CN100386313C - 新的除草剂 - Google Patents

新的除草剂 Download PDF

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CN100386313C
CN100386313C CNB998148857A CN99814885A CN100386313C CN 100386313 C CN100386313 C CN 100386313C CN B998148857 A CNB998148857 A CN B998148857A CN 99814885 A CN99814885 A CN 99814885A CN 100386313 C CN100386313 C CN 100386313C
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CN1331675A (zh
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J·谢策尔
A·德梅斯马克
S-F·李
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Abstract

式I化合物及其农业上可接受的盐、异构体和对映体，以及所述化合物的农业上可接受的盐/N-氧化物/异构体/对映体，它们特别适于用作除草剂，其中各取代基的定义如权利要求1中所述。

Description

新的除草剂
本发明涉及新的除草活性苯甲酰基衍生物，它们的制备方法，含有所述化合物的组合物及其它们控制杂草的用途，特别是在栽培植物的农作物中控制杂草的用途及抑制植物生长的用途。
除草活性的苯甲酰基衍生物例如在US-A-5094685中被描述，目前发现了有除草和抑制生长性质的新的苯甲酰基衍生物。
因此本发明的目的是提供式I化合物：
Figure C9981488500041
其中
X是L1-Y1-R4，L2-Y2-L3-Y3-R5或L4-Y4-L5-Y5-L6-Y6-R6；
L1，L2，L3，L4，L5，L6彼此独立地是C1-C6亚烷基，它们可以被C1-C4烷基，卤素，C1-C4烷氧基，C2-C6链烯基或C2-C6炔基取代；或者是C3-C6亚链烯基，它们可以被C1-C4烷基，卤素，C1-C4烷氧基，C2-C6链烯基或C2-C6炔基取代；或者是C3-C6亚炔基，它们可以被C1-C4烷基，卤素，C1-C4烷氧基，C2-C6链烯基或C2-C6炔基取代；
Y1，Y3，Y6彼此独立地是氧，硫，SO，SO2，NR7，OC(O)，NR8SO2或OSO2；
Y2，Y4，Y5彼此独立地是氧，硫，SO，SO2，NR9，OC(O)，NR10SO2；
R7，R8，R9和R10彼此独立地是氢或C1-C6烷基；
R1和R2彼此独立地是卤素，氰基，硝基，氨基，C1-C6烷基，C1-C6烷氧基，C1-C4-烷氧基-C1-C4烷基，C1-C6卤代烷基，C2-C6链烯基，C2-C6炔基，C1-C6烷氧基羰基，C1-C6烷基羰基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C6二烷基氨基磺酰基，C1-C6烷基氨基磺酰基，C1-C4烷基磺酰基氨基，C1-C6卤代烷氧基，OSO2-C1-C4烷基，C1-C6卤代烷硫基，C1-C6卤代烷基亚磺酰基，C1-C6卤代烷基磺酰基，苯硫基，苯基亚磺酰基或苯基磺酰基；
R3是氢，C1-C4烷基或卤素；
R4，R5和R6彼此独立地是氢；C1-C6烷基；它们可以被基团A1取代；C3-C7环烷基，它们可以被基团A2取代；C3-C7环烷基，它们可以含有1或2个氧原子、硫或NR11；C2-C6链烯基，它们可以被基团A3取代；C3-C6炔基，它们可以被基团A4取代；C3-C7环烷基-C1-C4烷基，其中的环烷基可以含有1或2个氧原子、硫或NR12；苄基或苯基，它们又可以被卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，氰基，硝基，C1-C4卤代烷氧基，C1-C4烷硫基，C1-C4烷基亚磺酰基，C1-C4烷基磺酰基，C1-C4二烷基氨基，C1-C4烷基羰基，C1-C4二烷基氨基磺酰基或NR13-CO-R14取代；
R11和R12彼此独立地是氢或C1-C4烷基；
R13和R14彼此独立地是氢或C1-C4烷基；
A1，A2，A3，A4彼此独立地是羟基，甲酰基，COOH，C1-C6烷氧基，C1-C4烷硫基，C1-C4烷基亚磺酰基，C1-C4烷基磺酰基，OSO2-C1-C4烷基，C1-C6烷基氨基，C1-C6二烷基氨基，C1-C6烷基氨基羰基，C1-C6二烷基氨基羰基，硝基，卤素，氰基，C1-C4烷氧基卤素，C1-C4烷基羰基，C1-C4烷氧基羰基或苯基，其中苯基又可以被卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，氰基，硝基，C1-C4卤代烷氧基，C1-C4烷硫基，C1-C4烷基亚磺酰基，C1-C4烷基磺酰基，C1-C4烷基羰基，C1-C4二烷基氨基磺酰基或NR15-CO-R16取代；
R15和R16彼此独立地是氢或C1-C4烷基；
Q是基团Q1：
Figure C9981488500051
其中
R39是羟基，卤素，C1-C6烷氧基，C1-C6烷基羰氧基，C1-C6烷氧基羰氧基，C1-C6二烷基氨基，COOH，C1-C6链烯硫基，C1-C6链烯基亚磺酰基，C1-C6链烯基磺酰基，OSO2-C1-C6烷基，苯甲酰氧基或OSO2-苯基，其中苯基和苯甲酰基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，卤素，硝基，COOH或氰基取代；V是C1-C4亚烷基，氧，硫，SO或SO2；
R17，R18，R19，R20，R21和R22彼此独立地是氢，C1-C6烷基，C1-C6烷氧羰基，C2-C6链烯基，C2-C6炔基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基氨基磺酰基，C1-C4卤代烷基，C1-C4烷基氨基，C1-C4二烷基氨基，C1-C6烷氧基，氰基，硝基，卤素或苯基；
q是1或2；
或者Q是基团Q2：
其中
R23是羟基，卤素，C1-C6烷氧基，C1-C6烷基羰氧基，C1-C6烷氧基羰氧基，C1-C6二烷基氨基，COOH，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷氧羰基-C1-C4烷硫基，C1-C4烷氧羰基-C1-C4烷基亚磺酰基，C1-C4烷氧羰基-C1-C4烷基磺酰基，C1-C6链烯硫基，C1-C6链烯基亚磺酰基，C1-C6链烯基磺酰基，OSO2-C1-C6烷基，苯甲酰氧基，苯硫基，苯基亚磺酰基，苯基磺酰基或OSO2-苯基，其中苯基和苯甲酰基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，卤素，硝基，COOH或氰基取代；R24和R25彼此独立地是氢，羟基，C1-C6烷基，C1-C4烷氧基-C1-C4烷基，C2-C6链烯基，C2-C6炔基，C1-C6烷氧羰基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基氨基磺酰基，C1-C4卤代烷基，C1-C6烷基氨基，C1-C6二烷基氨基，C1-C6烷氧基，氰基，硝基，卤素或苯基，苯基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，氨基，C1-C4烷基氨基，C1-C4二烷基氨基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基-S(O)2O，C1-C4卤代烷硫基，C1-C4卤代烷基亚磺酰基，C1-C4卤代烷基磺酰基，C1-C4卤代烷基-S(O)2O，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，卤素，硝基，COOH或氰基取代；或者R24和R25一起形成C2-C6亚烷基桥；R26是氢，C1-C4烷基，C1-C4烷氧羰基或苯基，苯基又可以被C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基，C1-C6卤代烷氧基，C1-C6烷基羰基，C1-C6烷氧基羰基，氨基，C1-C4烷基氨基，C1-C4二烷基氨基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4-烷基-S(O)2O，C1-C4卤代烷硫基，C1-C4卤代烷基亚磺酰基，C1-C4卤代烷基磺酰基，C1-C4卤代烷基-S(O)2O，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，卤素，硝基，COOH或氰基取代；
或者Q是基团Q3：
其中
R27是羟基，卤素，C1-C6烷氧基，C1-C6烷基羰氧基，C1-C6烷氧基羰氧基，C1-C6二烷基氨基，COOH，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷氧羰基-C1-C4烷硫基，C1-C4烷氧羰基-C1-C4烷基亚磺酰基，C1-C4烷氧羰基-C1-C4烷基磺酰基，C1-C6链烯硫基，C1-C6链烯基亚磺酰基，C1-C6链烯基磺酰基，OSO2-C1-C6烷基，苯甲酰氧基，苯硫基，苯基亚磺酰基，苯基磺酰基或OSO2-苯基，其中苯基和苯甲酰基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，卤素，硝基，COOH或氰基取代；R28，R29和R40彼此独立地是氢，羟基，C1-C6烷基，C1-C4烷氧基-C1-C4烷基，C2-C6链烯基，C2-C6炔基，C1-C6烷氧羰基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基氨基磺酰基，C1-C4卤代烷基，C1-C6烷基氨基，C1-C6二烷基氨基，C1-C6烷氧基，氰基，硝基，卤素或苯基，苯基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧羰基，氨基，C1-C4烷基氨基，C1-C4二烷基氨基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基-S(O)2O，C1-C4卤代烷硫基，C1-C4卤代烷基亚磺酰基，C1-C4卤代烷基磺酰基，C1-C4卤代烷基-S(O)2O，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，卤素，硝基，COOH或氰基取代；或者R28和R29一起形成C2-C6亚烷基桥；
R30是可以被基团A5取代的C1-C6烷基；可以被基团A6取代的C2-C6链烯基；可以被基团A7取代的C2-C6炔基；
A5，A6和A7彼此独立地是羟基，甲酰基，COOH，C1-C6烷氧基，C1-C4烷硫基，C1-C4烷基亚磺酰基，C1-C4烷基磺酰基，OSO2-C1-C4烷基，C1-C6烷基氨基，C1-C6二烷基氨基，C1-C6烷基氨基羰基，C1-C6二烷基氨基羰基，硝基，卤素，氰基，C1-C4烷氧基卤素，C1-C4烷基羰基，C1-C4烷氧基羰基或苯基，苯基又可以被卤素，C1-C4烷基，C1-C4烷氧基，C1-C4卤代烷基，氰基，硝基，C1-C4卤代烷基，C1-C4烷硫基，C1-C4烷基亚磺酰基，C1-C4烷基磺酰基，C1-C4烷基羰基，C1-C4二烷基氨基磺酰基或NR31-COR32取代；
R31，R32彼此独立地是氢或C1-C4烷基；
或者Q是基团Q4：
Figure C9981488500081
其中
R33是羟基，卤素，C1-C6烷氧基，C1-C6烷基羰氧基，C1-C6烷氧基羰氧基，C1-C5二烷基氨基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷氧羰基-C1-C4烷硫基，C1-C4烷氧羰基-C1-C4烷基亚磺酰基，C1-C4烷氧羰基-C1-C4烷基磺酰基，C1-C6链烯硫基，C1-C6链烯基亚磺酰基，C1-C6链烯基磺酰基，OSO2-C1-C6烷基，苯甲酰氧基，苯硫基，苯基亚磺酰基，苯基磺酰基或OSO2-苯基，其中苯基和苯甲酰基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，卤素，硝基，COOH或氰基取代；W是氧，硫，SO，SO2，NR38或C＝O；
R38是氢或C1-C6烷基；
R34，R35，R36和R37彼此独立地是氢，羟基，C1-C6烷基，C1-C4烷氧基-C1-C4烷基，C2-C6链烯基，C2-C6炔基，C1-C6烷氧羰基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基氨基磺酰基，C1-C4卤代烷基，C1-C6烷基氨基，C1-C6二烷基氨基，C1-C6烷氧基，氰基，硝基，卤素或苯基，苯基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，氨基，C1-C4烷基氨基，C1-C4二烷基氨基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷基-S(O)2O，C1-C4卤代烷硫基，C1-C4卤代烷基亚磺酰基，C1-C4卤代烷基磺酰基，C1-C4卤代烷基-S(O)2O，C1-C4烷基-S(O)2NH，C1-C4烷基-S(O)2N(C1-C4烷基)，卤素，硝基，COOH或氰基取代；或者R34和R35一起形成C2-C6亚烷基桥；以及上述化合物的农业上可接受的盐、异构体和对映体。
本发明也涉及式I化合物，特别是其中R23，R27，R33和R39是羟基的式I化合物和胺、碱金属及碱土金属或季铵碱形成的盐。
在作为形成盐的组份的碱金属和碱土金属氢氧化物中，锂，钠，钾，镁或钙的氢氧化物是值得注意的，特别是氢氧化钠和氢氧化钾。
适合于形成铵盐的胺的实例可以是氨和伯，仲，叔-C1-C18烷基胺，C1-C4羟烷基胺和C2-C4烷氧基烷基胺，例如甲基胺，乙基胺，正丙基胺，异丙基胺，四个异构体的丁基胺，正戊基胺，异戊基胺，己基胺，庚基胺，辛基胺，壬基胺，癸基胺，十五烷基胺，十六烷基胺，十七烷基胺，十八烷基胺，甲基乙基胺，甲基异丙基胺，甲基己基胺，甲基壬基胺，甲基十五烷基胺，甲基十八烷基胺，乙基丁基胺，乙基庚基胺，乙基辛基胺，己基庚基胺，己基辛基胺，二甲基胺，二乙基胺，二正丙基胺，二异丙基胺，二正丁基胺，二正戊基胺，二异戊基胺，二己基胺，二庚基胺，二辛基胺，乙醇胺，正丙醇胺，异丙醇胺，N，N-二乙醇胺，N-乙基丙醇胺，N-丁基乙醇胺，烯丙基胺，n-丁烯基-2-胺，n-戊烯基-2-胺，2，3-二甲基丁烯基-2-胺，二丁烯基-2-胺，n-己烯基-2-胺，丙二胺，三甲胺，三乙胺，三正丙基胺，三异丙基胺，三正丁基胺，三异丁基胺，三仲丁基胺，三正戊基胺，甲氧基乙基胺，和乙氧基乙基胺；杂环胺，例如吡啶，喹啉，异喹啉，吗啉，哌啶，吡咯烷，二氢吲哚，喹宁环和吖庚因；伯芳基胺，例如苯胺，甲氧基苯胺，乙氧基苯胺，邻-，间-，对-甲苯胺，苯二胺，联苯胺，萘胺和邻-，间-，对-氯苯胺；特别是三乙基胺、异丙基胺和二异丙基胺。
取代基定义中的烷基和亚烷基可以是直链或支链的，例如甲基，乙基，正丙基，异丙基，正丁基，仲丁基，异丁基，叔丁基，戊基和己基及其支链异构体；烷氧基，链烯基，亚链烯基，炔基和亚炔基从上述烷基衍生，所述链烯基，亚链烯基，炔基和亚炔基可以是单或多不饱和的。
卤素通常是指氟，氯，溴或碘，这也同样适用于和其它定义相结合的卤素，例如卤代烷基或卤代苯基中的卤素。
卤代烷基优选链长1-6个碳原子，卤代烷基例如是氟甲基，二氟甲基，三氟甲基，氯甲基，二氯甲基，三氯甲基，2，2，2-三氟乙基，2-氟乙基，2-氯乙基，五氟乙基，1，1-二氟-2，2，2-三氯乙基，2，2，3，3-四氟乙基和2，2，2-三氯乙基，优选三氯甲基，二氟氯甲基，二氟甲基，三氟甲基和二氯氟甲基。
烷氧基优选链长1-6个碳原子，烷氧基的实例是甲氧基，乙氧基，丙氧基，异丙氧基，正丁氧基，异丁氧基，仲丁氧基和叔丁氧基以及戊氧基和己氧基及其异构体，优选甲氧基和乙氧基。烷基羰基优选乙酰基和丙酰基。烷氧羰基例如是指甲氧羰基，乙氧羰基，丙氧羰基，异丙氧羰基，正丁氧羰基，异丁氧羰基，仲丁氧羰基或叔丁氧羰基，优选甲氧羰基或乙氧羰基。卤代烷氧基优选链长1-6个碳原子，卤代烷氧基例如是氟甲氧基，二氟甲氧基，三氟甲氧基，2，2，2-三氟乙氧基，1，1，2，2-四氟乙氧基，2-氟乙氧基，2-氯乙氧基，2，2-二氟乙氧基和2，2，2-三氯乙氧基，优选二氟甲氧基，2-氯乙氧基和三氟甲氧基。烷硫基优选链长1-6个碳原子，烷硫基例如是甲硫基，乙硫基，丙硫基，异丙硫基，正丁硫基，异丁硫基，仲丁硫基或叔丁硫基，优选甲硫基和乙硫基。烷基亚磺酰基例如是甲基亚磺酰基，乙基亚磺酰基，丙基亚磺酰基，异丙基亚磺酰基，正丁基亚磺酰基，异丁基亚磺酰基，仲丁基亚磺酰基，叔丁基亚磺酰基，优选甲基亚磺酰基和乙基亚磺酰基。
含有氧的C3-C7环烷基例如是环氧乙烷基，环氧丁烷基，四氢呋喃基，二氧戊环基，氧杂环己基，二氧杂环己基，氧杂环庚基或二氧杂环庚基。
含有氧的C3-C7-环烷基-C1-C3烷基例如是环氧乙烷-甲基，环氧丁烷-乙基，四氢呋喃-正丙基，二氧戊环-C1-C3烷基，氧杂环己基-C1-C3烷基，二氧杂环己基-C1-C3烷基，氧杂环庚基-C1-C3烷基或二氧杂环庚基-C1-C3烷基。
烷基磺酰基例如是甲基磺酰基，乙基磺酰基，丙基磺酰基，异丙基磺酰基，正丁基磺酰基，异丁基磺酰基，仲丁基磺酰基或叔丁基磺酰基，优选甲基磺酰基和乙基磺酰基。烷氧基烷氧基基团优选链长2-4个碳原子。
烷氧基烷氧基的实例是：甲氧甲氧基，甲氧乙氧基，甲氧丙氧基，乙氧甲氧基，乙氧乙氧基，丙氧甲氧基或丁氧丁氧基。
烷基氨基例如是甲基氨基，乙基氨基，丙基氨基，异丙基氨基或丁基氨基的各异构体。二烷基氨基例如是二甲基氨基，甲基乙基氨基，二乙基氨基，正丙基甲基氨基，二丁基氨基和二异丙基氨基，烷基氨基优选链长1-4个碳原子。烷氧基烷基优选具有2-4个碳原子，烷氧基烷基例如是指甲氧基甲基，甲氧基乙基，乙氧基甲基，乙氧基乙基，正丙氧基甲基，正丙氧基乙基，异丙氧基甲基或异丙氧基乙基。烷硫基烷基优选具有2-4个碳原子，烷硫基烷基是指例如甲硫基甲基，甲硫基乙基，乙硫基甲基，乙硫基乙基，正丙硫基甲基，正丙硫基乙基，异丙硫基甲基，异丙硫基乙基，丁硫基甲基，丁硫基乙基或丁硫基丁基。环烷基优选有具3-6个环碳原子，例如环丙基，环丁基，环戊基和环己基。苯基和作为取代基一部分的苯基，如苯氧基，苄基，苄氧基，苯甲酰基，苯硫基，苯基烷基或苯氧基烷基中的苯基可以取代的形式存在。
优选的式I化合物是：其中R1和R2彼此独立地是卤素，氰基，硝基，氨基，C1-C6烷基，C1-C6烷氧基，C1-C4烷氧基-C1-C4烷基，C1-C6卤代烷基，C2-C6链烯基，C2-C6炔基，C1-C6烷氧羰基，C1-C6烷基羰基，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C6二烷基氨基磺酰基，C1-C6烷基氨基磺酰基，C1-C6卤代烷氧基，OSO2-C1-C4烷基，C1-C6卤代烷硫基，C1-C6卤代烷基亚磺酰基，C1-C6卤代烷基磺酰基，苯硫基，苯基亚磺酰基或苯基磺酰基，和
R33表示羟基，卤素，C1-C6烷氧基，C1-C6烷基羰氧基，C1-C6烷氧基羰氧基，C1-C6二烷基氨基，COOH，C1-C6烷硫基，C1-C6烷基亚磺酰基，C1-C6烷基磺酰基，C1-C4烷氧羰基-C1-C4烷硫基，C1-C4烷氧羰基-C1-C4烷基亚磺酰基，C1-C4烷氧羰基-C1-C4烷基磺酰基，C1-C6链烯基硫基，C1-C6链烯基亚磺酰基，C1-C6链烯基磺酰基，OSO2C1-C6烷基，苯甲酰氧基，苯硫基，苯基亚磺酰基，苯基磺酰基或OSO2-苯基，其中的苯基和苯甲酰基又可以被C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，C1-C4烷基羰基，C1-C4烷氧基羰基，卤素，硝基，COOH或氰基取代。
更优选的式I化合物的特征为Q是Q1或Q2，在基团Q2中，R24，R25和R26优选为氢或C1-C6烷基，R23和R39特别是羟基。还值得注意是这些式I化合物，即，其中X是L1-Y1-R4。在该组中，其中L1是亚甲基的化合物是优选的。在式I化合物的更优选的组中，R2是C1-C6烷基磺酰基，还有兴趣是其中R1表示甲基的式I化合物。
式I范围内的特别优选的个别化合物是：4-羟基-3-(4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酰基)-双环[3.2.1]辛-3-烯-2-酮和5-羟基-4-(4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酰基)-2，6，6-三甲基-6H-[1.2]噁嗪-3-酮。
式I化合物可以用公知方法制备，例如US-A-5,565,410；US-A-5,608,101和EP-A-0 282 944记载的，例如将式II化合物：
Figure C9981488500131
其中R1，R2，R3和X具有在式I中给出的含义，Z表示离去基，优选卤素，特别是氯或氰基；
和式III化合物反应：
其中取代基的定义和基团Q1中的定义相同，
或者和式IV化合物反应：
Figure C9981488500133
其中取代基的定义和基团Q2中的定义相同，
或者和式V化合物反应：
Figure C9981488500141
其中取代基的定义和基团Q3中的定义相同，
或者和式VI化合物反应：
Figure C9981488500142
其中取代基的定义和基团Q4中的定义相同，并且相应地R39、R23、R27和R33表示羟基，反应可任选在碱存在下进行。式II、III、IV或V化合物是US-A-5,565,410；US-A-5,608,101和EP-A-0 282 944中公开的或者可以类似地按照其中公开的方法制备。
制备式I化合物的反应可有利地在非质子惰性有机溶剂中进行，所述有机溶剂是烃类如苯，甲苯，二甲苯或环已烷，氯代烃类如二氯甲烷，三氯甲烷，四氯化碳或氯苯；醚类如乙醚，乙二醇二甲醚，二甘醇二甲醚，四氢呋喃或二噁烷；腈类如乙腈或丙腈；酰胺如N，N-二甲基甲酰胺，二乙基甲酰胺或N-甲基吡咯烷酮。反应温度优选-20℃到+120℃，反应通常稍稍放热，一般可以在室温下进行。可以将反应混合物短时间加热到沸点以便缩短反应时间，或者也是为了引发反应。加入几滴碱作为催化剂也可以缩短反应时间。特别合适的碱优选为叔胺如三甲胺，三乙胺，喹宁环，1，4-二氮杂双环[2.2.2]辛烷，1，5-二氮杂双环[4.3.0]壬-5-烯，1，5-二氮杂双环[5.4.0]十一碳-7-烯，也合适的碱是无机碱，一般是氢化物如氢化钠或氢化钙；氢氧化物如氢氧化钠或氢氧化钾；碳酸盐如碳酸钠或碳酸钾或者碳酸氢盐如碳酸氢钠或碳酸氢钾。
式I化合物可以通过常规方法分离，例如浓缩反应混合物和/或通过蒸馏除去溶剂，和通过重结晶或在不溶解它们的溶剂中研磨固体残留物，一般使用醚类，芳香烃或氯代烃。
按照本发明式I化合物或含有它们的组合物通过所有标准使用方法可以用于农业，包括芽前使用、苗后使用及浸种，也可以通过各种方法和技术如控制释放来施用。对于控制释放，将除草剂溶液施加到矿物颗粒载体上或者聚合物颗粒上(脲/甲醛)，然后干燥。也可以使用包衣技术(包衣颗粒)，使活性成分在一定的时间周期内以控制速度释放。
式I化合物本身可以例如以合成时得到的形式用作除草剂，但是优选使用制剂技术经常使用的助剂按照常规方法加工成乳油，直接可喷雾或稀释的溶液，稀乳液，可温性粉剂，可溶性粉末，粉尘剂或颗粒剂或微胶囊剂。所述制剂在WO97/34485的第9-13页中有记载。如同制剂的类型一样，如喷雾，弥雾，喷粉，浸种，撒施或浇泼等施用方法可以根据其使用对象及流行的环境选择。
例如含有式I化合物或至少一种式I化合物及一种或一种以上的常用液体或固体制剂辅助剂的药剂、剂型、组合物的制剂可以通过常规方法制备，例如均匀混合和/或研磨除草剂和所述制剂辅助剂，一般是溶剂或固体载体。表面活性化合物(表面活性剂)也可以用于制备剂型，溶剂和固体载体的实例记载于WO9 7/34485的第6页。
依赖于加工配制成制剂的式I除草剂，合适的表面活性化合物是有良好的乳化性、分散性和润湿性的非离子、阳离子和/或阴离子表面活性剂以及表面活性剂混合物。
合适的阴离子、非离子和阳离子表面活性剂的实例记载于WO97/34485的第7-8页。
制剂领域常规的表面活性剂，以及尤其是记载于：《McCutcheon洗涤剂和乳化剂年鉴》(“McCutcheon’s Detergentsand Emulsifiers Annual”)MC Publeshing Corp.，RidgewoodNew Jersey，1981，Stache，H.，《表面活性剂手册》[“Tensid-Taschenbuch”(Handbook of Surfactants)]，Carl HanserVerlag，Munich/Vienna，1981，以及M.以及J.Ash，表面活性剂大全》(“Encycloedia of Surfactants”)，第I-III卷，Chemical Publishing Co.，New York，1980-81中的表面活性剂也适用于制备本发明的除草剂剂型。
除草剂组合物一般含有0.1-99％重量，优选0.1-95％重量的除草剂，1-99.9％重量，优选5-99.8％重量的固体或液体辅助剂，以及0-25％重量，优选0.1-25％重量的表面活性剂。尽管作为商品优选配制成浓缩物，但是最终的使用者通常使用其稀释的制剂。组合物也可以含有其它成分如稳定剂，例如合适的话，可以是环氧化的植物油(环氧化椰子油、菜籽油或大豆油)；消泡剂，一般是硅油；防腐剂；粘度调节剂；粘合剂和胶粘剂，以及肥料和其它化学试剂。
式I化合物通常成功地用于植物或植物生长场所，其浓度为0.001-4kg/ha，优选0.005-2kg/ha。达到所需作用的浓度可以通过试验确定。依赖于作用类型、载培作物和杂草的生长阶段及施用方式(场所、时间和施用方法)，这些变化的结果导致浓度范围很宽。
式I化合物具有优异的除草和抑制生长活性，适用于作物植物，特别是谷物，棉花，大豆，甜菜，甘蔗，人工林(plantations)，油菜，玉米和稻的种植中，以及用于非选择性地控制杂草。作物应理解为还包括通过常规育种或基因工程方法使其对除草剂或一类除草剂有耐受性的作物。欲防除的杂草可以是单子叶或双子叶杂草，典型地有繁缕属，豆瓣菜属，剪股颖属，马塘属，燕麦属，狗尾草属，白芥属，黑麦草属，茄属，稗属，蒸草属，雨久花属，慈姑属，雀麦属，看麦娘属，蜀黍属，石茅高梁，简轴茅属，莎草属，茼麻属，黄花稔属，苍耳属，苋属，藜属，番薯属，茼蒿属，猪殃殃属，堇菜属和婆婆纳属。
本发明用以下非限制性实施例进行说明。
制备实施例
实施例P1：4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酰氯的制备
Figure C9981488500171
将按照EP-A-0 282 944得到的1.5g(5.8mmol)4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酸在15ml二氯甲烷中的溶液于20℃和2滴DMF混合。然后，在稍稍冷却的同时，滴加1.0ml(11.6mmol)草酰氯在2ml二氯甲烷中的溶液，搅拌反应混合物直到不再放出气体，然后蒸馏出溶剂。得到的4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酰氯无需提纯直接用于下一步反应。
实施例P2：4-羟基-3-(4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酰 基)-双环[3.2.1]辛-3-烯-2-酮的制备
Figure C9981488500172
在20℃下，将0.8g(5.8mmol)双环[3.2.1]辛烷-2，4-二酮(其制备例如描述在US-A-5,608,101以及其中所引用的参考文献中)溶于15ml二氯甲烷中。所得溶液与0.97ml三乙胺混合并冷却至0℃。然后滴加1.6g(5.8mmol)4-甲基磺酰基-3-甲氧基甲基-2-甲基苯酰氯在10ml二氯甲烷中的溶液。0℃搅拌反应混合物0.5小时，然后用二氯甲烷稀释。洗涤和干燥后，通过蒸发浓缩有机相，得到非晶形式的2.23g4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酸-4-氧代-双环[3.2.1]辛-2-烯-2-基酯。产物不用提纯直接可用于下一步反应。
将2.23g(5.8mmol)4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酸-4-氧代-双环[3.2.1]辛-2-烯-2-基酯和1.6ml(11.6mmol)三乙胺溶于20ml乙腈中。于20℃加入0.2ml乙酰氰醇(acetocyanohydrin)。搅拌20小时后，将混合物进行后处理，并用薄层色谱纯化粗产物，得到非晶形式的1.0g 4-羟基-3-(4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酰基)-双环[3.2.1]辛-3-烯-2-酮。
实施例P3：5-羟基-4-(4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酰 基)-2，6，6-三甲基-6.H.-[1.2]噁嗪-3-酮的制备
Figure C9981488500181
准备0.79g(5.04mmol)2，6，6-三甲基-2H-1，2-噁嗪-3，5-二酮(其制备方法例如描述于US-A-5,565,410中)、15ml二氯甲烷和0.97ml三乙胺，于0℃滴加1.3g(4.7mmol)4-甲基磺酰基-3-甲氧基甲基-2-甲基苯甲酰氯在10ml二氯甲烷中的溶液。搅拌30分钟后，用二氯甲烷稀释所得溶液。反应溶液然后用稀盐酸酸化，分离有机相、干燥并且浓缩，得到非晶形式的2.0g 4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酸-2，6，6-三甲基-5-氧代-5，6-二氢-2.H.-[1.2]噁嗪-3-基酯。产品无需纯化直接进一步使用。
将2.0g(5.04mmol)4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酸-2，6，6-三甲基-5-氧代-5，6-二氢-2.H.-[1.2]噁嗪-3-基酯溶于35ml乙腈和10ml二氯甲烷的混合物中。然后，加入1.4ml(10.08mmol)三乙胺和0.18ml乙酰氰醇。于20℃搅拌20小时后，进行后处理、重结晶，最终得到5-羟基-4-(4-甲基磺酰基-3-甲氧基甲基-2-甲基-苯甲酰基)-2，6，6-三甲基-6.H.-[1.2]噁嗪-3-酮，熔点为157℃。
下表1-4中命名的物质也可按照类似于上述的方法制备。在表1-4中，X表示下述基团：
X1＝CH2OCH3，X2＝CH2OC2H5，X3＝CH2OH，X4＝CH2CH2OCH3，X5＝CH2CH2OC2H5，X6＝CH2CH2OCH2CH2OCH3，X7＝CH2CH2OCH2CH2OC2H5，X8＝CH(CH3)OC2H5，X10＝CH2OCH2CH＝CH2，X11＝CH2OCH2CH2CH3，X12＝CH(C2H5)OC2H5，X13＝C(CH3)2OH，X14＝CH2CH2OCH(CH3)2，X15＝CH2SO2CH3，X16＝CH2N(CH3)C2H5，X17＝CH2NHCH3，X18＝CH2OCH(CH3)2，X19＝C(CH3)2OCH3，X20＝CH2CH2OH，X21＝CH2OCH2CCH，X22＝C(CH3)2OC2H5，X23＝CH(C2H5)OCH3，X24＝CH(CH3)OH，X25＝CH(OH)C2H5，X26＝CH2SCH3，X27＝CH2N(CH3)2，X28＝CH2CH2N(CH3)2，X29＝CH2OCOCH3，X30＝CH2OPh，X31＝CH2CH2OPh，X32＝CH2OCH2CH2OCH3，X33＝CH2OCH2CH2OC2H5，
Figure C9981488500191
表1：式(Ia)化合物：
Figure C9981488500201
化合物  V     R17   R22    R1     X     R2        物理数据
序号
1,001   CH2   H     H      CH3    X1    SO2CH3    树脂状
1,002   CH2   H     H      CH3    X2    SO2CH3    -
1,003   CH2   H     H      CH3    X3    SO2CH3    -
1,004   CH2   H     H      CH3    X4    SO2CH3    -
1,005   CH2   H     H      CH3    X5    SO2CH3    -
1,006   CH2   H     H      CH3    X6    SO2CH3    -
1,007   CH2   H     H      CH3    X7    SO2CH3    -
1,008   CH2   H     H      CH3    X8    SO2CH3    -
1,009   CH2   H     H      CH3    X9    SO2CH3    -
1,010   CH2   H     H      CH3    X10   SO2CH3    -
1,011   CH2   H     H      CH3    X11   SO2CH3    -
1,012   CH2   H     H      CH3    X12   SO2CH3    -
1,013   CH2   H     H      CH3    X13   SO2CH3    -
1,014   CH2   H     H      CH3    X14   SO2CH3    -
1,015   CH2   H     H      CH3    X15   SO2CH3    -
1,016   CH2   H     H      CH3    X16   SO2CH3    -
1,017   CH2   H     H      CH3    X17   SO2CH3    -
1,018   CH2   H     H      CH3    X18   SO2CH3    -
1,019   CH2   H     H      CH3    X19   SO2CH3    -
1,020   CH2   H     H      CH3    X20   SO2CH3    -
1,021   CH2   H     H      CH3    X21   SO2CH3    -
1,022   CH2   H     H      CH3    X22   SO2CH3    -
1,023   CH2   H     H      CH3    X23   SO2CH3    -
1,024   CH2   H     H      CH3    X24   SO2CH3    -
化合物   V      R17  R22  R1     X      R2       物理数据
序号
1,025    CH2    H    H    CH3    X25    SO2CH3    -
1,026    CH2    H    H    CH3    X26    SO2CH3    -
1,027    CH2    H    H    CH3    X27    SO2CH3    -
1,028    CH2    H    H    CH3    X28    SO2CH3    -
1,029    CH2    H    H    CH3    X29    SO2CH3    -
1,030    CH2    H    H    CH3    X30    SO2CH3    -
1,031    CH2    H    H    CH3    X31    SO2CH3    -
1,032    CH2    H    H    CH3    X32    SO2CH3    -
1,033    CH2    H    H    CH3    X33    SO2CH3    -
1,034    CH2    H    H    CH3    X34    SO2CH3    -
1,035    CH2    H    H    CH3    X35    SO2CH3    -
1,036    CH2    H    H    CH3    X36    SO2CH3    -
1,037    CH2    H    H    CH3    X37    SO2CH3    -
1,038    CH2    H    H    CH3    X38    SO2CH3    -
1,039    CH2    H    H    CH3    X39    SO2CH3    -
1,040    CH2    H    H    CH3    X40    SO2CH3    -
1,041    CH2    H    H    CH3    X41    SO2CH3    -
1,042    CH2    H    H    CH3    X42    SO2CH3    -
1,043    CH2    H    H    CH3    X1     SCH3      -
1,044    CH2    H    H    CH3    X2     SCH3      -
1,045    CH2    H    H    CH3    X3     SCH3      -
1,046    CH2    H    H    CH3    X4     SCH3      -
1,047    CH2    H    H    CH3    X5     SCH3      -
1,048    CH2    H    H    CH3    X6     SCH3      -
1,049    CH2    H    H    CH3    X7     SCH3      -
1,050    CH2    H    H    CH3    X10    SCH3      -
1,051    CH2    H    H    CH3    X15    SCH3      -
1,052    CH2    H    H    CH3    X20    SCH3      -
1,053    CH2    H    H    CH3    X21    SCH3      -
1,054    CH2    H    H    CH3    X26    SCH3      -
1,055    CH2    H    H    CH3    X27    SCH3      -
化合物   V      R17    R22    R1     X      R2        物理数据
序号
1,056    CH2    H      H      CH3    X29    SCH3      -
1,057    CH2    H      H      CH3    X30    SCH3      -
1,058    CH3    CH3    CH3    CH3    X1     SO2CH3    -
1,059    CH3    CH3    CH3    CH3    X2     SO2CH3    -
1,060    CH3    CH3    CH3    CH3    X4     SO2CH3    -
1,061    CH3    CH3    CH3    CH3    X10    SO2CH3    -
1,062    CH3    CH3    CH3    CH3    X15    SO2CH3    -
1,063    CH3    CH3    CH3    CH3    X21    SO2CH3    -
1,064    CH3    CH3    CH3    CH3    X26    SO2CH3    -
1,065    O      CH3    CH3    CH3    X1     SO2CH3    -
1,066    O      CH3    CH3    CH3    X2     SO2CH3    -
1,067    O      CH3    CH3    CH3    X4     SO2CH3    -
1,068    O      CH3    CH3    CH3    X10    SO2CH3    -
1,069    O      CH3    CH3    CH3    X15    SO2CH3    -
1,070    O      CH3    CH3    CH3    X21    SO2CH3    -
1,071    O      CH3    CH3    CH3    X26    SO2CH3    -
1,072    CH2    H      H      Cl     X1     SO2CH3
1,073    CH2    H      H      Cl     X2     SO2CH3
1,074    CH2    H      H      Cl     X3     SO2CH3
1,075    CH2    H      H      Cl     X4     SO2CH3
1,076    CH2    H      H      Cl     X5     SO2CH3
1,077    CH2    H      H      Cl     X6     SO2CH3
1,078    CH2    H      H      Cl     X7     SO2CH3
1,079    CH2    H      H      Cl     X8     SO2CH3
1,080    CH2    H      H      Cl     X9     SO2CH3
1,081    CH2    H      H      Cl     X10    SO2CH3
1,082    CH2    H      H      Cl     X11    SO2CH3
1,083    CH2    H      H      Cl     X12    SO2CH3
1,084    CH2    H      H      Cl     X13    SO2CH3
1,085    CH2    H      H      Cl     X14    SO2CH3
1,086    CH2    H      H      Cl     X15    SO2CH3
化合物   V      R17  R22  R1    X      R2     物理数据
序号
1,087    CH2    H    H    Cl    X16    SO2CH3
1,088    CH2    H    H    Cl    X17    SO2CH3
1,089    CH2    H    H    Cl    X18    SO2CH3
1,090    CH2    H    H    Cl    X19    SO2CH3
1,091    CH2    H    H    Cl    X20    SO2CH3
1,092    CH2    H    H    Cl    X21    SO2CH3
1,093    CH2    H    H    Cl    X22    SO2CH3
1,094    CH2    H    H    Cl    X23    SO2CH3
1,095    CH2    H    H    Cl    X24    SO2CH3
1,096    CH2    H    H    Cl    X25    SO2CH3
1,097    CH2    H    H    Cl    X26    SO2CH3
1,098    CH2    H    H    Cl    X27    SO2CH3
1,099    CH2    H    H    Cl    X28    SO2CH3
1,100    CH2    H    H    Cl    X29    SO2CH3
1,101    CH2    H    H    Cl    X30    SO2CH3
1,102    CH2    H    H    Cl    X31    SO2CH3
1,103    CH2    H    H    Cl    X32    SO2CH3
1,104    CH2    H    H    Cl    X33    SO2CH3
1,105    CH2    H    H    Cl    X34    SO2CH3
1,106    CH2    H    H    Cl    X35    SO2CH3
1,107    CH2    H    H    Cl    X36    SO2CH3
1,108    CH2    H    H    Cl    X37    SO2CH3
1,109    CH2    H    H    Cl    X38    SO2CH3
1,110    CH2    H    H    Cl    X39    SO2CH3
1,111    CH2    H    H    Cl    X40    SO2CH3
1,112    CH2    H    H    Cl    X41    SO2CH3
1,113    CH2    H    H    Cl    X42    SO2CH3
1,114    CH2    H    H    CH3   X1     CF3
1,115    CH2    H    H    CH3   X2     CF3
1,116    CH2    H    H    CH3   X3     CF3
1,117    CH2    H    H    CH3   X4     CF3
化合物    V     R17   R22  R1     X      R2    物理数据
序号
1,118    CH2    H     H    CH3    X5     CF3
1,119    CH2    H     H    CH3    X6     CF3
1,120    CH2    H     H    CH3    X7     CF3
1,121    CH2    H     H    CH3    X10    CF3
1,122    CH2    H     H    CH3    X15    CF3
1,123    CH2    H     H    CH3    X20    CF3
1,124    CH2    H     H    CH3    X21    CF3
1,125    CH2    H     H    CH3    X26    CF3
1,126    CH2    H     H    CH3    X27    CF3
1,127    CH2    H     H    CH3    X29    CF3
1,128    CH2    H     H    CH3    X30    CF3
1,129    CH2    H     H    CH3    X1     Br
1,130    CH2    H     H    CH3    X2     Br
1,131    CH2    H     H    CH3    X3     Br
1,132    CH2    H     H    CH3    X4     Br
1,133    CH2    H     H    CH3    X5     Br
1,134    CH2    H     H    CH3    X6     Br
1,135    CH2    H     H    CH3    X7     Br
1,136    CH2    H     H    CH3    X10    Br
1,137    CH2    H     H    CH3    X15    Br
1,138    CH2    H     H    CH3    X20    Br
1,139    CH2    H     H    CH3    X21    Br
1,140    CH2    H     H    CH3    X26    Br
1,141    CH2    H     H    CH3    X27    Br
1,142    CH2    H     H    CH3    X29    Br
1,143    CH2    H     H    CH3    X30    Br
1,144    CH2    H     H    CH3    X1     CN
1,145    CH2    H     H    CH3    X2     CN
1,146    CH2    H     H    CH3    X3     CN
1,147    CH2    H     H    CH3    X4     CN
1,148    CH2    H     H    CH3    X6     CN
化合物   V      R17  R22  R1     X      R2      物理数据
序号
1,149    CH2    H    H    CH3    X10    CN
1,150    CH2    H    H    CH3    X15    CN
1,151    CH2    H    H    CH3    X21    CN
1,152    CH2    H    H    CH3    X26    CN
1,153    CH2    H    H    CH3    X30    CN
1,154    CH2    H    H    CF3    X1     SO2CH3
1,155    CH2    H    H    CF3    X2     SO2CH3
1,156    CH2    H    H    CF3    X3     SO2CH3
1,157    CH2    H    H    CF3    X4     SO2CH3
1,158    CH2    H    H    CF3    X6     SO2CH3
1,159    CH2    H    H    CF3    X10    SO2CH3
1,160    CH2    H    H    CF3    X15    SO2CH3
1,161    CH2    H    H    CF3    X21    SO2CH3
1,162    CH2    H    H    CF3    X26    SO2CH3
1,163    CH2    H    H    CF3    X30    SO2CH3
1,164    CH3    CH3  CH3  CF3    X1     SO2CH3
1,165    CH3    CH3  CH3  CF3    X2     SO2CH3
1,166    CH3    CH3  CH3  CF3    X4     SO2CH3
1,167    CH3    CH3  CH3  CF3    X10    SO2CH3
1,168    CH3    CH3  CH3  CF3    X15    SO2CH3
1,169    CH3    CH3  CH3  CF3    X21    SO2CH3
1,170    CH3    CH3  CH3  CF3    X26    SO2CH3
1,171    CH2    H    H    SO2CH3 X1     CF3
1,172    CH2    H    H    SO2CH3 X2     CF3
1,173    CH2    H    H    SO2CH3 X3     CF3
1,174    CH2    H    H    SO2CH3 X4     CF3
1,175    CH2    H    H    SO2CH3 X6     CF3
1,176    CH2    H    H    SO2CH3 X10    CF3
1,177    CH2    H    H    SO2CH3 X15    CF3
1,178    CH2    H    H    SO2CH3 X21    CF3
1,179    CH2    H    H    SO2CH3 X26    CF3
化合物   V      R17   R22  R1     X      R2      物理数据
序号
1,180    CH2    H     H    SO2CH3 X30    CF3
1,181    CH2    H     H    CH3    X1     Cl
1,182    CH2    H     H    CH3    X2     Cl
1,183    CH2    H     H    CH3    X3     Cl
1,184    CH2    H     H    CH3    X4     Cl
1,185    CH2    H     H    CH3    X6     Cl
1,186    CH2    H     H    CH3    X10    Cl
1,187    CH2    H     H    CH3    X15    Cl
1,188    CH2    H     H    CH3    X21    Cl
1,189    CH2    H     H    CH3    X26    Cl
1,190    CH2    H     H    CH3    X30    Cl
1,191    CH2    H     H    NO2    X1     SO2CH3
1,192    CH2    H     H    NO2    X2     SO2CH3
1,193    CH2    H     H    NO2    X4     SO2CH3
1,194    CH2    H     H    NO2    X10    SO2CH3
1,195    CH2    H     H    NO2    X15    SO2CH3
1,196    CH2    H     H    NO2    X21    SO2CH3
1,197    CH2    H     H    NO2    X26    SO2CH3
表2：式(Ib)化合物：
化合物   R24    R25    R26    R1     X     R2        m.p.
序号                                                 (℃)
2,001    CH3    CH3    CH3    CH3    X1    SO2CH3    157℃
2,002    CH3    CH3    CH3    CH3    X2    SO2CH3    -
2,003    CH3    CH3    CH3    CH3    X3    SO2CH3    -
化合物   R24    R25    R26    R1     X      R2        m.p.
序号                                                 (℃)
2,004    CH3    CH3    CH3    CH3    X4     SO2CH3    -
2,005    CH3    CH3    CH3    CH3    X5     SO2CH3    -
2,006    CH3    CH3    CH3    CH3    X6     SO2CH3    -
2,007    CH3    CH3    CH3    CH3    X7     SO2CH3    -
2,008    CH3    CH3    CH3    CH3    X8     SO2CH3    -
2,009    CH3    CH3    CH3    CH3    X9     SO2CH3    -
2,010    CH3    CH3    CH3    CH3    X10    SO2CH3    -
2,011    CH3    CH3    CH3    CH3    X11    SO2CH3    -
2,012    CH3    CH3    CH3    CH3    X12    SO2CH3    -
2,013    CH3    CH3    CH3    CH3    X13    SO2CH3    -
2,014    CH3    CH3    CH3    CH3    X14    SO2CH3    -
2,015    CH3    CH3    CH3    CH3    X15    SO2CH3    -
2,016    CH3    CH3    CH3    CH3    X16    SO2CH3    -
2,017    CH3    CH3    CH3    CH3    X17    SO2CH3    -
2,018    CH3    CH3    CH3    CH3    X18    SO2CH3    -
2,019    CH3    CH3    CH3    CH3    X19    SO2CH3    -
2,020    CH3    CH3    CH3    CH3    X20    SO2CH3    -
2,021    CH3    CH3    CH3    CH3    X21    SO2CH3    -
2,022    CH3    CH3    CH3    CH3    X22    SO2CH3    -
2,023    CH3    CH3    CH3    CH3    X23    SO2CH3    -
2,024    CH3    CH3    CH3    CH3    X24    SO2CH3    -
2,025    CH3    CH3    CH3    CH3    X25    SO2CH3    -
2,026    CH3    CH3    CH3    CH3    X26    SO2CH3    -
2,027    CH3    CH3    CH3    CH3    X27    SO2CH3    -
2,028    CH3    CH3    CH3    CH3    X28    SO2CH3    -
2,029    CH3    CH3    CH3    CH3    X29    SO2CH3    -
2,030    CH3    CH3    CH3    CH3    X30    SO2CH3    -
2,031    CH3    CH3    CH3    CH3    X31    SO2CH3    -
2,032    CH3    CH3    CH3    CH3    X32    SO2CH3    -
2,033    CH3    CH3    CH3    CH3    X33    SO2CH3    -
2,034    CH3    CH3    CH3    CH3    X34    SO2CH3    -
化合物    R24    R25    R26    R1    X      R2        m.p.
序号                                                  (℃)
2,035    CH3    CH3    CH3    CH3    X35    SO2CH3    -
2,036    CH3    CH3    CH3    CH3    X36    SO2CH3    -
2,037    CH3    CH3    CH3    CH3    X37    SO2CH3    -
2,038    CH3    CH3    CH3    CH3    X38    SO2CH3    -
2,039    CH3    CH3    CH3    CH3    X39    SO2CH3    -
2,040    CH3    CH3    CH3    CH3    X40    SO2CH3    -
2,041    CH3    CH3    CH3    CH3    X41    SO2CH3    -
2,042    CH3    CH3    CH3    CH3    X42    SO2CH3    -
2,043    CH3    CH3    CH3    Cl     X1     SO2CH3    -
2,044    CH3    CH3    CH3    Cl     X2     SO2CH3    -
2,045    CH3    CH3    CH3    Cl     X3     SO2CH3    -
2,046    CH3    CH3    CH3    Cl     X4     SO2CH3    -
2,047    CH3    CH3    CH3    Cl     X5     SO2CH3    -
2,048    CH3    CH3    CH3    Cl     X6     SO2CH3    -
2,049    CH3    CH3    CH3    Cl     X7     SO2CH3    -
2,050    CH3    CH3    CH3    Cl     X10    SO2CH3    -
2,051    CH3    CH3    CH3    Cl     X15    SO2CH3    -
2,052    CH3    CH3    CH3    Cl     X20    SO2CH3    -
2,053    CH3    CH3    CH3    Cl     X21    SO2CH3    -
2,054    CH3    CH3    CH3    Cl     X26    SO2CH3    -
2,055    CH3    CH3    CH3    Cl     X27    SO2CH3    -
2,056    CH3    CH3    CH3    Cl     X29    SO2CH3    -
2,057    CH3    CH3    CH3    Cl     X30    SO2CH3    -
2,058    CH3    CH3    CH3    CH3    X1     SCH3      -
2,059    CH3    CH3    CH3    CH3    X2     SCH3      -
2,060    CH3    CH3    CH3    CH3    X3     SCH3      -
2,061    CH3    CH3    CH3    CH3    X4     SCH3      -
2,062    CH3    CH3    CH3    CH3    X5     SCH3      -
2,063    CH3    CH3    CH3    CH3    X6     SCH3      -
2,064    CH3    CH3    CH3    CH3    X7     SCH3      -
2,065    CH3    CH3    CH3    CH3    X10    SCH3      -
化合物   R24    R25    R26     R1     X      R2        m.p.
序号    (℃)
2,066    CH3    CH3    CH3     CH3    X15    SCH3      -
2,067    CH3    CH3    CH3     CH3    X20    SCH3      -
2,068    CH3    CH3    CH3     CH3    X21    SCH3      -
2,069    CH3    CH3    CH3     CH3    X26    SCH3      -
2,070    CH3    CH3    CH3     CH3    X27    SCH3      -
2,071    CH3    CH3    CH3     CH3    X29    SCH3      -
2,072    CH3    CH3    CH3     CH3    X30    SCH3      -
2,073    H      H      C2H5    CH3    X1     SO2CH3    -
2,074    H      H      C2H5    CH3    X2     SO2CH3    -
2,075    H      H      C2H5    CH3    X4     SO2CH3    -
2,076    H      H      C2H5    CH3    X10    SO2CH3    -
2,077    H      H      C2H5    CH3    X15    SO2CH3    -
2,078    H      H      C2H5    CH3    X21    SO2CH3    -
2,079    H      H      C2H5    CH3    X26    SO2CH3    -
2,080    H      H      C3H7    CH3    X1     SO2CH3    -
2,081    H      H      C3H7    CH3    X2     SO2CH3    -
2,082    H      H      C3H7    CH3    X4     SO2CH3    -
2,083    H      H      C3H7    CH3    X10    SO2CH3    -
2,084    H      H      C3H7    CH3    X15    SO2CH3    -
2,085    H      H      C3H7    CH3    X21    SO2CH3    -
2,086    H      H      C3H7    CH3    X26    SO2CH3    -
2,087    CH3    CH3    CH3     Cl     X1     SCH3      -
2,088    CH3    CH3    CH3     Cl     X2     SCH3      -
2,089    CH3    CH3    CH3     Cl     X4     SCH3      -
2,090    CH3    CH3    CH3     Cl     X26    SCH3      -
2,091    CH3    CH3    CH3     CH3    X1     CF3       -
2,092    CH3    CH3    CH3     CH3    X2     CF3       -
2,093    CH3    CH3    CH3     CH3    X3     CF3       -
2,094    CH3    CH3    CH3     CH3    X4     CF3       -
2,095    CH3    CH3    CH3     CH3    X6     CF3       -
2,096    CH3    CH3    CH3     CH3    X10    CF3       -
化合物   R24    R25    R26    R1     X      R2        m.p.
序号                                                  (℃)
2,097    CH3    CH3    CH3    CH3    X15    CF3       -
2,098    CH3    CH3    CH3    CH3    X21    CF3       -
2,099    CH3    CH3    CH3    CH3    X26    CF3       -
2,100    CH3    CH3    CH3    CH3    X30    CF3       -
2,101    CH3    CH3    CH3    SO2CH3 X1     CF3       -
2,102    CH3    CH3    CH3    SO2CH3 X2     CF3       -
2,103    CH3    CH3    CH3    SO2CH3 X4     CF3       -
2,104    CH3    CH3    CH3    SO2CH3 X26    CF3       -
2,105    CH3    CH3    CH3    NO2    X1     CF3       -
2,106    CH3    CH3    CH3    NO2    X2     CF3       -
2,107    CH3    CH3    CH3    NO2    X4     CF3       -
2,108    CH3    CH3    CH3    NO2    X26    CF3       -
2,109    CH3    CH3    CH3    NO2    X1     SO2CH3    -
2,110    CH3    CH3    CH3    NO2    X2     SO2CH3    -
2,111    CH3    CH3    CH3    NO2    X4     SO2CH3    -
2,112    CH3    CH3    CH3    NO2    X26    SO2CH3    -
2,113    CH3    CH3    CH3    Br     X1     SO2CH3    -
2,114    CH3    CH3    CH3    Br     X2     SO2CH3    -
2,115    CH3    CH3    CH3    Br     X4     SO2CH3    -
2,116    CH3    CH3    CH3    Br     X26    SO2CH3    -
表3：式(Ic)化合物：
Figure C9981488500301
化合物   R28    R29    R30    R1     X      R2        物理数据
序号
3,001    CH3    CH3    CH3    CH3    X1     SO2CH3    -
化合物   R28    R29    R30    R1     X      R2       物理数据
序号
3,002    CH3    CH3    CH3    CH3    X2     SO2CH3    -
3,003    CH3    CH3    CH3    CH3    X3     SO2CH3    -
3,004    CH3    CH3    CH3    CH3    X4     SO2CH3    -
3,005    CH3    CH3    CH3    CH3    X5     SO2CH3    -
3,006    CH3    CH3    CH3    CH3    X6     SO2CH3    -
3,007    CH3    CH3    CH3    CH3    X7     SO2CH3    -
3,008    CH3    CH3    CH3    CH3    X8     SO2CH3    -
3,009    CH3    CH3    CH3    CH3    X9     SO2CH3    -
3,010    CH3    CH3    CH3    CH3    X10    SO2CH3    -
3,011    CH3    CH3    CH3    CH3    X11    SO2CH3    -
3,012    CH3    CH3    CH3    CH3    X12    SO2CH3    -
3,013    CH3    CH3    CH3    CH3    X13    SO2CH3    -
3,014    CH3    CH3    CH3    CH3    X14    SO2CH3    -
3,015    CH3    CH3    CH3    CH3    X15    SO2CH3    -
3,016    CH3    CH3    CH3    CH3    X16    SO2CH3    -
3,017    CH3    CH3    CH3    CH3    X17    SO2CH3    -
3,018    CH3    CH3    CH3    CH3    X18    SO2CH3    -
3,019    CH3    CH3    CH3    CH3    X19    SO2CH3    -
3,020    CH3    CH3    CH3    CH3    X20    SO2CH3    -
3,021    CH3    CH3    CH3    CH3    X21    SO2CH3    -
3,022    CH3    CH3    CH3    CH3    X22    SO2CH3    -
3,023    CH3    CH3    CH3    CH3    X23    SO2CH3    -
3,024    CH3    CH3    CH3    CH3    X24    SO2CH3    -
3,025    CH3    CH3    CH3    CH3    X25    SO2CH3    -
3,026    CH3    CH3    CH3    CH3    X26    SO2CH3    -
3,027    CH3    CH3    CH3    CH3    X27    SO2CH3    -
3,028    CH3    CH3    CH3    CH3    X28    SO2CH3    -
3,029    CH3    CH3    CH3    CH3    X29    SO2CH3    -
3,030    CH3    CH3    CH3    CH3    X30    SO2CH3    -
3,031    CH3    CH3    CH3    CH3    X31    SO2CH3    -
3,032    CH3    CH3    CH3    CH3    X32    SO2CH3    -
化合物   R28    R29    R30    R1     X      R2        物理数据
序号
3,033    CH3    CH3    CH3    CH3    X33    SO2CH3    -
3,034    CH3    CH3    CH3    CH3    X34    SO2CH3    -
3,035    CH3    CH3    CH3    CH3    X35    SO2CH3    -
3,036    CH3    CH3    CH3    CH3    X36    SO2CH3    -
3,037    CH3    CH3    CH3    CH3    X37    SO2CH3    -
3,038    CH3    CH3    CH3    CH3    X38    SO2CH3    -
3,039    CH3    CH3    CH3    CH3    X39    SO2CH3    -
3,040    CH3    CH3    CH3    CH3    X40    SO2CH3    -
3,041    CH3    CH3    CH3    CH3    X41    SO2CH3    -
3,042    CH3    CH3    CH3    CH3    X42    SO2CH3    -
3,043    CH3    CH3    CH3    CH3    X1     SCH3      -
3,044    CH3    CH3    CH3    CH3    X2     SCH3      -
3,045    CH3    CH3    CH3    CH3    X3     SCH3      -
3,046    CH3    CH3    CH3    CH3    X4     SCH3      -
3,047    CH3    CH3    CH3    CH3    X5     SCH3      -
3,048    CH3    CH3    CH3    CH3    X6     SCH3      -
3,049    CH3    CH3    CH3    CH3    X7     SCH3      -
3,050    CH3    CH3    CH3    CH3    X10    SCH3      -
3,051    CH3    CH3    CH3    CH3    X15    SCH3      -
3,052    CH3    CH3    CH3    CH3    X20    SCH3      -
3,053    CH3    CH3    CH3    CH3    X21    SCH3      -
3,054    CH3    CH3    CH3    CH3    X26    SCH3      -
3,055    CH3    CH3    CH3    CH3    X27    SCH3      -
3,056    CH3    CH3    CH3    CH3    X29    SCH3      -
3,057    CH3    CH3    CH3    CH3    X30    SCH3      -
3,058    CH3    CH3    CH3    Cl     X1     SO2CH3    -
3,059    CH3    CH3    CH3    Cl     X2     SO2CH3    -
3,060    CH3    CH3    CH3    Cl     X3     SO2CH3    -
3,061    CH3    CH3    CH3    Cl     X4     SO2CH3    -
3,062    CH3    CH3    CH3    Cl     X5     SO2CH3    -
3,063    CH3    CH3    CH3    Cl     X6     SO2CH3    -
化合物   R28    R29    R30    R1    X      R2       物理数据
序号
3,064    CH3    CH3    CH3    Cl    X7     SO2CH3    -
3,065    CH3    CH3    CH3    Cl    X8     SO2CH3    -
3,066    CH3    CH3    CH3    Cl    X9     SO2CH3    -
3,067    CH3    CH3    CH3    Cl    X10    SO2CH3    -
3,068    CH3    CH3    CH3    Cl    X11    SO2CH3    -
3,069    CH3    CH3    CH3    Cl    X12    SO2CH3    -
3,070    CH3    CH3    CH3    Cl    X13    SO2CH3    -
3,071    CH3    CH3    CH3    Cl    X14    SO2CH3    -
3,072    CH3    CH3    CH3    Cl    X15    SO2CH3    -
3,073    CH3    CH3    CH3    Cl    X16    SO2CH3    -
3,074    CH3    CH3    CH3    Cl    X17    SO2CH3    -
3,075    CH3    CH3    CH3    Cl    X18    SO2CH3    -
3,076    CH3    CH3    CH3    Cl    X19    SO2CH3    -
3,077    CH3    CH3    CH3    Cl    X20    SO2CH3    -
3,078    CH3    CH3    CH3    Cl    X21    SO2CH3    -
3,079    CH3    CH3    CH3    Cl    X22    SO2CH3    -
3,080    CH3    CH3    CH3    Cl    X23    SO2CH3    -
3,081    CH3    CH3    CH3    Cl    X24    SO2CH3    -
3,082    CH3    CH3    CH3    Cl    X25    SO2CH3    -
3,083    CH3    CH3    CH3    Cl    X26    SO2CH3    -
3,084    CH3    CH3    CH3    Cl    X27    SO2CH3    -
3,085    CH3    CH3    CH3    Cl    X28    SO2CH3    -
3,086    CH3    CH3    CH3    Cl    X29    SO2CH3    -
3,087    CH3    CH3    CH3    Cl    X30    SO2CH3    -
3,088    CH3    CH3    CH3    Cl    X31    SO2CH3    -
3,089    CH3    CH3    CH3    Cl    X32    SO2CH3    -
3,090    CH3    CH3    CH3    Cl    X33    SO2CH3    -
3,091    CH3    CH3    CH3    Cl    X34    SO2CH3    -
3,092    CH3    CH3    CH3    Cl    X35    SO2CH3    -
3,093    CH3    CH3    CH3    Cl    X36    SO2CH3    -
3,094    CH3    CH3    CH3    Cl    X37    SO2CH3    -
化合物   R28    R29    R30    R1     X      R2        物理数据
序号
3,095    CH3    CH3    CH3    Cl     X38    SO2CH3    -
3,096    CH3    CH3    CH3    Cl     X39    SO2CH3    -
3,097    CH3    CH3    CH3    Cl     X40    SO2CH3    -
3,098    CH3    CH3    CH3    Cl     X41    SO2CH3    -
3,099    CH3    CH3    CH3    Cl     X42    SO2CH3    -
3,100    CH3    CH3    CH3    CH3    X1     CF3       -
3,101    CH3    CH3    CH3    CH3    X2     CF3       -
3,102    CH3    CH3    CH3    CH3    X3     CF3       -
3,103    CH3    CH3    CH3    CH3    X4     CF3       -
3,104    CH3    CH3    CH3    CH3    X6     CF3       -
3,105    CH3    CH3    CH3    CH3    X10    CF3       -
3,106    CH3    CH3    CH3    CH3    X15    CF3       -
3,107    CH3    CH3    CH3    CH3    X21    CF3       -
3,108    CH3    CH3    CH3    CH3    X26    CF3       -
3,109    CH3    CH3    CH3    CH3    X30    CF3       -
3,110    CH3    CH3    CH3    NO2    X1     SO2CH3    -
3,111    CH3    CH3    CH3    NO2    X2     SO2CH3    -
3,112    CH3    CH3    CH3    NO2    X4     SO2CH3    -
3,113    CH3    CH3    CH3    NO2    X26    SO2CH3    -
3,114    CH3    CH3    CH3    NO2    X1     CF3       -
3,115    CH3    CH3    CH3    NO2    X2     CF3       -
3,116    CH3    CH3    CH3    NO2    X4     CF3       -
3,117    CH3    CH3    CH3    NO2    X26    CF3       -
3,118    CH3    C2H5   CH3    CH3    X1     SO2CH3    -
3,119    CH3    C2H5   CH3    CH3    X2     SO2CH3    -
3,120    CH3    C2H5   CH3    CH3    X3     SO2CH3    -
3,121    CH3    C2H5   CH3    CH3    X4     SO2CH3    -
3,122    CH3    C2H5   CH3    CH3    X6     SO2CH3    -
3,123    CH3    C2H5   CH3    CH3    X10    SO2CH3    -
3,124    CH3    C2H5   CH3    CH3    X15    SO2CH3    -
3,125    CH3    C2H5   CH3    CH3    X21    SO2CH3    -
化合物   R28    R29     R30    R1    X      R2        物理数据
序号
3,126    CH3    C2H5    CH3    CH3   X26    SO2CH3    -
3,127    CH3    C2H5    CH3    CH3   X30    SO2CH3    -
3,128    C2H5   C2H5    CH3    CH3   X1     SO2CH3    -
3,129    C2H5   C2H5    CH3    CH3   X2     SO2CH3    -
3,130    C2H5   C2H5    CH3    CH3   X4     SO2CH3    -
3,131    C2H5   C2H5    CH3    CH3   X10    SO2CH3    -
3,132    C2H5   C2H5    CH3    CH3   X15    SO2CH3    -
3,133    C2H5   C2H5    CH3    CH3   X21    SO2CH3    -
3,134    C2H5   C2H5    CH3    CH3   X26    SO2CH3    -
3,135    CH3    CH3     CH3    Cl    X1     SCH3      -
3,136    CH3    CH3     CH3    Cl    X2     SCH3      -
3,137    CH3    CH3     CH3    Cl    X3     SCH3      -
3,138    CH3    CH3     CH3    Cl    X4     SCH3      -
3,139    CH3    CH3     CH3    Cl    X5     SCH3      -
3,140    CH3    CH3     CH3    Cl    X6     SCH3      -
3,141    CH3    CH3     CH3    Cl    X7     SCH3      -
3,142    CH3    CH3     CH3    Cl    X10    SCH3      -
3,143    CH3    CH3     CH3    Cl    X15    SCH3      -
3,144    CH3    CH3     CH3    Cl    X20    SCH3      -
3,145    CH3    CH3     CH3    Cl    X21    SCH3      -
3,146    CH3    CH3     CH3    Cl    X26    SCH3      -
3,147    CH3    CH3     CH3    Cl    X27    SCH3      -
3,148    CH3    CH3     CH3    Cl    X29    SCH3      -
3,149    CH3    CH3     CH3    Cl    X30    SCH3      -
表4：式(Id)化合物：
化合物   R36    R37    W    R1     X      R2        物理数据
序号
4,001    CH3    CH3    O    CH3    X1     SO2CH3    -
4,002    CH3    CH3    O    CH3    X2     SO2CH3    -
4,003    CH3    CH3    O    CH3    X3     SO2CH3    -
4,004    CH3    CH3    O    CH3    X4     SO2CH3    -
4,005    CH3    CH3    O    CH3    X5     SO2CH3    -
4,006    CH3    CH3    O    CH3    X6     SO2CH3    -
4,007    CH3    CH3    O    CH3    X7     SO2CH3    -
4,008    CH3    CH3    O    CH3    X8     SO2CH3    -
4,009    CH3    CH3    O    CH3    X9     SO2CH3    -
4,010    CH3    CH3    O    CH3    X10    SO2CH3    -
4,011    CH3    CH3    O    CH3    X11    SO2CH3    -
4,012    CH3    CH3    O    CH3    X12    SO2CH3    -
4,013    CH3    CH3    O    CH3    X13    SO2CH3    -
4,014    CH3    CH3    O    CH3    X14    SO2CH3    -
4,015    CH3    CH3    O    CH3    X15    SO2CH3    -
4,016    CH3    CH3    O    CH3    X16    SO2CH3    -
4,017    CH3    CH3    O    CH3    X17    SO2CH3    -
4,018    CH3    CH3    O    CH3    X18    SO2CH3    -
4,019    CH3    CH3    O    CH3    X19    SO2CH3    -
4,020    CH3    CH3    O    CH3    X20    SO2CH3    -
4,021    CH3    CH3    O    CH3    X21    SO2CH3    -
4,022    CH3    CH3    O    CH3    X22    SO2CH3    -
4,023    CH3    CH3    O    CH3    X23    SO2CH3    -
4,024    CH3    CH3    O    CH3    X24    SO2CH3    -
4,025    CH3    CH3    O    CH3    X25    SO2CH3    -
4,026    CH3    CH3    O    CH3    X26    SO2CH3    -
4,027    CH3    CH3    O    CH3    X27    SO2CH3    -
4,028    CH3    CH3    O    CH3    X28    SO2CH3    -
4,029    CH3    CH3    O    CH3    X29    SO2CH3    -
4,030    CH3    CH3    O    CH3    X30    SO2CH3    -
4,031    CH3    CH3    O    CH3    X31    SO2CH3    -
化合物 R36    R37    W    R1     X      R2        物理数据
序号
4,032  CH3    CH3    O    CH3    X32    SO2CH3    -
4,033  CH3    CH3    O    CH3    X33    SO2CH3    -
4,034  CH3    CH3    O    CH3    X34    SO2CH3    -
4,035  CH3    CH3    O    CH3    X35    SO2CH3    -
4,036  CH3    CH3    O    CH3    X36    SO2CH3    -
4,037  CH3    CH3    O    CH3    X37    SO2CH3    -
4,038  CH3    CH3    O    CH3    X38    SO2CH3    -
4,039  CH3    CH3    O    CH3    X39    SO2CH3    -
4,040  CH3    CH3    O    CH3    X40    SO2CH3    -
4,041  CH3    CH3    O    CH3    X41    SO2CH3    -
4,042  CH3    CH3    O    CH3    X42    SO2CH3    -
4,043  CH3    CH3    O    CH3    X1     SCH3      -
4,044  CH3    CH3    O    CH3    X2     SCH3      -
4,045  CH3    CH3    O    CH3    X3     SCH3      -
4,046  CH3    CH3    O    CH3    X4     SCH3      -
4,047  CH3    CH3    O    CH3    X5     SCH3      -
4,048  CH3    CH3    O    CH3    X6     SCH3      -
4,049  CH3    CH3    O    CH3    X7     SCH3      -
4,050  CH3    CH3    O    CH3    X10    SCH3      -
4,051  CH3    CH3    O    CH3    X15    SCH3      -
4,052  CH3    CH3    O    CH3    X20    SCH3      -
4,053  CH3    CH3    O    CH3    X21    SCH3      -
4,054  CH3    CH3    O    CH3    X26    SCH3      -
4,055  CH3    CH3    O    CH3    X27    SCH3      -
4,056  CH3    CH3    O    CH3    X29    SCH3      -
4,057  CH3    CH3    O    CH3    X30    SCH3      -
4,058  CH3    CH3    O    Cl     X1     SO2CH3    -
4,059  CH3    CH3    O    Cl     X2     SO2CH3    -
4,060  CH3    CH3    O    Cl     X3     SO2CH3    -
4,061  CH3    CH3    O    Cl     X4     SO2CH3    -
4,062  CH3    CH3    O    Cl     X5     SO2CH3    -
化合物   R36    R37    W    R1    X      R2        物理数据
序号
4,063    CH3    CH3    O    Cl    X6     SO2CH3    -
4,064    CH3    CH3    O    Cl    X7     SO2CH3    -
4,065    CH3    CH3    O    Cl    X8     SO2CH3    -
4,066    CH3    CH3    O    Cl    X9     SO2CH3    -
4,067    CH3    CH3    O    Cl    X10    SO2CH3    -
4,068    CH3    CH3    O    Cl    X11    SO2CH3    -
4,069    CH3    CH3    O    Cl    X12    SO2CH3    -
4,070    CH3    CH3    O    Cl    X13    SO2CH3    -
4,071    CH3    CH3    O    Cl    X14    SO2CH3    -
4,072    CH3    CH3    O    Cl    X15    SO2CH3    -
4,073    CH3    CH3    O    Cl    X16    SO2CH3    -
4,074    CH3    CH3    O    Cl    X17    SO2CH3    -
4,075    CH3    CH3    O    Cl    X18    SO2CH3    -
4,076    CH3    CH3    O    Cl    X19    SO2CH3    -
4,077    CH3    CH3    O    Cl    X20    SO2CH3    -
4,078    CH3    CH3    O    Cl    X21    SO2CH3    -
4,079    CH3    CH3    O    Cl    X22    SO2CH3    -
4,080    CH3    CH3    O    Cl    X23    SO2CH3    -
4,081    CH3    CH3    O    Cl    X24    SO2CH3    -
4,082    CH3    CH3    O    Cl    X25    SO2CH3    -
4,083    CH3    CH3    O    Cl    X26    SO2CH3    -
4,084    CH3    CH3    O    Cl    X27    SO2CH3    -
4,085    CH3    CH3    O    Cl    X28    SO2CH3    -
4,086    CH3    CH3    O    Cl    X29    SO2CH3    -
4,087    CH3    CH3    O    Cl    X30    SO2CH3    -
4,088    CH3    CH3    O    Cl    X31    SO2CH3    -
4,089    CH3    CH3    O    Cl    X32    SO2CH3    -
4,090    CH3    CH3    O    Cl    X33    SO2CH3    -
4,091    CH3    CH3    O    Cl    X34    SO2CH3    -
4,092    CH3    CH3    O    Cl    X35    SO2CH3    -
4,093    CH3    CH3    O    Cl    X36    SO2CH3    -
化合物   R36    R37    W    R1     X      R2        物理数据
序号
4,094    CH3    CH3    O    Cl     X37    SO2CH3    -
4,095    CH3    CH3    O    Cl     X38    SO2CH3    -
4,096    CH3    CH3    O    Cl     X39    SO2CH3    -
4,097    CH3    CH3    O    Cl     X40    SO2CH3    -
4,098    CH3    CH3    O    Cl     X41    SO2CH3    -
4,099    CH3    CH3    O    Cl     X42    SO2CH3    -
4,100    CH3    CH3    O    CH3    X1     CF3       -
4,101    CH3    CH3    O    CH3    X2     CF3       -
4,102    CH3    CH3    O    CH3    X3     CF3       -
4,103    CH3    CH3    O    CH3    X4     CF3       -
4,104    CH3    CH3    O    CH3    X6     CF3       -
4,105    CH3    CH3    O    CH3    X10    CF3       -
4,106    CH3    CH3    O    CH3    X15    CF3       -
4,107    CH3    CH3    O    CH3    X21    CF3       -
4,108    CH3    CH3    O    CH3    X26    CF3       -
4,109    CH3    CH3    O    CH3    X30    CF3       -
4,110    CH3    CH3    O    NO2    X1     SO2CH3    -
4,111    CH3    CH3    O    NO2    X2     SO2CH3    -
4,112    CH3    CH3    O    NO2    X4     SO2CH3    -
4,113    CH3    CH3    O    NO2    X26    SO2CH3    -
4,114    CH3    CH3    O    NO2    X1     CF3       -
4,115    CH3    CH3    O    NO2    X2     CF3       -
4,116    CH3    CH3    O    NO2    X4     CF3       -
4,117    CH3    CH3    O    NO2    X26    CF3       -
4,118    CH3    C2H5   O    CH3    X1     SO2CH3    -
4,119    CH3    C2H5   O    CH3    X2     SO2CH3    -
4,120    CH3    C2H5   O    CH3    X3     SO2CH3    -
4,121    CH3    C2H5   O    CH3    X4     SO2CH3    -
4,122    CH3    C2H5   O    CH3    X6     SO2CH3    -
4,123    CH3    C2H5   O    CH3    X10    SO2CH3    -
4,124    CH3    C2H5   O    CH3    X15    SO2CH3    -
化合物 R36    R37    W    R1     X     R2        物理数据
序号
4,125  CH3    C2H5   O    CH3    X21   SO2CH3    -
4,126  CH3    C2H5   O    CH3    X26   SO2CH3    -
4,127  CH3    C2H5   O    CH3    X30   SO2CH3    -
4,128  C2H5   C2H5   O    CH3    X1    SO2CH3    -
4,129  C2H5   C2H5   O    CH3    X2    SO2CH3    -
4,130  C2H5   C2H5   O    CH3    X4    SO2CH3    -
4,131  C2H5   C2H5   O    CH3    X10   SO2CH3    -
4,132  C2H5   C2H5   O    CH3    X15   SO2CH3    -
4,133  C2H5   C2H5   O    CH3    X21   SO2CH3    -
4,134  C2H5   C2H5   O    CH3    X26   SO2CH3    -
4,135  CH3    CH3    O    Cl     X1    SCH3      -
4,136  CH3    CH3    O    Cl     X2    SCH3      -
4,137  CH3    CH3    O    Cl     X3    SCH3      -
4,138  CH3    CH3    O    Cl     X4    SCH3      -
4,139  CH3    CH3    O    Cl     X5    SCH3      -
4,140  CH3    CH3    O    Cl     X6    SCH3      -
4,141  CH3    CH3    O    Cl     X7    SCH3      -
4,142  CH3    CH3    O    Cl     X10   SCH3      -
4,143  CH3    CH3    O    Cl     X15   SCH3      -
4,144  CH3    CH3    O    Cl     X20   SCH3      -
4,145  CH3    CH3    O    Cl     X21   SCH3      -
4,146  CH3    CH3    O    Cl     X26   SCH3      -
4,147  CH3    CH3    O    Cl     X27   SCH3      -
4,148  CH3    CH3    O    Cl     X29   SCH3      -
4,149  CH3    CH3    O    Cl     X30   SCH3      -
4,150  CH3    CH3    S    CH3    X1    SO2CH3    -
4,151  CH3    CH3    S    CH3    X2    SO2CH3    -
4,152  CH3    CH3    S    CH3    X4    SO2CH3    -
4,153  CH3    CH3    S    CH3    X26   SO2CH3    -
4,154  CH3    CH3    S    Cl     X1    SO2CH3    -
4,155  CH3    CH3    S    Cl     X2    SO2CH3    -
化合物  R36    R37    W     R1     X      R2        物理数据
序号
4,156   CH3    CH3    S     Cl     X4     SO2CH3    -
4,157   CH3    CH3    S     Cl     X26    SO2CH3    -
4,158   CH3    CH3    NCH3  CH3    X1     SO2CH3    -
4,159   CH3    CH3    NCH3  CH3    X2     SO2CH3    -
4,160   CH3    CH3    NCH3  CH3    X4     SO2CH3    -
4,161   CH3    CH3    NCH3  CH3    X26    SO2CH3    -
4,162   H      H      O     CH3    X1     SO2CH3    -
4,163   H      H      O     CH3    X2     SO2CH3    -
4,164   H      H      O     CH3    X4     SO2CH3    -
4,165   H      H      O     CH3    X26    SO2CH3    -
生物学实施例
实施例B1：芽前除草活性
单子叶和双子叶试验植物种植在塑料盆里的标准土壤中。种植后立即喷洒浓度为2kg活性物质/公顷的试验化合物的水悬浮液(按照WO97/34485的25％可湿性粉剂(实施例F3，b)制备)，或者试验化合物的乳液[由25％的乳油(实施例F1c)制备](500L水/公顷)。然后将试验植物于最佳条件下在温室中培育，3周以后按照1-9级进行评价 实验结果：(1＝全部损害，9＝无作用)，1-4级(特别是1-3级)说明除草效果良好至很好。
表B1：芽前活性
试验植物    狗尾草属  莎草属  白芥属     茄属  繁缕属  剂量
                             (Sinapsis)(Solanig)       [g/AS/ha]
活性成分
序号
1,001       3         3       3          2      2      2000
2,001       3         3       2          2      2      2000
按照WO97/34485实施例F2和F4-F8方法加工配制式I化合物，得到同样的结果。
实施例B2：苗后除草活性
在温室中，将单子叶和双子叶试验植物种植在塑料盆里的标准土壤中，在4-6叶期用从25％可湿性粉剂[WO97/34485(实施例F3，b)]制备的式I试验化合物的水悬浮液喷雾，或者用从25％乳油[WO97/34485(实施例F1c)]制备的式I试验化合物的乳液喷雾，喷洒浓度为2kg活性物质/公顷(500L水/公顷)。在温室中于最佳条件下进一步培育试验植物。18天以后按照1-9级进行评价实验结果：(1＝全部损害，9＝无作用)，1-4级(特别是1-3级)说明除草效果良好至很好。在上述试验中，式I化合物表现出杰出的除草活性。
表B2：苗后活性
试验植物    狗尾草属    莎草属    白芥属   茄属   繁缕属   剂量
                                                          [g/AS/ha]
活性成分
序号
1,001        2          3          2        2      2       2000
2,001        3          3          2        2      4       2000
按照WO97/34485实施例F2和F4-F8方法加工配制式I化合物，得到同样的结果。

Claims (7)

1.式I化合物：
Figure C998148850002C1
其中
X是L1-Y1-R4；
L1是C1-C6亚烷基；
Y1是氧；
R1和R2彼此独立地是C1-C6烷基或C1-C6烷基磺酰基；
R3是氢；
R4是C1-C6烷基；
Q是基团Q1：
Figure C998148850002C2
其中
R39是羟基；
V是C1-C4亚烷基；
R17、R18、R19、R20、R21和R22彼此独立地是氢；
q是1；
或者Q是基团Q2：
Figure C998148850003C1
其中
R23是羟基；
R24和R25彼此独立地是C1-C6烷基；
R26是C1-C4烷基；
以及上述化合物的农业上可接受的盐。
2.根据权利要求1的化合物，其中L1是亚甲基。
3.根据权利要求1的化合物，其中R2是C1-C6烷基磺酰基。
4.一种除草和植物生长抑制组合物，其中包括除草有效量的式I化合物和惰性载体。
5.一种控制不需要的植物生长的方法，包括使用除草有效量的式I化合物或者含有所述化合物的组合物处理植物或其生长场所。
6.一种抑制不需要的植物生长的方法，包括使用除草有效量的式I化合物或者含有所述化合物的组合物处理植物或其生长场所。
7.根据权利要求4的组合物在控制不需要的植物生长上的用途。
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