本发明涉及新的具有含硫基的N-氰芳基氮杂环化合物，多种的有关 这些化合物的制备方法以及这些化合物作为除草剂和杀虫剂的应用。

已知某些N-氰芳基氮杂环类具有杀草活性(参见：WO-A91/00278， WO-A92/11244，EP-A408382，EP-A438209，EP-A473551， DE-A4237920)。然而，以前已知的N-氰芳基氮杂环，其杀草活性及 与栽培植物的相容性并不完全令人满意。

现在找到了以下列通式(I)表示的新的具有含硫基的N-氰芳基氮杂 环类化合物，以及式(I)化合物的盐 其中 Q1代表氧或硫， R1代表氢或卤素， R2代表卤素，氰基，硝基，氨基或-N(A1)SO2A，其中A在各自情况下代 表可任意取代的烷基，链烯基，炔基，二烷氨基，环烷基，环烷烷基， 芳基或芳烷基；

A1代表氢，甲酰基，或在各自情况下代表可任意取代的烷基，链烯基， 炔基，烷羰基，烷氧羰基或烷基磺酰基，或与A一起代表亚烷基， R3代表氢，卤素，氰基或任意取代的烷基， R4代表任意取代的烷基，或与R3一起代表亚烷基， Z代表下列基团中的一种 其中 Q2代表氧或硫，

R5代表氢，或在各自情况下代表任意取代的烷基，链烯基，炔基或烷 羰基， 以上各款以Q1或Q2至少有一个代表硫为条件。

因此，通式(I)代表了下列通式(IA)和(IB)所示的异构化合物

通式(I)表示的这类新的具有含硫基的N-氰芳基氮杂环化合物是通 过下述方法得到的： (a)在有或没有反应辅助剂存在以及有或没有稀释剂存在的情况下，通式 (II)表示的氨基链烯(硫)酯

其中：

Q1，R3，R4和R5的意义同上，

R代表烷基

与通式(III)表示的氰芳基异(硫)氰酸酯反应

其中：Q2，R1和R2的意义同上。 或 (b)在有或没有一个酸的受体存在以及有或没有稀释剂存在的情况下，通 式(IA)或(IB)所表示的N-氰芳基氮杂环(其中R5代表氢，Q1，Q2，R1，R2， R3和R4的意义同上)与通式(IV)或(V)所表示的烷基化剂(其中R5

       X-R5(IV)    R5-O-SO2-O-R5(V)

在各自情况下代表任意取代的烷基，链烯基或炔基)反应，可制备式 (IA)和/或式(IB)所代表的化合物(其中R5在各自情况下代表可任选地被 取代的烷基，链烯基或炔基，Q1，Q2，R1，R2，R3和R4的意义同上)。 或 (c)在有或没有酸的受体存在以及有或没有稀释剂存在的情况下，通式(I) 所表示的N-氰芳基氮杂环(其中R2代表卤素，Q1，Q2，R1，R3，R4和Z 的意义同上)与通式(VI)

                HN(A1)SO2A        (VI)

所表示的氨或氨化物(其中A和A1的意义同上)反应，可制备式(I)所 代表的化合物(其中R2代表氨基或-N(A1)SO2A基，A，A1，Q1，Q2，R1，R3， R4和Z的意义同上)。

用类似于上述(a)的方法，使前面式(II)所表示的氨基链烯(硫)酯与 式(IIIa)所代表的氰芳基(硫)氨基甲酸酯反应，也可得到式(I)的化合 物。

其中

Q2，R1和R2的意义同上，

R代表烷基(特别是甲基)或芳基(特别是苯基)。

通式(I)所表示的这类新的具有含硫基的N-氰芳基氮杂环类化合物 具有很高的杀草效能。

在定义中，其饱和的或不饱和的烃链，如烷基，亚烷基，链烯基或炔 基，各自为直链或支链的。

卤素一般指氟，氯，溴或碘，尤其指氟，氯或溴，特别指氟或氯。

本发明特别涉及式(I)所代表的那些化合物， 其中 Q1代表氧或硫， R1代表氢，氟，氯或溴， R2代表氟，氯，溴，氰基，硝基，氨基或-N(A1)SO2A基，其中

A代表一个基团，这个基团可以是烷基，链烯基，炔基或二烷氨基， 它们各自可有最多达10个碳原子，并且每一个都可任选地被氟，氯，溴， 氰基或C1-C4烷氧基任意取代，

A还可代表环烷基或环烷基烷基，它们各自可被氟，氯，溴，氰基或 C1-C4烷基任意取代，并且其环烷基部分具有3-8个碳原子，合适的 话，其烷基部分具有1-4个碳原子，

A还可代表芳基或芳烷基，它们各自可被氟，氯，溴，氰基，硝基， 羧基，氨基甲酰基任意取代，可被C1-C4烷基，C1-C4烷氧基，C1-C4 烷硫基，C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(这些基各自可任意 被氟和/或氯取代)任意取代，可被二甲氨基磺酰基或二乙氨基磺酰基任 意取代，可被C1-C4烷氧基-羰基(该基可任意被氟，氯，溴，甲氧基或 乙氧基取代)任意取代，可被苯基或苯氧基(它们各自可任意被氟，氯， 溴，氰基，甲基，甲氧基，三氟甲基和/或三氟甲氧基取代)任意取代， 这些芳基或芳烷基的芳基部分具有6个或10个碳原子，合适的话，其烷 基部分具有1-4个碳原子，

A1代表氢或甲酰基，或可任意被氟和/或氯、氰基或C1-C4烷氧基羰 基取代的C1-C4烷基，或各自可被氟，氯或C1-C4烷氧基任意取代的C1 -C4烷基羰基或C1-C4烷氧羰基、或可任意被氟和/或氯取代的C1-C4 烷基磺酰基，或与A一起代表具有2-8个碳原子的亚烷基， R3代表氢，氟，氯，溴，氰基或具有1-4个碳原子，可任意被氟和/或 氯取代的烷基， R4代表具有1-6个碳原子可被氟、氯、溴、甲氧基或乙氧基任意取代 的烷基，或与R3一起代表具有2-8个碳原子的亚烷基， Z代表下列两式所示基团中的一个

其中

Q2代表氧或硫，

R5代表氢或各自具有至多6个碳原子，并可任意被氟、氯、溴、氰基、 C1-C4烷氧基、C1-C4烷基羰基或C1-C4烷氧基羰基取代的烷基、链烯 基、炔基或烷羰基，一个前提条件，即Q1或Q2至少有一个代表硫。

本发明更涉及式(I)化合物的钠盐、钾盐、钙盐、铵盐、C1-C4烷基 铵盐、双-(C1-C4烷基)铵盐、三-(C1-C4烷基)-铵盐、环戊基或环 己基铵盐和四-(C1-C4烷基)铵盐，其中Q1、R1、R2、R3、R4和Z的意 义和如上所给出的并注明“特别是”的部分。

本发明尤其涉及式(I)所代表的那些化合物， 其中 Q1代表氧或硫， R1代表氢、氟或氯， R2代表氟、氯、溴、氰基、氨基或-N(A1)SO2A，

其中

A代表可任意被氟和氯取代的甲基、乙基、正或异丙基、正或异丁基、 仲或叔丁基、乙烯基、丙烯基、丁烯基或代表二甲氨基，

A还代表可任意被氟、氯、溴和/或乙基取代的环丙基、环戊基、环 己基、环丙甲基、环戊甲基或环己甲基，

A还代表苯基、萘基、苯甲基或苯乙基，它们各自均可被下列基团任 意取代：氟、氯、溴、氰基、硝基、羧基、甲基、三氟甲基、甲氧基、 乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、乙硫基、甲基亚磺酰基、 乙基亚磺酰基、甲基磺酰基、乙基磺酰基、二甲氨基磺酰基、甲氧羰基、 乙氧羰基、丙氧羰基或苯基，

A1代表氢、甲酰基、甲基、乙基、乙酰基、丙酰基、甲氧羰基、乙氧 羰基、甲基磺酰基或乙基磺酰基，或与A一起代表三亚甲基或四亚甲基， R3代表氢、氟、氯、溴、甲基、三氟甲基、乙基、正或异丙基， R4代表甲基、乙基、正或异丙基，它们各自均可被氟或氯任意取代，

或与R3一起代表三亚甲基或四亚甲基， Z代表下列两种基中的一个

其中

Q2代表氧或硫，

R5代表氢、甲基、二氟甲基、氰甲基、乙基、氟乙基、氯乙基、二氟 乙基、二氯乙基、三氟乙基、氯二氟乙基、氰乙基、正或异丙基、氟丙 基、氯丙基、氰基丙基、烯丙基、氯烯丙基、炔丙基、乙酰基、丙酰基、 氟乙酰基、氯乙酰基、二氟乙酰基、二氯乙酰基、三氟乙酰基或三氯乙 酰基， 前提条件是，Q1或Q2至少有一个代表硫。

本发明中式(I)所表示的化合物尤其是指式(IA)所代表的化合物，其 中Q1代表氧，Q2代表硫，R1，R2，R3，R4和R5与上述注明“特别是”项中 相应符号的意义相同。

本发明中式(I)所表示的化合物更加尤其是指式(IB)所代表的化合 物，其中Q1代表氧，Q2代表硫，R1，R2，R3，R4和R5与上述注明“特别是” 项中相应符号的意义相同。

上述各基团的一般定义或属优先考虑的定义不仅适用于式(I)的最终 产物，也相应地适用于制备过程中所必须的各种初始物或中间产物。这 些基团的定义可以任何方式互相组合，在优先考虑的化合物所给定的范 围之间这些基团的定义也可以任何方式互相组合。

下列表1给出了本发明中式(IA)所代表的化合物的例子-此表中各 组的Q1都代表氧，Q2都代表硫。

表1  式(IA)化合物示例

R1        R2       R3        R4         R5

F          F          H          CH3        H

F          F          H          CH3        CH3

F          F          H          CH3        CHF2

F       NHSO2C2H5 H          CH3        CH3

F       NHSO2CH3   H          CH3        CHF2

F          F          H          CF3        CH3

F          F          H          CF3        C3H7

Cl         F          CH3       CF3        CHF2

F       NHSO2CH3   H          CF3        CH3

F       NHSO2C2H5 H          CF3        CH3

F       NHSO2CH3   H          CF3        CH2-C≡CH

F       NHSO2C2H5 H          CF2Cl      CH3

F          F          H          CF2CF3    H

F          F          H          CF2CF3    CH3

H          F          H          CF2CF3    C2H5

H          F          H          CF2CF3    CH2CH＝CH2

F       NHSO2CH3   H          CF2CF3    CH3

R1        R2           R3        R4         R5

F       NHSO2C2H5     H         CF2CF3     CH3

F          F              H         CHF2        H

F          F              H         CHF2        CH3

F          F              H         CHF2        CHF2

F       NHSO2CH3       H         CHF2        CH3

F       NHSO2CH3       H         CHF2        CHF2

F       NHSO2C2H5     Cl        CHF2        CH2CH＝CH2

F       NHSO2CF3       H         CH3         CH3

F       N(K)SO2CH3     H         CF3         CH3

F       N(Na)SO2CH3    H         CF3         CH3

F       N(K)SO2C2H5  H         CF3         CH3

F       N(Na)SO2C2H5 H         CF3         CH3

F       NHSO2CH3      H         CF3         H

F            H          CF3        CH3

F             H          CF3        CH3

F            H          CF3        CH3

R1     R2                       R3     R4      R5

F                    H       CF3     CH3

F                     H       CF3     CH3

F                       H       CF3     CH3

H    NHSO2CH3                  H       CH3     CH3

H    NHSO2C2H5                H       CH3     CH3

H    NHSO2C3H7-n              H       CH3     CH3

H    NHSO2C3H7-i              H       CH3     CH3

H                 H       CH3     CH3

H    NHSO2C4H9-n              H       CH3     CH3

H    NHSO2C6H5                H       CH3     CH3

H      H       CH3     CH3

F    NHSO2CH3                  H       CH3     CH3

F    NHSO2C2H5                H       CH3     CH3

F    NHSO2C3H7-n              H       CH3     CH3

F    NHSO2C3H7-i              H       CH3     CH3

F                 H       CH3     CH3

R1     R2                      R3     R4      R5

F    NHSO2C4H9-n              H       CH3     CH3

F    NHSO2C6H5                H       CH3     CH3

F      H       CH3     CH3

F    NHSO2CH3                  CH3    CH3     CH3

F    NHSO2C2H5                CH3    CH3     CH3

F    NHSO2C3H7-n              CH3    CH3     CH3

F    NHSO2C3H7-i              CH3    CH3     CH3

F                 CH3     CH3     CH3

F    NHSO2C4H9-n              CH3     CH3     CH3

F    NHSO2C6H5                CH3     CH3     CH3

F      CH3    CH3     CH3

F    NHSO2CH3                  Cl       CH3     CH3

F    NHSO2C2H5                Cl       CH3     CH3

F    NHSO2C3H7-n              Cl       CH3     CH3

F    NHSO2C3H7-i              Cl       CH3     CH3

F                 Cl       CH3     CH3

F    NHSO2C4H9-n              Cl       CH3     CH3

R1     R2                          R3       R4        R5

F    NHSO2C6H5                    Cl       CH3       CH3

F      Cl       CH3       CH3

F    NHSO2CH3                      F        CH3       CH3

F    NHSO2C2H5                    F        CH3       CH3

F    NHSO2C3H7-n                  F        CH3       CH3

F    NHSO2C3H7-i                  F        CH3       CH3

F                    F        CH3       CH3

F    NHSO2C4H9-n                  F        CH3       CH3

F    NHSO2C6H5                    F        CH3       CH3

F       F        CH3       CH3

H    NHSO2CH3                      H        CH3       CHF2

H    NHSO2C2H5                    H        CH3       CHF2

H    NHSO2C3H7-n                  H        CH3       CHF2

H    NHSO2C3H7-i                  H        CH3       CHF2

H                    H        CH3       CHF2

H    NHSO2C4H9-n                  H        CH3       CHF2

H    NHSO2C6H5                    H        CH3       CHF2

R1     R2                       R3      R4      R5

H      H       CH3     CHF2

F    NHSO2CH3                   H       CH3     CHF2

F    NHSO2C2H5                H       CH3     CHF2

F    NHSO2C3H7-n              H       CH3     CHF2

F    NHSO2C3H7-i              H       CH3     CHF2

F                  H       CH3     CHF2

F    NHSO2C4H9-n              H       CH3     CHF2

F    NHSO2C6H5                H       CH3     CHF2

F      H       CH3     CHF2

F    NHSO2CH3                  CH3    CH3     CHF2

F    NHSO2C2H5                CH3    CH3     CHF2

F    NHSO2C3H7-n              CH3    CH3     CHF2

F    NHSO2C3H7-i              CH3    CH3     CHF2

F                 CH3     CH3     CHF2

F    NHSO2C4H9-n              CH3     CH3     CHF2

F    NHSO2C6H5                CH3     CH3     CHF2

R1       R2                      R3     R4      R5

F      CH3    CH3     CHF2

F      NHSO2CH3                 Cl      CH3     CHF2

F      NHSO2C2H5               Cl      CH3     CHF2

F      NHSO2C3H7-n             Cl      CH3     CHF2

F      NHSO2C3H7-i             Cl      CH3     CHF2

F                  Cl      CH3     CHF2

F      NHSO2C4H9-n             Cl      CH3     CHF2

F      NHSO2C6H5               Cl      CH3     CHF2

F      Cl      CH3     CHF2

F      NHSO2CH3                 F       CH3     CHF2

F      NHSO2C2H5               F       CH3     CHF2

F      NHSO2C3H7-n             F       CH3     CHF2

F      NHSO2C3H7-i             F       CH3     CHF2

F                  F       CH3     CHF2

F      NHSO2C4H9-n             F       CH3     CHF2

F      NHSO2C6H5               F       CH3     CHF2

R1       R2                     R3     R4     R5

F      F       CH3     CHF2

F      NHSO2CH3                H       CH3     C2H5

F      NHSO2C2H5              H       CH3     C2H5

F      NHSO2C3H7-n            H       CH3     C2H5

F      NHSO2C3H7-i            H       CH3     C2H5

F                 H       CH3     C2H5

F      NHSO2C4H9-n            H       CH3     C2H5

F      NHSO2C6H5              H       CH3     C2H5

F      H       CH3     C2H5

H      NHSO2CH3                H       CF3     CH3

H      NHSO2CF3                H       CF3     CH3

H      NHSO2C2H5              H       CF3     CH3

H      NHSO2CH2CF3            H       CF3     CH3

H      NHSO2C3H7-n            H       CF3     CH3

H      NHSO2C3H7-i            H       CF3     CH3

H                 H       CF3     CH3

H      NHSO2CH2CH2CH2Cl     H       CF3     CH3

R1        R2                    R3     R4      R5

H       NHSO2C4H9-n           H       CF3     CH3

H       NHSO2C4H9-sec         H       CF3     CH3

H       NHSO2C4H9-iso         H       CF3     CH3

H       NHSO2C5H11-n          H       CF3     CH3

H            H       CF3     CH3

H     H       CF3     CH3

H      H       CF3     CH3

F      NHSO2CH3               H       CF3     CH3

F      NHSO2CF3               H       CF3     CH3

F      NHSO2C2H5             H       CF3     CH3

F      NHSO2CH2CF3           H       CF3     CH3

F      NHSO2C3H7-n           H       CF3     CH3

F      NHSO2C3H7-i           H       CF3     CH3

F                H       CF3     CH3

F      NHSO2CH2CH2CH2Cl    H       CF3     CH3

F      NHSO2C4H9-n          H       CF3     CH3

R1         R2                  R3     R4      R5

F    NHSO2C4H9-sec            H       CF3     CH3

F    NHSO2C4H9-iso            H       CF3     CH3

F    NHSO2C5H11-n             H       CF3     CH3

F             H       CF3     CH3

F      H       CF3     CH3

F       H       CF3     CH3

H               H       CF3     CH3

H                    H       CF3     CH3

H                  H       CF3     CH3

H                H       CF3     CH3

H                H       CF3     CH3

H                 H       CF3     CH3

R1       R2                      R3      R4      R5

H                 H       CF3     CH3

H            H       CF3     CH3

H                   H       CF3     CH3

H                H       CF3     CH3

H                H       CF3     CH3

H            H       CF3     CH3

H     H       CF3     CH3

H      H       CF3     CH3

F                    H       CF3     CH3

F                  H       CF3     CH3

F                   H       CF3     CH3

R1         R2                    R3      R4      R5

F                 H        CF3     CH3

F                  H        CF3     CH3

F                   H        CF3     CH3

F                 H        CF3     CH3

F            H        CF3     CH3

F                  H        CF3     CH3

F                H        CF3     CH3

F                H        CF3     CH3

F             H        CF3     CH3

F     H        CF3     CH3

F       H        CF3     CH3

R1         R2                      R3     R4      R5

H                       H       CF3     CH3

H                       H       CF3     CH3

H                      H       CF3     CH3

H                   H       CF3     CH3

H                    H       CF3     CH3

H                    H       CF3     CH3

H                   H       CF3     CH3

H                    H       CF3     CH3

H                  H       CF3     CH3

H                  H       CF3     CH3

H              H       CF3     CH3

R1       R2                      R3   R4    R5

H     H     CF3    CH3

F                     H     CF3    CH3

F                    H     CF3    CH3

F                   H     CF3    CH3

F                H     CF3    CH3

F                 H     CF3    CH3

F                  H     CF3    CH3

F                H     CF3    CH3

F                  H     CF3    CH3

F                H     CF3    CH3

F                H     CF3    CH3

R1     R2                        R3   R4     R5

F            H     CF3    CH3

F     H     CF3    CH3

F       H     CF3    CH3

F                    H     CF3    C2H5

F                    H     CF3    C2H5

F                   H     CF3    C2H5

F                H     CF3    C2H5

F                 H     CF3    C2H5

F                 H     CF3    C2H5

F               H     CF3    C2H5

F                 H     CF3    C2H5

R1     R2                        R3   R4      R5

F                 H    CF3     C2H5

F                 H    CF3     C2H5

F             H    CF3     C2H5

F      H    CF3     C2H5

H    NHSO2CH3                    H    CF3     C2H5

H    NHSO2CF3                    H    CF3     C2H5

H    NHSO2C2H5                  H    CF3     C2H5

H    NHSO2CH2CF3                H    CF3     C2H5

H    NHSO2C3H7-n                H    CF3     C2H5

H    NHSO2C3H7-i                H    CF3     C2H5

H                    H    CF3     C2H5

H    NHSO2CH2CH2CH2Cl          H    CF3     C2H5

H    NHSO2C4H9-n                H    CF3     C2H5

H    NHSO2C4H9-sec              H    CF3     C2H5

H    NHSO2C4H9-iso              H    CF3     C2H5

R1       R2                     R3      R4      R5

H      NHSO2C5H11-n            H       CF3     C2H5

H             H       CF3     C2H5

H      H       CF3     C2H5

F     NHSO2CH3                  H       CF3     C2H5

F     NHSO2CF3                  H       CF3     C2H5

F     NHSO2C2H5                H       CF3     C2H5

F     NHSO2CH2CF3              H       CF3     C2H5

F     NHSO2C3H7-n              H       CF3     C2H5

F     NHSO2C3H7-i              H       CF3     C2H5

F                  H       CF3     C2H5

F     NHSO2CH2CH2CH2Cl        H       CF3     C2H5

F     NHSO2C4H9-n              H       CF3     C2H5

F     NHSO2C4H9-sec            H       CF3     C2H5

F     NHSO2C4H9-iso            H       CF3     C2H5

F     NHSO2C5H11-n             H       CF3     C2H5

F             H       CF3     C2H5

R1       R2                    R3      R4      R5

F      H       CF3     C2H5

H     NHSO2CH3                 CH3     CF3     CH3

H     NHSO2CF3                 CH3     CF3     CH3

H     NHSO2C2H5               CH3     CF3     CH3

H     NHSO2CH2CF3             CH3     CF3     CH3

H     NHSO2C3H7-n             CH3     CF3     CH3

H     NHSO2C3H7-i             CH3     CF3     CH3

H                 CH3     CF3     CH3

H    NHSO2CH2CH2CH2Cl       CH3     CF3     CH3

H    NHSO2C4H9-n              CH3     CF3     CH3

H    NHSO2C4H9-sec            CH3     CF3     CH3

H    NHSO2C4H9-iso            CH3     CF3     CH3

H    NHSO2C5H11-n             CH3     CF3     CH3

H            CH3     CF3     CH3

H     CH3     CF3     CH3

F   NHSO2CH3                   CH3     CF3     CH3

R1       R2                   R3      R4      R5

F      NHSO2CF3               CH3     CF3     CH3

F      NHSO2C2H5             CH3     CF3     CH3

F      NHSO2CH2CF3           CH3     CF3     CH3

F      NHSO2C3H7-n           CH3     CF3     CH3

F      NHSO2C3H7-i           CH3     CF3     CH3

F                 CH3     CF3     CH3

F      NHSO2CH2CH2CH2Cl     CH3     CF3     CH3

F      NHSO2C4H9-n           CH3     CF3     CH3

F      NHSO2C4H9-sec         CH3     CF3     CH3

F      NHSO2C4H9-iso         CH3     CF3     CH3

F      NHSO2C5H11-n          CH3     CF3     CH3

F            CH3     CF3     CH3

F     CH3     CF3     CH3

F      NHSO2CH3                Cl      CF3     CH3

F      NHSO2CF3                Cl      CF3     CH3

F      NHSO2C2H5              Cl      CF3     CH3

F      NHSO2CH2CF3            Cl      CF3     CH3

R1       R2                   R3     R4      R5

F      NHSO2C3H7-n           Cl      CF3     CH3

F      NHSO2C3H7-i           Cl      CF3     CH3

F                Cl      CF3     CH3

F      NHSO2CH2CH2CH2Cl     Cl      CF3     CH3

F      NHSO2C4H9-n           Cl      CF3     CH3

F      NHSO2C4H9-sec         Cl      CF3     CH3

F      NHSO2C4H9-iso         Cl      CF3     CH3

F      NHSO2C5H11-n          Cl      CF3     CH3

F            Cl      CF3     CH3

F      Cl      CF3     CH3

F      NHSO2CH3                F       CF3     CH3

F      NHSO2CF3                F       CF3     CH3

F      NHSO2C2H5              F       CF3     CH3

F      NHSO2CH2CF3            F       CF3     CH3

F      NHSO2C3H7-n            F       CF3     CH3

F      NHSO2C3H7-i            F       CF3     CH3

F                  F       CF3     CH3

R1       R2                    R3     R4      R5

F    NHSO2CH2CH2CH2Cl       F       CF3     CH3

F    NHSO2C4H9-n             F       CF3     CH3

F    NHSO2C4H9-sec           F       CF3     CH3

F    NHSO2C4H9-iso           F       CF3     CH3

F    NHSO2C5H11-n            F       CF3     CH3

F            F       CF3     CH3

F     F       CF3     CH3

F                   CH3     CF3     CH3

F                   CH3     CF3     CH3

F                  CH3     CF3     CH3

F               CH3     CF3     CH3

F                CH3     CF3     CH3

F                 CH3     CF3     CH3

R1       R2                   R3     R4      R5

F              CH3     CF3     CH3

F         CH3     CF3     CH3

F                CH3     CF3     CH3

F              CH3     CF3     CH3

F              CH3     CF3     CH3

F           CH3     CF3     CH3

F    CH3     CF3     CH3

F                    Cl       CF3     CH3

F                  Cl       CF3     CH3

F                 Cl       CF3     CH3

F               Cl       CF3     CH3

R1       R2                  R3     R4      R5

F              Cl      CF3     CH3

F               Cl      CF3     CH3

F              Cl      CF3     CH3

F                Cl      CF3     CH3

F              Cl      CF3     CH3

F              Cl      CF3     CH3

F            Cl      CF3     CH3

F     Cl      CF3     CH3

F                     F       CF3     CH3

F                     F       CF3     CH3

F                   F       CF3     CH3

R1       R2                     R3     R4      R5

F                F       CF3     CH3

F                 F       CF3     CH3

F                  F       CF3     CH3

F                F       CF3     CH3

F           F       CF3     CH3

F                  F       CF3     CH3

F               F       CF3     CH3

F               F       CF3     CH3

F                 F       CF3     CH3

F            F       CF3     CH3

F     F       CF3     CH3

R1       R2                    R3     R4      R5

F      NHSO2CH3                H       CF3     CHF2

F      NHSO2CF3                H       CF3     CHF2

F      NHSO2C2H5              H       CF3     CHF2

F      NHSO2CH2CF3            H       CF3     CHF2

F      NHSO2C3H7-n            H       CF3     CHF2

F      NHSO2C3H7-i            H       CF3     CHF2

F                  H       CF3     CHF2

F      NHSO2CH2CH2CH2Cl      H       CF3     CHF2

F      NHSO2C4H9-n            H       CF3     CHF2

F      NHSO2C4H9-sec          H       CF3     CHF2

F      NHSO2C4H9-iso          H       CF3     CHF2

F      NHSO2C5H11-n           H       CF3     CHF2

F            H       CF3     CHF2

F     H       CF3     CHF2

F                  H       CF3     CHF2

F                   H       CF3     CHF2

R1       R2                     R3     R4      R5

F                   H       CF3     CHF2

F                H       CF3     CHF2

F                 H       CF3     CHF2

F                  H       CF3     CHF2

F                H       CF3     CHF2

F           H       CF3     CHF2

F                  H       CF3     CHF2

F                H       CF3     CHF2

F                H       CF3     CHF2

F            H       CF3     CHF2

F     H       CF3     CHF2

R1       R2                     R3     R4      R5

F      NHSO2CH3                CH3     CF3     CHF2

F      NHSO2CF3                CH3     CF3     CHF2

F      NHSO2C2H5              CH3     CF3     CHF2

F      NHSO2CH2CF3            CH3     CF3     CHF2

F      NHSO2C3H7-n            CH3     CF3     CHF2

F      NHSO2C3H7-i            CH3     CF3     CHF2

F                  CH3     CF3     CHF2

F      NHSO2CH2CH2CH2Cl      CH3     CF3     CHF2

F      NHSO2C4H9-n            CH3     CF3     CHF2

F      NHSO2C4H9-sec          CH3     CF3     CHF2

F      NHSO2C4H9-iso          CH3     CF3     CHF2

F      NHSO2C5H11-n           CH3     CF3     CHF2

F             CH3     CF3     CHF2

F      CH3     CF3     CHF2

H      NHSO2CH3                 H        CHF2    CH3

H      NHSO2CF3                 H        CHF2    CH3

H      NHSO2C2H5               H        CHF2    CH3

R1       R2                    R3     R4      R5

H    NHSO2CH2CF3             H       CHF2    CH3

H    NHSO2C3H7-n             H       CHF2    CH3

H    NHSO2C3H7-i             H       CHF2    CH3

H                 H       CHF2    CH3

H    NHSO2CH2CH2CH2Cl       H       CHF2    CH3

H    NHSO2C4H9-n             H       CHF2    CH3

H    NHSO2C4H9-sec           H       CHF2    CH3

H    NHSO2C4H9-iso           H       CHF2    CH3

H    NHSO2C5H11-n            H       CHF2    CH3

H            H       CHF2    CH3

H     H       CHF2    CH3

F    NHSO2CH3                 H       CHF2    CH3

F    NHSO2CF3                 H       CHF2    CH3

F    NHSO2C2H5               H       CHF2    CH3

F    NHSO2CH2CF3             H       CHF2    CH3

F    NHSO2C3H7-n             H       CHF2    CH3

F    NHSO2C3H7-i             H       CHF2    CH3

R1       R2                   R3     R4      R5

F                H       CHF2    CH3

F      NHSO2CH2CH2CH2Cl     H       CHF2    CH3

F      NHSO2C4H9-n           H       CHF2    CH3

F      NHSO2C4H9-sec         H       CHF2    CH3

F      NHSO2C4H9-iso         H       CHF2    CH3

F      NHSO2C5H11-n          H       CHF2    CH3

F            H       CHF2    CH3

F     H       CHF2    CH3

H                   H       CHF2    CH3

H                   H       CHF2    CH3

H                  H       CHF2    CH3

H               H       CHF2    CH3

H                H       CHF2    CH3

R1       R2                       R3     R4      R5

H                    H       CHF2    CH3

H                  H       CHF2    CH3

H                    H       CHF2    CH3

H                  H       CHF2    CH3

H                  H       CHF2    CH3

H               H       CHF2    CH3

H        H       CHF2    CH3

F                       H       CHF2    CH3

F                       H       CHF2    CH3

F                      H       CHF2    CH3

F                   H       CHF2    CH3

R1       R2                         R3     R4      R5

F                     H       CHF2    CH3

F                      H       CHF2    CH3

F                    H       CHF2    CH3

F              H       CHF2    CH3

F                     H       CHF2    CH3

F                   H       CHF2    CH3

F                   H       CHF2    CH3

F               H       CHF2    CH3

F       H       CHF2    CH3

H                       H       CHF2    CH3

H                      H       CHF2    CH3

R1       R2                       R3     R4      R5

H                     H       CHF2    CH3

H                 H       CHF2    CH3

H                  H       CHF2    CH3

H                   H       CHF2    CH3

H                 H       CHF2    CH3

H                  H       CHF2    CH3

H                H       CHF2    CH3

H                H       CHF2    CH3

H            H       CHF2    CH3

H     H       CHF2    CH3

F                    H       CHF2    CH3

R1       R2                      R3     R4      R5

F                     H       CHF2    CH3

F                    H       CHF2    CH3

F                 H       CHF2    CH3

F                  H       CHF2    CH3

F                   H       CHF2    CH3

F                  H       CHF2    CH3

F             H       CHF2    CH3

F                    H       CHF2    CH3

F                  H       CHF2    CH3

F                  H       CHF2    CH3

F              H       CHF2    CH3

R1       R2                       R3     R4      R5

F       H       CHF2    CH3

F                      H       CHF2    C2H5

F                      H       CHF2    C2H5

F                     H       CHF2    C2H5

F                  H       CHF2    C2H5

F                   H       CHF2    C2H5

F                    H       CHF2    C2H5

F                  H       CHF2    C2H5

F                    H       CHF2    C2H5

F                  H       CHF2    C2H5

F                  H       CHF2    C2H5

R1       R2                     R3     R4      R5

F            H       CHF2    C2H5

F     H       CHF2    C2H5

H      NHSO2CH3                 H       CHF2    C2H5

H      NHSO2CF3                 H       CHF2    C2H5

H      NHSO2C2H5               H       CHF2    C2H5

H      NHSO2CH2CF3             H       CHF2    C2H5

H      NHSO2C3H7-n             H       CHF2    C2H5

H      NHSO2C3H7-i             H       CHF2    C2H5

H                  H       CHF2    C2H5

H      NHSO2CH2CH2CH2Cl      H       CHF2    C2H5

H      NHSO2C4H9-n             H       CHF2    C2H5

H      NHSO2C4H9-sec           H       CHF2    C2H5

H      NHSO2C4H9-iso           H       CHF2    C2H5

H      NHSO2C5H10-n            H       CHF2    C2H5

H             H       CHF2    C2H5

R1       R2                    R3   R4      R5

H     H     CHF2    C2H5

F      NHSO2CH3                H     CHF2    C2H5

F      NHSO2CF3                H     CHF2    C2H5

F      NHSO2C2H5              H     CHF2    C2H5

F      NHSO2CH2CF3            H     CHF2    C2H5

F      NHSO2C3H7-n            H     CHF2    C2H5

F      NHSO2C3H7-i            H     CHF2    C2H5

F                 H     CHF2    C2H5

F      NHSO2CH2CH2CH2Cl     H     CHF2    C2H5

F      NHSO2C4H9-n            H     CHF2    C2H5

F      NHSO2C4H9-sec          H     CHF2    C2H5

F      NHSO2C4H9-iso          H     CHF2    C2H5

F      NHSO2C5H11-n           H     CHF2    C2H5

F            H     CHF2    C2H5

F     H     CHF2    C2H5

H      NHSO2CH3                CH3  CHF2    CH3

R1       R2                     R3      R4      R5

H      NHSO2CF3                 CH3     CHF2    CH3

H      NHSO2C2H5               CH3     CHF2    CH3

H      NHSO2CH2CF3             CH3     CHF2    CH3

H      NHSO2C3H7-n             CH3     CHF2    CH3

H      NHSO2C3H7-i             CH3     CHF2    CH3

H                   CH3     CHF2    CH3

H      NHSO2CH2CH2CH2Cl       CH3     CHF2    CH3

H      NHSO2C4H9-n             CH3     CHF2    CH3

H      NHSO2C4H9-sec           CH3     CHF2    CH3

H      NHSO2C4H9-iso           CH3     CHF2    CH3

H      NHSO2C5H11-n            CH3     CHF2    CH3

H             CH3     CHF2    CH3

H      CH3     CHF2    CH3

F      NHSO2CH3                 CH3     CHF2    CH3

F      NHSO2CF3                 CH3     CHF2    CH3

F      NHSO2C2H5               CH3     CHF2    CH3

F      NHSO2CH2CF3             CH3     CHF2    CH3

R1       R2                     R3     R4      R5

F      NHSO2C3H7-n            CH3     CHF2    CH3

F      NHSO2C3H7-i            CH3     CHF2    CH3

F                 CH3     CHF2    CH3

F      NHSO2CH2CH2CH2Cl      CH3     CHF2    CH3

F      NHSO2C4H9-n            CH3     CHF2    CH3

F      NHSO2C4H9-sec          CH3     CHF2    CH3

F      NHSO2C4H9-iso          CH3     CHF2    CH3

F      NHSO2C5H11-n           CH3     CHF2    CH3

F             CH3     CHF2    CH3

F      CH3     CHF2    CH3

F      NHSO2CH3                 Cl       CHF2    CH3

F      NHSO2CF3                 Cl       CHF2    CH3

F      NHSO2C2H5               Cl       CHF2    CH3

F      NHSO2CH2CF3             Cl       CHF2    CH3

F      NHSO2C3H7-n             Cl       CHF2    CH3

F      NHSO2C3H7-i             Cl       CHF2    CH3

F                  Cl       CHF2    CH3

R1       R2                     R3   R4      R5

F      NHSO2CH2CH2CH2Cl      Cl    CHF2    CH3

F      NHSO2C4H9-n            Cl    CHF2    CH3

F      NHSO2C4H9-sec          Cl    CHF2    CH3

F      NHSO2C4H9-iso          Cl    CHF2    CH3

F      NHSO2C5H11-n           Cl    CHF2    CH3

F            Cl    CHF2    CH3

F     Cl    CHF2    CH3

F      NHSO2CH3                F     CHF2    CH3

F      NHSO2CF3                F     CHF2    CH3

F      NHSO2C2H5              F     CHF2    CH3

F      NHSO2CH2CF3            F     CHF2    CH3

F      NHSO2C3H7-n            F     CHF2    CH3

F      NHSO2C3H7-i            F     CHF2    CH3

F                 F     CHF2    CH3

F      NHSO2CH2CH2CH2Cl      F     CHF2    CH3

F      NHSO2C4H9-n            F     CHF2    CH3

F      NHSO2C4H9-sec          F     CHF2    CH3

R1       R2                       R3   R4      R5

F     NHSO2C4H9-iso              F    CHF2    CH3

F     NHSO2C5H11-n               F    CHF2    CH3

F               F    CHF2    CH3

F        F    CHF2    CH3

F                      CH3  CHF2    CH3

F                      CH3  CHF2    CH3

F                     CH3  CHF2    CH3

F               CH3  CHF2    CH3

F                  CH3  CHF2    CH3

F                   CH3  CHF2    CH3

F                 CH3  CHF2    CH3

F                  CH3  CHF2    CH3

R1       R2                       R3     R4      R5

F                 CH3     CHF2    CH3

F                 CH3     CHF2    CH3

F             CH3     CHF2    CH3

F      CH3     CHF2    CH3

F                      Cl       CHF2    CH3

F                     Cl       CHF2    CH3

F                    Cl       CHF2    CH3

F                 Cl       CHF2    CH3

F                  Cl       CHF2    CH3

F                   Cl       CHF2    CH3

F                 Cl       CHF2    CH3

R1       R2                      R3     R4      R5

F                   Cl      CHF2    CH3

F                Cl      CHF2    CH3

F                Cl      CHF2    CH3

F             Cl      CHF2    CH3

F      Cl      CHF2    CH3

F                      F       CHF2    CH3

F                      F       CHF2    CH3

F                     F       CHF2    CH3

F                 F       CHF2    CH3

F                  F       CHF2    CH3

F                   F       CHF2    CH3

R1       R2                     R3     R4      R5

F                F       CHF2    CH3

F                  F       CHF2    CH3

F                F       CHF2    CH3

F                F       CHF2    CH3

F            F       CHF2    CH3

F     F       CHF2    CH3

F      NHSO2CH3                  H       CHF2    CHF2

F      NHSO2CF3                  H       CHF2    CHF2

F      NHSO2C2H5                H       CHF2    CHF2

F      NHSO2CH2CF3              H       CHF2    CHF2

F      NHSO2C3H7-n              H       CHF2    CHF2

F      NHSO2C3H7-i              H       CHF2    CHF2

F                  H       CHF2    CHF2

F      NHSO2CH2CH2CH2Cl       H       CHF2    CHF2

R1       R2                    R3   R4      R5

F     NHSO2C4H9-n             H    CHF2    CHF2

F     NHSO2C4H9-sec           H    CHF2    CHF2

F     NHSO2C4H9-iso           H    CHF2    CHF2

F     NHSO2C5H11-n            H    CHF2    CHF2

F            H    CHF2    CHF2

F     H    CHF2    CHF2

F                   H    CHF2    CHF2

F                   H    CHF2    CHF2

F                  H    CHF2    CHF2

F               H    CHF2    CHF2

F                H    CHF2    CHF2

F                 H    CHF2    CHF2

F               H    CHF2    CHF2

R1       R2                         R3     R4      R5

F                      H       CHF2    CHF2

F                   H       CHF2    CHF2

F                   H       CHF2    CHF2

F           H       CHF2    CHF2

F       H       CHF2    CHF2

F      NHSO2CH3                   CH3    CHF2    CHF2

F      NHSO2CF3                   CH3    CHF2    CHF2

F      NHSO2C2H5                CH3    CHF2    CHF2

F      NHSO2CH2CF3              CH3    CHF2    CHF2

F      NHSO2C3H7-n              CH3    CHF2    CHF2

F      NHSO2C3H7-i              CH3    CHF2    CHF2

F                   CH3    CHF2    CHF2

F      NHSO2CH2CH2CH2Cl        CH3    CHF2    CHF2

F      NHSO2C4H9-n              CH3    CHF2    CHF2

F      NHSO2C4H9-sec            CH3    CHF2    CHF2

R1       R2                    R3    R4     R5

F     NHSO2C4H9-iso          CH3   CHF2    CHF2

F     NHSO2C5H11-n           CH3   CHF2    CHF2

F            CH3   CHF2    CHF2

F     CH3   CHF2    CHF2

H     NHSO2CH3                H     C2F5    CH3

H     NHSO2CF3                H     C2F5    CH3

H     NHSO2C2H5              H     C2F5    CH3

H     NHSO2CH2CF3            H     C2F5    CH3

H     NHSO2C3H7-n            H     C2F5    CH3

H     NHSO2C3H7-i            H     C2F5    CH3

H                H     C2F5    CH3

H     NHSO2CH2CH2CH2Cl     H     C2F5    CH3

H     NHSO2C4H9-n            H     C2F5    CH3

H     NHSO2C4H9-sec          H     C2F5    CH3

H     NHSO2C4H9-iso          H     C2F5    CH3

H     NHSO2C5H11-n           H     C2F5    CH3

R1       R2                      R3    R4      R5

H              H      C2F5    CH3

H       H      C2F5    CH3

F      NHSO2CH3                  H      C2F5    CH3

F      NHSO2CF3                  H      C2F5    CH3

F      NHSO2C2H5                H      C2F5    CH3

F      NHSO2CH2CF3              H      C2F5    CH3

F      NHSO2C3H7-n              H      C2F5    CH3

F      NHSO2C3H7-i              H      C2F5    CH3

F                    H      C2F5    CH3

F      NHSO2CH2CH2CH2Cl        H      C2F5    CH3

F      NHSO2C4H9-n              H      C2F5    CH3

F      NHSO2C4H9-sec            H      C2F5    CH3

F      NHSO2C4H9-iso            H      C2F5    CH3

F      NHSO2C5H11-n             H      C2F5    CH3

F               H      C2F5    CH3

R1       R2                    R3     R4      R5

F     H       C2F5    CH3

H                   H       C2F5    CH3

H                   H       C2F5    CH3

H                  H       C2F5    CH3

H               H       C2F5    CH3

H                H       C2F5    CH3

H                 H       C2F5    CH3

H               H       C2F5    CH3

H                 H       C2F5    CH3

H               H       C2F5    CH3

H               H       C2F5    CH3

R1       R2                     R3     R4      R5

H            H       C2F5    CH3

H     H       C2F5    CH3

F                    H       C2F5    CH3

F                    H       C2F5    CH3

F                  H       C2F5    CH3

F                H       C2F5    CH3

F                 H       C2F5    CH3

F                  H       C2F5    CH3

F                 H       C2F5    CH3

F                  H       C2F5    CH3

F                H       C2F5    CH3

R1       R2                       R3     R4      R5

F                 H       C2F5    CH3

F             H       C2F5    CH3

F      H       C2F5    CH3

H                      H       C2F5    CH3

H                      H       C2F5    CH3

H                     H       C2F5    CH3

H                  H       C2F5    CH3

H                   H       C2F5    CH3

H                    H       C2F5    CH3

H                  H       C2F5    CH3

H                    H       C2F5    CH3

R1       R2                     R3     R4      R5

H               H       C2F5    CH3

H               H       C2F5    CH3

H           H       C2F5    CH3

H    H       C2F5    CH3

F                    H       C2F5    CH3

F                    H       C2F5    CH3

F                   H       C2F5    CH3

F                H       C2F5    CH3

F                 H       C2F5    CH3

F                  H       C2F5    CH3

F               H       C2F5    CH3

R1       R2                      R3     R4      R5

F                   H       C2F5    CH3

F                 H       C2F5    CH3

F                 H       C2F5    CH3

F             H       C2F5    CH3

F      H       C2F5    CH3

F                      H       C2F5    C2H5

F                      H       C2F5    C2H5

F                     H       C2F5    C2H5

F                   H       C2F5    C2H5

F                    H       C2F5    C2H5

F                  H       C2F5    C2H5

R1       R2                     R3     R4      R5

F                H       C2F5    C2H5

F                  H       C2F5    C2H5

F                H       C2F5    C2H5

F                H       C2F5    C2H5

F            H       C2F5    C2H5

F     H       C2F5    C2H5

H     NHSO2CH3                  H       C2F5    C2H5

H     NHSO2CF3                  H       C2F5    C2H5

H     NHSO2C2H5                H       C2F5    C2H5

H     NHSO2CH2CF3              H       C2F5    C2H5

H     NHSO2C3H7-n              H       C2F5    C2H5

H     NHSO2C3H7-i              H       C2F5    C2H5

H                  H       C2F5    C2H5

H    NHSO2CH2CH2CH2Cl        H       C2F5    C2H5

R1       R2                     R3   R4      R5

H     NHSO2C4H9-n             H    C2F5    C2H5

H     NHSO2C4H9-sec           H    C2F5    C2H5

H     NHSO2C4H9-iso           H    C2F5    C2H5

H     NHSO2C5H11-n            H    C2F5    C2H5

H             H    C2F5    C2H5

H      H    C2F5    C2H5

F     NHSO2CH3                 H    C2F5    C2H5

F     NHSO2CF3                 H    C2F5    C2H5

F     NHSO2C2H5               H    C2F5    C2H5

F     NHSO2CH2CF3             H    C2F5    C2H5

F     NHSO2C3H7-n             H    C2F5    C2H5

F     NHSO2C3H7-i             H    C2F5    C2H5

F                 H    C2F5    C2H5

F     NHSO2CH2CH2CH2Cl       H    C2F5    C2H5

F     NHSO2C4H9-n             H    C2F5    C2H5

F     NHSO2C4H9-sec           H    C2F5    C2H5

F     NHSO2C4H9-iso           H    C2F5    C2H5

R1       R2                      R3      R4      R5

F     NHSO2C5H11-n              H       C2F5    C2H5

F              H       C2F5    C2H5

F       H       C2F5    C2H5

H     NHSO2CH3                   CH3    C2F5    CH3

H     NHSO2CF3                   CH3    C2F5    CH3

H     NHSO2C2H5                 CH3    C2F5    CH3

H     NHSO2CH2CF3               CH3    C2F5    CH3

H     NHSO2C3H7-n               CH3    C2F5    CH3

H     NHSO2C3H7-i               CH3    C2F5    CH3

H                   CH3    C2F5    CH3

H     NHSO2CH2CH2CH2Cl        CH3    C2F5    CH3

H     NHSO2C4H9-n               CH3    C2F5    CH3

H     NHSO2C4H9-sec             CH3    C2F5    CH3

H     NHSO2C4H9-iso             CH3    C2F5    CH3

H     NHSO2C5H11-n              CH3    C2F5    CH3

H              CH3    C2F5    CH3

R1       R2                      R3      R4       R5

H       CH3     C2F5    CH3

F    NHSO2CH3                   CH3     C2F5    CH3

F    NHSO2CF3                   CH3     C2F5    CH3

F    NHSO2C2H5                 CH3     C2F5    CH3

F    NHSO2CH2CF3               CH3     C2F5    CH3

F    NHSO2C3H7-n               CH3     C2F5    CH3

F    NHSO2C3H7-i               CH3     C2F5    CH3

F                  CH3     C2F5    CH3

F    NHSO2CH2CH2CH2Cl        CH3     C2F5    CH3

F    NHSO2C4H9-n               CH3     C2F5    CH3

F    NHSO2C4H9-sec             CH3     C2F5    CH3

F    NHSO2C4H9-iso             CH3     C2F5    CH3

F    NHSO2C5H11-n              CH3     C2F5    CH3

F              CH3     C2F5    CH3

F       CH3     C2F5    CH3

F    NHSO2CH3                   Cl        C2F5    CH3

R1       R2                    R3      R4      R5

F     NHSO2CF3                 Cl      C2F5    CH3

F     NHSO2C2H5               Cl      C2F5    CH3

F     NHSO2CH2CF3             Cl      C2F5    CH3

F     NHSO2C3H7-n             Cl      C2F5    CH3

F     NHSO2C3H7-i             Cl      C2F5    CH3

F                  Cl      C2F5    CH3

F     NHSO2CH2CH2CH2Cl       Cl      C2F5    CH3

F     NHSO2C4H9-n             Cl      C2F5    CH3

F     NHSO2C4H9-sec           Cl      C2F5    CH3

F     NHSO2C4H9-iso           Cl      C2F5    CH3

F     NHSO2C5H11-n            Cl      C2F5    CH3

F             Cl      C2F5    CH3

F      Cl      C2F5    CH3

F     NHSO2CH3                  F       C2F5    CH3

F     NHSO2CF3                  F       C2F5    CH3

F     NHSO2C2H5                F       C2F5    CH3

F     NHSO2CH2CF3              F       C2F5    CH3

R1       R2                     R3      R4      R5

F      NHSO2C3H7-n             F       C2F5    CH3

F      NHSO2C3H7-i             F       C2F5    CH3

F                  F       C2F5    CH3

F      NHSO2CH2CH2CH2Cl       F       C2F5    CH3

F      NHSO2C4H9-n             F       C2F5    CH3

F      NHSO2C4H9-sec           F       C2F5    CH3

F      NHSO2C4H9-iso           F       C2F5    CH3

F      NHSO2C5H11-n            F       C2F5    CH3

F              F       C2F5    CH3

F       F       C2F5    CH3

F                     CH3     C2F5    CH3

F                   CH3     C2F5    CH3

F                   CH3     C2F5    CH3

F                CH3     C2F5    CH3

R1       R2                      R3      R4       R5

F                  CH3     C2F5    CH3

F                   CH3     C2F5    CH3

F                 CH3     C2F5    CH3

F                   CH3     C2F5    CH3

F                 CH3     C2F5    CH3

F                 CH3     C2F5    CH3

F             CH3     C2F5    CH3

F      CH3     C2F5    CH3

F                      Cl       C2F5    CH3

F                      Cl       C2F5    CH3

F                    Cl       C2F5    CH3

R1       R2                       R3     R4      R5

F                  Cl      C2F5    CH3

F                 Cl      C2F5    CH3

F                    Cl      C2F5    CH3

F                  Cl      C2F5    CH3

F                    Cl      C2F5    CH3

F                  Cl      C2F5    CH3

F                  Cl      C2F5    CH3

F              Cl      C2F5    CH3

F        Cl      C2F5    CH3

F                   F       C2F5    CH3

F                       F       C2F5    CH3

R1       R2                     R3     R4      R5

F                   F       C2F5    CH3

F                F       C2F5    CH3

F                 F       C2F5    CH3

F                  F       C2F5    CH3

F                 F       C2F5    CH3

F                   F       C2F5    CH3

F                 F       C2F5    CH3

F                 F       C2F5    CH3

F             F       C2F5    CH3

F      F       C2F5    CH3

F     NHSO2CH3                   H       C2F5    CHF2

F     NHSO2CF3                   H       C2F5    CHF2

R1       R2                      R3     R4       R5

F      NHSO2C2H5                H       C2F5    CHF2

F      NHSO2CH2CF3              H       C2F5    CHF2

F      NHSO2C3H7-n              H       C2F5    CHF2

F      NHSO2C3H7-i              H       C2F5    CHF2

F                   H       C2F5    CHF2

F      NHSO2CH2CH2CH2Cl        H       C2F5    CHF2

F      NHSO2C4H9-n              H       C2F5    CHF2

F      NHSO2C4H9-sec            H       C2F5    CHF2

F      NHSO2C4H9-iso            H       C2F5    CHF2

F      NHSO2C5H11-n             H       C2F5    CHF2

F               H       C2F5    CHF2

F        H       C2F5    CHF2

F                     H       C2F5    CHF2

F                     H       C2F5    CHF2

F                    H       C2F5    CHF2

R1       R2                     R3     R4      R5

F                H       C2F5    CHF2

F                 H       C2F5    CHF2

F                  H       C2F5    CHF2

F                H       C2F5    CHF2

F                  H       C2F5    CHF2

F                H       C2F5    CHF2

F                H       C2F5    CHF2

F                 H       C2F5    CHF2

F            H       C2F5    CHF2

F     H       C2F5    CHF2

F     NHSO2CH3                  CH3    C2F5    CHF2

F    -NHSO2CF3                  CH3    C2F5    CHF2

R1       R2                     R3      R4       R5

F      NHSO2C2H5              CH3     C2F5    CHF2

F      NHSO2CH2CF3            CH3     C2F5    CHF2

F      NHSO2C3H7-n            CH3     C2F5    CHF2

F      NHSO2C3H7-i            CH3     C2F5    CHF2

F                  CH3     C2F5    CHF2

F     NHSO2CH2CH2CH2Cl       CH3     C2F5    CHF2

F     NHSO2C4H9-n             CH3     C2F5    CHF2

F     NHSO2C4H9-sec           CH3     C2F5    CHF2

F     NHSO2C4H9-iso           CH3     C2F5    CHF2

F     NHSO2C5H11-n            CH3     C2F5    CHF2

F             CH3     C2F5    CHF2

F      CH3    C2F5     CHF2

H      NHSO2CH3                 H       CF2Cl     CH3

H      NHSO2CF3                 H       CF2Cl     CH3

H      NHSO2C2H5               H       CF2Cl     CH3

H      NHSO2CH2CF3             H       CF2Cl     CH3

H      NHSO2C3H7-n             H       CF2Cl     CH3

R1       R2                     R3     R4     R5

H     NHSO2C3H7-i             H       CF2Cl   CH3

H                 H       CF2Cl   CH3

H     NHSO2CH2CH2CH2Cl       H       CF2Cl   CH3

H     NHSO2C4H9-n             H       CF2Cl   CH3

H     NHSO2C4H9-sec           H       CF2Cl   CH3

H     NHSO2C4H9-iso           H       CF2Cl   CH3

H     NHSO2C5H11-n            H       CF2Cl   CH3

H             H       CF2Cl   CH3

H      H       CF2Cl   CH3

F     NHSO2CH3                  H       CF2Cl   CH3

F     NHSO2CF3                  H       CF2Cl   CH3

F     NHSO2C2H5                H       CF2Cl   CH3

F     NHSO2CH2CF3              H       CF2CL   CH3

F     NHSO2C3H7-n              H       CF2Cl   CH3

F     NHSO2C3H7-i              H       CF2Cl   CH3

F                  H       CF2Cl   CH3

F     NHSO2CH2CH2CH2Cl       H       CF2Cl   CH3

R1       R2                     R3     R4      R5

F     NHSO2C4H9-n              H       CF2Cl   CH3

F     NHSO2C4H9-sec            H       CF2Cl   CH3

F     NHSO2C4H9-iso            H       CF2Cl   CH3

F     NHSO2C5H11-n             H       CF2Cl   CH3

F              H       CF2Cl   CH3

F       H       CF2Cl   CH3

H                    H       CF2Cl   CH3

H                     H       CF2Cl   CH3

H                    H       CF2Cl   CH3

H                 H       CF2Cl   CH3

H                  H       CF2Cl   CH3

H                   H       CF2Cl   CH3

H                H       CF2Cl   CH3

R1       R2                      R3     R4       R5

H                   H       CF2Cl    CH3

H                 H       CF2Cl    CH3

H                 H       CF2Cl    CH3

H                  H       CF2Cl    CH3

H             H       CF2Cl    CH3

H      H       CF2Cl    CH3

F                      H       CF2Cl    CH3

F                      H       CF2Cl    CH3

F                     H       CF2Cl    CH3

F                  H       CF2Cl    CH3

F                   H       CF2Cl    CH3

R1       R2                      R3     R4       R5

F                   H       CF2Cl    CH3

F                 H       CF2Cl    CH3

F                   H       CF2Cl    CH3

F                 H       CF2Cl    CH3

F                 H       CF2Cl    CH3

F                  H       CF2Cl    CH3

F             H       CF2Cl    CH3

F      H       CF2Cl    CH3

H                     H       CF2Cl    CH3

H                     H       CF2Cl    CH3

H                    H       CF2Cl    CH3

R1       R2                    R3     R4     R5

H               H      CF2Cl   CH3

H                H      CF2Cl   CH3

H                 H      CF2Cl   CH3

H                H      CF2Cl   CH3

H                  H      CF2Cl   CH3

H                H      CF2Cl   CH3

H                H      CF2Cl   CH3

H                 H      CF2Cl   CH3

H            H      CF2Cl   CH3

H     H      CF2Cl   CH3

F                     H      CF2Cl   CH3

R1       R2                     R3     R4       R5

F                    H       CF2Cl    CH3

F                   H       CF2Cl    CH3

F                H       CF2Cl    CH3

F                 H       CF2Cl    CH3

F                  H       CF2Cl    CH3

F                 H       CF2Cl    CH3

F                  H       CF2Cl    CH3

F                H       CF2Cl    CH3

F                H       CF2Cl    CH3

F                 H       CF2Cl    CH3

F            H       CF2Cl    CH3

R1       R2                      R3     R4       R5

F     H       CF2Cl    CH3

F                  H       CF2Cl    C2H5

F                    H       CF2Cl    C2H5

F                   H       CF2Cl    C2H5

F               H       CF2Cl    C2H5

F                H       CF2Cl    C2H5

F                 H       CF2Cl    C2H5

F               H       CF2Cl    C2H5

F               H       CF2Cl    C2H5

F              H       CF2Cl    C2H5

F              H       CF2Cl    C2H5

R1       R2                      R3    R4       R5

F                 H     CF2Cl    C2H5

F            H     CF2Cl    C2H5

F     H     CF2Cl    C2H5

H      NHSO2CH3                 H     CF2Cl    C2H5

H      NHSO2CF3                 H     CF2Cl    C2H5

H      NHSO2C2H5               H     CF2Cl    C2H5

H      NHSO2CH2CF3             H     CF2Cl    C2H5

H      NHSO2C3H7-n             H     CF2Cl    C2H5

H      NHSO2C3H7-i             H     CF2CL    C2H5

H                  H     CF2Cl    C2H5

H     NHSO2CH2CH2CH2Cl       H     CF2Cl    C2H5

H     NHSO2C4H9-n             H     CF2Cl    C2H5

H     NHSO2C4H9-sec           H     CF2Cl    C2H5

H     NHSO2C4H9-iso           H     CF2Cl    C2H5

H     NHSO2C5H11-n             H     CF2Cl    C2H5

R1       R2                      R3   R4       R5

H               H    CF2Cl    C2H5

H        H    CF2Cl    C2H5

F      NHSO2CH3                  H    CF2Cl    C2H5

F      NHSO2CF3                  H    CF2Cl    C2H5

F      NHSO2C2H5                H    CF2Cl    C2H5

F      NHSO2CH2CF3              H    CF2Cl    C2H5

F      NHSO2C3H7-n              H    CF2Cl    C2H5

F      NHSO2C3H7-i              H    CF2Cl    C2H5

F                   H    CF2Cl    C2H5

F     NHSO2CH2CH2CH2Cl        H    CF2Cl    C2H5

F     NHSO2C4H9-n               H    CF2Cl    C2H5

F     NHSO2C4H9-sec             H    CF2Cl    C2H5

F     NHSO2C4H9-iso             H    CF2Cl    C2H5

F     NHSO2C5H11-n              H    CF2Cl    C2H5

F              H    CF2Cl    C2H5

R1       R2                        R3     R4       R5

F        H        CF2Cl    C2H5

H      NHSO2CH3                  CH3     CF2Cl    CH3

H      NHSO2CF3                  CH3     CF2Cl    CH3

H      NHSO2C2H5                CH3     CF2Cl    CH3

H      NHSO2CH2CF3              CH3     CF2Cl    CH3

H      NHSO2C3H7-n              CH3     CF2Cl    CH3

H      NHSO2C3H7-i              CH3     CF2Cl    CH3

H                   CH3     CF2Cl    CH3

H      NHSO2CH2CH2CH2Cl       CH3     CF2Cl    CH3

H      NHSO2C4H9-n              CH3     CF2Cl    CH3

H      NHSO2C4H9-sec            CH3     CF2Cl    CH3

H      NHSO2C4H9-iso            CH3     CF2Cl    CH3

H      NHSO2C5H11-n             CH3     CF2Cl    CH3

H               CH3     CF2Cl    CH3

H       CH3     CF2Cl    CH3

F      NHSO2CH3                  CH3     CF2Cl    CH3

R1       R2                     R3     R4       R5

F      NHSO2CF3                CH3     CF2Cl    CH3

F      NHSO2C2H5              CH3     CF2Cl    CH3

F      NHSO2CH2CF3            CH3     CF2Cl    CH3

F      NHSO2C3H7-n            CH3     CF2Cl    CH3

F      NHSO2C3H7-i            CH3     CF2Cl    CH3

F                 CH3     CF2Cl    CH3

F     NHSO2CH2CH2CH2Cl       CH3     CF2Cl    CH3

F     NHSO2C4H9-n             CH3     CF2Cl    CH3

F     NHSO2C4H9-sec           CH3     CF2Cl    CH3

F     NHSO2C4H9-iso           CH3     CF2Cl    CH3

F     NHSO2C5H11-n            CH3     CF2Cl    CH3

F             CH3     CF2Cl    CH3

F      CH3     CF2Cl    CH3

F      NHSO2CH3                 Cl       CF2Cl    CH3

F      NHSO2CF3                 Cl       CF2Cl    CH3

F      NHSO2C2H5               Cl       CF2Cl    CH3

F      NHSO2CH2CF3             Cl       CF2Cl    CH3

R1       R2                     R3   R4      R5

F      NHSO2C3H7-n            Cl    CF2Cl    CH3

F      NHSO2C3H7-i            Cl    CF2Cl    CH3

F                 Cl    CF2Cl    CH3

F      NHSO2CH2CH2CH2Cl      Cl    CF2Cl    CH3

F      NHSO2C4H9-n            Cl    CF2Cl    CH3

F      NHSO2C4H9-sec          Cl    CF2Cl    CH3

F      NHSO2C4H9-iso          Cl    CF2Cl    CH3

F      NHSO2C5H11-n           Cl    CF2Cl    CH3

F             Cl    CF2Cl    CH3

F      Cl    CF2Cl    CH3

F      NHSO2CH3                 F     CF2Cl    CH3

F      NHSO2CF3                 F     CF2Cl    CH3

F      NHSO2C2H5               F     CF2Cl    CH3

F      NHSO2CH2CF3             F     CF2Cl    CH3

F      NHSO2C3H7-n             F     CF2Cl    CH3

F      NHSO2C3H7-i             F     CF2Cl    CH3

F                 F     CF2Cl    CH3

R1      R2                       R3     R4       R5

F     NHSO2CH2CH2CH2Cl        F       CF2Cl    CH3

F     NHSO2C4H9-n              F       CF2Cl    CH3

F     NHSO2C4H9-sec            F       CF2Cl    CH3

F     NHSO2C4H9-iso            F       CF2Cl    CH3

F     NHSO2C5H11-n             F       CF2Cl    CH3

F              F       CF2Cl    CH3

F       F       CF2Cl    CH3

F                     CH3     CF2Cl    CH3

F                     CH3     CF2Cl    CH3

F                    CH3     CF2Cl    CH3

F                 CH3     CF2Cl    CH3

F                 CH3     CF2Cl    CH3

F                 CH3     CF2Cl    CH3

R1       R2                       R3      R4     R5

F                  CH3     CF2Cl   CH3

F                    CH3     CF2Cl   CH3

F                  CH3     CF2Cl   CH3

F                  CH3     CF2Cl   CH3

F              CH3     CF2Cl   CH3

F       CH3     CF2Cl   CH3

F                       Cl       CF2Cl   CH3

F                       Cl       CF2Cl   CH3

F                      Cl       CF2Cl   CH3

F                   Cl       CF2Cl   CH3

F                    Cl       CF2Cl   CH3

R1       R2                     R3      R4      R5

F                  Cl      CF2Cl    CH3

F                Cl      CF2Cl    CH3

F                  Cl      CF2Cl    CH3

F                Cl      CF2Cl    CH3

F                Cl      CF2Cl    CH3

F                 Cl      CF2Cl    CH3

F            Cl      CF2Cl    CH3

F     Cl      CF2Cl    CH3

F                    F       CF2Cl    CH3

F                     F       CF2Cl    CH3

F                  F       CF2Cl    CH3

R1        R2                     R3      R4      R5

F                 F       CF2Cl    CH3

F                  F       CF2Cl    CH3

F                   F       CF2Cl    CH3

F                  F       CF2Cl    CH3

F                   F       CF2Cl    CH3

F                 F       CF2Cl    CH3

F                 F       CF2Cl    CH3

F             F       CF2Cl    CH3

F      F       CF2Cl    CH3

F      NHSO2CH3                  H       CF2Cl    CHF2

F      NHSO2CF3                  H       CF2Cl    CHF2

F      NHSO2C2H5                H       CF2Cl    CHF2

R1       R2                     R3     R4       R5

F     NHSO2CH2CF3              H       CF2Cl    CHF2

F     NHSO2C3H7-n              H       CF2Cl    CHF2

F     NHSO2C3H7-i              H       CF2Cl    CHF2

F                   H       CF2Cl    CHF2

F     NHSO2CH2CH2CH2Cl        H       CF2Cl    CHF2

F     NHSO2C4H9-n              H       CF2Cl    CHF2

F     NHSO2C4H9-sec            H       CF2Cl    CHF2

F     NHSO2C4H9-iso            H       CF2Cl    CHF2

F     NHSO2C5H11-n             H       CF2Cl    CHF2

F              H       CF2Cl    CHF2

F       H       CF2Cl    CHF2

F                  H       CF2Cl    CHF2

F                     H       CF2Cl    CHF2

F                    H       CF2Cl    CHF2

R1       R2                      R3      R4      R5

F                 H       CF2Cl    CHF2

F                  H       CF2Cl    CHF2

F                   H       CF2Cl    CHF2

F                 H       CF2Cl    CHF2

F                   H       CF2Cl    CHF2

F                H       CF2Cl    CHF2

F                H       CF2Cl    CHF2

F                 H       CF2Cl    CHF2

F            H       CF2Cl    CHF2

F     H       CF2Cl    CHF2

F    NHSO2CH3                   CH3    CF2Cl    CHF2

F    NHSO2CF3                   CH3    CF2Cl    CHF2

R1        R2                       R3      R4       R5

F       NHSO2C2H5                CH3     CF2Cl    CHF2

F       NHSO2CH2CF3              CH3     CF2Cl    CHF2

F       NHSO2C3H7-n              CH3     CF2Cl    CHF2

F       NHSO2C3H7-i              CH3     CF2Cl    CHF2

F                    CH3     CF2Cl    CHF2

F       NHSO2CH2CH2CH2Cl        CH3     CF2Cl    CHF2

F       NHSO2C4H9-n              CH3     CF2Cl    CHF2

F       NHSO2C4H9-sec            CH3     CF2Cl    CHF2

F       NHSO2C4H9-iso            CH3     CF2Cl    CHF2

F       NHSO2C5H11-n             CH3     CF2Cl    CHF2

F               CH3     CF2Cl    CHF2

F        CH3     CF2Cl    CHF2

H     -N(SO2CH3)2                H        CF3      CH3

H     -N(SO2CH3)(SO2C2H5)     H        CF3      CH3

H     -N(SO2C2H5)2             H        CF3      CH3

H     -N(SO2CH3)(SO2C3H7)     H        CF3      CH3

R1       R2                      R3   R4     R5

H     -N(SO2C3H7)2             H    CF3    CH3

H     -N(SO2CH3)(SO2C3H7-i)   H    CF3    CH3

H     -N(SO2C3H7-i)2           H    CF3    CH3

F     -N(SO2CH3)2               H    CF3    CH3

F     -N(SO2CH3)2               H    CF3    C2H5 

F     -N(SO2CH3)(SO2C2H5)     H    CF3    CH3

F     -N(SO2C2H5)2             H    CF3    CH3

F     -N(SO2CH3)(SO2C3H7)     H    CF3    CH3

F     -N(SO2C3H7)2              H    CF3    CH3

F     -N(SO2CH3)(SO2C3H7-i)   H    CF3    CH3

F     -N(SO2C3H7-i)2           H    CF3    CH3

F     -N(SO2C2H5)(SO2C3H7)   H    CF3    CH3

F                    H    CF3    CH3

R1         R2                   R3    R4     R5

F                   H     CF3    CH3

F    -N(SO2CH3)(SO2C4H9)    H     CF3    CH3

F    -N(SO2C4H9)2            H     CF3    CH3

F    -N(SO2CH3)(SO2CF3)      H     CF3    CH3

F    -N(SO2CF3)2              H     CF3    CH3

F    -                            H     CF3    CH3

     N(SO2CH3)(SO2CH2CF3)

F    -N(SO2CH2CF3)2          H     CF3    CH3

F    -N(SO2CH3)(SO2C3H6Cl)  H     CF3    CH3

F    -N(SO2CH2CH2CH2Cl)2    H     CF3    CH3

F    -N(SO2CH3)(SO2C6H5)    H     CF3    CH3

F    -N(SO2C6H5)2            H     CF3    CH3

F    -N(SO2C2H5)(SO2C6H5)  H     CF3    CH3

R1      R2                      R3   R4      R5

F     H    CF3     CH3

F    -N(SO2CH3)2              H    CHF2    CH3

F    -N(SO2CH3)2              H    CHF2    C2H5

F    -N(SO2C2H5)2            H    CHF2    CH3

F    -N(SO2CH3)(SO2C3H7)    H    CHF2    CH3

F    -N(SO2C3H7)2            H    CHF2    CH3

F    -N(SO2CH3)(SO2C3H7-i)  H    CHF2    CH3

F    -N(SO2C3H7-i)2          H    CHF2    CH3

F                 H    CHF2    CH3

F                 H    CHF2    CH3

F    -N(SO2CH3)(SO2C4H9)   H    CHF2    CH3

F    -N(SO2C4H9)2           H    CHF2    CH3

R1          R2                   R3   R4       R5

F    -N(SO2CH3)(SO2CF3)       H    CHF2     CH3

F    -N(SO2CF3)2               H    CHF2     CH3

F    -                             H    CHF2     CH3

     N(SO2CH3)(SO2CH2CF3)

F    -N(SO2CH2CF3)2           H    CHF2     CH3

F    -N(SO2CH3)(SO2C6H5)     H    CHF2     CH3

F    -N(SO2C6H5)2             H    CHF2     CH3

F    -N(SO2C2H5)(SO2C6H5)   H    CHF2     CH3

F      H    CHF2     CH3

F    -N(SO2CH3)2               H    CF2Cl    CH3

F    -N(SO2CH3)2               H    CF2Cl    C2H5

F    -N(SO2C2H5)2             H    CF2Cl    CH3

F    -N(SO2CH3)(SO2C3H7)     H    CF2Cl    CH3

F    -N(SO2C3H7)2             H    CF2Cl    CH3

R1           R2                  R3   R4      R5

F    -N(SO2CH3)(SO2C3H7-i)   H    CF2Cl    CH3

F    -N(SO2C3H7-i)2           H    CF2Cl    CH3

F                   H    CF2Cl    CH3

F                   H    CF2Cl    CH3

F    -N(SO2CH3)(SO2C4H9)     H    CF2Cl    CH3

F    -N(SO2C4H9)2             H    CF2Cl    CH3

F    -N(SO2CH3)(SO2CF3)       H    CF2Cl    CH3

F    -N(SO2CF3)2               H    CF2Cl    CH3

F    -                             H    CF2Cl    CH3

     N(SO2CH3)(SO2CH2CF3)

F    -N(SO2CH2CF3)2           H    CF2Cl    CH3

F    -N(SO2CH2CH2CH2Cl)2     H    CF2Cl    CH3

F    -N(SO2CH3)(SO2C6H5)     H    CF2Cl    CH3

F    -N(SO2C6H5)2             H    CF2Cl    CH3

R1       R2                    R3   R4      R5

F      H    CF2Cl    CH3

F    -N(SO2CH3)2              H    C2F5    CH3

F    -N(SO2CH3)2              H    C2F5    C2H5

F    -N(SO2C2H5)2            H    C2F5    CH3

F    -N(SO2CH3)(SO2C3H7)    H    C2F5    CH3

F    -N(SO2C3H7)2            H    C2F5    CH3

F    -N(SO2CH3)(SO2C3H7-i)  H    C2F5    CH3

F    -N(SO2C3H7-i)2          H    C2F5    CH3

F                  H    C2F5    CH3

F    -N(SO2CH3)(SO2C4H9)    H    C2F5    CH3

F    -N(SO2C4H9)2            H    C2F5    CH3

F    -N(SO2CH3)(SO2CF3)      H    C2F5    CH3

F    -N(SO2CF3)2              H    C2F5    CH3

R1        R2                    R3    R4     R5

F    -N(SO2CH2CF3)2          H     C2F5   CH3

F    -N(SO2CH3)(SO2C6H5)    H     C2F5   CH3

F    -N(SO2C6H5)2            H     C2F5   CH3

F      H     C2F5   CH3

F    -N(SO2CH3)2              CH3  CF3     CH3

F    -N(SO2CH3)2              CH3  CF3     C2H5

F    -N(SO2C2H5)2            CH3  CF3     CH3

F    -N(SO2CH3)2              Cl    CF3     CH3

F    -N(SO2CH3)2              Cl    CF3     C2H5

F    -N(SO2CH3)(SO2C2H5)    Cl    CF3     CH3

F    -N(SO2C2H5)2            Cl    CF3     CH3

F    -N(SO2CH3)(COOCH3)       H     CF3     CH3

F    -N(SO2CH3)(COOC2H5)     H     CF3     CH3

R1           R2               R3    R4     R5

F    -N(SO2CH3)(COOC4H9-t) H      CF3    CH3

F    -N(SO2CH3)(COOC6H5)   H      CF3    CH3

F    -N(SO2CH3)(COCH3)      H      CF3    CH3

F    -N(SO2CH3)(COCF3)      H      CF3    CH3

F    -N(SO2CH3)(CHO)         H      CF3    CH3

H                    H      CF3    CH3

H                    H      CF3    C2H5

H                    CH3   CF3    CHF2

F                    H      CF3    CH3

F                    H      CF3    C2H5

F                    CH3   CF3    CHF2

R1     R2              R3      R4     R5

F              Cl      CF3     CH3

H             H       CF3     CH3

H             H       CF3     C2H5

H             H       CF3     CHF2

F             H       CF3     CH3

F             H       CF3     C2H5

F             H       CF3     CHF2

F             CH3    CF3     CH3

F             Cl      CF3     CH3

R1        R2          R3   R4     R5

H    NHSO2CH＝CH2     H     CF3    CH3

F    NHSO2CH＝CH2     H     CF3    CH3

H    NHSO2CH＝CH2     H     CF3    C2H5

F    NHSO2CH＝CH2     H     CF3    C2H5

H    NHSO2CH＝CH2     Cl    CF3    CH3

F    NHSO2CH＝CH2     CH3  CF3    CHF2

H    NHSO2N(CH3)2    H     CF3    CH3

F    NHSO2N(CH3)2    H     CF3    CH3

H    NHSO2N(CH3)2    H     CF3    C2H5

F    NHSO2N(CH3)2    H     CF3    C2H5

H    NHSO2N(CH3)2    Cl    CF3    CH3

F    NHSO2N(CH3)2    CH3  CF3    CH3 其中：n＝正，i＝iso＝异，sec＝仲，

例如，若用3-氨基丁烯酸甲酯和4-氰基-2，5-二氟苯基异硫 基氰酸酯为反应初始物，则本发明中(a)法的反应过程可以下列反应式表 示：

例如，若用1-(3-氯-4-氰基-苯基)-3，6-二氢-6-氧 代-2-硫代-4-三氟甲基-1(2H)嘧啶和甲基溴为反应初始物，则本 发明中(b)法的反应过程可以下列反应式表示：

例如，若用1-(4-氰基-2，5-二氟-苯基)-3，6-二氢-3， 4-二甲基-2-氧代-6-硫代-1(2H)-嘧啶和乙磺酰胺为反应初始 物，则本发明中(c)法的反应过程可以下列反应式表示：

式(II)表示按本发明(a)法制备式(I)化合物时用作初始物的氨基链 烯酸(硫代)酯。

式(II)中Q1，R3和R4所优先代表或特别代表的基团，即上述为本发明 式(I)化合物的Q1，R3和R4所规定的那些优先代表或特别代表的基团。

R优先代表C1-C4烷基，特别是甲基或乙基。

式(II)的初始物是已知的和/或能通过已知方法(见J.Heterocycl. Chem.9(1972)，513-522)制备的。

式(III)表示本发明(a)法中用作初始物的氰基芳基异(硫代)氰酸 酯。

式(III)中Q2、R1和R2所优先代表或特别代表的基团，即上述为本 发明式(I)化合物的Q2，R1和R2所规定的那些优先代表或特别代表的基 团。

式(III)的初始物是已知的和/或能通过已知方法(见J.Qrg.Chem. 30(1965)，2465-2466；又见DE-P4327743和DE-P4335438)制 备的。

在有或没有反应辅助剂(如碳酸钙)存在以及有或没有稀释剂(如二氯 甲烷、甲苯、氯苯以及，合适的话，水)存在的情况下，温度为0℃-150 ℃之间，使以通式(VII)表示的相应的氰基芳基胺与碳酰氯或硫代碳酰氯 反应，可得到式(III)的氰基芳基异(硫代)氰酸酯(见制备实施例)

其中R1和R2的意义同上。

以本发明的(a)法制备式(I)所示的新化合物时最好用稀释剂。实际上 所有的惰性有机溶剂在这里都是适宜的稀释剂。这些稀释剂尤其包括脂 肪族和芳香族的非卤代烃或卤代烃(如：戊烷、己烷、庚烷、环己烷、石 油醚、汽油、粗汽油、苯、甲苯、三甲苯、二氯甲烷、氯乙烯、氯仿、 四氯甲烷、氯代苯和邻二氯苯)，醚如乙醚和丁醚，乙二醇二甲醚和二甘 醇二甲醚，四氢呋喃和二噁烷，酮如丙酮，甲基乙基酮，甲基异丙酮和 甲基异丁酮，酯如甲酸甲酯和乙酸乙酯，腈(如乙腈和丙腈)，酰胺(如二 甲基甲酰胺，二甲基乙酰胺)，N-甲基吡咯烷酮，二甲基亚砜，四亚甲 基砜和六甲基磷酰三胺。

进行本发明(a)法的反应时最好有反应辅助剂存在。这里适用的反应 辅助剂主要是酸的受体。所用的辅助剂有碱金属氢化物和碱土金属氢化 物，例如氢化锂、氢化钠、氢化钾和氢化钙；碱金属的氢氧化物和碱土 金属的氢氧化物，例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙；碱 金属的碳酸盐和碳酸氢盐以及碱土金属的碳酸盐或碳酸氢盐，例如碳酸 钠或碳酸氢钠，碳酸钾或碳酸氢钾以及碳酸钙；碱金属的乙酸盐，例如 乙酸钠和乙酸钾；碱金属的醇盐，例如甲醇钠、乙醇钠、丙醇钠、异丙 醇钠、丁醇钠、异丁醇钠和叔丁醇钠以及甲醇钾、乙醇钾、丙醇甲、异 丙醇钾、丁醇钾、异丁醇钾和叔丁醇钾；此外还有碱性的氮化合物，例 如三甲胺，三乙胺，三丙胺，三丁胺，二异丁胺，二环己胺，乙基二异 丙胺，乙基二环己胺，N，N-二甲基苄胺，N，N-二甲基苯胺，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，1，5-二氮杂二环[4，3， 0]-壬-5-烯(DBN)，1，8-二氮杂二环-[5，4，0]-十一碳-7- 烯(DBU)和1，4-二氮杂二环-[2，2，2]-辛烷(DABCO)。

本发明(a)法中的反应温度可在相对较宽的范围内变动。一般所用温 度范围为-120℃-+100℃，优选的温度范围为-70℃-+80℃。

本发明(a)法中的反应一般是正常大气压下进行，但也可提高或降低 压力。

在进行本发明(a)法中的反应时，在各种情况下所需的初始物一般是 用大约等摩尔的量。但也可在每种情况下所用的两种化合物中使一种的 量大于另一种。反应一般是在有反应助剂存在的情况下在适宜的稀释剂 中进行的，在各自要求的温度下将反应混合物搅拌数小时。本发明(a) 法中的反应在各种情况下都是按常规方法完成的(参见制备实施例)。

式(IA)和式(IB)代表了以本发明的(b)法制备式(I)化合物时用作初 始物的N-氰基芳基氮杂环化合物，此处的R3代表氢。

式(IA)和式(IB)中Q1，Q2，R1，R2，R3和R4所优先代表或特别代表的 基团，亦即上述本发明的式(I)化合物中的Q1，Q2，R1，R2，R3和R4所优先 代表或特别代表的基团。

式(IA)和式(IB)所表示的(b)法中所用的初始物是本发明的新化合 物，它们可通过本发明的(a)法来制备。

式(IV)和式(V)代表本发明(b)法中进而用作初始物的烷基化剂。

在式(IV)和式(V)中，R5所优先代表或特别代表的基团，亦即上述本 发明式(I)化合物中的R5所优先代表或特别代表的基团。

式(IV)和式(V)的初始物为已知的合成有机化合物。

本发明中(b)法最好是用稀释剂。本发明的(a)法中所提到的那些稀释 剂基本上对(b)法也是适用的。

可用于本发明(b)法的酸的受体全都是酸性粘合剂，常规情况下它们 对这些反应是有用的。优选的可用基团包括：碱金属的氢化物和碱土金 属的氢化物(例如氢化锂、氢化钠、氢化钾和氢化钙)，碱金属的氢氧化 物和碱土金属的氢氧化物(例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化 钙)；碱金属的碳酸盐和碳酸氢盐以及碱土金属的碳酸盐和碳酸氢盐(例 如碳酸钠或碳酸氢钠、碳酸钾或碳酸氢钾以及碳酸钙)；碱金属的乙酸 盐，如乙酸钠和乙酸钾；碱金属的醇盐，如甲醇钠、乙醇钠、丙醇钠、 异丙醇钠、丁醇钠、异丁醇钠、叔丁醇钠、甲醇钾、乙醇钾、丙醇钾、 异丙醇钾、丁醇钾、异丁醇钾和叔丁醇钾；此外还包括碱性的氮化合物， 如三甲胺、三乙胺、三丙胺、三丁胺、二异丁胺、二环己胺、乙基二异 丙胺、乙基二环己胺、N，N-二甲基苄胺、N，N-二甲基苯胺、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、1，5-二氮杂二环[4，3， 0]-壬-5-烯(DBN)，1，8-二氮杂二环[5，4，0]十一碳-7-烯(DBU) 和1，4-二氮杂二环-[2，2，2]-辛烷(DABCO)。

本发明(b)法中的反应温度可在较宽的范围内变动。一般地，用0℃ -120℃的温度，优选的温度范围为10℃-100℃。

本发明(b)法中的反应一般是在1个大气压下进行，但也可在较高和 较低的压力下进行。

在进行本发明(b)法中的反应时，每次所需的初始物一般是用大约等 摩尔的量。但每次也可使所用的两种化合物中一种的量大于另一种。反 应一般是在有一种酸性受体存在的情况下在适宜的稀释剂中进行的，在 各自要求的温度下将反应混合物搅拌数小时。本发明(b)法中的反应在各 种情况下都是按常规方法完成的(参见制备实施例)。

以R2代表卤素为条件，式(I)则代表了用本发明的(c)法制备式(I)化 合物时用作初始物的N-氰基芳基氮杂环化合物。

式(I)中，Q1，Q2，R1，R3，R4和Z所优先代表或特别代表的基团，亦 即上述本发明的式(I)化合物中的Q1，Q2，R1，R3，R4和Z所优先代表或特 别代表的基团。

(c)法中式(I)的初始物是本发明的新化合物，它们可用本发明的(a) 法和(b)法来制备。

式(VI)一般地代表了本发明的(c)法中进而用作初始物的胺类。

式(VI)中，A和A1所优先代表或特别代表的基团，亦即上述本发明 式(I)化合物中的A和A1所优先代表或特别代表的基团。

式(VI)的初始物为已知的合成有机化合物。

本发明中(c)法的反应最好是用稀释剂。本发明的(a)法中所提到的那 些稀释剂基本上对(c)法也是适用的。

本发明(c)法中的反应是在有或没有一种酸性受体存在的情况下进行 的。在叙述本发明的(b)法时所提到的那些酸性受体在这里也是适用的。

本发明(c)法中的反应温度可在较宽的范围内变动。一般用0℃-200 ℃，优选的温度范围为20℃-180℃。

本发明中(c)法的反应一般是在正常大气压下进行，但也可在较高和 较低的压力下进行。

在进行本发明(c)法中的反应时，每次所需的初始物一般是用大约等 摩尔的量。但每次也可使所用的两种化合物中一种的量大于另一种。反 应一般是在有一种酸性受体存在的情况下在适宜的稀释剂中进行的，在 各自要求的温度下将反应混合物搅拌数小时。本发明(c)法中的反应在各 种情况下都是按常规方法完成的(参见制备实施例)。

本发明的活性化合物可用作脱叶剂，干燥剂，杀草剂，特别是用作除 杂草剂。从最广泛的意义上说，所谓杂草，即指所有那些生长在人们不 希望它们生长的地方的植物。本发明中的化合物是起完全的除草作用抑 或选择性的除草作用，则基本上取决于使用比率。

例如，本发明的活性化合物可被用在下述植物上：

下列各属的双子叶杂草：欧白芥属，独行菜属，拉拉藤属，繁缕属， 母菊属，春黄菊属，牛膝菊属，藜属，荨麻属，千里光属，蓖属，马齿 苋属，苍耳属，旋花属，番薯属，蓼属，田菁属，豚草属，蓟属，飞廉 属，苦苣菜属，茄属，蔊菜属，节节菜属，母草属，野芝麻属，婆婆纳 属，苘麻属，刺酸模属，曼陀罗属，堇菜属，鼬瓣花属，罂粟属，矢车 菊属，车轴草属，毛莨属和蒲公英属。

下列各属的双子叶栽培植物：草棉属，大豆属，甜菜属，胡萝卜属， 菜豆属，豌豆属，茄属，亚麻属，番薯属，蚕豆属，烟草属，番茄属， 落花生属，芸苔属，莴苣属，甜瓜属和南瓜属。

下列各属的单子叶杂草：稗属，狗尾草属，黍属，马磨属，梯牧草属， 早熟禾属，羊茅属，属，臂形草属，毒麦属，雀麦属，燕麦属，莎草 属，高梁属，冰草属，狗牙根属，雨久花属，瓢拂草属，慈姑属，荸荠 属，藨草属，雀稗属，鸭嘴草属，密穗桔梗属，龙爪茅属，剪股颖属， 看麦粮属和野猪草属。

下列各属的单子叶栽培植物：稻属，玉蜀黍属，小麦属，大麦属，燕 麦属，黑麦属，高梁属，黍属，甘蔗属，凤梨属，天门冬属和葱属。

但是，本发明的活性化合物并不仅限于用在这些属的植物上，它们也 以相同的方式用在其它植物上。

这些化合物(决定于其使用浓度)适用于全面的除草，例如在工厂区和 铁路线上的除草，在有树或没有树的小路和地面的除草。同样，这些化 合物也可用于下列场所的除草，例如树林，观赏林地，果园，葡萄园， 桔园，坚果园，香蕉园，咖啡园，茶园，橡胶园，油棕榈园，可可园， 浆果园和蛇麻草田，观赏草坪，运动场，牧地以及年度作物耕地的选择 性除草。

本发明的化合物特别适用于单子叶作物和双子叶作物耕地中、在杂草 出现前和出现后有选择性地清除其中的单子叶和双子叶杂草。

这些活性化合物也适用于消灭有害动物，尤其是节肢动物和线虫，特 别是那些发生在农业上、林业上、储物防护以及卫生方面的有害昆虫和 蜘蛛纲的动物。它们可防治敏感的种类和有抗性的种类，并对所有各虫 期或某些虫期有效。上面提到的害虫包括：

等足目的潮虫、鼠妇和粗潮虫。

倍足目的具斑马陆。

唇足目的蜈蚣和蚰蜒。

综合目的庭园么蚰。

缨尾目的衣鱼。

弹尾目的武装棘跳虫。

直翅目的东方蠊，美洲大蠊，马德拉蠊，德国小蠊，家蟋蟀，蝼 蛄属的种类，非洲飞蝗，异黑蝗和沙漠蝗。

革翅目的欧洲球螋。

等翅目散白蚁属的种类。

虱目的葡萄根瘤蚜，瘿绵蚜属种类，体虱，血虱属种类和毛虱属种类。

食毛目中羽虱属和畜虱属的种类。

缨翅目的温室纹蓟马和烟蓟马。

异翅目的扁盲蝽属种类，介中棉红蝽，方背皮蝽，温带臭虫，长红猎 蝽和雉猎蝽属的种类。

同翅目的甘蓝粉虱，木薯粉虱，温室粉虱，棉蚜，甘蓝蚜，茶藨隐瘤 蚜，甜菜蚜，波密一条角蚜，苹果绵蚜，梅大尾蚜，麦长管蚜，瘤蚜属 的种类，忽布疣蚜，禾谷缢管蚜，小绿叶蝉属种类，二叶叶蝉，黑尾叶 蝉，水木坚蚧，乌盔蚧，灰飞虱，褐飞虱，红肾圆盾蚧，常春藤圆盾蚧， 粉蚧属和木虱属的种类。

鳞翅目的棉红铃虫，松尺蠖，苹细蛾，苹果巢蛾，菜蛾，黄褐天幕毛 虫，黄毒蛾，毒蛾属种类，棉潜蛾，桔潜蛾，地老虎属种类，切根虫属 种类，夜蛾属种类，埃及金刚钻，实夜蛾属种类，甜菜夜蛾，甘蓝夜蛾， 松夜蛾，斜纹夜蛾，灰翅夜蛾属种类，粉纹夜蛾，菜粉蝶属，禾草螟属 种类，玉米螟，地中海粉斑螟，大蜡螟，幕谷蛾，袋谷蛾，褐织蛾，亚 麻黄卷蛾，网织烟卷蛾，枞色卷蛾，葡萄果蠹蛾，茶长卷蛾和栎绿卷蛾。

鞘翅目的家具窃蠹，谷蠹，大豆象，覆雉胸豆象，北美家天牛，桤木 萤叶甲，马铃薯叶甲，辣根猿叶甲，叶甲属种类，油菜金头跳甲，墨西 哥大豆飘虫，隐食甲属种类，锯谷盗，花象属的种类，谷象属的种类， 黑葡萄耳象，香蕉根颈象，白菜籽龟象，紫苜蓿叶象，皮蠹属种类，斑 皮蠹属种类，圆皮蠹属种类，毛皮蠹属种类，粉蠹属种类，油菜花露尾 甲，蛛甲属种类，黄蛛甲，裸蛛甲，拟谷盗属的种类，黄粉虫，叩头虫 属种类，宽胸叩头虫属的种类，西方五月鳃角金龟，马铃薯鳃角金龟和 褐新西兰肋翅鳃角金龟。

膜翅目的锯角叶蜂属的种类，樱叶蜂属种类，蚁属的种类，小黄家蚁 和胡蜂属种类。

双翅目的伊蚊属种类，按蚊属种类，库蚊属种类，黑尾果蝇，家蝇属 种类，厕蝇属种类，红头丽蝇，绿蝇属种类，金蝇属种类，疽蝇属种类， 胃蝇属的种类，厩螫蝇属种类，狂蝇属种类，皮蝇属种类，虻属种类， 园艺毛蚊，瑞典麦杆蝇，种蝇属种类，甜菜泉蝇，地中海蜡实蝇，橄榄 实蝇和欧洲大蚊。

蚤目的印鼠客蚤和角叶蚤属的种类。

蛛形目黑蠍和毒沼虾。

蜱螨目的粗脚粉螨，锐缘蜱属种类，纯缘蜱属种类，鸡皮刺螨，硬瘿 螨，梏皱叶刺瘿螨，牛蜱属种类，扇头蜱种类，花蜱属种类，璃眼蜱属 种类，硬蜱属种类，瘙螨属种类，痒螨属种类，疥螨属种类，跗线螨属 种类，苜蓿苔螨，金爪螨属种类和叶螨属的种类。

植物病原线虫包括短体线虫属种类，相似穿孔线虫，起绒草茎线虫， 半穿刺线虫，异皮线虫属种类，根结线虫属种类，滑刃线虫属种类，长 针线虫属种类，剑线虫属种类和毛刺线虫属的种类。

这些活性化合物可被加工成常规剂型，如溶液，乳剂，可湿性粉剂， 悬浮剂，粗粉，细粉，膏剂，可溶性粉剂，颗粒剂，悬浮剂，用该活性 化合物浸泡的天然织物和合成织物以及用聚合物制成的微胶囊。

这些剂型是用已知的方法制备的，例如在使用或不使用表面活性剂 (乳化剂和/或分散剂和/或发泡剂)的情况下将这些活性化合物与增量剂 (液态溶剂和/或固态的载体)混合起来。

在用水作增量剂的情况下，例如有机溶剂也可用作加溶剂。基本的适 用液体溶剂有：芳香剂，例如二甲苯，甲苯或烷基萘，氯代芳族化合物 和氯代脂族烃，例如氯代苯，氯乙烯或二氯甲烷；脂族烃，例如环己烷 或链烷烃(矿物油馏分，矿物油和植物油)；醇类，例如丁醇或乙二醇及 其醚和酯；酮类，例如丙酮，甲基乙基酮，甲基异丁酮或环己酮；强极 性溶剂，例如二甲基亚甲胺和二甲基亚砜，以及水。

适用的固态载体有；例如铵盐和天然石粉，例如高岭土，粘土，滑石 粉，白垩，石英，活性白土，蒙脱土或硅藻土和合成的石粉，例如高分 散硅，氧化铝和硅酸盐；适用作颗粒剂的固态载体有：碾碎和磨细的天 然石料，例如方解石，大理石，浮石，海泡石，白云石以及用无机或 有机的粉末制成的颗粒，和有机物(例如锯末，花生壳，玉米芯和烟草杆) 的碎屑；乳化剂和/或发泡剂有：非离子乳化剂和阴离子乳化剂，例如聚 氧乙烯脂肪酸酯，聚氧乙稀脂肪醇醚，如烷芳基聚乙二醇醚，烷基亚磺 酸酯，烷基磺酸酯，芳基亚磺酸酯和蛋白质的水解物；适用的分散剂有 木素亚硫酸盐溶液和甲基纤维素。

在这些剂型中可以使用粘合剂(例如羧甲基纤维素)，天然的和合成的 粉状、颗粒状或胶乳状聚合物(例如阿拉伯树脂，聚乙烯醇，聚乙酸乙烯 酯)以及天然的磷脂(例如脑磷脂和卵磷脂)和合成的磷脂。其它的添加剂 可以是矿物油和植物油。

可以使用着色剂，例如无机色素(如氧化铁，钛白，普鲁士兰)和有机 着色剂(如茜素，偶氮染料和金属酞菁染料)以及微量营养素(如铁盐、锰 盐、硼盐、铜盐、钴盐、钼盐和锌盐)。

这些配方中一般含有0.1％-95％(W/W)的活性化合物，优选的含量 是0.5％-90％。

本发明的活性化合物本身就可以使用，也可与已知的除草剂混合起来 用于除灭杂草，也可制成即开即用的剂型或罐装的混合制剂。

已知适用于与本发明的活性化合物混配的除草剂有：N-酰苯胺类 (如二氟非草康(doflufenican)和敌稗)；芳基羧酸类(如二氯吡啶甲酸、 甲氧二氯苯酸和毒草定)；芳氧基链烷酸类(如2，4-滴，2，4-滴丁 酸，2，4-滴丙酸，氟羟基丙酮酸(fluroxypyr)，2甲4氯，2甲4氯 丙酸钾和乙氯草定)；芳氧基-苯氧基-链烷酸酯(如甲基二氯伏草丹 (diclofop-methyl)，乙基涕丙酯(fenoxaprop-ethyl)，丁基氟草丹 (fluazifop-butyl)，甲基金草丹(holoxyfop-methyl)和乙基醌草丹 (quizalofop-ethyl))；连氮杂苯类(如氯哒酮和氟哒酮)；氨基甲酸酯 类(如氯苯胺灵，甜草灵，甲二威灵和苯胺灵)；乙酰氯苯胺类(如杂草锁， 乙基乙草安，丁草锁，甲吖草安，甲氧草安，先利草安和毒草安)；二硝 基苯胺类(如磺胺乐灵，偏二甲灵和氟乐灵)；二苯醚类(如acifluorfen， 甲酯除草醚，氟甘醚，福灭杀醚，卤杀醚，乳草醚和氧氟草醚)；脲类(如 绿麦隆，敌草隆，伏草隆，异丙隆，利谷隆和噻唑隆)；羟胺类(如阿洛 氧草敌，克利乙氧草敌，环氧敌，丝乙氧草敌和三烷氧草敌)；咪唑啉酮 类(如imazethapyr，imazamethabenz，imazapyr和imazaquin)；腈类 (如溴草腈，敌草腈和碘草腈)；羟乙酰胺类(如mefenacet)；磺酰脲类(如 氨基磺酰脲，甲基苯磺酰脲，乙基氯化磺酰脲，氯磺酰脲，华磺酰脲， 甲基介磺酰脲，烟磺酰脲，本初磺酰脲，乙基吡唑磺酰脲，甲基三酚磺 酰胺，三磺酰脲和甲基三苯脲)；巯氨基甲酸酯类(如异丁草丹，环己丹， 二氯烯丹，丙草丹)，esprocarb，环草丹，甲硫磺氨基甲酸酯，硫苯氨 基甲酸酯和三氯烯丹)；三嗪类(如阿特拉津，丙腈津，西玛津，西玛净， 特丁草净和特丁津)；三嗪农类(如双三嗪农，甲苯嗪和赛克嗪)；其它类 (如氨三唑，benfuresate，苯达松，别甲啉，clomazone，clopyralid， 草吡唑，dithiopyr，甜菜呋，氯氟酮，glufosinate，glyphosate， isoxaben，pyridate，quinclorac，quinmerae，sulphosate和 fridiphane)。

本发明的活性化合物也可与其它已知的活性化合物(例如杀真菌剂、 杀虫剂、杀螨剂、杀线虫剂、驱乌剂、植物营养素和土壤结构改良剂) 混配使用。

本发明的化合物可以本身的形式使用，可以其配方的形式使用，也可 通过进一步稀释制成实用形式，如即开即用溶液，悬浮液，乳液粉，膏 和颗粒。这些化合物是用常规方法使用的，如泼撒、喷淋、喷雾、撒播 等。

本发明的活性化合物可以在植物出土之前或出土之后使用，以可在播 种前将此化合物施用到土壤中。

该活性化合物的用量变动范围较大，基本上取决于希望它起什么样的 作用。一般地，其用量为每公顷土地施用10g-10kg，优先考虑的用 量为50g-5kg/公顷。

本发明的活性化合物的制备和使用如下述实施例所示。 制备实施例 实施例1 (方法(a))

在30ml二甲基甲酰胺和2ml甲苯中加入1.8g(10mmol)3-氨基 -4，4，4-三氟-丁烯酸乙酯，在0℃-5℃的温度下加入0.4g(10 mmol)氢化钠(强度80％)。在此特定温度下将混合物搅拌30分钟。冷却 到-70℃后，加入1.0g(5mmol)4-氰基-2，5-二氟-苯基异硫氰 酸酯，在-70℃下将反应混合物搅拌2小时，然后在20℃下继续搅拌 15小时，最后在50℃下再搅拌4小时。然后在混合物中加入2ml乙酸， 用水稀释成原量的大约2倍，用乙酸乙酯提取。将有机相浓集起来，用 柱层析法将残渣样的粗产物进行提纯(硅胶；开始用废弃的二氯甲烷洗， 用乙酸乙酯洗出主要部分)。将洗出的主要部分浓缩，用乙醚浸提法将残 渣(产物)结晶出来。

获得0.3g(理论收率9％)1-(4-氰基-2，5-二氟-苯基)-3， 6-二氢-2-硫代-6-氧代-4-三氟甲基-1(2H)-嘧啶，熔点187 ℃。 实施例2 (方法(b))

在10ml丙酮中加入0.9g(2.7mmol)1-(4-氰基-2，5-二氟 -苯基)-3，6-二氢-2-硫代-6-氧代-4-三氟甲基-1(2H) -嘧啶和0.37g(2.7mmol)碳酸钾，在-10℃下再加入0.38g(2.7mmol) 甲基碘。将反应混合物在20℃下搅拌15小时，然后过滤。用喷水吸气 泵将溶剂小心地从滤液中蒸馏出来。

得到1.0g(约为理论收率的100％)油状的1-(4-氰基-2，5- 二氟-苯基)-1，6-二氢-2-甲硫基-6-氧代-4-三氟甲基- 嘧啶。

1H-NMR(二甲基亚砜D6，δ)：7.02ppm。 实施例3 (方法(a))

在100ml二甲基甲酰胺和10ml甲苯的混合物中加入9.9g(50mmol) 3-甲氨基-4，4，4-三氟丁烯酸乙酯，在-15℃下再加入2.0g(50 mmol)氢化钠(浓度60％)。在此特定温度下将反应混合物搅拌15分钟， 然后加入5.0g(25mmol)4-氰基-2，5-二氟苯基异硫氰酸酯，在20 ℃下将反应混合物搅拌15小时。

然后加入6ml乙酸，用水将反应混合物稀释到约为原量的两倍，再 用乙酸乙酯提取。将有机相浓集，用柱层析法将残渣状的粗产物提纯(硅 胶，二氯甲烷)。将洗脱的主要部分浓集起来，用二异丙基醚通过浸提的 方法从浓集的残渣中将产物结晶出来。

得到1.1g(理论收率的13％)熔点为191℃的1-(4-氰基-2，5 -二氟-苯基)-3，6-二氢-2-硫代-6-氧代-3-甲基-4- 三氟甲基-1(2H)-嘧啶。 实施例4 (方法(a))

在50ml二甲基甲酰胺和5ml甲苯的混合物中加入2.1g(10.5mmol) 3-甲氨基-4，4，4-三氟-丁烯酸乙酯，在-70℃下加入0.4g(10.9 mmol)氢化钠(浓度60％)。在此特定温度下将混合物搅拌15分钟，然后 再加入2.0g(7mmol)4-氰基-2-氟-5-乙基磺酰基-氨基-苯基 异硫氰酸酯。然后将反应混合物在-60℃下搅拌4小时，尔后再加入6ml 乙酸，并用水将混合物稀释到原量的大约两倍。将有机相分离出来并浓 集。用二异丙基醚通过浸提法从浓集的残渣中将产物结晶出来。

得到0.7g(理论收率25％)熔点为150℃的1-(4-氰基-2-氟 -5-乙基磺酰氨基-苯基)-3，6-二氢-2-硫代-6-氧代-3 -甲基-4-三氟甲基-1(2H)-嘧啶。

按照对本发明的制备方法所做的一般性叙述，采用与实施例1-4 相似的步骤，也可制备下面表2所列之式(I)-或式(IA)或(IB)-所示的 化合物，例如

表2：式(I)化合物示例   例号  通式  Q1  Q2  R1     R2             R3 R4     R5    熔点(℃)

5    IA    O    S    F    -NHSO2C3H7     H   CF3    CH3    162

6    IA    O    S    F    -NHSO2CH3       H   CF3    H

7    IB    O    S    F    -NHSO2CH3       H   CF3    CH3

8    IA    O    S    F    -NHSO2CH3       H   CF3    CH3    214

9    IB    O    S    F    -N(CH3)SO2CH3  H   CF3    CH3

10   IB    O    S    F    -NHSO2C2H5     H   CF3    CH3

11   IB    O    S    F    -NHSO2CH3       H   CF3    C2H5

12   IB    O    S    F    -NHSO2C2H5     H   CF3    C3H7

13   IB    O    S    F    -NHSO2C3H7     H   CF3    CHF2

14   IB    O    S    F    -NHSO2CH(CH3)2 H   CF3    CH3   例号  通式   Q1  Q2  R1        R2          R3  R4    R5    熔点(℃)

15    IA    O    S    F    -NHSO2CH(CH3)2  H   CF3    CH3    114

16    IA    O    S    F    -NHSO2CH3        H   CF3    C2H5

17    IA    O    S    F    -NHSO2CH3        H   CF3    C3H7

18    IA    O    S    F    -NHSO2C2H5      H   CF3    CHF2

19    IA    O    S    F    -N(C2H5)SO2CH3 H   CF3    CH3

20    IA    O    S    F        H   CF3    CH3    208

21    IA    O    S    F    -NHSO2C4H9      H   CF3    CH3    161

22    IA    O    S    F  H   CF3    CH3

23    IA    O    S    F    -NHSO2CH3        H   CHF2   CH3

24    IA    O    S    F    -NHSO2CH3        H   CF2Cl  CH3

25    IA    O    S    F    -NHSO2C2H5      H   CF2Cl  CH3

26    IA    O    S    F    -NHSO2C2H5      H   CF3    C2H5

27    IA    O    S    H    -NHSO2CH3        H   CF3    CH3

28    IA    O    S    H    -NHSO2C2H5      H   CF3    CH3

29    IA    O    S    Cl   -NHSO2CH3        H   CF3   

30    IA    O    S    Cl   -NHSO2C3H7      H   CF3    CH3    例号  通式  Q1  Q2  R1   R2               R3 R4    R5    熔点(℃)

31    IA    O    S    F    -NHSO2C2H5      H  CF3   C2H5   177

32    IA    O    S    F        H  CF3   CH3     122

33    IA    O    S    F    -N(CH3)SO2C2H5 H  CF3   CH3     68

34    IA    O    S    F    -N(CH3)SO2CH3   H  CF3   CH3

35    IA    O    S    F    -NHSO2CH3        H  CHF2  CH3     220

表2中例32的化合物可按下列步骤制备：

将2.0g(4.4mmol)1-(4-氰基-2-氟-5-乙基磺酰氨基-苯 基)-3，6-二氢-2-硫代-6-氧代-3-甲基-4-三氟甲基- 1(2H)-嘧啶、0.64g(5.6mmol)甲磺酰氯、0.8g(8mmol)三乙胺和50 ml乙腈的混合物在20℃下搅拌15小时，然后再喷水真空泵使此混合物 浓集。在残留物中加水搅拌，用过滤法将生成的结晶状产物分离出来。

得到2.3g(理论收率的100％)熔点为122℃的1-(4-氰基-2 -氟-5-(N-乙基磺酰基-N-甲基磺酰基-氨基)-苯基)-3，6 -二氢-2-硫代-6-氧代-3-甲基-4-三氟甲基-1(2H)-嘧 啶。

例如，表2中例33的化合物可按下列步骤制备：

将1.5g(3.4mmol)1-(4-氰基-2-氟-5-乙基磺酰氨基-苯 基)-3，6-二氢-2-硫代-6-氧代-3-甲基-4-三氟甲基- 1(2H)-嘧啶、0.5g(3.8mmol)碳酸钾和30ml乙腈的混合物在20℃下 搅拌30分钟，然后加入0.5g(3.8mmol)硫酸二甲酯。然后在20℃下将 反应混合物回流5小时，再搅拌60小时。用喷水真空泵将此混合物浓集， 将残留物加水搅拌，将所生成的结晶状产物过滤分离出来。

得到1.2g(理论收率的78％)熔点为68℃的1-(4-氰基-2-氟 -5-(N-乙基磺酰基-N-甲基-氨基)-苯基)-3，6-二氢-2 -硫代-6-氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶。 式(III)的初始物 例(III-1)

将10.0g(65mmol)4-氰基-2，5-二氟-苯胺加入到100ml甲 苯中，将此混合物加热到80-90℃，慢慢加入8.2g(71mmol)二氯硫 化碳。将此反应混合物回流约40小时。用减压法将溶剂小心地蒸馏掉以 后，即得赭石色的产物4-氰基-2，5-二氟-苯基异硫氰酸酯。

1H-NMR(CDCl3，δ)：7.03ppm。 应用实施例 例A 出苗前试验

溶剂：5份(重量)丙酮

乳化剂：1份(重量)烷芳基聚乙二醇醚

为制备便于使用的活性化合物制剂，将1份(重量)活性化合物与特定 量的溶剂混合，再加入特定量的乳化剂，用水将此制剂稀释到所希望的 浓度。

将试验植物的种子播撒到标准化的土壤中，24小时后浇水，同时浇 洒活性化合物制剂。在此期间单位面积的浇水量要保持恒定。制剂中活 性化合物的浓度并不重要，只有每单位面积中活性化合物的施用率才是 关键性的。三周后，通过与未经活性化合物制剂处理的对照植株的发育 情况进行比较来评价试验植株的受损害程度(以％表示)：

0％表示无影响(如未处理的对照)

100％表示全部破坏

在这项试验中，由制备实施例3、4、7和8所示的那些化合物与栽 培植物(如小麦)有很好的相容性(0％)，而对杂草，在用量为60g/公顷 时，则表现很强的破坏作用，如对苘麻(80-100％)，对苋(70-100 ％)，对脲草(95-100％)，对牛膝菊(90-100％)，对马齿苋(90- 100％)，对茄科杂草(80-100％)。 例B 出苗后试验

溶剂：5份(重量)丙酮

乳化剂：1份(重量)烷芳基聚乙二醇醚

为制备便于使用的活性化合物制剂，将1份(重量)活性化合物与特定 量的溶剂混合，再加入特定量的乳化剂，用水将此制剂稀释到所希望的 浓度。

对已经长到5-15cm高的试验植物喷洒活性化合物制剂，每次在单 位面积内活性化合物的量按所要求的施用。三周后，通过与未经活性化 合物制剂处理的对照植株的发育情况进行比较来评价试验植株的受损害 程度(以％表示)。

评价标准：

0％表示无影响(如未处理的对照)

100％表示全部破坏

在这项试验中，由制备实施例3、4和8所示的那些化合物与栽培植 物(如小麦)有很好的相容性(5％)，而对杂草，在用量为30g/公顷时， 则毫无例外地表现出很强的破坏作用，如对苘麻(100％)，藜(100％)， 番薯(100％)，茄属杂草(100％)，对婆婆纳属杂草(100％)。 例C 猿叶虫属幼虫试验

溶剂：7份(重量)二甲基甲酰胺

乳化剂：1份(重量)烷芳基聚乙二醇醚

为制备合适的活性化合物制剂，将1重量份活性化合物与特定量的溶 剂和特定量的乳化剂混合，并将浓缩物用水稀释至所需浓度。

将活性化合物制剂配成所要求的浓度，将菜苔的叶子在配好的制剂内 浸蘸一下，在叶子仍显湿润的情况下将辣根猿叶虫的幼虫放到叶子上 去。

经过一段所要求的时间后，检查试虫受损情况(以％表示)。100％表 示所有受试的幼虫都已死亡，0％则表示没有受试幼虫死亡。

在这项试验中，制备实施例3所示的活性化合物，在浓度为0.1％时， 3天后对受试幼虫的破坏率为100％。