CN1040754C - 3－(取代的酮和醇)－2－(2－咪唑啉－2－基)吡啶和喹啉、制备方法和除草剂 - Google Patents

3－(取代的酮和醇)－2－(2－咪唑啉－2－基)吡啶和喹啉、制备方法和除草剂 Download PDF

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CN1040754C
CN1040754C CN93106165.2A CN93106165A CN1040754C CN 1040754 C CN1040754 C CN 1040754C CN 93106165 A CN93106165 A CN 93106165A CN 1040754 C CN1040754 C CN 1040754C
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P·J·韦普罗
小A·D·克鲁斯
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Abstract

本发明记述了能有效防治不需要植物种类的3-(取代的酮和醇)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物。同时也记述了该化合物的用于除草及其制备方法。

Description

3－(取代的酮和醇)－2－(2－咪唑啉－2－基)吡啶和喹啉、制备方法和除草剂
本发明涉及新颖的3-(取代的酮和醇)-2-(2-咪唑啉-2-基)吡啶和喹啉、它们的制备方法以及它们作为除草剂的应用。
杂草由于降低作物的产率和质量而引起全球范围巨大的经济损失。在美国，作物必须与1,800种不同的杂草竞争。因而，在本技术领域正开展着研究以发明更有效和/或更具选择性的除草剂。
美国专利4,798,619揭示了大量有效的除草剂，包括3-(苯甲酰基和羟烷基)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物。尽管这些化合物和其它已知除草剂可能是有效的除草剂，但环境已日益受到关注，因而人们已加倍努力着手发现更有效的除草剂，即那些能以低比率使用却仍对广谱的不需要植物品种具有相同或更好的控制。
本发明的目的是提供可非常有效地防治不需要的植物种类的化合物。
具体地说，本发明提供作为有益于防治不需要的植物种类的除草剂的3-(取代的酮和醇)-2-(2-咪唑啉-2-基)-吡啶和喹啉化合物及它们的制备方法。
本发明的目的还在于提供含上述3-(取代的醇和醇)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物的除草剂组合物以及使用上述化合物防治不需要植物种类的方法。
本发明的3-(取代的酮)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物如式I所示，本发明的3-(取代的醇)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物如式II所示：
Figure C9310616500101
其中：R是C1-C4烷基；R1是C1-C4烷基或C3-C6环烷基；当R和R1与它们连接的碳原子合在一起时，它们代表可被甲基任意取代的C3-C6环烷基；Q是R2、R3和R4独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基或可被一或二个卤原子、C1-C4烷基或卤代烷基或C1-C4烷氧基或卤代烷氧基任意取代的苯基；m是1或2的整数；A是O、S或NR5；条件是m是2，A是O；R5是C1-C4烷基；B是氢、COR6或SO2R7；R6是C1-C11烷基、氯甲基或可被一个氯、一个硝基或一个甲氧基任意取代的苯基；R7是C1-C4烷基或可被一个甲基任意取代的苯基；W是O或S；X是氢、卤素或甲基；Y和Z独立地是氢、卤素、C1-C6烷基、C1-C4烷氧甲基、C1-C6烷氧基、C1-C4烷硫基、苯氧基、C1-C4卤代烷基、硝基、氰基、C1-C4烷基磺酰基或可被一个C1-C4烷基、C1-C4烷氧基或卤素任意取代的苯基；并且当它们联在一起，Y和Z可形成环即YZ，其结构式是：-(CH2)n-，其中n选自整数3和4；或其中R8、R9、R10和R11独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基、硝基、氰基、苯基、苯氧基、氨基、氯苯基、甲苯基或可被一个氯、三氟甲基、硝基或甲基取代的苯氧基，条件是仅R8、R9、R10和R11中的一个可代表除氢、卤素、C1-C4烷基或C1-C4烷氧基以外的取代基；以及当R和R1不同时，它们的光学异构体。
尽管3-(苯甲酰基和羟烷基)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物是已知的，出乎意料地，本发明的3-(取代的酮和醇)-2-(2-咪唑啉-2-基)嘧啶和喹啉化合物在低剂量即能较好地防治不需要的植物种类。
出人意料地，已发现本发明的式I和式II化合物在低剂量使用时，尤其在芽后用药，是比现有技术中已知的3-(苯甲酰基和羟烷基)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物更有效的除草剂。与3-(苯甲酰基羟烷基)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物相比，本发明还具有可在更低的剂量防治更广泛的不需要的植物种类的优点。自然，低剂量是理想的，因为这意味着增加了对农民和环境的安全性。
对防治不需要的植物种类特别有效的本发明优选的3-(取代的酮和醇)-2-(2-咪唑啉-2-基)吡啶和喹啉化合物如式III和IV所示：其中R2、R3、R4和m如上所述；A是O或S；Y和Z独立地是氢、卤素、C1-C6烷基、C1-C4烷氧甲基或C1-C6烷氧基，并且当联在一起时，Y和Z可形成环即YZ，其结构如下：
              -CH＝CH-CH＝CH-。
本发明特别优选的化合物是式中R3是氢且R2和R4独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基或C1-C4卤代烷氧基的式III化合物。
以上所述的卤素是例如氟、氯、溴和碘。术语“卤代烷基”所定义的是具式CpHqMr的化合物，其中M是卤素，p、q和r为整数且q+r＝2p+1。术语“卤代烷氧基”所定义的是具式CpHqMrO的化合物，其中M是卤素，p，q和r是整数且q+r＝2p+1。
式中m是2的式I和式II化合物可以如流程图I所示制备。
         流程图I
Figure C9310616500131
将被适当取代的式V的2-(2-咪唑基-2-基)吡啶或喹啉酸，在非质子传递溶剂如二氯甲烷或四氢呋喃的存在下，最好于约20-32℃，与约1当量的脱水剂如二异丙基碳化二亚胺或二环己基碳化二亚胺(DCC)反应，生成式VI化合物。然后在有机溶剂如四氢呋喃的存在下，最好在约-78至30℃，将所述的式VI化合物与1当量或大于1当量的被适当取代的式VII的锂试剂反应，得到所需的式I和式II化合物。
式中m是1的式II化合物可以如流程图II所示制备。
          流程图II
Figure C9310616500141
将被适当取代的式VIII的咪唑啉酮化合物在惰性溶剂如四氢呋喃的存在下，最好在约-80℃至0℃，与至少约2.0摩尔当量C1-C4烷基锂(所述C1-C4烷基锂可选自正丁基钾和甲基锂)反应。然后将所生成的盐在惰性溶剂如四氢呋喃中，最好在约-80℃至40℃，与至少约1.0摩尔当量的被适当取代的式IX的醛化合物反应，得到所需的式II化合物。
有利地，将由此生成的式中m是1的式III化合物在惰性溶剂如氯仿存在下，最好在约20-80℃，与氧化剂如二氧化锰(IV)反应，生成式I化合物。反应式如流程图III所示。
         流程III
Figure C9310616500142
式V、VI和VIII化合物及它们的制法已在美国专利4,798,619中说明。
式I和式II的N-取代衍生物(式中B是COR6或SO2R7；m是2；且R、R1、Q、R2、R3、R4、A、R5、W、X、Y和Z如上所述)可通过将B是氢的适当取代的式I或式II化合物与过量的酰基卤、酸酐或磺酰卤独自或在溶剂如吡啶或甲苯中，在约50-125℃进行反应而加以制备。
m是1且B是COR6或SO2R7的式II化合物可以通过用还原剂如硼氢化钠还原式中B是COR6或SO2R7的式I化合物来制备。
本发明的式I的3-(取代的酮)-2-(2-咪唑啉-2-基)吡啶和喹啉以及式II的3-(取代的醇)-2-(2-咪唑啉-2-基)吡啶和喹啉是有效的除草剂，可广谱防治不同的草本和木本的、一年生和多年生的、单子叶和双子叶植物。这些化合物对生长于旱地和潮湿地域的杂草均能有效地防治。当施用于上述植株的叶部或土壤或含种子的水或所述植株其它繁殖器官如匍匐茎，块茎或根茎，化合物对防治上述植物是有效的，其使用比率为约0.0016-4.0kg/ha，最好为约0.125-4.0kg/ha。
已经发现本发明的化合物最适于用作广谱除草剂，尤其适用于芽后杂草防治。然而这并不是说，本发明的所有化合物是无选择性的。实际上，本发明的一些化合物是对豆科作物具有选择性，例如大豆。
本发明的式I或II化合物可以以固态或液态除草组合物的形式施用于作物，所述组合物包含分散或溶解于惰性固体或液体载体中的除草有效量的式I或II化合物。配成的制剂可作杂草的芽前或芽后处理。
式I和式II化合物可配成浓缩乳剂、可湿性粉剂、颗粒剂、胶悬剂等等。
为了便于进一步理解本发明，给出下列实施例以说明其更具体的细节。本发明并未由此得到限制，除非在权利要求书中限定。
        实施例1
4-异丙基-4-甲基-2-[5-甲基-3-(2-噻吩甲酰基)-2-吡啶基]-2-咪唑啉
         -5-酮的制备
Figure C9310616500161
将噻吩(3.3mL)的无水四氢呋喃(150mL)溶液冷却至-78℃，并用2.5摩尔正丁基锂的己烷(16.8mL)溶液处理30分钟。加入2-异丙基-2，7-二甲基-5H-咪唑并[1′，2′：1，2]吡咯并[3，4-b]吡啶-3(2H)，5-二酮(10.19g，0.0396摩尔)，室温搅拌反应混合物三天，用水稀释并用乙酸乙酯萃取。用盐水洗涤合并的有机萃取液，干燥(Na2SO4)并真空浓缩得到无色油状物。用硅胶和含30％己烷的乙醚混合物将该油状物层析分离，得到为白色固体的2-[3-〔羟基二(2-噻吩甲基)〕-5-甲基-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮(1.0g，mp 190-191℃)及为白色固体的4-异丙基-4-甲基-2-[5-甲基-3-(2-噻吩甲酰基)-2-吡啶基]-2-咪唑啉-5-酮(0.45g，mp168-170℃)。
采用基本相同的步骤并使用适当取代的5H-咪唑并[1′，2′：1，2]吡咯并[3，4-b]吡啶-3(2H)，5-二酮和适当的噻吩或呋喃，得到下列化合物。A       Y                 Z          mp°O       H                 H          145-146S       H                 H          144-145O       CH3              H          159-160O       C2H5            H          108-110S       C2H5            H          153-154O       CH2OCH3         H          123-125S       CH2OCH3         H          144-147S         -CH＝CH-CH＝CH-             235-238A       Y                Z                mp°O       H                H                138-139O       CH3             H                133-134O       CH2OCH3        H                138-140
         实施例2
2-[3-(α-羟基-5-甲基-2-噻吩甲基)
-5-甲基-2-吡啶基]-4-异丙基-4-
甲基-2-咪唑啉-5-酮的制备
将搅拌的4-异丙基-4-甲基-2-(5-甲基-2-吡啶基)-2-咪唑啉-5-酮(10.0g，0.043mol)的无水四氢呋喃(200mL)溶液冷却至-78℃，并用1.5mol甲基锂的乙醚(60.6mL)溶液处理。将生成的悬浮液在-78℃搅拌30分钟，在0℃搅拌30分钟。再将反应混合物冷却至-78℃，滴加5-甲基-2-噻吩甲醛(15.35g，0.043mol)。30分钟后，移去冷却浴并在室温将该反应混合物搅拌过夜，然后用水稀释。用乙酸将该含水混合物酸化至pH6并用乙醚萃取。合并的有机萃取液用水洗涤，干燥(Na2SO4)并真空浓缩以得到橙色油状物。将该油状物用硅胶和含20％乙醚的二氯甲烷混合物进行层析，得到黄色油状物，将其与乙醚共研，得到标题产物，为白色固体(2.0g，mp 147-148℃)。
采用基本相同的步骤并使用适当取代的2-(2-吡啶基)-2-咪唑啉-5-酮和适当的2-噻吩甲醛或2-呋喃醛，得到下列化合物：
Figure C9310616500191
A     Y         Z           R2       R3     R4      mp℃O     H         H           H         H       H       151-158O     H         H           CH3      H       H       玻璃状S     H         H           H         H       CH3    玻璃状O     CH3      H           H         H       H       163-175O     CH3      H           CH3      H       H       130-135O     CH3      H           C2H5   H       H       油状物S     CH3      H           H         H       CH3    123-127O     C2H5    H           H         H       H       115-121S     C2H5    H           H         H       H       140-155O     C2H5    H           CH3      H       H       液体S     C2H5    H           CH3      H       H       120-122O     C2H5    H           C2H5   H       H       118-121S     C2H5    H           H         H       CH3    121-123S     C2H5    H           Cl        H       H       131-133S     -CH＝CH-CH＝CH-       H         H       H       168-170S     -CH＝CH-CH＝CH-       CH3      H       H       179-185
        实施例3
4-异丙基-4-甲基-2-[5-甲基-3-(5-甲基-2-噻吩甲酰基)-2-吡啶基]-2-
     咪唑啉-5-酮的制备
将2-[(3-(α-羟基-5-甲基-2-噻吩甲基)-5-甲基-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮(1.35g，0.0038mol)的氯仿(75mL)溶液用二氧化锰(10g，0.12mol)处理并加热至60℃。10分钟后，再加入二氧化锰(10g)并在60C搅拌该反应混合物2小时，冷却至室温并通过硅藻土过滤。真空浓缩滤液，得到残余物，用乙醚结晶，得到标题产物，为白色固体(1.2g，mp 173-175℃)。
采用基本相同的步骤并使用适当取代的2-{3-[α-羟基-2-(噻吩甲基或糠基)]-2-吡啶基}-2-咪唑啉-5-酮，得到下列化合物：
Figure C9310616500202
A       Y                R2          R3        R4      mp℃S       H                H            H          CH3     150-152S       CH3             H            H          CH3     173-178O       C2H5          CH3         H          H        106-108S       C2H5          CH3         H          H        140-142S       C2H5          H            H          CH3     玻璃状S       C2H5          Cl           H          H        玻璃状
实施例4
实验化合物的芽前除草评估
通过下列实验举例说明本发明化合物的芽前除草活性，实验中将大量的单子叶和双子叶植物的种子分别与盆栽土混合并植入各量杯中约1英寸的土的表面上。植入后，用充足量的含所选实验化合物的含水丙酮溶液喷洒这些杯子，以提供每杯相当于每公顷约0.125-4.0kg实验化合物。然后将处理后的杯子放在暖房架上，按常规暖房步骤浇灌并管理。处理后的4-5星期起，中止实验，检查每个杯子并按上述评估系统评价。所得的数据列于下述表I中。当一个已知化合物进行不止一次实验时，则将数据平均。
在这些评估中使用的植物种类用词首缩写、俗名和学名记录。
在此芽前除草评估中及其芽后除草评估的实施例中所使用的化合物被编号并以其名称区分。表I中数据以化合物编号列出。除草评价等级
除草评估的结果以评价等级(0-9)来表达。等级是以与对照相比，目测到的植株直立、存活、畸形、大小、枯黄和总体植株外形为依据的。等级            含义                        ％与对组照相比
                                        的％率防治9               完全杀死                    1008               几乎完全杀死                91-997               良好的除草效果              80-906               有除草效果                  65-795               一定的杀伤作用              45-644               有杀伤作用                  30-443               有中等作用                  16-292               有轻微作用                  6-151               几乎无效                    1-50               无效                        0
                     除草评估中所用的植物种类词首缩写                 俗名                      学名Barnydgr                 稗                        ECHINOCHLOA CRUS-
                                               GALLI，(L)BEAUFoxtail Sp               狗尾草                    SETAIA SPP.Wild Oats                野燕麦                    AVENA FATUA，L.Quackgrass               硬叶冰草                  AGROPYRON REPENS，
                                               (L)BEAUVFld Bindwd               田旋花                    CONVOLVULUS AR-
                                               VENSIS，(RHIZOME)L.Mrnglry Sp               牵牛属                    IPOMOEA SPPWild Mustd               田芥菜                    BRASSICA KABER，(DC)
                                               L.C.WHEELRVelvetleaf               苘麻                      ABUTILON
                                               THEOPHRASTI，MEDIC.Wht Fenman Fenman        小麦                      TRITICUM AESTIVUM，
                                               FENMANCorn Field，             大田玉米                  ZEA MAYS，L.Cotton                   棉花                      GOSSYPIUM HIRSU-
                                               TUM，L.Soybean                  大豆                      GLYCINE MAX
               作为除草剂评估的化合物化合物编号1        2-[3-(2-糠酰基)-2-吡啶基]-4-异丙基-4-甲基-2-咪唑
     啉-5-酮2        4-异丙基-4-甲基-2-[3-(3-甲基-2-噻吩甲酰基)-2-吡
     啶基]-2-咪唑啉-5-酮3        4-异丙基-4-甲基-2-[3-(2-噻吩甲酰基)-2-吡啶基]-2-
     咪唑啉-5-酮4        2-[3-(2-糠酰基)-5-甲基-2-吡啶基]-4-异丙基-4-甲基
     -2-咪唑啉-5-酮5        4-异丙基-4-甲基-2-[5-甲基-3-(2-噻吩甲酰基)-2-吡
     啶基]-2-咪唑啉-5-酮6        4-异丙基-4-甲基-2-[5-甲基-3-(5-甲基-2-噻吩甲酰
     基)-2-吡啶基]-2-咪唑啉-5-酮7        4-异丙基-4-甲基-2-[5-甲基-3-(3-甲基-2-噻吩甲酰
     基)-2-吡啶基]-2-咪唑啉-5-酮8        2-[5-乙基-3-(2-糠酰基)-2-吡啶基]-4-异丙基-4-甲基
     -4-甲基-2-咪唑啉-5-酮9        2-[5-乙基-3-(2-噻吩甲酰基)-2-吡啶基]-4-异丙基-4-
     甲基-2-咪唑啉-5-酮10       2-[5-乙基-3-(5-甲基-2-糠酰基]-4-异丙基-4-甲基-2-
     咪唑啉-5-酮11       2-[5-乙基-3-(5-甲基-2-噻吩甲酰基)-2-吡啶基]-4-异
     丙基-4-甲基-2-咪唑啉-5-酮12       2-[5-乙基-3-(3-甲基-2-噻吩甲酰基)-2-吡啶基]-4-异
     丙基-4-甲基-2-咪唑啉-5-酮13       2-[3-(5-氯代-2-噻吩甲酰基)-5-乙基)-2-吡啶基]-4-
     异丙基-4-甲基-2-咪唑啉-5-酮14       2-[3-(2-糠酰基)-5-(甲氧甲基)-2-吡啶基]-4-异丙基-
     4-甲基-2-咪唑啉-5-酮15       4-异丙基-2-[5-(甲氧苯基)-3-(2-噻吩甲酰基)-2-吡啶
     基-4-甲基-2-咪唑啉-5-酮16       4-异丙基-4-甲基-2-[3-(2-噻吩甲酰基)-2-喹啉基]-2-
     咪唑啉-5-酮17       2-[3-(α-羟基糠基)-2-吡啶基]-4-异丙基-4-甲基-2-
     咪唑啉-5-酮18       2-[3-(α-羟基-5-甲基糠基)-2-吡啶基]-4-异丙基-4-甲
     基-2-咪唑啉-5-酮19       2-[3-(α-羟基-3-甲基-2-噻吩甲基)-2-吡啶基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮20       2-[3-(α-羟基糠基)-5-甲基-2-吡啶基]-4-异丙基-4-甲
     基-2-咪唑啉-5-酮21       2-[3-(α-羟基-5-甲基糠基)-5-甲基-2-吡啶基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮22       2-[3-(α-羟基-5-甲基-2-噻吩甲基)-5-甲基-2-吡啶
     基]-4-异丙基-4-甲基-2-咪唑啉-5-酮23       2-[3-(5-乙基-α-羟基糠基)-5-甲基-2-吡啶基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮24       2-[3-(α-羟基-3-甲基-2-噻吩甲基)-5-甲基-2-吡啶
     基]-4-异丙基-4-甲基-2-咪唑啉-5-酮25       2-[5-乙基-3-(α-羟基糠基)-2-吡啶基]-4-异丙基-4-甲
     基-2-咪唑啉-5-酮26       2-[5-乙基-3-(α-羟基-2-噻吩甲基)-2-吡啶基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮27       2-[5-乙基-3-(α-羟基-5-甲基糠基)-2-吡啶基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮28       2-[5-乙基-3-(α-羟基-5-甲基-2-噻吩甲基)-2-吡啶
     基]-4-异丙基-4-甲基-2-咪唑啉-5-酮29       2-[5-乙基-3-(5-乙基-α-羟基糠基)-2-吡啶基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮30       2-[5-乙基-3-(α-羟基-3-甲基-2-噻吩甲基)-2-吡啶
     基]-4-异丙基-4-甲基-2-咪唑啉-5-酮31       2-[3-(5-氯代-α-羟基-2-噻吩甲基)-5-乙基-2-吡啶
     基]-4-异丙基-4-甲基-2-咪唑啉-5-酮32       2-[3-(α-羟基-2-噻吩甲基)-2-喹啉基]-4-异丙基-4-甲
     基-2-咪唑啉-5-酮33       2-[3-(α-羟基-5-甲基-2-噻吩甲基)-2-喹啉基]-4-异丙
     基-4-甲基-2-咪唑啉-5-酮34       2-{3-[二(2-呋喃基)羟基甲基]-2-吡啶基}-4-异丙基
     -4-甲基-2-咪唑啉-5-酮35       2-{3-〔二(2-呋喃基)羟基甲基〕-5-甲基-2-吡啶基}-4-
     异丙基-4-甲基-2-咪唑啉-5-酮36       2-{3-〔二(2-呋喃基)羟基甲基〕-5-甲氧甲基-2-吡啶
     基}-4-异丙基-4-甲基-2-咪唑啉-5-酮
                                      表I
                             供试化合物芽前除草评估
        使用比率 Barny     Foxta   Wild   Quack   Fld B   Mrngl   Wild    Velve   Wht F   Corn    Cot    Soy化合物编号
        (kg/ha)  ardgr     il Sp   oats   grass   indwd   ry Sp   mustd   tleaf   enman   field   ton    bean1            4.000    8.0      -       7.0    9.0     9.0     8.0     9.0     8.0     -       -       -      -
         .500     7.0      9.0     9.0    9.0     9.0     9.0     9.0     9.0     9.0     9.0     9.0    8.0
         .125     6.0      9.0     9.0    9.0     9.0     8.0     9.0     9.0     9.0     9.0     9.0    7.02            4.000    9.0      -       8.0    9.0     9.0     8.0     9.0     8.0     -       -       -      -
         .500     7.0      9.0     9.0    7.0     9.0     7.0     9.0     8.0     9.0     9.0     9.0    8.0
          .125    1.4      4.0     0.0    2.0     4.0     1.7     8.0     2.0     8.0     7.0     4.0    0.03            4.000    8.0      7.0     9.0    9.0     7.0     9.0     8.0     -       -       -       -      -
         .500     7.0      9.0     9.0    9.0     9.0     8.0     9.0     9.0     9.0     9.0     9.0    7.0
         .125     5.0      5.0     7.0    9.0     9.0     5.0     9.0     8.0     7.0     4.0     7.0    4.04            .500     9.0      9.0     9.0    9.0     9.0     9.0     9.0     9.0     9.0     9.0     9.0    8.0
         .125     6.0      7.0     9.0    0.0     9.0     6.0     9.0     8.0     6.0     8.0     8.0    8.05            .500     8.0      8.0     8.0    0.0     8.0     8.0     9.0     8.0     5.0     8.0     6.0    7.0
         .125     0.0      2.0     0.0    0.0     0.0     0.0     8.0     2.0     0.0     0.0     0.0    0.0
                                    表I(续)化合物
    使用比率  Barny   Foxta   Wild    Quack   Fld B   Mrngl   Wild    Velve   Wht F   Corn   Cot    Soy编号
    (kg/ha)   ardgr   il Sp   oats    grass   indwd   ry Sp   mustd   tleaf   enman   field  ton    bean6       4.000    8.0     -       8.0     9.0     9.0     8.0     9.0     9.0     -       -      -      -
     .500     5.0     4.0     1.5     1.5     4.5     4.7     4.5     4.0     1.5     2.0    3.0    2.0
     .125     1.4     1.5     0.0     0.0     4.5     0.7     4.0     3.5     0.0     0.0    1.0    0.57       .500     8.0     9.0     3.0     2.0     9.0     8.0     9.0     9.0     0.0     2.0    8.0    2.0
     .125     0.0     0.0     0.0     0.0     4.0     0.0     7.0     2.0     0.0     0.0    0.0    0.08       .500     8.0     8.0     8.0     9.0     9.0     7.0     9.0     8.0     6.0     7.0    7.0    0.0
     .125     0.0     0.0     4.0     0.0     9.0     0.0     9.0     7.0     0.0     2.0    0.0    0.09       .500     6.0     2.0     4.0     9.0     9.0     0.0     9.0     5.0     1.0     2.0    3.0    0.0
     .125     0.0     0.0     0.0     0.0     9.0     0.0     6.0     0.0     0.0     0.0    0.0    0.010       4.000    8.0     -       9.0     9.0     9.0     8.0     9.0     9.0     -       -      -      -
     .500     8.0     9.0     9.0     9.0     9.0     8.0     9.0     9.0     8.0     8.0    9.0    2.0
     .125     3.0     3.0     1.0     3.0     9.0     4.0     9.0     8.0     1.0     2.0    4.0    0.0
                                 表I(续)化合物
   使用比率   Barny   Foxta    Wild   Quack    Fld B  Mrngl   Wild   Velve   Wht F   corn   Cot    Soy编号   (kg/ha)    ardgr   il Sp    oats   grass    indwd  ry Sp   mustd  tleaf   enman   field  ton    bean11      4.000      8.0     -        8.0     8.0     9.0    7.0    9.0     8.0     -       -      -      -
     .500      1.0     2.0      1.0     1.5     4.5    1.0    5.0     3.5     1.0     1.0    2.0    0.0
     .125      0.0     0.0      0.0     0.0     0.0    0.0    2.0     0.5     0.0     0.0    0.0    0.012       .500      1.0     4.0      0.0     4.0     9.0    0.0    9.0     8.0     0.0     0.0    2.0    0.0
     .125      0.0     0.0      0.0     0.0     6.0    0.0    0.0     1.0     0.0     0.0    0.0    0.013       .500      4.0     4.0      4.0     5.0     9.0    6.0    8.0     7.0     2.0     3.0    2.0    0.0
     .125      0.0     4.0      0.0     0.0     2.0    0.0    8.0     4.0     0.0     0.0    -      0.014       .500      7.0     8.0      9.0     9.0     9.0    7.0    9.0     8.0     9.0     9.0    9.0    2.0
     .125      0.0     2.0      7.0     6.0     4.0    0.0    7.0     4.0     8.0     7.0    0.0    0.015       .500      4.0     8.0      9.0     7.0     9.0    4.0    9.0     7.0     8.0     7.0    7.0    2.0
     .125      0.0     7.0      2.0     4.0     4.0    0.0    5.0     5.0     3.0     3.0    0.0    0.0
                               表I(续)化合物编号 使用比率    Barny    Foxta    Wild    Quack    Fld B    Mrngl   Wild    Velve    Wht F    Corn      Cot     Soy
       (kg/ha)     ardgr    il Sp    oats    grass    indwd    ry sp   mustd   tleaf    enman    field     ton     bean16          4.000       2.0      -        4.0     6.0      2.0      1.0     9.0     4.0      -        -         -       -17          .500        8.0      9.0      9.0     9.0      9.0      9.0     9.0     9.0      9.0      9.0       9.0     8.0
        .125        6.0      9.0      9.0     9.0      9.0      8.0     9.0     8.0      9.0      9.0       8.0     7.018          4.000       9.0      -        8.0     9.0      9.0      7.0     9.0     8.0      -        -         -       -
        .500        9.0      9.0      9.0     9.0      9.0      9.0     9.0     9.0      9.0      9.0       9.0     8.0
        .125        2.0      9.0      9.0     9.0      9.0      9.0     9.0     8.0      9.0      9.0       9.0     7.019          4.000       8.0      -        8.0     8.0      9.0      8.0     9.0     8.0      -        -         -        -
        .500        2.2      7.0      8.0     7.0      6.0      5.5     9.0     8.0      9.0      7.0       5.0     5.0
        .125        0.4      0.0      0.0     0.0      0.0      1.7     0.0     0.0      0.0      0.0       0.0     0.020          4.000       9.0      -        8.0     9.0      9.0      8.0     9.0     9.0      -        -         -       -
        .500        8.5      9.0      9.0     9.0      8.5      9.0     8.5     9.0      9.0      8.0       7.5     7.0
        .125        9.0      9.0      7.0     7.0      9.0      8.0     9.0     8.0      5.0      7.0       9.0     6.0
                                        表I(续)
       使用比率   Barny  Foxta    Wild    Quack    Fld B   Mrngl    Wild     Velve    Wht F    Corn     cot    Soy化合物编号  (kg/ha)   ardgr  il Sp    oats    grass    indwd   ry Sp    mustd    tleaf    enman    field    ton    bean21           4.000     9.0    -        8.0     9.0      9.0     9.0      9.0      9.0      -        -        -      -
         .500      8.5    9.0      9.0     9.0      9.0     8.3      9.0      9.0      8.5      9.0      9.0    7.5
         .125      5.5    8.5      8.0     3.0      9.0     6.0      8.5      8.0      4.0      5.5      8.5    4.022           4.000     8.0    -        8.0     9.0      9.0     8.0      9.0      8.0      -        -        -      -
         .500      3.3    8.0      8.0     5.0      9.0     4.0      9.0      8.0      2.0      3.0      8.0    1.0
         .125      0.0    0.0      0.0     0.0      2.0     0.0      7.0      5.0      0.0      0.0      2.0    0.023           4.000     9.0    -        8.0     9.0      9.0     8.0      9.0      9.0      -        -        -      -
         .500      8.0    9.0      9.0     9.0      9.0     7.7      9.0      8.5      8.5      9.0      9.0    7.5
         .125      4.0    7.5      7.5     4.5      9.0     5.3      9.0      8.5      3.5      7.0      8.5    5.024           .500      0.0    8.0      3.0     2.0      4.0     2.0      7.0      7.0      1.0      1.0      6.0    3.025           .500      9.0    9.0      8.0     9.0      9.0     8.0      9.0      9.0      9.0      9.0      8.0    1.0
         .125      8.0    8.0      7.0     8.0      9.0     7.0      9.0      9.0      2.0      5.0      7.0    1.0
                                表I(续)
       使用比率    Barny    Foxta    Wild    Quack    Fld B    Mrngl    Wild     Velve    Wht F    Corn     Cot    Soy化合物编号 (kg/ha)     ardgr    il Sp    oats    grass    indwd    ry Sp    mustd    tleaf    enman    field    ton    bean26          4.000      7.0      8.0      9.0     9.0      6.0      9.0      7.0      -        -        -        -      -
        .500       4.0      6.0      0.0     0.0      4.0      0.0      8.0      3.0      0.0      0.0      0.0    0.027          .500       9.0      9.0      6.0     9.0      9.0      8.0      9.0      8.0      7.0      9.0      8.0    2.0
        .125       7.0      9.0      2.0     4.0      9.0      1.0      8.0      7.0      3.0      3.0      6.0    0.028          4.000      8.0      -        6.0     6.0      9.0      6.0      8.0      7.0      -        -        -      -
        .500       7.0      7.0      0.0     0.0      9.0      0.0      8.0      7.0      0.0      1.0      2.0    0.0
        .125       0.0      0.0      0.0     0.0      0.0      0.0      1.0      0.0      0.0      0.0      0.0    0.029          .500       9.0      9.0      7.0     9.0      9.0      7.0      9.0      8.0      8.0      7.0      8.0    2.0
        .125       7.0      8.0      2.0     5.0      9.0      2.0      8.0      7.0      3.0      3.0      8.0    0.030          .500       2.0      6.0      2.0     2.0      8.0      2.0      7.0      7.0      1.0      4.0      3.0    3.0
                             表I(续)
       使用比率   Barny   Foxta     Wild    Quack    Fld B    Mrngl    Wild     Velve     Wht F    corn     cot    Soy化合物编号 (kg/ha)    ardgr   il Sp     oats    grass    indwd    ry Sp    mustd    tleaf     enman    field    ton    bean31          .500      0.0     4.0       0.0     0.0      4.0      2.0      9.0      8.0       0.0      0.0      0.0    0.0
        .125      0.0     0.0       0.0     0.0      0.0      0.0      4.0      0.0       0.0      0.0      0.0    0.032          4.000     9.0     -         9.0     8.0      9.0      6.0      9.0      6.0       -        -        -      -33          4.000     8.0     -         7.0     9.0      9.0      8.0      9.0      6.0       -        -        -      -
        .500      0.0     0.0       1.0     6.0      1.0      2.0      8.0      5.0       1.0      7.0      4.0    0.034          4.000     8.0     -         7.0     9.0      9.0      6.0      9.0      7.0       -        -        -      -
        .500      8.0     9.0       9.0     9.0      9.0      9.0      9.0      9.0      9.0      8.0      9.0     7.0
        .125      6.0     9.0       9.0     8.0      8.0      7.0      9.0      8.0       8.0      8.0      8.0    3.035          .500      7.0     8.0       9.0     6.0      9.0      8.0      9.0      9.0       6.0      9.0      7.0    7.0
        .125      0.0     7.0       3.0     2.0      9.0      4.0      8.0      7.0       0.0      2.0      2.0    1.0
                           表I(续)
        使用比率   Barny    Foxta    Wild    Quack    Fld B    Mrngl    Wild     Velve    Wht F    Corn    Cot    Soy化合物编号  (kg/ha)    ardgr    il Sp    oats    grass    indwd    ry Sp    mustd    tleaf    enman    field   ton    bean36           .500      4.0      9.0      8.0     9.0      9.0      7.0      9.0      8.0      9.0      9.0     7.0    2.0
         .125      0.0      4.0      4.0     4.0      2.0      0.0      5.0      3.0      6.0      2.0     4.0    0.0
                    实施例5供试化合物芽后除草评估
通过下列实验说明本发明化合物的杂草芽后除草活性，供试化合物均以丙酮水溶液混合物喷洒处理大量的单子叶和双子叶植物。实验中，将植株秧苗种于jiffy flats，约二周。将实验化合物分散于50/50丙酮/水混合物中，混合物中含有0.5％吐温_20，为AttasChemical Industries的聚氧乙烯脱水山梨糖醇单月桂酸酯表面活性剂，当将混合物通过喷嘴施用于植株，在40psi进行预定的时间其量充足以提供相当于约0.125-4.0kg/ha活性化合物。喷洒后，将植株放于暖房架上并以通常方式管理，即以常规暖房操作。处理后4-5周，检查秧苗并按上述实施例4中提供的分级系统将其分级。得到的数据记录干下表II中。被评估的化合物以实施例4中给出的化合物编号记述。
                                    表II
                         供试化合物芽后除草活性评估
        使用比率   Barny   Foxta   Wild    Quack    Fld B    Mrngl   wild     Velve     Wht F    Corn     cot     Soy化合物编号  (kg/ha)    ardgr   il Sp   oats    grass    indwd    ry Sp   mustd    tleaf     enman    field    ton     bean1            4.000     9.0     -       9.0     9.0      9.0      9.0     9.0      9.0       -        -        -       -
         .500      9.0     9.0     9.0     9.0      9.0      9.0     9.0      9.0       9.0      9.0      9.0     9.0
         .125      8.0     9.0     9.0     8.0      9.0      9.0     9.0      9.0       9.0      9.0      8.0     7.02            4.000     9.0     -       8.0     0.0      6.0      6.0     9.0      8.0       -        -        -       -
         .500      7.4     9.0     9.0     6.0      7.0      7.7     9.0      7.0       9.0      9.0      8.0     7.0
         .125      4.4     8.0     9.0     4.0      6.0      6.3     9.0      8.0       8.0      9.0      8.0     7.03            4.000     9.0     -       9.0     9.0      9.0      9.0     9.0      9.0       -        -        -       -
         .500      9.0     9.0     9.0     9.0      9.0      9.0     9.0      9.0       9.0      9.0      9.0     8.0
         .125      7.0     9.0     9.0     8.0      8.0      9.0     9.0      9.0       9.0      9.0      9.0     8.04            .500      9.0     9.0     9.0     8.0      9.0      9.0     9.0      9.0       9.0      9.0      9.0     8.0
         .125      9.0     9.0     8.0     3.0      8.0      9.0     9.0      9.0       9.0      8.0      7.0     3.05            .500      8.0     9.0     9.0     4.0      9.0      9.0     9.0      9.0       9.0      9.0      7.0     7.0
         .125      8.0     9.0     6.0     2.0      9.0      8.0     9.0      9.0       7.0      9.0      7.0     7.0
                                          表II续)
       使用比率   Barny   Foxta   Wild   Quack    Fld B    Mrngl    Wild     Velve    Wht F    Corn     Cot    Soy化合物编号  (kg/ha)   ardgr   il Sp   oats   grass    indwd    ry Sp    mustd    tleaf    enman    field    ton    bean6           4.000     9.0     -      9.0    1.0      8.0       6.0      9.0      8.0     -         -       -      -
         .500      8.3     9.0    9.0    3.5      9.0       8.7      9.0      9.0     8.5       8.5     9.0    7.0
         .125      6.5     8.0    8.0    1.0      7.5       7.3      7.0      8.0     7.0       6.5     8.5    4.57           .500      8.0     9.0    8.0    0.0      8.0       7.0      8.0      9.0     9.0       8.0     8.0    7.0
         .125      8.0     8.0    8.0    0.0      2.0       7.0      7.0      8.0     6.0       5.0     8.0    0.08           .500      7.0     8.0    3.0    9.0      9.0       5.0      9.0      9.0     9.0       9.0     4.0    2.0
         .125      4.0     2.0    2.0    4.0      9.0       4.0      9.0      3.0     8.0       8.0     3.0    0.09           .500      4.0     7.0    4.0    7.0      9.0       4.0      9.0      6.0     2.0       3.0     0.0    0.0
         .125      2.0     2.0    2.0    0.0      4.0       0.0      8.0      0.0     0.0       0.0     0.0    0.010          4.000     9.0     -      9.0    7.0      9.0       9.0      9.0      9.0     -         -       -      -
         .500      9.0     9.0    9.0    4.0      8.0       8.0      9.0      9.0     9.0       9.0     9.0    3.0
         .125      8.0     9.0    8.0    2.0      8.0       6.0      9.0      8.0     6.0       7.0     9.0    1.0
                               表II(续)
       使用比率    Barny   Foxta    Wild    Quack    Fld B    Mrngl    Wild      Velve       Wht F      Corn       Cot      Soy化合物编号  (kg/ha)    ardgr   il Sp    oats    grass    indwd    ry Sp    mustd      tleaf      enman      field      ton      bean11           4.000     9.0     9.0      4.0      9.0      8.0      9.0      9.0        -         -          -          -
         .500      8.0     8.0      6.5      3.0      7.0      6.0      9.0        7.5       6.0        7.5        7.0      0.5
         .125      6.5     7.0      4.0      1.0      5.5      2.0      8.0        6.0       3.0        2.5        5.5      0.512           .500      8.0     8.0      6.0      0.0      8.0      4.0      8.0        7.0       2.0        2.0        7.0      0.0
         .125      4.0     2.0      4.0      0.0      2.0      0.0      4.0        0.0       1.0        2.0        2.0      0.013           .500      8.0     9.0      7.0      4.0      9.0      6.0      9.0        8.0       7.0        6.0        4.0      1.0
         .125      4.0     6.0      4.0      2.0      4.0      0.0      7.0        2.0       2.0        3.0        -        0.014           .500      9.0     9.0      9.0      9.0      9.0      8.0      9.0        9.0       9.0        9.0        9.0      3.0
         .125      7.0     9.0      5.0      8.0      7.0      8.0      9.0        9.0       8.0        9.0        9.0      2.015           .500      2.0     9.0      9.0      8.0      9.0      7.0      9.0        9.0       9.0        9.0        8.0      0.0
         .125      2.0     9.0      2.0      8.0      6.0      0.0      2.0        8.0       8.0        8.0        6.0      0.0
                                             表II(续)
      使用比率   Barny   Foxta    Wild    Quack    Fld B    Mrngl    Wild       Velve     Wht F      corn       cot      Soy化合物编号 (kg/ha)   ardgr   il Sp    oats    grass    indwd    ry Sp    mustd      tleaf     enman      field      ton      bean16          4.000    6.0     -        7.0     8.0      8.0      0.0      9.0        1.0        -         -          -        -17          .500     9.0     9.0      9.0     7.0      8.0      9.0      9.0        9.0        9.0       9.0        9.0      8.0
        .125     5.0     8.0      5.0     6.0      9.0      9.0      9.0        9.0        8.0       9.0        8.0      7.018          4.000    9.0     -        9.0     8.0      9.0      9.0      9.0        9.0        -         -          -        -
        .500     9.0     9.0      9.0     9.0      7.0      9.0      9.0        9.0        9.0       9.0        8.0      7.0
        .125     7.0     8.0      7.0     7.0      5.0      6.0      9.0        9.0        9.0       9.0        7.0      5.019          4.000    9.0     -        4.0     0.0      2.0      6.0      8.0        8.0        -         -          -        -
        .500     4.8     9.0      8.0     6.0      7.0      5.0      8.0        8.0        8.0       7.0        7.0      3.0
        .125     2.2     0.0      5.0     4.0      2.0      0.7      8.0        7.0        2.0       2.0        7.0      1.020          4.000    6.0     -        6.0     0.0      4.0      4.0      8.0        5.0        -         -          -        -
        .500     9.0     9.0      8.0     7.0      7.5      6.5      9.0        9.0        8.0       9.0        7.0      7.0
        .125     9.0     9.0      7.0     4.0      5.0      8.0      9.0        9.0        7.0       8.0        7.0      4.0
                                 表III(续)
       使用比率  Barny    Foxta    Wild    Quack    Fld B    Mrngl    Wild       Velve      Wht F      Corn       Cot      Soy化合物编与 (kg/ha)   ardgr    il Sp    oats    grass    indwd    ry Sp    mustd      tleaf      enman      field      ton      bean21          4.000    9.0      9.0      2.0     7.0      6.0      9.0      8.0        -          -          -          -        -
        .500     9.0      9.0      9.0     2.0      9.0      8.5      9.0        9.0        9.0        9.0        9.0      7.0
        .125     8.3      9.0      9.0     2.0      7.0      7.3      9.0        8.0        6.5        4.5        8.5      3.522          4.000    9.0      -        9.0     2.0      7.0      6.0      8.0        9.0        -          -          -        -
        .125     4.0      2.0      6.0     0.0      6.0      8.0      7.0        0.0        2.0        2.0        8.0      8.023          4.000    9.0      9.0      2.0     7.0      6.0      9.0      9.0        -          -          -          -        -
        .500     9.0      9.0      8.5     6.5      9.0      8.7      9.0        9.0        8.5        8.5        8.0      6.5
        .125     7.5      8.0      8.0     3.0      5.0      6.0      7.5        7.5        8.0        3.0        7.5      1.524          .500     8.0      8.0      2.0     0.0      2.0      6.0      6.0        7.0        2.0        2.0        6.0      0.0
        .125     2.0      6.0      0.0     0.0      0.0      0.0      0.0        0.0        0.0        0.0        0.0      0.025          .500     9.0      9.0      7.0     8.0      7.0      7.0      9.0        8.0        9.0        8.0        7.0      0.0
        .125     8.0      9.0      2.0     4.0      4.0      4.0      9.0        7.0        3.0        3.0        3.0      0.0
                                  表II(续)
        使用比率   Barny   Foxta   Wild    Quack   Fld B   Mrngl   Wild      Velve     Wht F     Corn      Cot      Soy化合物编号  (kg/ha)    ardgr   il Sp   oats    grass   indwd   ry Sp   mustd     tleaf     enman     field     ton      bean26           4.000     9.0     4.0     6.0     9.0     1.0     9.0     4.0       -         -         -         -        -
         .500      6.0     8.0     4.0     2.0     8.0     3.0     9.0       4.0       0.0       0.0       4.0      0.0
         .125      0.0     0.0     0.0     0.0     0.0     0.0     3.0       0.0       0.0       0.0       0.0      0.027           .500      9.0     8.0     6.0     6.0     7.0     7.0     8.0       8.0       6.0       6.0       7.0      0.0
         .125      8.0     7.0     2.0     4.0     4.0     0.0     6.0       6.0       1.0       1.0       2.0      0.028           4.000     7.0     5.0     4.0     4.0     4.0     9.0     5.0       -         -         -         -        -
         .500      8.0     7.0     2.0     1.0     7.0     2.0     7.0       4.0       3.0       2.0       6.0      0.0
         .125      2.0     5.0     0.0     0.0     2.0     0.0     3.0       0.0       0.0       0.0       0.0      0.029           .500      9.0     9.0     8.0     8.0     9.0     4.0     9.0       7.0       8.0       9.0       7.0      1.0
         .125      7.0     7.0     4.0     0.0     2.0     0.0     4.0       2.0       2.0       3.0       4.0      0.030           .500      2.0     4.0     0.0     0.0     4.0     0.0     8.0       0.0       0.0       0.0       0.0      0.0
                              表II(续)
      使用比率   Barny  Foxta   Wild   Quack   Fld B   Mrngl   Wild    Velve     Wht F     Corn      Cot     Soy化合物编号 (kg/ha)   ardgr  il Sp   otts   grass   indwd   ry Sp   mustd   tleaf     enman     field     ton     bean31           .500    2.0    4.0     0.0    2.0     4.0     0.0     8.0     7.0       1.0       2.0       3.0     0.0
         .125    0.0    2.0     0.0    0.0     0.0     0.0     6.0     2.0       0.0       0.0       0.0     0.032           4.000   8.0    -       9.0    9.0     9.0     2.0     9.0     3.0       -         -         -       -33           4.000   9.0    -       8.0    0.0     4.0     6.0     8.0     5.0       -         -         -       -
         .500    2.3    7.0     4.0    2.0     0.0     0.0     8.0     2.0       2.0       7.0       7.0     0.0
         .125    0.0    0.0     2.0    0.0     0.0     0.0     8.0     2.0       0.0       6.0       6.0     0.034           4.000   9.0    -       9.0    9.0     9.0     7.0     9.0     9.0       -         -         -       -
         .500    9.0    9.0     9.0    8.0     9.0     9.0     9.0     9.0       9.0       9.0       9.0     8.0
         .125    4.0    8.0     8.0    8.0     8.0     9.0     9.0     9.0       -         -         8.0     6.035           .500    9.0    9.0     8.0    7.0     9.0     9.0     9.0     9.0       9.0       9.0       8.0     8.0
         .125    7.0    8.0     7.0    2.0     7.0     2.0     9.0     9.0       6.0       8.0       6.0     4.0
                                             表II(续)
         使用比率   Barny    Foxta    Wild    Quack    Fld B    Mrngl     Wild     Velve     Wht F     Corn      Cot     Soy化合物编号   (kg/ha)    ardgr    il Sp    oats    grass    indwd    ry Sp     mustd    tleaf     enman     field     ton     bean36            .500      7.0      9.0      4.0     8.0       4.0     6.0       9.0      8.0       9.0       9.0       7.0     3.0
          .125      4.0      8.0      2.0     7.0       4.0     2.0       7.0      7.0       7.0       8.0       7.0     1.0

Claims (10)

1.一种具有下式结构的化合物
Figure C9310616500021
其中：R是C1-C4烷基；R1是C1-C4烷基或C3-C6环烷基；当R和R1与它们连接的碳原子合在一起时，它们代表可被甲基任意取代的C3-C6环烷基；Q是
Figure C9310616500022
R2、R3和R4独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基或可被一或二个卤原子、C1-C4烷基或卤代烷基或C1-C4烷氧基或卤代烷氧基任意取代的苯基；m是1或2的整数；A是O、S或NR5；条件是m是2，A是O；R5是C1-C4烷基；B是氢、COR6或SO2R7；R6是C1-C11烷基、氯甲基或可被一个氯、一个硝基或一个甲氧基任意取代的苯基；R7是C1-C4烷基或可被一个甲基任意取代的苯基；W是O或S；X是氢、卤素或甲基；Y和Z独立地是氢、卤素、C1-C6烷基、C1-C4烷氧甲基、C1-C6烷氧基、C1-C4烷硫基、苯氧基、C1-C4卤代烷基、硝基、氰基、C1-C4烷基磺酰基或可被一个C1-C4烷基、C1-C4烷氧基或卤素任意取代的苯基；并且当它们联在一起，Y和Z可形成环即YZ，其结构式是：-(CH2)n-，其中n选自整数3和4；或
Figure C9310616500031
其中R8、R9、R10和R11独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基、硝基、氰基、苯基、苯氧基、氨基、氯苯基、甲苯基或可被一个氯、三氟甲基、硝基或甲基取代的苯氧基，条件是仅R8、R9、R10和R11中的一个可代表除氢、卤素、C1-C4烷基或C1-C4烷氧基以外的取代基；以及当R和R1不同时，它们的光学异构体。
2.如权利要求1所述具有下列结构的化合物
Figure C9310616500041
其特征在于，其中：A是O或S；Y和Z独立地是氢、卤素、C1-C6烷基、C1-C4烷氧甲基或C1-C6烷氧基，并且当联在一起时，Y和Z可形成环即YZ，其结构如下：
              -CH＝CH-CH＝CH-  。
3.如权利要求2所述具有下列结构的化合物
Figure C9310616500042
其特征在于，其中：R2和4独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基或C1-C4卤代烷氧基。
4.如权利要求2所述的化合物，其特征在于，其中，它们是2-[3-(2-糠酰基)-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮；2-[3-(2-糠酰基)-5-甲基-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮；2-[3-(α-羟基糠基)-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮；2-[3-(α-羟基糠基)-5-甲基-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮；2-[3-(α-羟基-5-甲基糠基)-5-甲基-2-吡啶基]-4-异丙基-4-甲基-2-咪唑啉-5-酮；或2-{3-[二(2-呋喃基)羟基甲基]-2-吡啶基}-4-异丙基-4-甲基-2-咪唑啉-5-酮。
5.一种防治不需要植物种类的方法，其特征在于，包括向所述植株的叶部或含种子或它们的其它繁殖器官的土壤或水施用除草有效量的如权利要求1所述的化合物。
6.如权利要求5所述的方法，其特征在于：所述的化合物具有下列结构其中A是O或S；Y和Z独立地是氢、卤素、C1-C6烷基、C1-C4烷氧甲基或C1-C6烷氧基，并且当联在一起时，Y和Z可形成环即YZ，其结构如下：
             -CH＝CH-CH＝CH-。
7.如权利要求5所述的方法，其特征在于，包括施用所述化合物的比率为约0.016-4.0Kg/ha。
8.一种除草剂组合物，其特征在于，包括惰性固体或液体稀释剂以及除草有效量的如权利要求1所述的化合物。
9.制备具下式结构的3-(取代的酮)-2-(2-咪唑啉-2-基)吡啶或喹啉化合物的方法
Figure C9310616500061
其中：R是C1-C4烷基R1是C1-C4烷基或C3-C6环烷基；当R和R1与它们连接的碳原子合在一起时，它们代表可被甲基任意取代的C3-C6环烷基；Q是R2、R3和R4独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基或可被一或二个卤原子、C1-C4烷基或卤代烷基或C1-C4烷氧基或卤代烷氧基任意取代的苯基；A是O、S或NR5；条件是m是2，A是O；R5是C1-C4烷基；X是氢、卤素或甲基；Y和Z独立地是氢、卤素、C1-C6烷基、C1-C4烷氧甲基、C1-C6烷氧基、C1-C4烷硫基、苯氧基、C1-C4卤代烷基、硝基、氰基、C1-C4烷基磺酰基或可被一个C1-C4烷基、C1-C4烷氧基或卤素任意取代的苯基；并且当它们联在一起，Y和Z可形成环即YZ，其结构式是：-(CH2)n-，其中n选自整数3和4；或
Figure C9310616500071
其中R8、R9、R10和R11独立地是氢、卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基、硝基、氰基、苯基、苯氧基、氨基、氯苯基、甲苯基或可被一个氯、三氟甲基、硝基或甲基取代的苯氧基，条件是仅R8、R9、R10和R11中的一个可代表除氢、卤素、C1-C4烷基或C1-C4烷氧基以外的取代基；以及当R和R1不同时，它们的光学异构体。其特征在于，包括将具有下式结构的咪唑啉酮化合物
Figure C9310616500072
其中X、Y、Z、R和R1如上所述与至少约2.0摩尔当量的C1-C4烷基锂在惰性溶剂的存在下反应，生成盐并将该盐与至少1.0摩尔当量的具有结构 的醛化合物，
其中Q如上所述，在惰性溶剂存在下反应，生成具有下式结构的3-(取代醇)-2-(2-咪唑啉-2-基)吡啶或喹啉化合物
Figure C9310616500081
其中R，R1，Q，X，Y和Z如上所述，并将所述3-(取代醇)-2-(2-咪唑啉-2-基)吡啶或喹啉化合物与氧化剂在惰性有机溶剂的存在下反应，形成3-(取代酮)-2-(2-咪唑啉-2-基)吡啶或喹啉化合物。
10.如权利要求9所述的方法，其特征在于，其中氧化剂是二氧化锰(IV)，C1-C4烷基锂可选自正丁基锂和甲基锂，且Q是
Figure C9310616500082
CN93106165.2A 1992-06-03 1993-05-20 3－(取代的酮和醇)－2－(2－咪唑啉－2－基)吡啶和喹啉、制备方法和除草剂 Expired - Fee Related CN1040754C (zh)

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