A0110152700805
  182272       -    S    C2H5   (6-)CF3   112
表1-续实施例号  A    Q      R1        (位置)      R3
                               R2                    熔点(℃)273       -    S    C2H5      (6-)CF3    167274       -    S    C2H5      (6-)CF3
Figure A0110152700812
  152275       -    S    n-C3H7    (6-)CF3
Figure A0110152700813
  119276       -    S    n-C3H7    (6-)CF3   157277       -    S    n-C3H7    (6-)CF3
Figure A0110152700815
 154
表1-续实施例号  A    Q      R1        (位置)      R3
                             R2                    熔点(℃)278       -    S    i-C3H7    (6-)CF3   137279       -    S    i-C3H7    (6-)CF3
Figure A0110152700822
  167280       -    S    i-C3H7    (6-)CF3
Figure A0110152700823
  137281       -    O    C2H5      (6-)CF3
Figure A0110152700824
  154282       -    O    C2H5      (6-)CF3
Figure A0110152700825
 160
表1-续实施例号  A    Q      R1        (位置)       R3
                                R2                 熔点(℃)283       -    O    C2H5      (6-)CF3
Figure A0110152700831
 139284       -    O    C2H5      (6-)CF3
Figure A0110152700832
  134285       -    O    C2H5      (6-)CF3  142286       -    O    C2H5      (6-)CF3
Figure A0110152700834
 120287       -    O    n-C3H7    (6-)CF3
Figure A0110152700835
  130
表1-续实施例号  A    Q      R1        (位置)        R3
                              R2                       熔点(℃)288       -    O    n-C3H7    (6-)CF3
Figure A0110152700841
  127289       -    O    n-C3H7    (6-)CF3   116290       -    O    n-C3H7    (6-)CF3
Figure A0110152700843
   126291       -    O    n-C3H7    (6-)CF3   113292       -    O    i-C3H7    (6-)CF3
Figure A0110152700845
   151
表1-续实施例号  A    Q      R1        (位置)       R3
                               R2                    熔点(℃)293       -    O    i-C3H7    (6-)CF3
Figure A0110152700851
  157294       -    O    i-C3H7    (6-)CF3   171295       -    O    i-C3H7    (6-)CF3
Figure A0110152700853
   137296       -    O    i-C3H7    (6-)CF3   125297       -    O    n-C3H7    (6-)CF3
Figure A0110152700855
   109
表1-续实施例号  A    Q      R1        (位置)      R3
                             R2                     熔点(℃)298       -    O    n-C3H7    (6-)CF3   138299       -    O    i-C3H7    (6-)CF3
Figure A0110152700862
  130300       -    O    C2H5      (6-)CF3
Figure A0110152700863
  165301       -    O    i-C3H7    (6-)CF3
Figure A0110152700864
   148302       -    O    i-C3H7    (6-)CF3  147
表1-续实施例号  A    Q       R1        (位置)      R3
                               R2                     熔点(℃)303       -    O    i-C3H7    (6-)CF3    172304       -    O    i-C3H7    (6-)CF3   147305       -    O    i-C3H7    (6-)CF3    136306       -    O    C2H5      (6-)CF3
Figure A0110152700874
   124307       -    O    C2H5      (6-)CF3    98
表1-续实施例号  A    Q      R1        (位置)     R3
                               R2                   熔点(℃)308       -    O    C2H5      (6-)CF3
Figure A0110152700881
   125309       -    O    C2H5      (6-)CF3
Figure A0110152700882
   179310       -    O    C2H5      (6-)CF3   153311       -    O    C2H5      (6-)CF3    171312       -    O    n-C3H7    (6-)CF3
Figure A0110152700885
   113
表1-续实施例号  A    Q      R1        (位置)      R3
                             R2                      熔点(℃)313       -    O    n-C3H7    (6-)CF3    138314       -    O    n-C3H7    (6-)CF3
Figure A0110152700892
  110315       -    O    n-C3H7    (6-)CF3   134316       -    O    i-C3H7    (6-)CF3   167317       -    O    i-C3H7    (6-)CF3   120表1-续实施   A    Q      R1        (位置)     R3例号                          R2                       熔点(℃)318    -    O    i-C3H7    (6-)CF3
Figure A0110152700901
  117319    -    O    i-C3H7    (6-)CF3
Figure A0110152700902
  160320    -    O    i-C3H7    (6-)CF3
Figure A0110152700903
 154321    -    O    i-C3H7    (6-)CF3
Figure A0110152700904
  159322    -    O    n-C3H7    (6-)CF3
Figure A0110152700905
  141表1-续实施   A    Q      R1      (位置)            R3例号                         R2                               熔点(℃)323    -    O    i-C3H7   (6-)CF3            146324    -    O    i-C3H7   (6-)CF3        
Figure A0110152700912
   134325    -    O    i-C3H7   (6-)CF3           168326    -    O    CH3       (6-)C3H7-n       158327    -    O    CH3       (6-)C3H7-n        172表1-续实施   A    Q     R1        (位置)             R3例号                          R2                           熔点(℃)328    -    O    CH3        (6-)C3H7-n  
Figure A0110152700921
  147329    -    O    C2H5      (6-)CF3   
Figure A0110152700922
     66330    -    O    C2H5      (6-)CH3   
Figure A0110152700923
       134331    -    O    C2H5      (6-)CH3   
Figure A0110152700924
      149332    -    O    n-C3H7    (6-)CH3   
Figure A0110152700925
      114333    -    O    H           (6-)Cl            102表1-续实施   A    Q      R1           (位置)     R3例号                              R2                    熔点(℃)334    -    O    H               (6-)Cl     143335    -    O    
Figure A0110152700932
    (6-)Cl
Figure A0110152700933
    130336    -    O    -CH2C6H5    (6-)Cl     143337    -    O    -CH2C6H5    (6-)Cl
Figure A0110152700935
    99338    -    O    -CH2C≡CH     (6-)Cl
Figure A0110152700936
    161表1-续实施   A    Q      R1                   (位置)       R3例号                                      R2                     熔点(℃)339    -    O    n-C3H7               (6-)CH3
Figure A0110152700941
  133340    -    O    H                       (6-)CH3    100341    -    O    H                       (6-)CH3
Figure A0110152700943
   147342    -    O    -CH2C6H5            (6-)CH3    157343    -    O                 (6-)CH3
Figure A0110152700946
  150表1-续实施   A    Q      R1         (位置)       R3例号                           R2                       熔点(℃)344    -    O    -CH2C≡CH   (6-)CH3
Figure A0110152700951
    172345    -    O    i-C3H7     (6-)CH3
Figure A0110152700952
    346    -    O    C2H5       (6-)CH3   136347    -    O    i-C3H7     (6-)CH3   113348    -    O    i-C3H7     (6-)CH3     175349    -    O    i-C3H7     (6-)CH3   135
表1-续实施例号  A    Q       R1      (位置)      R3
                             R2                     熔点(℃)350       -    O    i-C3H7   (6-)CH3
Figure A0110152700961
  78351       -    O    i-C3H7   (6-)CH3   125352       -    O    i-C3H7   (6-)CH3
Figure A0110152700963
  140353       -    O    CH3       (6-)CH3   161354       -    O    CH3       (6-)CH3
Figure A0110152700965
  142355       -    O    CH3       (6-)CH3
Figure A0110152700966
  124
表1-续实施例号  A    Q    R1     (位置)       R3
                          R2                    熔点(℃)356       -    O    CH3    (6-)CH3
Figure A0110152700971
  153357       -    O    CH3    (6-)CH3
Figure A0110152700972
  170358       -    O    CH3    (6-)CH3
Figure A0110152700973
  116359       -    O    CH3    (6-)CH3  120360       -    O    CH3    (5-)Cl     172
表1-续实施例号  A    Q    R1     (位置)     R3
                         R2                      熔点(℃)361       -    O    CH3    (5-)Cl
Figure A0110152700981
   175362       -    O    CH3    (5-)Cl
Figure A0110152700982
    192363       -    O    CH3    (5-)Cl
Figure A0110152700983
    195364       -    O    CH3    (5-)Cl
Figure A0110152700984
   174365       -    O    CH3    (5-)Cl
Figure A0110152700985
   160366       -    O    CH3    (5-)Cl      214
表1-续实施例号  A     Q    R1        (位置)      R3
                             R2                      熔点(℃)367       -     O    CH3       (5-)Cl 
Figure A0110152700991
  185368       -     O    CH3       (5-)Cl 
Figure A0110152700992
  191369       NH    O    CH3       (6-)CH3    161370       NH    O    i-C3H7   (6-)CH3
Figure A0110152700994
   132371       NH    O    CH3       (6-)OCH3
Figure A0110152700995
  151372       NH    O    CH3       (6-)CH3   161
表1-续实施例号  A     Q      R1      (位置)      R3
                             R2                     熔点(℃)373       NH    O    i-C3H7   (6-)CH3
Figure A0110152701001
    128374       NH    O    CH3       (6-)CH3
Figure A0110152701002
    140375       -     S    i-C3H7   (6-)CH3     108376       -     O    CHF2      (4-)CH3       131377       -     O    CH3       (6-)CF3
Figure A0110152701005
   187378       -     O    CH3       (6-)CF3     154
表1-续实施例号  A    Q      R1      (位置)        R3
                           R2                       熔点(℃)379       -    O    CH3     (6-)C2H5
Figure A0110152701011
  179380       -    O    CH3     (6-)C2H5
Figure A0110152701012
  178381       -    O    CH3     (6-)C2H5
Figure A0110152701013
  167382       -    O    C2H5   (6-)C2H5  135383       -    O    C2H5   (6-)C2H5
Figure A0110152701015
 146
表1-续实施例号  A    Q      R1      (位置)       R3
                           R2                       熔点(℃)384       -    O    C2H5   (6-)C2H5     174385       -    O    CH3     (6-)C2H5     130386       -    O    CH3     (6-)C2H5      195387       -    O    CH3     (6-)C2H5
Figure A0110152701024
     183388       -    O    C2H5   (6-)C3H7-n
Figure A0110152701025
 135
表1-续实施例号  A    Q      R1      (位置)          R3
                           R2                          熔点(℃)389       -    O    C2H5   (6-)C3H7-n
Figure A0110152701031
  149390       -    O    CH3     (6-)C3H7-n
Figure A0110152701032
  19339l       -    O    CH3     (6-)C3H7-n
Figure A0110152701033
  125392       -    O    CH3     (6-)C3H7-n
Figure A0110152701034
  182393       -    O    C2H5   (6-)C3H7-n   120
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                         熔点(℃)394       -    O    C2H5      (6-)C3H7-n
Figure A0110152701041
   158395       -    O    i-C3H7    (6-)CH3  
Figure A0110152701042
    180396       -    O    n-C4H9    (6-)CH3  
Figure A0110152701043
    132397       -    O    n-C4H9    (6-)CH3  
Figure A0110152701044
    143398       -    O    n-C4H9    (6-)CH3  
Figure A0110152701045
    106
表1-续实施例号  A    Q      R1        (位置)      R3
                              R2                    熔点(℃)399       -    O    n-C4H9   (6-)CH3    98400       -    O    n-C4H9   (6-)CH3
Figure A0110152701052
   140401       -    O    CH3       (6-)CH3
Figure A0110152701053
  147402       -    O    CH3       (6-)CH3
Figure A0110152701054
  123403       -    O    CH3       (6-)CH3   185404       -    O    CH3       (6-)CH3
Figure A0110152701056
  154
表1-续实施例号  A    Q      R1         (位置)       R3
                               R2                      熔点(℃)405       NH    O    i-C3H7    (6-)CH3 
Figure A0110152701061
   150406       -     O    C2H5      (6-)C2H5   135407       -     O    C2H5      (6-)C2H5   134408       -     O    C2H5      (6-)C2H5
Figure A0110152701064
  178409       -     O    C3H7-i    (6-)C2H5   109
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                      熔点(℃)410       -    O    C3H7-i    (6-)C2H5   125411       -    O    C3H7-i    (6-)C2H5
Figure A0110152701072
  161412       -    O    C3H7-i    (6-)C2H5
Figure A0110152701073
  114413       -    O    C3H7-i    (6-)C2H5
Figure A0110152701074
  142414       -    O    C3H7-i    (6-)C2H5
Figure A0110152701075
  124415       -    O    CH3        (6-)C2H5
Figure A0110152701076
表1-续实施例号  A    Q      R1      (位置)          R3
                           R2                          熔点(℃)416       -    O    C2H5   (6-)C3H7-n    126417       -    O    C2H5   (6-)C3H7-n
Figure A0110152701082
   121418       -    O    CH3     (6-)C3H7-n    109419       -    O    CH3     (6-)C3H7-n
Figure A0110152701084
  145420       -    O    CH3     (6-)C3H7-n   126
表1-续实施例号  A    Q      R1       (位置)           R3
                             R2                           熔点(℃)421       -    O    CH3        (6-)C3H7-n
Figure A0110152701091
  130422       -    O    CH3        (6-)C3H7-n
Figure A0110152701092
  155423       -    O    CH3        (6-)C3H7-n
Figure A0110152701093
    133424       -    O    CH3        (6-)C3H7-n
Figure A0110152701094
  145425       -    O    -SO2CH3   (6-)CH3 
Figure A0110152701095
      95426       -    O    -SO2CH3   (6-)CH3        153
表1-续实施例号  A    Q      R1         (位置)       R3
                              R2                    熔点(℃)427       -    O    C4H9-n     (6-)CH3
Figure A0110152701101
  154428       -    O    -CH2C≡CH   (6-)CH3
Figure A0110152701102
  167429       -    O    -CH2C≡CH   (6-)CH3
Figure A0110152701103
  170430       -    O    -CH2C≡CH   (6-)CH3
Figure A0110152701104
  153431       -    O    C4H9-i     (6-)CH3
Figure A0110152701105
 123432       -    O    C4H9-i     (6-)CH3   145
表1-续实施例号  A    Q      R1        (位置)        R3
                               R2                    熔点(℃)433       -    O    C4H9-i    (6-)CH3
Figure A0110152701111
    143434       -    O    C3H7-i    (6-)CH3
Figure A0110152701112
  138435       -    O    C3H7-i    (6-)CH3   161436       -    O    C3H7-i    (6-)CH3
Figure A0110152701114
  128437       -    O    C3H7-i    (6-)CH3
Figure A0110152701115
    177438       -    O    C3H7-i    (6-)CH3   165表1-续实施   A    Q      R1    (位置)      R3例号                      R2                     熔点(℃)439    -    O    CH3    (6-)CH3   157440    -    O    CH3    (6-)CH3
Figure A0110152701122
  168441    -    O    CH3    (6-)CH3
Figure A0110152701123
  164442    -    O    CH3    (6-)CH3
Figure A0110152701124
  125443    -    O    CH3    (6-)CH3    162444    -    O    CH3    (6-)OCH3
Figure A0110152701126
    154
表1-续实施例号  A    Q      R1   (位置)           R3
                         R2                         熔点(℃)445       -    S    CH3    (4-)C3H7-i
Figure A0110152701131
  116446       -    S    CH3    (4-)C3H7-i   110447       -    S    CH3    (4-)C3H7-i
Figure A0110152701133
  134448       -    O    CH3    (4-)C3H7-i   152449       -    O    CH3    (4-)C3H7-i
Figure A0110152701135
  159450       -    O    CH3    (4-)C3H7-i
Figure A0110152701136
  150
表1-续实施例号  A    Q      R1      (位置)       R3
                            R2                     熔点(℃)451       -    O    C2H5    (6-)OCH3
Figure A0110152701141
  107452       -    O    C2H5    (6-)OCH3   104453       -    O    C2H5    (6-)OCH3
Figure A0110152701143
100454       -    S    C2H5    (6-)OCH3
Figure A0110152701144
  103455       -    S    C2H5    (6-)OCH3   95
表1-续实施例号  A    Q      R1        (位置)      R3
                             R2                           熔点(℃)456       -    S    C2H5      (6-)OCH3 
Figure A0110152701151
      105457       -    O    C2H5      (6-)OC2H5      130458       -    O    C2H5      (6-)OC2H5       100459       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701154
   114460       -    O    C3H7-i    (6-)OC3H7-i   125461       -    S    C3H7-i    (6-)OC3H7-i   143
表1-续实施例号  A    Q      R1           (位置)       R3
                                R2                      熔点(℃)462       -    O    C2H5        (6-)OC2H5
Figure A0110152701161
 120463       -    O    -CF2CHFCl    (6-)CH3 
Figure A0110152701162
  124464       -    O    -CF2CHFCl    (6-)CH3 
Figure A0110152701163
  115465       -    O    -CF2CHFCl    (6-)CH3 
Figure A0110152701164
  150466       -    O    CH3          (3-)CH3    178
表1-续
      A    Q      R1      (位置)      R3实施例号                       R2                    熔点(℃)467       -    O    CH3      (3-)Cl    188468       -    O    C2H5    (3-)Cl    159469       -    O    CH3      (3-)F 
Figure A0110152701173
   176470       -    O    C2H5    (6-)CF3  124471       -    O    C2H5    (6-)CF3  34
表1-续
      A    Q      R1        (位置)     R3实施例号                          R2                       熔点(℃)472       -    O    C2H5      (6-)CF3
Figure A0110152701181
   68473       -    O    C3H7-i    (6-)CF3
Figure A0110152701182
   41474       -    O    C2H5      (6-)CF3     127475       -    O    H           (6-)CF3       125476       -    S    C2H5      (6-)CH3
Figure A0110152701185
表1-续
      A      Q       R1        (位置)     R3实施例号                            R2                       熔点(℃)477       NH     O     C2H5      (6-)CH3   128478       NH     O     C2H5      (6-)CH3
Figure A0110152701192
    148479       NH     O     C3H7-n    (6-)CH3     127480       NH     O     C3H7-n    (6-)CH3
Figure A0110152701194
     57481       NH     O     C2H5      (6-)CH3
Figure A0110152701195
     125
表1-续
      A      Q      R1        (位置)       R3实施例号                            R2                    熔点(℃)482       NH     O    C3H7-n    (6-)CH3
Figure A0110152701201
   115483       NH     O    C3H5-n    (6-)CH3    151484       NH     O    C2H5      (5-)CH3   132485       NH     O    C2H5      (5-)CH3
Figure A0110152701204
  106486       NH     O    C2H5      (5-)CH3
Figure A0110152701205
  163
表1-续
      A    Q      R1           (位置)       R3实施例号                             R2                          熔点(℃)487       NH   O    C2H5          (5-)CH3 
Figure A0110152701211
       137488       -    O    C2H5          (6-)C3H7-i
Figure A0110152701212
  166489       -    O    C2H5          (6-)C3H7-i    169490       -    O    C2H5          (6-)C3H7-i     130491       NH   O    
Figure A0110152701215
      (6-)CH3 
Figure A0110152701216
      148
表1-续
      A       Q       R1    (位置)        R3实施例号                          R2                        熔点(℃)492       NH      O 
Figure A0110152701221
  (6-)CH3 
Figure A0110152701222
    138493       NH      O    (6-)CH3 
Figure A0110152701224
    147494       -       O    (6-)CH3 
Figure A0110152701226
    124495       -       O 
Figure A0110152701227
  (6-)CH3 
Figure A0110152701228
    152496       -       O    (6-)CH3 
Figure A01101527012210
  141表1-续
         A       Q       R1             (位置)     R3实施例号                                      R2                        熔点(℃)497          -       O     
Figure A0110152701231
        (6-)CH3
Figure A0110152701232
    127498          -       O              (6-)CH3     144499          -       O              (6-)CH3     107500          -       O     C3H7-n          (6-)CH3
Figure A0110152701237
501          -       O     C2H5            (6-)CH3 表1-续
            A    Q      R1        (位置)      R3实施例号                                R2                        熔点(℃)502             -    O    C3H7-i    (6-)CH3 503             -    O
Figure A0110152701242
      (6-)CH3   73504             -    O    C3H7-i    (6-)CH3
Figure A0110152701244
505             -    O    C3H7-i    (6-)CH3      140506             -    O    C4H9-s    (6-)CH3
Figure A0110152701246
     120
表1-续
      A    Q      R1        (位置)     R3实施例号                         R2                      熔点(℃)507       -    O    C4H9-s    (6-)CH3
Figure A0110152701251
    117508       -    O    C4H9-s    (6-)CH3     128509       -    O    C4H9-s    (6-)CH3     232510       -    O    C4H9-s    (6-)CH3    268511       -    O    C4H9-s    (6-)CH3   130
表1-续
      A    Q      R1        (位置)     R3实施例号                          R2                          熔点(℃)512       -    O    C4H9-s    (6-)CH3
Figure A0110152701261
       137513       -    O    C4H9-s    (6-)CH3
Figure A0110152701262
       145514       -    O    C4H9-s    (6-)CH3
Figure A0110152701263
       164515       -    O    C4H9-s    (6-)CH3      89516       -    O    C4H9-s    (6-)CH3
Figure A0110152701265
 86
表1-续
      A    Q    R1        (位置)        R3实施例号                        R2                      熔点(℃)517       -    O  C4H9-s    (6-)CH3
Figure A0110152701271
 98518       -    O  C4H9-s    (6-)CH3
Figure A0110152701272
  122519       -    O  C4H9-s    (6-)CH3
Figure A0110152701273
    135520       -    O  C2H5      (6-)CH3
Figure A0110152701274
    142521       -    O  CH3        (6-)CH3
Figure A0110152701275
    157
表1-续
      A    Q      R1        (位置)     R3实施例号                          R2                      熔点(℃)522       -    O    C3H7-n    (6-)CH3
Figure A0110152701281
     126523       -    O    C4H9-s    (6-)CH3
Figure A0110152701282
     140524       -    O    C2H5      (6-)CH3
Figure A0110152701283
  164525       -    O    CH3        (6-)CH3
Figure A0110152701284
   166526       -    O    C3H7-n    (6-)CH3    145表1-续
      A    Q      R1      (位置)        R3实施例号                        R2                            熔点(℃)527       -    O    CH3       (6-)CH3 
Figure A0110152701291
528       -    O    C3H7-n   (6-)CH3  529       -    O    C2H5     (6-)CH3 
Figure A0110152701293
530       -    O    CH3       (6-)C3H7-i   166531       -    O    CH3       (6-)C3H7-i
Figure A0110152701295
  178
表1-续
      A    Q      R1        (位置)        R3实施例号                          R2                        熔点(℃)532       -    O    C3H7-i    (6-)C3H7-i  131533       -    O    C3H7-i    (6-)C3H7-i
Figure A0110152701302
 130534       -    O    C3H7-i    (6-)C3H7-i
Figure A0110152701303
 133535       -    O    C3H7-i    (6-)C3H7-i  116536       -    O    CH3        (6-)C3H7-i
Figure A0110152701305
 192表1-续
      A    Q      R1   (位置)        R3实施例号                     R2                           熔点(℃)537       -    O    CH3    (6-)C3H7-i     200538       -    O    CH3    (6-)C3H7-i     200539       -    O    CH3    (6-)C3H7-i
Figure A0110152701313
 105540       -    O    CH3    (6-)C3H7-i
Figure A0110152701314
  154541       -    O    CH3    (6-)C3H7-i
Figure A0110152701315
  152
表1-续
      A    Q      R1        (位置)         R3实施例号                          R2                                   熔点(℃)542       -    O    C3H7-n    (6-)C3H7-i
Figure A0110152701321
     132543       -    O    C3H7-n    (6-)C3H7-i      129544       -    O    C3H7-n    (6-)C3H7-i      179545       -    O    CH3        (6-)C3H7-i
Figure A0110152701324
546       -    O    C3H7-n    (6-)C3H7-i
表1-续
      A    Q     R1      (位置)           R3实施例号                       R2                           熔点(℃)547       -    O    C2H5    (6-)C3H7-i     200548       -    O    C2H5    (6-)C3H7-i     147549       -    O    C2H5    (6-)C3H7-i
Figure A0110152701333
    149550       -    O    C2H5    (6-)C3H7-i
Figure A0110152701334
 136551       -    O    C2H5    (6-)C3H7-i   134
表1-续
      A    Q    R1          (位置)           R3实施例号                          R2                         熔点(℃)552       -    O    C3H7-i    (6-)C3H7-i  175553       -    O    C3H7-i    (6-)C3H7-i   147554       -    O    C3H7-i    (6-)C3H7-i  167555       -    O    C3H7-i    (6-)C3H7-i
Figure A0110152701344
   173556       -    O    C3H7-i    (6-)CH3 
Figure A0110152701345
  188
表1-续
      A    Q     R1       (位置)           R3实施例号                        R2                         熔点℃557       NH   O    CH3        (6-)CH3
Figure A0110152701351
   181558       NH   O    C3H7-i    (6-)CH3    136559       -    O    CH3        (6-)CH3 560       NH   O    C3H7-n    (6-)CH3    129561       -    O    C3H7-i    (6-)OCH3    94
表1-续
      A    Q      R1       (位置)         R3实施例号                         R2                        熔点℃562       -    O    C3H7-i    (6-)OCH3 
Figure A0110152701361
 80563       -    O    C3H7-i    (6-)OC2H5  68564       -    O    C3H7-i    (6-)OC2H5  91565       -    O    C3H7-n    (6-)OCH3  123566       -    O    C3H7-n    (6-)OCH3 
Figure A0110152701365
 104
表1-续
      A    Q      R1        (位置)      R3实施例号                         R2                        熔点℃567       -    O    C3H7-n    (6-)OCH3
Figure A0110152701371
    90568       -    S    C3H7-n    (6-)OCH3     107569       -    O    C3H7-n    (6-)OCH3
Figure A0110152701373
      70570       -    O    C2H5      (6-)OC2H5
Figure A0110152701374
 132571       -    S    CH3        (6-)OCH3
Figure A0110152701375
   150
表1-续
       A    Q      R1        (位置)          R3实施例号                            R2                            熔点℃572        -    O    C2H5      (6-)OCH3 
Figure A0110152701381
          127573        -    O    C3H7-i    (6-)OC3H7-i     110574        -    S    C3H7-n    (6-)OC3H7-n     130575        -    S    C3H7-n    (6-)OC3H7-n     135576        -    S    C3H7-n    (6-)OC3H7-n
Figure A0110152701385
表1-续
      A    Q      R1        (位置)       R3实施例号                         R2                            熔点℃577       -    O    C2H5      (6-)OC2H5
Figure A0110152701391
     173578       -    O    C2H5      (6-)OCH3       168579       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701393
  125580       -    O    C3H7-n    (6-)OC2H5      140581       -    O    C3H7-n    (6-)OCH3 
Figure A0110152701395
     115
表1-续
      A    Q      R1        (位置)         R3实施例号                         R2                    熔点℃582       -    S    C3H7-n    (6-)OCH3 
Figure A0110152701401
 111583       -    S    C3H7-n    (6-)OCH3 
Figure A0110152701402
 138584       -    O    C3H7-i    (6-)OCH3 
Figure A0110152701403
 127585       -    O    C3H7-i    (6-)OC2H5  142586       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701405
 143
表1-续
      A    Q      R1      (位置)      R3实施例号                        R2                        熔点℃587       -    O    C2H5    (6-)OCH3
Figure A0110152701411
   104588       -    O    C2H5    (6-)OCH3
Figure A0110152701412
   118589       -    O    C2H5    (6-)OCH3
Figure A0110152701413
 70590       -    O    C2H5    (6-)OCH3
Figure A0110152701414
   110591       -    O    C2H5    (6-)OCH3
Figure A0110152701415
   156
表1-续
      A    Q     R1        (位置)       R3实施例号                        R2                          熔点℃592       -    O    C3H7-n    (6-)OCH3
Figure A0110152701421
   140593       -    O    C3H7-n    (6-)OCH3
Figure A0110152701422
   148594       -    O    C3H7-n    (6-)OCH3
Figure A0110152701423
 145595       -    O    C2H5      (6-)OCH3
Figure A0110152701424
 120596       -    O    C2H5      (6-)OCH3   100
表1-续
      A    Q     R1         (位置)        R3实施例号                          R2                       熔点℃597       -    O    C2H5      (6-)OCH3    130598       -    O    C2H6      (6-)OCH3   103599       -    O    C2H5      (6-)OCH3
Figure A0110152701433
 104600       -    O    C3H7-n    (6-)OCH3
Figure A0110152701434
   185601       -    O    C3H7-n    (6-)OCH3  100
表1-续
      A    Q      R1        (位置)         R3实施例号                          R2                     熔点℃602       -    O    C3H7-n    (6-)OCH3    138603       -    O    C3H7-n    (6-)OCH3
Figure A0110152701442
   106604       -    O    C3H7-n    (6-)OCH3    112605       -    O    C3H7-n    (6-)OCH3
Figure A0110152701444
 140606       -    O    C3H7-n    (6-)OCH3
Figure A0110152701445
    160
表1-续
      A    Q      R1        (位置)          R3实施例号                          R2                       熔点℃607       -    O    C3H7-n    (6-)OCH3
Figure A0110152701451
   180608       -    O    C3H7-n    (6-)OCH3
Figure A0110152701452
 142609       -    O    C3H7-n    (6-)OCH3
Figure A0110152701453
   158610       -    O    C3H7-n    (6-)OCH3
Figure A0110152701454
 134611       -    O    C3H7-i    (6-)OCH3
Figure A0110152701455
   140
表1-续
      A    Q      R1        (位置)        R3实施例号                          R2                          熔点℃612       -    O    C3H7-i    (6-)OCH3      142613       -    O    C3H7-i    (6-)OCH3    148614       -    O    C3H7-i    (6-)OCH3     146615       -    O    C3H7-i    (6-)OCH3     104616       -    O    C2H5      (6-)OC2H5
Figure A0110152701465
   123
表1-续
      A    Q      R1        (位置)           R3实施例号                          R2                           熔点℃617       -    O    C3H7-n    (6-)OC3H7-n   123618       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701472
 82619       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701473
  81620       -    S    C3H7-n    (6-)OC3H7-n
Figure A0110152701474
  88621       -    S    C2H5      (6-)OCH3 
Figure A0110152701475
    145
表1-续
      A    Q      R1        (位置)        R3实施例号                          R2                          熔点℃622       -    S    C2H5      (6-)OC2H5    147623       -    S    C3H7-n    (6-)OCH3 
Figure A0110152701482
   205624       -    S    C3H7-n    (6-)OC2H5
Figure A0110152701483
   202625       -    S    C3H7-i    (6-)OC3H7-i 152626       -    S    C2H5      (6-)OC2H5     168
表1-续
      A    Q      R1        (位置)           R3实施例号                          R2                          熔点℃627       -    S    C3H7-n    (6-)C3H7-n
Figure A0110152701491
  145628       -    S    C3H7-n    (6-)OCH3 
Figure A0110152701492
    158629       -    S    C3H7-i    (6-)OC3H7-i  155630       -    O    C3H7-i    (6-)OCH3     145631       -    O    C3H7-i    (6-)OCH3   111
表1-续
      A    Q      R1        (位置)         R3实施例号                          R2                         熔点℃632       -    O    C3H7-i    (6-)OCH3     122633       -    O    C3H7-i    (6-)OCH3 
Figure A0110152701502
   171634       -    O    C3H7-i    (6-)OCH3     160635       -    O    C3H7-i    (6-)OCH3 
Figure A0110152701504
  142636       -    O    C2H5      (6-)OC2H5
Figure A0110152701505
  106
表1-续
      A    Q      R1      (位置)          R3实施例号                        R2                          熔点℃637       -    O    C2H5    (6-)OC2H5
Figure A0110152701511
 106638       -    O    C2H5    (6-)OC2H5
Figure A0110152701512
  159639       -    O    C2H5    (6-)OC2H5
Figure A0110152701513
  148640       -    O    C2H5    (6-)OC2H5
Figure A0110152701514
  126641       -    O    C2H5    (6-)OC2H5
Figure A0110152701515
   111
表1-续
      A    Q      R1        (位置)          R3实施例号                          R2                          熔点℃642       -    O    C2H5      (6-)OC2H5
Figure A0110152701521
   171643       -    O    C2H5      (6-)OC2H5
Figure A0110152701522
  127644       -    O    C2H5      (6-)OC2H5
Figure A0110152701523
    148645       -    O    C2H5      (6-)OC2H5
Figure A0110152701524
  123646       -    O    C3H7-n    (6-)OC3H7-n  138
表1-续
      A    Q      R1        (位置)       R3实施例号                          R2                            熔点℃647       -    O    C3H7-n    (6-)OC3H7-n  95648       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701532
   130649       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701533
  74650       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701534
  109651       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701535
   75
表1-续
      A    Q      R1        (位置)             R3实施例号                          R2                              熔点℃652       -    O    C3H7-n    (6-)OC3H7-n    147653       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701542
 99654       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701543
   102655       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701544
 98656       -    O    C3H7-i    (6-)OC3H7-i    138
表1-续
      A    Q      R1        (位置)           R3实施例号                          R2                              熔点℃657       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701551
     127658       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701552
   160659       -    O    C3H7-i    (6-)OC3H7-i      115660       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701554
 108661       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701555
    154
表1-续
      A    Q      R1          (位置)            R3实施例号                            R2                             熔点℃662       -    O    C3H7-i       (6-)OC3H7-i
Figure A0110152701561
 144663       -    O    C2H4OC2H5  (6-)OCH3      124664       -    O    C2H4OC2H5  (6-)OCH3      138665       -    O    C4H9-n       (6-)OCH3 
Figure A0110152701564
     130666       -    O    C4H9-n       (6-)OCH3 
Figure A0110152701565
     132
表1-续
      A    Q      R1        (位置)          R3实施例号                           R2                            熔点℃667       -    O    C3H7-i    (6-)OC3H7-i    100668       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701572
 108669       -    O    C3H7-i    (6-)OC3H7-i     130670       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701574
   133671       -    O    C3H7-i    (6-)OC3H7-i  125
表1-续
      A    Q      R1        (位置)           R3实施例号                          R2                            熔点℃672       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701581
  108673       -    O    C3H7-i    (6-)OC3H7-i 110674       -    O    C4H9-n    (6-)OCH3 
Figure A0110152701583
     144675       -    O    C4H9-n    (6-)OCH3       116676       -    O    C4H9-n    (6-)OCH3       139
表1-续
      A    Q      R1        (位置)         R3实施例号                          R2                        熔点℃677       -    O    C4H9-n    (6-)OCH3
Figure A0110152701591
    174678       -    O    C4H9-n    (6-)OCH3  149679       -    O    C4H9-n    (6-)OCH3
Figure A0110152701593
   104680       -    O    C4H9-n    (6-)OCH3
Figure A0110152701594
   98681       -    O    C4H9-n    (6-)OCH3
Figure A0110152701595
   112
表1-续
      A    Q      R1        (位置)      R3实施例号                          R2                       熔点℃682       -    O    C4H9-n    (6-)OCH3  100683       -    O    C4H9-n    (6-)OCH3    92684       -    O    C4H9-n    (6-)OCH3   115685       -    O    C4H9-n    (6-)OCH3  99686       -    O    C4H9-n    (6-)OCH3
Figure A0110152701605
   102
表1-续
      A    Q      R1            (位置)          R3实施例号                              R2                            熔点℃687       -    O    C4H9-n       (6-)OCH3 
Figure A0110152701611
     106688       -    O    C2H4OC2H5  (6-)OCH3 
Figure A0110152701612
      120689       -    O    C2H4OC2H5  (6-)OCH3 
Figure A0110152701613
      98690       -    O    C2H4OC2H5  (6-)OCH3   138691       -    O    C4H9-i       (6-)OC2H5
Figure A0110152701615
     118
表1-续
      A    Q      R1           (位置)          R3实施例号                             R2                         熔点℃692       -    O    C2H4OC2H5  (6-)OCH3
Figure A0110152701621
   138693       -    O    C2H4OC2H5  (6-)OCH3
Figure A0110152701622
   94694       -    O    C2H4OC2H5  (6-)OCH3    94695       -    O    C2H4OC2H5  (6-)OCH3
Figure A0110152701624
   65696       -    O    C2H4OC2H5  (6-)OCH3
Figure A0110152701625
 60
表1-续
      A    Q      R1           (位置)         R3实施例号                             R2                          熔点℃697       -    O    C2H4OC2H5  (6-)OCH3 
Figure A0110152701631
   104698       -    O    C4H9-n       (6-)OC4H9-n  104699       -    O    C4H9-n       (6-)OC4H9-n  137700       -    O    C4H9-n       (6-)OC4H9-n
Figure A0110152701634
 70701       -    O    C4H9-n       (6-)OC4H9-n  110
表1-续
      A    Q      R1        (位置)           R3实施例号                          R2                             熔点℃702       -    O    C4H9-n    (6-)OC4H9-n
Figure A0110152701641
   102703       -    O    C3H7-i    (6-)OC3H7-i   137704       -    O    C3H7-i    (6-)OCH3       160705       -    O    C3H7-n    (6-)OC3H7-n   94706       -    O    C3H7-n    (6-)OC2H5
Figure A0110152701645
      155
表1-续
      A    Q      R1        (位置)       R3实施例号                          R2                          熔点℃707       -    O    C3H7-n    (6-)OCxH5     130708       -    O    C3H7-n    (6-)OC2H5  142709       -    O    C3H7-n    (6-)OC2H5
Figure A0110152701653
 85710       -    O    C3H7-n    (6-)OC2H5   106711       -    O    C3H7-n    (6-)OC2H5    87
表1-续
      A    Q      R1          (位置)          R3实施例号                            R2                            熔点℃712       -    S    C3H7-i       (6-)OCH3      120713       -    S    C4H9-n       (6-)OCH3 
Figure A0110152701662
    143714       -    S    C3H7-i       (6-)OC3H7-i  152715       -    S    C2H4OC2H5  (6-)OCH3 
Figure A0110152701664
    112716       -    S    C3H7-i       (6-)OCH3       130
表1-续
      A    Q      R1          (位置)          R3实施例号                           R2                             熔点℃717       -    S    C3H7-i      (6-)OCH3        165718       -    S    C3H7-i      (6-)OC3H7-i
Figure A0110152701672
 161719       -    S    C4H9-n      (6-)OCH3  
Figure A0110152701673
     111720       -    S    C2H5        (6-)OCH3        156721       -    S    C2H4OC2H5  (6-)OCH3       137
表1-续
      A    Q      R1         (位置)       R3实施例号                           R2                           熔点℃722       -    S    CH3        (6-)OCH3 
Figure A0110152701681
     163723       -    S    C3H7-n    (6-)OCH3 
Figure A0110152701682
     113724       -    S    C3H7-n    (6-)OCH3     130725       -    S    C4H9-n    (6-)OCH3 
Figure A0110152701684
    154726       -    S    C3H7-i    (6-)OC3H7-i
Figure A0110152701685
 157
表1-续
      A    Q      R1        (位置)        R3实施例号                          R2                           熔点℃727       -    S    C3H7-n    (6-)OC3H7-n
Figure A0110152701691
 142728       -    S    C2H5      (6-)OC2H5
Figure A0110152701692
    162729       -    S    CH3        (6-)OCH3     157730       -    S    C2H5      (6-)OCH3     108731       -    S    CH3        (6-)OCH3 
Figure A0110152701695
     172
表1-续
      A    Q      R1        (位置)           R3实施例号                          R2                           熔点℃732       -    S    CH3        (6-)OCH3 
Figure A0110152701701
      147733       -    S    C3H7-n    (6-)OC3H7-n  160734       -    S    C3H7-n    (6-)OC3H7-n  103735       -    O    C3H7-n    (6-)OC3H7-n
Figure A0110152701704
  172736       -    S    C2H5      (6-)OC2H5      137
表1-续
      A    Q      R1           (位置)          R3实施例号                             R2                          熔点℃737       -    S    C2H5         (6-)OC2H5     156738       -    S    C2H4OC2H5  (6-)OCH3 
Figure A0110152701712
    103739       -    S    C3H7-i       (6-)OC3H7-i
Figure A0110152701713
 134740       -    S    C4H9-n       (6-)OC4H9-n  87741       -    S    C4H9-n       (6-)OC4H9-n
Figure A0110152701715
 110
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                            熔点℃742       -    S    C4H9-n    (6-)OC4H9-n
Figure A0110152701721
    88743       -    S    C4H9-n    (6-)OC4H9-n
Figure A0110152701722
   98744       -    S    C4H9-n    (6-)OC4H9-n
Figure A0110152701723
   98745       -    S    C4H9-n    (6-)OC4H9-n
Figure A0110152701724
    88746       -    S    C4H9-n    (6-)OC4H9-n
Figure A0110152701725
  104
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                           熔点℃747       -    S    C4H9-n    (6-)OC4H9-n  75748       -    O    C2H5      (6-)OC2H5
Figure A0110152701732
      145749       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701733
     131750       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701734
     158751       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701735
    132
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                        熔点℃752       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701741
 142753       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701742
  130754       -    S    C3H7-i    (6-)OC2H5  170755       -    S    C3H7-n    (6-)OC2H5
Figure A0110152701744
  152756       -    S    C3H7-n    (6-)OC2H5   138
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                         熔点℃757       -    S    C3H7-n    (6-)OC2H5     130758       -    S    C3H7-n    (6-)OC2H5
Figure A0110152701752
  150759       -    S    C3H7-n    (6-)OC2H5
Figure A0110152701753
   156760       -    S    C3H7-n    (6-)OC2H5
Figure A0110152701754
    110761       -    S    C3H7-n    (6-)OC2H5
Figure A0110152701755
    120
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                         熔点℃762       -    S    C4H9-n    (6-)OC4H9-n
Figure A0110152701761
 104763       -    S    C3H7-i    (6-)OCH3 
Figure A0110152701762
    105764       -    S    C3H7-n    (6-)OC3H7-n
Figure A0110152701763
 120765       -    S    C3H7-n    (6-)OCH3      135766       -    S    C3H7-n    (6-)OC3H7-n
Figure A0110152701765
 116
表1-续实施例号  A    Q      R1           (位置)        R3
                                 R2                           熔点℃767       -    S    C3H7-i       (6-)OC3H7-i 110768       -    S    C2H4OC2H5  (6-)OCH3 
Figure A0110152701772
   95769       -    S    C3H7-i       (6-)OCH3     112770       -    O    C3H7-i       (6-)OC2H5
Figure A0110152701774
   70771       -    O    C3H7-i       (6-)OC2H5   132
表1-续实施例号  A    Q     R1        (位置)        R3
                              R2                         熔点℃772       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701781
 75773       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701782
   118774       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701783
 85775       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701784
   130776       -    O    C3H7-i    (6-)OC2H5    120
表1-续实施例号  A    Q      R1        (位置)        R3
                              R2                           熔点℃777       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701791
  124778       -    O    C3H7-i    (6-)OC2H5    130779       -    O    C3H7-i    (6-)OC2H5
Figure A0110152701793
   100780       -    O    C2H5      (6-)OCH3 
Figure A0110152701794
   172781       -    O    C2H5      (6-)OCH3 
Figure A0110152701795
   164
表1-续实施例号  A    Q      R1        (位置)         R3
                              R2                           熔点℃782       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701801
 118783       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701802
 88784       -    O    C4H9-s    (6-)OCH3      124785       -    O    C4H9-s    (6-)OCH3      100786       -    O    C4H9-n    (6-)OC2H5    106
表1-续实施例号  A    Q      R1        (位置)        R3
                              R2                         熔点℃787       -    O    C4H9-n    (6-)OC2H5
Figure A0110152701811
   108788       -    O    C4H9-n    (6-)OC2H5    105789       -    O    C4H9-s    (6-)OCH3 
Figure A0110152701813
   112790       -    O    C4H9-n    (6-)OC2H5    80791       -    O    C4H9-s    (6-)OCH3 
Figure A0110152701815
  130
表1-续实施例号  A    Q      R1        (位置)         R3
                             R2                             熔点℃792       -    O    C4H9-n    (6-)OC2H5
Figure A0110152701821
  120793       -    O    C4H9-n    (6-)OC2H5
Figure A0110152701822
   95794       -    O    C4H9-n    (6-)OC2H5
Figure A0110152701823
   96795       -    O    C4H9-s    (6-)OCH3    130796       -    O    C4H9-s    (6-)OCH3 
Figure A0110152701825
   118
表1-续实施例号  A    Q      R1        (位置)          R3
                              R2                          熔点℃797       -    O    C4H9-s    (6-)OCH3 
Figure A0110152701831
    134798       -    O    C4H9-s    (6-)OCH3      118799       -    O    C4H9-n    (6-)OC2H5
Figure A0110152701833
   90800       -    O    C4H9-s    (6-)OCH3     78801       -    O    C4H9-s    (6-)OCH3 
Figure A0110152701835
   112
表1-续实施例号  A    Q      R1        (位置)        R3
                              R2                           熔点℃802       -    O    C4H9-s    (6-)OCH3     78803       -    O    C4H9-s    (6-)OCH3 
Figure A0110152701842
     80804       -    O    C4H9-n    (6-)OC4H9-n  55805       -    O    C4H9-n    (6-)OC4H9-n
Figure A0110152701844
 100806       -    O    C4H9-n    (6-)OC4H9-n  92
表1-续实施例号  A    Q      R1        (位置)       R3
                              R2                          熔点℃807       -    O    C3H7-n    (6-)OC2H5
Figure A0110152701851
     74808       -    O    C3H7-n    (6-)OC2H5     143809       -    O    C3H7-n    (6-)OC2H5
Figure A0110152701853
  102810       -    O    C3H7-n    (6-)OC2H5     95811       -    O    C4H9-n    (6-)OC4H9-n  82
表1-续实施例号  A    Q      R1        (位置)        R3
                               R2                          熔点℃812       -    O    C4H9-n    (6-)OC2H5    92813       -    O    C4H9-n    (6-)OCH3     90814       -    O    C4H9-n    (6-)OCH3 
Figure A0110152701863
   124815       -    O    C4H9-n    (6-)OCH3     85816       -    O    C4H9-n    (6-)OCH3    90
表1-续实施例号  A    Q      R1           (位置)                R3
                                 R2                                  熔点℃817       -    O    C2H4OC2H5        (6-)OCH3  
Figure A0110152701871
    90818       -    O                (6-)OCH3        65819       -    O    
Figure A0110152701874
           (6-)OCH3     130820       -    O    
Figure A0110152701876
           (6-)OCH3  
Figure A0110152701877
     149821       -    O    C4H9-s             (6-)OC4H9-s    125
表1-续
      A    Q       R1      (位置)        R3实施例号                       R2                          熔点℃822       -    O   (6-)OCH3 
Figure A0110152701882
    112823       -    O   (6-)OCH3 
Figure A0110152701884
  156824       -    O 
Figure A0110152701885
 (6-)OCH3 
Figure A0110152701886
   148825       -    O   (6-)OCH3 
Figure A0110152701888
   145826       -    O   (6-)OCH3 
Figure A01101527018810
   156
表1-续
      A    Q      R1        (位置)              R3实施例号                        R2                                熔点℃827       -    O    
Figure A0110152701891
       (6-)OCH3 
Figure A0110152701892
   126828       -    O            (6-)OCH3     134829       -    O    
Figure A0110152701895
       (6-)OCH3   114830       -    O    
Figure A0110152701897
       (6-)OCH3 
Figure A0110152701898
  141831       -    O    C4H9-i   (6-)OC2H5          125
表1-续
      A    Q      R1        (位置)         R3实施例号                          R2                           熔点℃832       -    O    C4H9-i    (6-)OC2H5      128833       -    O    C4H9-i    (6-)OC2H5
Figure A0110152701902
   106834       -    O    C4H9-i    (6-)OC2H5    88835       -    O    C4H9-i    (6-)OC2H5    112836       -    O    C4H9-i    (6-)OC2H5    125
表1-续
      A    Q      R1        (位置)      R3实施例号                          R2                           熔点℃837       -    O    C4H9-i    (6-)OC2H5   106838       -    O    H            (6-)OH       
Figure A0110152701912
 172839       -    O    C4H9-i    (6-)OCH3  
Figure A0110152701913
   102840       -    O    C4H9-i    (6-)OCH3  
Figure A0110152701914
   114841       -    O    C4H9-i    (6-)OCH3  
Figure A0110152701915
   124
表1-续
      A    Q      R1        (位置)        R3实施例号                          R2                       熔点℃842       -    O    C4H9-i    (6-)OCH3
Figure A0110152701921
   98843       -    O    C4H9-i    (6-)OCH3
Figure A0110152701922
   146844       -    O    C4H9-i    (6-)OCH3
Figure A0110152701923
   97845       -    O    C4H9-i    (6-)OCH3
Figure A0110152701924
   117846       -    O    C4H9-i    (6-)OCH3
Figure A0110152701925
   142
表1-续
      A    Q      R1          (位置)        R3实施例号                            R2                       熔点℃847       -    O    C4H9-i      (6-)OCH3
Figure A0110152701931
   109848       -    S    C2H5        (6-)OCH3
Figure A0110152701932
    138849       -    S    C2H5        (6-)OCH3
Figure A0110152701933
   135850       -    S    C2H5        (6-)OCH3     155851       -    S    C2H5        (6-)OCH3
Figure A0110152701935
    160
表1-续
      A    Q      R1        (位置)       R3实施例号                         R2                       熔点℃852       -    S    C4H9-s    (6-)OCH3    108853       -    S    C4H9-s    (6-)OCH3    143854       -    S    C4H9-s    (6-)OCH3    105855       -    S    C4H9-s    (6-)OCH3
Figure A0110152701944
    65856       -    S    C4H9-s    (6-)OCH3
Figure A0110152701945
  114
表1-续
      A    Q      R1        (位置)       R3实施例号                         R2                        熔点℃857       -    O    C2H5      (3-)CH3
Figure A0110152701951
    179858       -    S    C4H9-s    (6-)OCH3
Figure A0110152701952
   146859       -    S    C3H7-i    (6-)OCH3    146860       -    S    C4H9-n    (6-)OCH3
Figure A0110152701954
   132861       -    S    C4H9-n    (6-)OCH3
Figure A0110152701955
 112
表1-续
      A    Q      R1        (位置)        R3实施例号                          R2                         熔点℃862       -    S    C4H9-n    (6-)OCH3 
Figure A0110152701961
  100863       -    S    C4H9-n    (6-)OCH3 
Figure A0110152701962
  138864       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701963
  155865       -    S    C3H7-i    (6-)OC2H5
Figure A0110152701964
 140866       -    S    C4H9-n    (6-)OCH3  
Figure A0110152701965
 140
表1-续
      A    Q      R1        (位置)       R3实施例号                         R2                           熔点℃867       -    O    C4H9-i    (6-)OCH3 
Figure A0110152701971
    131868       -    O    C4H9-i    (6-)OCH3      135869       -    O    C4H9-i    (6-)OCH3 
Figure A0110152701973
    137870       -    O    C4H9-n    (6-)OC4H9-n  123871       -    O    C4H9-n    (6-)OC2H5
Figure A0110152701975
    118
表1-续
      A    Q      R1        (位置)         R3实施例号                           R2                           熔点℃872       -    O    
Figure A0110152701981
  (6-)OCH3 
Figure A0110152701982
     164873       -    O    C3H7-i    (6-)OCH3 
Figure A0110152701983
    150874       -    O    C3H7-i    (6-)OC3H7-i  148875       -    O    C3H7-n    (6-)OCH3      147876       -    O    C2H5      (6-)OC2H5    108
表1-续
      A    Q      R1        (位置)         R3实施例号                          R2                          熔点℃877       -    O    C3H7-i    (6-)OC3H7-i   108878       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701992
 148879       -    O    C2H5      (6-)OC2H5
Figure A0110152701993
    176880       -    O    C3H7-n    (6-)OCH3 
Figure A0110152701994
    144881       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152701995
 167
表1-续
      A    Q      R1        (位置)          R3实施例号                          R2                           熔点℃882       -    O    C2H5      (6-)OC2H5   135883       -    O    C3H7-n    (6-)OCH3 
Figure A0110152702002
  100884       -    O    C2H5      (6-)OC2H5   158885       -    O    C3H7-n    (6-)OCH3 
Figure A0110152702004
 108
表1-续
      A    Q      R1        (位置)          R3实施例号                          R2                            熔点℃886       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152702011
 164887       -    O    C3H7-i    (6-)OC3H7-i  157888       -    O    C3H7-n    (6-)OCH3 
Figure A0110152702013
    113889       -    O    C3H7-i    (6-)OC3H7-i
Figure A0110152702014
 132890       -    O    C3H7-n    (6-)OCH3      92
表1-续
      A    Q      R1        (位置)          R3实施例号                         R2                             熔点℃891       -    O    C3H7-i    (6-)OC3H7-i   141892       -    O    C3H7-i    (6-)OC3H7-i  159893       -    O    C2H5      (6-)OC2H5
Figure A0110152702023
    139894       -    O    C2H5      (6-)OC2H5
Figure A0110152702024
   150895       -    O    C3H7-n    (6-)OCH3 
Figure A0110152702025
   126
表1-续
      A    Q      R1        (位置)       R3实施例号                          R2                           熔点℃896       -    O    C3H7-i    (6-)CH3
Figure A0110152702031
     148897       -    O    C3H7-i    (6-)CH3
Figure A0110152702032
     157898       -    O    C3H7-i    (6-)CH3
Figure A0110152702033
     125899       NH   O    CH3        (6-)OCH3        182900       NH   O    CH3        (6-)OCH3        175
表1-续
      A    Q      R1     (位置)      R3实施例号                       R2                        熔点℃901       -    O    CF3    (6-)CH3  902       -    O    CF3    (6-)CH3     129903       -    O    CF3    (6-)CH3 
Figure A0110152702043
    149904       -    O    CF3    (6-)CH3     163905       -    O    CF3    (6-)C2H5
Figure A0110152702045
   121
表1-续
      A    Q      R1        (位置)       R3实施例号                         R2                        熔点℃906       -    O    C3H7-i    (6-)CH3     170907       -    O    C3H7-i    (6-)CH3   125908       -    O    C3H7-i    (6-)CH3   129909       -    O    C3H7-i    (6-)CH3
Figure A0110152702054
     156910       -    O    CH3        (6-)OCH3
Figure A0110152702055
   157911       -    O    CH3        (6-)OCH3    177
表1-续
      A    Q      R1        (位置)      R3实施例号                         R2                        熔点℃912       -    O    CH3        (6-)OCH3    172913       -    O    C3H7-i    (6-)CH3
Figure A0110152702062
 132914       -    O    C3H7-i    (6-)CH3
Figure A0110152702063
  153915       -    O    C3H7-i    (6-)CH3   150916       -    O    C3H7-i    (6-)CH3  110
表1-续实施例号  A    Q      R1        (位置)      R3
                               R2                      熔点℃917       -    O    C3H7-i    (6-)CH3
Figure A0110152702071
  131918       -    O    C3H7-i    (6-)CH3
Figure A0110152702072
  133919       -    O    CH3        (6-)OCH3
Figure A0110152702073
 153920       -    O    C3H7-i    (6-)CH3    122921       -    O    C3H7-i    (6-)CH3
Figure A0110152702075
  147
表1-续实施例号  A    Q      R1        (位置)         R3
                               R2                     熔点℃922       -    O    CH3       (6-)OCH3      160923       -    O    CH3       (6-)OCH3
Figure A0110152702082
    182924       -    O    CH3       (6-)OCH3
Figure A0110152702083
    142925       -    O    CH3       (6-)OCH3   178926       -    O    C3H7-i   (6-)CH3
Figure A0110152702085
  151
表1-续实施例号  A    Q      R1     (位置)      R3
                          R2                        熔点℃927       -    O    CH3    (6-)OCH3
Figure A0110152702091
   178928       -    O    CH3    (6-)OCH3    130929       -    O    CH3    (6-)OCH3
Figure A0110152702093
   124930       -    O    CH3    (6-)OCH3    153931       -    O    CH3    (6-)OCH3
Figure A0110152702095
 157
表1-续实施例号  A    Q      R1      (位置)         R3
                            R2                        熔点℃932       -    O    CH3       (6-)OCH3  114933       -    O    CH3       (6-)OCH3
Figure A0110152702102
 130934       -    O    C3H7-i   (6-)CH3
Figure A0110152702103
  151935       -    O    C3H7-i   (6-)CH3   153936       -    O    CH3       (6-)OCH3
Figure A0110152702105
   167
表1-续实施例号  A    Q      R1          (位置)     R3
                                 R2                       熔点℃937       -    O    CF2Cl        (6-)CH3
Figure A0110152702111
938       -    O    CH3          (6-)OCH3
Figure A0110152702112
939       NH   O    CH2CH2F     (6-)CH3
Figure A0110152702113
     163940       NH   O    CH2CHF2     (6-)CH3      160941       NH   O    CF2CHFCl     (6-)CH3
Figure A0110152702115
     88
表1-续实施例号  A    Q      R1         (位置)     R3
                               R2                         熔点℃942       -    O    CH2CH2F    (6-)CH3     178943       -    O    CH2CH2F    (6-)CH3
Figure A0110152702122
    135944       -    O    CH2CH2F    (6-)CH3
Figure A0110152702123
    127945       -    O    CH2CH2F    (6-)CH3
Figure A0110152702124
    139946       -    O    CH2CH2F    (6-)CH3
表1-续实施例号  A    Q      R1         (位置)        R3
                              R2                         熔点℃947       -    O    CH2CH2F    (6-)CH3     171948       -    O    CH2CH2F    (6-)CH3
Figure A0110152702132
    144949       -    O    CH2CHF2    (6-)CH3
Figure A0110152702133
950       -    O    CH2CHF2    (6-)CH3
Figure A0110152702134
    181951       -    O    CH2CHF2    (6-)CH3
Figure A0110152702135
    142
表1-续实施例号  A    Q      R1         (位置)        R3
                              R2                           熔点℃952       -    O    CH2CHF2    (6-)CH3      114953       -    O    CH2CHF2    (6-)CH3      108954       -    O    CH2CHF2    (6-)CH3 
Figure A0110152702143
    185955       -    O    CH2CHF2    (6-)CH3 
Figure A0110152702144
    150956       -    O    CF3         (6-)C2H5
Figure A0110152702145
表1-续实施例号  A    Q      R1     (位置)     R3
                          R2                     熔点℃957       -    O    CF3    (6-)CH3
Figure A0110152702151
   155958       -    O    CF3    (6-)CH3
Figure A0110152702152
   112959       -    O    CF3    (6-)CH3
Figure A0110152702153
    166960       -    O    CF3    (6-)CH3
Figure A0110152702154
    137961       -    O    CF3    (6-)CH3
Figure A0110152702155
    132
表1-续实施例号  A    Q      R1      (位置)     R3
                             R2                     熔点℃962       -    O    CF3     (6-)CH3
Figure A0110152702161
   172963       -    O    CF3     (6-)CH3
Figure A0110152702162
   139964       -    O    CF3     (6-)CH3
Figure A0110152702163
     130965       -    O    C2H5   (3-)CH3      184可以例如如下制备表1中列出的化合物，如实施例9：(方法(b))
1.4g(0.01mol)5-乙氧基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮和2.4g(0.01mol)2-乙氧基-6-甲基-苯基磺酰基异氰酸盐在50ml乙腈中在20℃下搅拌15小时。蒸馏出溶剂，残余物与二乙醚搅拌，抽滤滤出沉淀。
得到3.3g(理论值85％)5-乙氧基-4-甲基-2-(2-乙氧基-6-甲基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点160℃。式(II)或(IIa)的起始原料：实施例(II-1)
64.6g(0.26mol)2-异丙氧基-6-甲基-苯磺酰氯在350ml25％强度氨水溶液中在20℃搅拌12小时。接着抽滤分离结晶产物
得到54g(理论值90％)2-异丙氧基-6-甲基-苯磺酰胺，熔点78℃。实施例(II-2)
1.9g(10mmol)2-羟基-6-甲基-苯磺酰胺，1.2g(10mmol)炔丙基溴(以80％强度甲苯溶液的形式)和1.4g(10mmol)碳酸钾在回流下加热2小时，然后过滤混合物，水泵真空下浓缩滤液，残余物溶解于石油醚中，由此溶液抽滤分离得到的结晶产物。
得到2.1g(理论值93％)6-甲基-2-炔丙基氧基-苯磺酰胺，熔点129℃。实施例(II-3)
在20℃，搅拌下向32.3g(0.15mol)2-乙氧基-6-甲基苯磺酰胺的300ml二氯甲烷的溶液中滴加188ml 1摩尔溴化硼(III)的二氯甲烷溶液，反应混合物在20℃下搅拌30分钟。然后自0℃至5℃(冰冷却)滴加300ml甲醇。加热到20℃后，反应混合物在水泵真空下浓缩，残余物与乙酸乙酯搅拌，用水洗涤得到的溶液，硫酸钠干燥，过滤水泵真空下浓缩滤液，残余物与石油醚搅拌结晶，并抽滤分离结晶产物。
得到20.3g(理论值72％)2-羟基-6-甲基-苯磺酰胺，熔点126℃。
类似于实施例(II-1)至(II-3)，并根据本发明制备方法的概括描述，也可以例如制备下面表2中列出的式(II)或(IIa)化合物。
Figure A0110152702191
表2：式(II)化合物的实施例实施例号   A    R1              (位置)
                              R2        熔点(℃)II-4       -    C2H5          (6-)CH3       104II-5       -    n-C3H7        (6-)CH3       63II-6       -    -CH2CH2Cl     (6-)CH3       102II-7       -    CH3            (6-)CH3       132II-8       -    -CH2C6H5     (6-)CH3       131II-9       -    -CH2COOCH3    (6-)CH3       90II-10      -    CH3            (6-)C3H7-n   108II-11      -    C2H5          (6-)C3H7-n   80II-12      -    C2H5          (5-)CH3       131II-13      -    CH3            (6-)Cl         166II-14      -    C2H5          (6-)Cl         121表1-续实施例号 A    R1           (位置)
                          R2         熔点(℃)II-15    -    H              (6-)Cl        118II-16    -    i-C3H7      (6-)Cl         85II-17    -    -CH2CH＝CH2 (6-)Cl         106II-18    -    -CH2C≡CH    (6-)Cl         181II-19    -    CF3          (5-)ClII-20    -    CHF2         (5-)CH3       127II-21    -    CHF2         (6-)CH3       89II-22    -    CH3          (5-)C(CH3)3  160II-23    -    CH3          (5-)ClII-24    -    CHF2         (4-)CH3       153II-25    -    -CF2CHFCl    (6-)CH3       85II-26    -    C2H5        (6-)CH2Cl式(IV)的起始原料实施例(IV-1)
Figure A0110152702211
21.5g(0.1mol)2-乙氧基-6-甲基-苯磺酰胺和10g(0.1mol)异氰酸正丁酯在100ml氯苯中加热至沸腾。在回流温度下，通入4小时光气。减压下浓缩澄清溶液，精馏残余物。在0.8毫巴的压力和135-140℃的顶空温度下，馏出2-乙氧基-6-甲基-苯基磺酰基异氰酸盐，其在接收器中固化。
得到7.9g 2-乙氧基-6-甲基-苯基磺酰基异氰酸盐，为无色产物，熔点40℃。式(VI)或(VIa)的起始原料：实施例(VI-1)
47.8g(0.29mol)2-异丙氧基-6-甲基苯胺溶解于87ml 1N盐酸和145ml浓盐酸的混合物中，将该溶液冷却到-5℃。在-5℃至0℃下，在搅拌下滴加22g(0.32mol)亚硝酸钠的87ml水溶液，并在大约0℃下将混合物再搅拌1小时。用氨基磺酸去除过量的亚硝酸盐后，在-5℃至0℃将得到的重氮盐溶液滴加到二氧化硫的175ml 1.2-二氯乙烷的饱和溶液中。大约30分钟后，加入1.7g氯化亚铜(I)和1.7g十二烷基-三甲铵溴化物，让反应混合物在大约60分钟中升至室温，再经1小时加热到大约40℃，并在该温度下搅拌大约12小时。在大约20℃时，加入14.2g 35％强度过氧化氢溶液，将混合物搅拌大约30分钟，接着与300ml二氯甲烷搅拌，分离有机相，用水洗涤，硫酸钠干燥并过滤、通过水泵真空蒸馏自滤液中小心去除溶剂。
得到65.9g(理论值90％)2-异丙氧基-6-甲基-苯磺酰氯，为亮棕色油状残余物。1H-NMR(CDCl3，TMS，δppm)：1.47(d，J＝6.1Hz，2xCH3)；2.68(s，CH3)；4.79(sept.，J＝6.1Hz，1H)；6.83(d，J＝7.5Hz，1H)；6.95(d，J＝8.4Hz，1H)；7.45(pseudo t，J＝8.3Hz，1H)。
类似于实施例(VI-1)，也可以例如制备下面表3中列出的式(VI)或(VIa)化合物。
Figure A0110152702221
表3：式(VI)化合物的实施例实施例号A    R1        (位置)     物理数据
                    R2VI-2    -    CH3      (6-)CH3    Fp：52℃VI-3    -    C2H5    (6-)CH3  1H-NMR(CDCl3，TMS，δ，ppm)：1.55
                              (t，J＝6,97Hz，CH3)，2,69(s，CH3)，
                              4,24(q，J＝6,97Hz，CH2)，6,87(d，
                              J＝7,68Hz，1H)，6,95(d，J＝8,34Hz，
                              1H)，7,46(pseudo t，J＝8,1Hz，1H)VI-4    -    n-C3H7  (6-)CH3  1H-NMR(CDCl3，TMS，δ，ppm)1.33
                              (t，J＝7,38Hz，CH3)，1,95(m，CH2)，
                              2,69(s，CH3)，4,12(t，J＝6,3Hz，
                              CH2)，6,86(d，J＝7,69Hz，1H)，6.94
                              (d，J＝8,37Hz，1H)，7,46(pseudo t，
                              J＝7,8Hz，1H)表3-续实施例号A    R1                 (位置)     物理数据
                                R2VI-5    -    -CH2CH2Cl        (6-)CH3  1H-NMR(CDCl3，TMS，δ，ppm)：2.71
                                       (s，CH3)，3,94(t，J＝6,1Hz，CH2)，
                                       4,41(t，J＝6,1Hz，CH2)，6,96(t，J＝7,1
                                       Hz，2H)，7,5(t，J＝7,8Hz，1H)VI-6    -    -CH2CH2OC2H5  (6-)CH3  1H-NMR(CDCl3，TMS，δ，ppm)：1.23
                                       (t，J＝7Hz，CH3)，2,69(s，CH3)，3,65
                                       (q，J＝7Hz，CH2)，3,91(t，J＝5,16Hz.
                                       CH2)，4,30(t，J＝5,16Hz，CH2)，6.89
                                       (d，J＝7,7Hz，1H)，7,0(d，J＝8,3Hz.
                                       1H)，7,47(pseudo t，J＝8,1Hz，1H)VI-7    -    C2H5             (5-)CH3  1H-NMR(CDCl3，TMS，δ，ppm)：1,53
                                       (t，J＝7Hz，CH3)，2,36(s，CH3)，4,25
                                       (q，J＝7Hz，CH2)，7,0(d，J＝8,53Hz.
                                       1H)，7,45(d，J1＝8,53Hz，J2＝2,15Hz.
                                       1H)，7,75(d，J＝2,15Hz，1H)VI-8    -    n-C3H7           (5-)CH3    1H-NMR(CDCl3，TMS，δ，ppm)：1,08
                                       (t，J＝7,38Hz，CH3)，1,85(m，CH2)，
                                       2,23(s，CH3)，3,99(t，J＝6,5Hz)，6,74
                                       (d，J＝8,2Hz，1H)，6,92(m，1H)，7,34
                                       (d，J＝1,65Hz，1H)VI-9    -    i-C3H7           (5-)CH3  1H-NMR(CDCl3，TMS，δ，ppm)：1.45
                                       (d，J＝6,06，2xCH3)，2,35(s，CH3)，
                                       4,77(sept.，J＝6,06Hz，1H)，6,99(d，
                                       J＝8,57Hz，1H)，7,43(dd，J1＝8,56Hz，
                                       1H，J2＝2,1Hz，1H)，7,74(d，J＝2.1
                                       Hz，1H)表3-续实施例号A     R1             (位置)       物理数据
                           R2VI-10    -    C2H5          (6-)CH2Cl   (Oil)VI-11    -    -CF2CHFCl      (6-)CH3    1H-NMR(CDCl3，TMS，δ，ppm)：2,78
                                       (s，CH3)，6,46(td，CHFCl)，7,2-7,6
                                       (Ar-H)VI-12    -    CHF2          (6-)CH3    1H-NMR(CDCl3，TMS，δ，ppm)：2,76
                                       (s，CH3)，6,61(t，CHF2)，7,27-7,59
                                       (Ar-H)VI-13    -    CH3           (5-)C(CH3)3Fp：62℃VI-14    -    CHF2          (4-)CH3    1H-NMR(CDCl3，TMS，δ，ppm)：2,50
                                       (s，CH3)，6,68(t，CHF2)，7,05-7,92
                                       (Ar-H)VI-15    -    CHF2           (5-)CH3    1H-NMR(CDCl3，TMS，δ，ppm)：2,45
                                       (s，CH3)，6,64(t，CHF2)，7,35-7,86
                                       (AR-H)VI-16    -    -CH2CH2Ci    (6-)CH3VI-17    -    -CH2CH＝CH2  (6-)CH3VI-18    -    -CH2C≡CH     (6-)CH3VI-19    -    -CH2C6H5    (6-)CH3式(X)的起始原料：实施例(X-1)步骤1：制备2-异丙氧基-6-甲基-硝基苯
153g(1.0mol)3-甲基-2-硝基-苯酚，172.5g(1.25mol)碳酸钾，170g(1.0mol)2-碘-丙烷和400ml丙酮在回流下加热12小时。接着在水泵真空下浓缩，残余物与400ml二氯甲烷搅拌，过滤混合物，用二氯甲烷洗涤过滤的产物。水泵真空蒸馏从滤液中小心去除溶剂。
得到l83.4g 2-异丙氧基-6-甲基-硝基苯，为黄色油状残余物。1H-NMR(CDCl3，TMS，δppm)：1.33(d，J＝6.1Hz，2xCH3)；2.28(s，CH3)；4.6(sept.，J＝6.1Hz，1H)；6.8(d，J＝7.7Hz，1H)；6.87(d，J＝8.4Hz，1H)；7.26(pseudo t，J＝8.1Hz，1H)。步骤2：制备2-异丙氧基-6-甲基苯胺
在40至60巴的氢压力下，在存在9.5g阮内镍下在1升乙酸乙酯中将183.3g(0.94mol)2-异丙氧基-6-甲基-硝基苯氢化5小时。然后过滤混合物，并通过水泵真空蒸馏从滤液中小心去除溶剂。
得到139.4g(理论值90％)2-异丙氧基-6-甲基-苯胺，为橙色油状残余物。1H-NMR(CDCl3，TMS，δppm)：1.36(d，J＝6.1Hz，2xCH3)；2.16(s，CH3)；3.72(s，NH2)，4.51(sept.，J＝6.1Hz，1H)；6.65-6.70(m，3H)。应用实施例
在应用实施例中，使用下面指定的化合物为对比物质：4，5-二甲氧基-2-(2-甲氧基苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮(EP 534266中公开)；4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮(EP 534266中公开)。实施例A苗前试验溶剂：5份重量丙酮乳化剂：1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适制剂，将1份重量的活性化合物与所述量的溶剂混合，加入所述量的乳化剂，用水将乳油稀释到所需浓度。
试验植物的种子种到正常土壤中，24小时后，用活性化合物制剂灌溉土壤。希望每单位面积保持恒定量的水。制剂中活性化合物的浓度并不重要，只有每单位面积施用的活性化合物的量是决定性的。
三星期后，与未处理的对照物的生长相比以损伤百分率测定对植物损伤的程度。数值表示：
0％＝没有作用(象未处理的对照物)
100％＝完全损伤。
在该项试验中，例如制备实施例1、7-21、23-41、46-49、51、54、55、57、60、62、65、68、72-74、76、78、79、88、89、199、207、209、222和901的化合物具有非常强的杀阔叶杂草的作用。实施例B苗后试验溶剂：5份重量丙酮乳化剂：1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适制剂，将1份重量的活性化合物与所述量的溶剂混合，加入所述量的乳化剂，用水将乳油稀释到所需浓度。
以一种方式用活性化合物的制剂对高5-15cm的试验植物喷雾，使每单位面积施用具体量的所期活性化合物。选择喷雾液浓度，使以2000升水/ha施用具体量的所期活性化合物。三星期后，与未处理对照物的生长相比较以损伤百分率测定对植物损伤的程度。数值表示：
0％＝没有作用(象未处理的对照物)
100％＝完全损伤。
在该项试验中，例如制备实施例1、7-10、12、13、15、16、17、25、30、31、38、40、41、46和47的化合物具有非常强的杀阔叶杂草的作用。

Claims (2)

1.式(XIII)苯磺酸衍生物其中E代表-NH2，-N＝C＝Q或-Cl，其中A1代表正-或异丙基、正-、异-、仲-或叔丁基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、乙氧基乙基或苄基，和A2代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
2.式(XIII)苯磺酸衍生物
Figure A0110152700022
其中E如权利要求1中所定义，A1和A2如下表中的组合所定义：  A1  A2  1 i-C3H7  -O-(i-C3H7)  2 C2H5  Cl  3 -CH2-CH2Cl  CH3
Figure A0110152700031
 A1  A2  26 n-C3H7 -O-(n-C3H7)  27 CF2Cl CH3  28 i-C3H7 i-C3H7  29 CH3 i-C3H7  30 C2H5 -O-(n-C4H9)  31 -CH2-CH2F CH3  32 s-C4H9 -OCH3  33 CH2-CHF2 CH3  34 n-C3H7 i-C3H7  35 i-C4H9 O-C2H5  36 i-C4H9 O-CH3  37 s-C4H9 s-C4H9  38 n-C4H9 O-CH3
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