CN1190651A - 带杂环的2-烷氧苯氧基硫酰脲类和它们作为除草剂或植物生长调节剂的应用 - Google Patents
带杂环的2-烷氧苯氧基硫酰脲类和它们作为除草剂或植物生长调节剂的应用 Download PDFInfo
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- CN1190651A CN1190651A CN97108749A CN97108749A CN1190651A CN 1190651 A CN1190651 A CN 1190651A CN 97108749 A CN97108749 A CN 97108749A CN 97108749 A CN97108749 A CN 97108749A CN 1190651 A CN1190651 A CN 1190651A
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- C07—ORGANIC CHEMISTRY
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- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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Abstract
式Ⅰ表示的化合物或其盐类(其中各基团和符号见说明书)具有突出的除草和调节植物生长的性质。
Description
已知道，带杂环的取代苯氧基硫酰脲类具有除草和调节植物生长的性能(EP-A 4 163，DE-A 3 151-450)。
现已令人惊异地发现，带杂环的取代氨基磺酸苯酯类，当它的苯酯部分由某些邻苯二酚单烷基醚构成时，能特别适合用作除草剂或植物生长调节剂。
因此，本发明涉及的是式(I)表示的化合物或它们的盐类：
其中，
R1代表乙基、丙基或异丙基，R2代表卤素、NO2、CF3、CN、(C1-C4)烷基、
(C1-C4)烷氧基、(C1-C4)烷硫基或(C1-C4烷氧基)羰基，n代表0、1、2或3，y代表O或S，R3代表氢、(C1-C8)烷基、(C2-C8)链烯基、(C2-C8)链炔基或(C1-C4)烷氧基，R4代表一个下式表示的杂环基团其中，E代表CH或N，G代表O或CH2，
R5、R6相互独立地代表氢、卤素、(C1-C6)烷基、(C1-C6)烷氧基或(C1-C6)烷硫基，这里提到的含烷基基团可被一个或多个卤素取代、或被1个或2个(C1-C4)烷氧基或(C1-C4)烷硫基取代，R5和R6还可代表一个下式表示的基团：-NR12R13、-OCHR7-CO2R12、(C3-C6)环烷基、(C3-C5)链烯基、(C2-C4)链炔基、(C3-C5)链烯氧基或(C3-C5)链炔氧基，
R7代表氢或(C1-C4)烷基，
R8代表(C1-C4)烷基、-CHF2或-CH2CF3，
R9、R10相互独立地代表氢、(C1-C4)烷基、(C1-C5)烷氧基或卤素，
R11代表氢、(C1-C4)烷基、-CHF2或者-CH2CF3，
R12、R13相互独立地代表氢、(C1-C4)烷基、(C2-C4)链烯基或(C3-C4)链炔基。
式(I)表示的化合物能够生成盐，在它们的盐上，-SO2-NH-基团上的氢被一个适于农用的阳离子代替，这些盐一般是金属盐、尤其是碱金属盐、碱土金属盐、必要时是烷基化的铵盐或有机胺盐。
在上面的定义中，较优先的卤素是氟、氯或溴。
优先选用的式(I)表示的化合物或它们的盐是这样的物质，它们中的n＝0或1，y＝0，R2定位在苯环的6位上且有如前所述意义(如果是卤素，则尤其以氟或氯为好)，R3为氢、(C1-C4)烷基或(C3-C4)链烯基，R4代表下式表示的一个杂环基团
其中，E＝CH或N，R5、R6代表卤素、(C1-C4)烷基、(C1-C4)烷氧基或(C1-C4)烷硫基，这里的含烷基基团可如前述被取代。
尤其优先选用的式(I)表示的化合物及其盐是这样的物质，其中n＝0或1，R2被定位在苯环的6位上，且代表氟、氯、(C1-C4)烷基、(C1-C4)烷氧基或(C1-C4)烷氧羰基，R3＝氢或甲基，R4代表下式表示的一个杂环基团
其中，E＝CH或N，R5和R6相互独立地代表氯、溴、(C1-C4)烷基、(C1-C4)烷氧基、OCHF2、OCH2CF3或CF3，尤其以(C1-C2)烷基或(C1-C2)烷氧基为好。
此外，本发明还涉及制备通式(I)表示的化合物或其盐的方法，其特征是，a)一种式(II)表示的化合物与一种式(III)表示的化合物进行反应
或b)一种式(IV)表示的化合物
与一种式(V)表示的氯磺酰脲反应或c)一种式(VI)表示的化合物
与一种式(VII)表示的氨基甲酸酯进行反应
其中，Z代表苯基或(C1-C6)烷基，
必要时将得到的式(I)表示的化合物转化成它们的盐。
化合物(II)和(III)的反应最好在惰性的非质子传递溶剂中，且在0℃至所用溶剂的沸点之间来进行，上述溶剂是如乙腈、二氯甲烷、甲苯、四氢呋喃或二噁烷。
式(II)表示的异氰酸苯氧磺酰酯可根据原则上是已知的方法，且相应从式(IV)表示的邻苯二酚单醚与异氰酸氯磺酰酯简单地制得(参照G.Lohaus，Chem.Ber.，105，2791(1972))。
式(III)的原料是已知的，原则上也可用已知的方法来制备，如用相应的胍衍生物与适当的取代的1，3-二酮进行环化来制备(这可参照如“The Chemistry of HeterocyclicCompounds”，Vol.XVI(1962)andSupplement I(1970))，或通过氰尿酰氯的衍生化而制备(这可参照如“The Chemistry of HeterocyclicCompounds”，L.Rapaport：“S-Triazines andDerivatives”(1959))。
化合物(IV)与氯磺酰脲(V)的反应最好是在惰性溶剂如二氯甲烷中、并在一种碱存在下(碱作为HCl缚酸剂)进行，反应温度介于-10℃至80℃之间。可用作这种碱的有，碱金属或碱土金属的碳酸盐或碳酸氢盐，如K2CO3、NaHCO3、Na2CO3或者用叔胺如吡啶或三乙胺。
邻苯二酚单醚(IV)可从文献得知，或根据文献公开的方法来制备。氯磺酰脲(V)可用式(III)表示的胺和异氰酸氯磺酰酯反应制得(EP-A 141，199)。
式(VI)表示的化合物与式(VII)表示的杂环氨基甲酸酯化合物的反应最好是在一种叔式有机碱(如1，8-二氮杂双环〔5.4.0〕十一碳-7-烯(DBU))存在下，在惰性溶剂如乙腈或二噁烷中、并在介于20℃至溶剂沸点之间的温度下进行(类似于EP-A 44，807)。
此外提及反应所需的(VII)式表示的氨基甲酸酯是文献公开了的，或可依照已知的方法制备(EP-A 70 804)。氨基磺酸酯(VI)可基本按照已知的方法由邻苯二酚单醚来制备(可参见如Synthesis 1978，357：Z.Chem.15，270(1975)：Chem.Ber.105，2791(1972))
式(I)表示的化合物的盐最好是在惰性溶剂如水、甲醇或丙酮中、在0-100℃的温度下制备。在制备本发明的盐时，对制备适用的碱是(如)碱金属的碳酸盐(如碳酸钾)、碱金属和碱土金属的氢氧化物、氨或乙醇胺。
式(I)表示的依本发明的化合物，对许多经济上重要的单子叶和双子叶有害植物具有优良的广谱除草效果。其有效成分对难以防除多年生杂草有同样好的药效，这些杂草的茎从根茎、细根茎(Wurzelstockchen)或其它多年生组织中萌发出来。在除去上述杂草时，当本发明物质用于播前时，芽前处理还是芽后处理的效果一样。下面列举一些有代表性的单子叶和双子叶杂草种群，它们能被本发明的有效成分控制，但并不意味着本发明的有效成分仅限于用在所列举的杂草种类上。
上述的单子叶杂草种属有如：燕麦属、毒麦属、看麦娘属、
草属、稗属、马唐属、狗毛草属等。还有一年生的莎草：多年生杂草种属有(如)：冰草属、狗牙根属、白茅属和高梁属等，还有多年生的莎草。可杀除的双子叶杂草种属包括一年生的猪殃殃属、堇菜属、婆婆婆纳属、野芝麻属、繁缕属、苋属、欧白芥属、番薯属、母菊属、麻属、黄花稔属等，多年生杂草包括旋花属、蓟属、酸模属、蒿属等。
在特定的耕作条件下，本发明的有效成分能很有效地控制稻田杂草，例如慈姑属、泽泻属、荸荠属、藨草属、莎草属等。
如果用本发明的化合物芽前施于芽前的土表，或可完全防止杂草实生苗的出土，或是杂草只长至子叶阶段就停止生长，三至四周后，这些植物最后完全死亡。
有效成分芽后施于植物的绿色部分后，在很短的时间内，植物生长就迅速停止，杂草停留在施用时的生长阶段，或经一段时间后，它们很快先后死亡。因此，采用依照本发明这种新药剂，在很早阶段就能够持效性地防止杂草危害作物。
尽管本发明的化合物具有很好的防除单子叶和双子叶杂草的活性，但对经济上重要的作物如小麦、大麦、黑麦、稻、玉米、甜菜、棉花和大豆，仅有可忽略的药害或根本无药害。因此，本发明的化合物非常适用于农作物田间选择性地控制杂草生长。
此外，本发明的化合物对作物具有调节植物生长的能力。它们对植物的新陈代谢具有调节作用，因此，可使用它们以便于作物收获，例如引起植物脱水干枯、落叶以及使植物生长矮化。它们还适宜于对不需要的营养生长作通常性的调节和抑制，同时不会损害作物。营养生长的抑制对许多单子叶和双子叶作物有重要意义，因为这可以减少倒伏，或完全防止倒伏。
依本发明的化合物可以以通常的制剂形式来使用，如可湿性粉剂、乳油、乳剂、直接喷洒剂、粉剂、种衣剂、分散剂(dispersions)粒剂或微粒剂。
可湿性粉剂是可均匀地分散在水中的制剂，除了有效成分外，它还含有湿润剂如聚氧乙基化的烷基酚，聚氧乙基化的脂肪醇、磺酸烷基酯或磺酸烷基苯酯，还含有分散剂如木素磺酸钠、2，2′-二萘甲烷-6，6 ′-二磺酸钠、二丁基萘磺酸钠，以及油酰甲基牛磺酸钠，如需要时还可包括稀释剂或惰性物质。制剂是用通常的方式如通过研磨和混合所含组分制备的。
乳油可通过将有效成分溶解于惰性有机溶剂中、并添加一种或多种乳化剂来制备，上述溶剂的例子有：丁醇、环己酮、二甲基甲酰胺、二甲苯，还有高沸点芳烃或链烃。若有效成分是液态的，能够省去所有的或部分溶剂。采用的乳化剂如有：烷芳基磺酸的钙盐如十二烷基苯磺酸钙，或是非离子型乳化剂如脂肪酸聚二醇酯，烷芳基聚二醇醚、脂肪醇聚二醇醚、环氧丙烷/环氧乙烷缩合物、脂肪醇/环氧丙烷/环氧乙烷缩合产物、烷基聚二醇醚、脂肪酸脱水山梨醇酯、脂肪酸聚氧乙烯脱水山梨醇酯或聚氧乙烯山梨醇酯。
粉剂是通过将有效成分与很细的固体物质如滑石或天然粘土一起研磨而制得的，天然粘土的例子有高岭土、膨润土、叶蜡石或硅藻土。
粒剂或是通过喷洒活性物质到吸附性的、已成粒的惰性材料上、或是借助粘结剂将有效成分的高浓度溶液施涂于赋形剂的表面而成，赋形剂的例子有砂、高岭土或粒状的惰性物质，粘结剂的例子有聚乙烯醇、聚丙烯酸的钠盐或不同的矿物油。适用的有效成分也可制粒，其方法是在肥料造粒中常用的，如需要的话，还可与肥料制成混剂。
可湿性粉剂中有效成分的浓度约在10-90％(重)之间：其余的重量含量为通常的配制成分占有。乳油中有效成分的浓度在约5-80％(重)之间。粉剂配方中通常含5-20％(重)的有效成分，直接喷洒剂中约含有2-20％(重)的有效成分。在粒剂中，有效成分的含量部分地取决于有效成分是液态还是固态，并取决于采用哪些成粒助剂、填料等。
此外，如合适的话，提到的有效成分配方中可含有粘合剂、湿润剂、分散剂、乳化剂、渗透剂、溶剂、填料或载体，在每一种配方中这些辅助物质都是通常的。
这些制剂的商品形式有效成分浓度较高，使用时有的需要按一般方法稀释。如对可湿性粉剂、乳油、分散剂，可用水稀释，在某些情况下，微粒剂也可用水稀释。粉剂和粒剂形式的制剂以及直接喷洒剂在使用前通常不需用惰性物质进一步稀释。
所需的施药量随外界条件而变化，如温度、湿度等。它可以在一个很宽的范围内，如0.005-10.0千克有效成分/公顷或用更多一些有效成分，但较好的是在0.01-5千克/公顷范围内。
需要时可与其它有效成分如杀虫剂、杀螨剂、除草剂、肥料、生长调节剂或杀菌剂混用或制成混剂。
以下实施例更详细地描述本发明。制剂实例A.将10份(重量、下同)有效成分和90份滑石或惰性物质混合并置于一个锤磨机中粉碎，可制得一种粉剂。B.一种便于分散在水中的可湿性粉剂可如下法制得：混合25份有效成分、64份不含石英砂的高岭土作为惰性物质，10份木素磺酸钾和1份油酰甲基牛磺酸钠作为湿润剂和分散剂，将该混合物置于一个气流粉碎机(Pinned disk mill)中研磨粉碎。C.便于分散在水中的悬浮剂可如下法制得：混合20份有效成分、6份烷基酚聚二醇醚(Triton X 207)，3份异十三醇聚二醇醚(8 EO)和71份石蜡油(其沸点范围约为255℃至377℃)，将该混合物置于一个砂磨机中研磨至5微米以下。D.乳油可由以下成份制得：15份有效成分、75份环己烷酮作为溶剂、10份氧乙烯化的壬基酚(10 EO)作为乳化剂。化合物实例例1异氰酸2-乙氧苯氧基磺酰酯
25℃下，67.9g(0.48mol)异氰酸氯磺酰酯滴加到一个由55.2g(0.4mol)2-乙氧苯酚溶于500ml二甲苯所形成的溶液中。滴加完成后，使混合液温度慢慢地升到140℃，并回流2.5小时。冷却该混合物，在一个旋转蒸发器上移去溶剂以及剩余的异氰酸氯磺酰酯。对剩下的黄色油状物(97.2g，产率100％)不作进一步提纯而使用。例23-(4，6-二甲氧基嘧啶-2-基)-1-(2-乙氧苯氧磺酰)脲
97.2g(0.4mol)例1中得到的产物溶于100ml二氯甲烷中，在25℃下把该溶液滴加到在600ml二氯甲烷中的62.0g(0.4mol)2-氨基-4，6-二甲氧嘧啶中。室温下连续搅拌16小时，用600ml二氯甲烷稀释上述混合物，其有机相用2N盐酸洗涤两次(每次500ml)，再用500ml水洗涤一次。在用无水硫酸钠干燥了该混合物。并在一个旋转蒸发器上移去溶剂后，剩下的油状物用乙醚净化而结晶。得到145.0g(产率为91％)的3-(4，6-二甲氧嘧啶-2-基)-1-(2-乙氧苯氧磺酰)脲，其熔点为145-147℃。例33-(4，6-二甲氧嘧啶-2-基)-1-(2-丙氧苯氧磺酰)脲
1.74g(0.008mol)氨基磺酸2-丙氧苯基酯在室温下加到2.32g(0.0084mol)溶于100ml乙腈中的N-(4，6-二甲氧嘧啶-2-基)氨基甲酸苯酯中。加入1.33g(0.0088mol)1，8-二氮杂双环〔5.4.0〕十一碳-7-烯(DBU)后，该反应混合物在室温下搅拌18小时，浓缩，用水稀释并用2N盐酸酸化至pH为3-4。吸滤出固体并干燥，得到2.85g(产率为86％)3-(4，6-二甲氧嘧啶-2-基)-1-(2-丙氧苯氧磺酰)脲，熔点为108-109℃。
下表中列出的化合物系用例1-3所示方法制得。
表1
实例序号 R1 R3 R5 R6 E n 熔点[℃]4 CH2CH3 H CH3 CH3 CH 0 1625 CH2CH3 H OCH3 CH3 CH 0 1256 CH2CH3 H CH3 CH3 N 07 CH2CH3 H OCH3 CH3 N 0 128-1298 CH2CH3 H OCH3 OCH3 N 0 169-1709 CH2CH3 H OCH3 SCH3 N 010 CH2CH3 H OCH3 Cl CH 0 134-13511 CH2CH3 H OCF2H CH3 CH 012 CH2CH3 H OCF2H OCF2H CH 0 14013 CH2CH3 H OCH3 Br CH 014 CH2CH3 H CH3 Cl CH 0 16315 CH2CH3 H OCH3 H CH 016 CH2CH3 H OCH3 NHCH3 CH 017 CH2CH3 H OCH3 NHCH3 N 018 CH2CH3 H CH3 NHCH3 CH 019 CH2CH3 H OC2H5 NHCH3 N 0 16820 CH2CH3 H OCH3 SCH3 CH 021 CH2CH3 H OCH3 OC2H5 CH 022 CH2CH3 H OCH3 OC3H7 CH 023 CH2CH3 H OCH3 OC2H5 N 024 CH2CH3 H Cl OC2H5 CH 025 CH2CH3 H OC2H5 OC2H5 CH 026 CH2CH3 H C2H5 OCH3 CH 027 CH2CH3 H CF3 OCH3 CH 028 CH2CH3 H OCH2CF3 CH3 CH 029 CH2CH3 H OCH2CF3 OCH3 CH 030 CH2CH3 H OCH2CF3 OCH2CF3 CH 0实例序号 R1 R3 R5 R6 E n 熔点[℃]31 CH2CH3 H OCH2CF3 NHCH3 CH 032 CH2CH3 H OCH2CF3 OCH3 N 0 17533 CH2CH3 H OCH2CF3 NHCH3 N 034 CH2CH3 H OCH3 NHC2H5 CH 035 CH2CH3 H OCH2CF3 NHC2H5 CH 036 CH2CH3 H OCH3 N(CH3)2 CH 037 CH2CH3 H OCH3 CH(OCH3)2 CH 038 CH2CH2CH3 H CH3 CH3 CH 0 113-11539 CH2CH2CH3 H OCH3 CH3 CH 0 101-10240 CH2CH2CH3 H CH3 CH3 N 041 CH2CH2CH3 H OCH3 CH3 N 0 93-12342 CH2CH2CH3 H OCH3 OCH3 N 043 CH2CH2CH3 H OCH3 Cl CH 0 121-12344 CH2CH2CH3 H OCF2H CH3 CH 0 12645 CH2CH2CH3 H OCF2H OCF2H CH 046 CH2CH2CH3 H OCH3 Br CH 047 CH2CH2CH3 H CH3 Cl CH 048 CH2CH2CH3 H OCH3 H CH 049 CH2CH2CH3 H OCH3 NHCH3 CH 050 CH2CH2CH3 H OCH3 NHCH3 N 051 CH2CH2CH3 H CH3 NHCH3 CH 052 CH2CH2CH3 H CH3 NHCH3 N 053 CH2CH2CH3 H OCH3 SCH3 CH 054 CH2CH2CH3 H OCH3 OC2H5 CH 0 127-13055 CH2CH2CH3 H OCH3 OC3H7 N 056 CH2CH2CH3 H OCH3 OC2H5 N 057 CH2CH2CH3 H Cl OC2H5 CH 058 CH2CH2CH3 H OC2H5 OC2H5 CH 059 CH2CH2CH3 H C2H5 OCH3 CH 060 CH2CH2CH3 H CF3 OCH3 CH 061 CH2CH2CH3 H OCH2CF3 CH3 CH 062 CH2CH2CH3 H OCH2CF3 OCH3 CH 063 CH2CH2CH3 H OCH2CF3 OCH2CF3 CH 0实例序号 R1 R3 R5 R6 E n 熔点[℃]64 CH2CH2CH3 H OCH2CF3 NHCH3 CH 065 CH2CH2CH3 H OCH2CF3 OCH3 N 066 CH2CH2CH3 H OCH2CF3 NHCH3 N 067 CH2CH2CH3 H OCH3 OCH3 CH 068 CH2CH2CH3 H OCH2CF3 NHC2H5 CH 069 CH2CH2CH3 H OCH3 N(CH3)2 CH 070 CH2CH2CH3 H OCH3 CH(OCH3)2 CH 071 CH(CH3)2 H CH3 CH3 CH 0 90-9272 CH(CH3)2 H OCH3 CH3 CH 0 135-13773 CH(CH3)2 H CH3 CH3 N 074 CH(CH3)2 H OCH3 CH3 N 0 108-11075 CH(CH3)2 H OCH3 OCH3 CH 0 141-14376 CH(CH3)2 H OCH3 Cl CH 0 121-12377 CH(CH3)2 H OCF2H CH3 CH 078 CH(CH3)2 H OCF2H OCF2H CH 0 135-13679 CH(CH3)2 H OCH3 Br CH 080 CH(CH3)2 H CH3 Cl CH 081 CH(CH3)2 H OCH3 H CH 082 CH(CH3)2 H OCH3 NHCH3 CH 083 CH(CH3)2 H OCH3 NHCH3 N 084 CH(CH3)2 H CH3 NHCH3 CH 085 CH(CH3)2 H CH3 NHCH3 N 086 CH(CH3)2 H OCH3 SCH3 CH 087 CH(CH3)2 H OCH3 OC2H5 CH 088 CH(CH3)2 H OCH3 OC3H7 CH 089 CH(CH3)2 H OCH3 OC2H5 N 090 CH(CH3)2 H Cl OC2H5 CH 091 CH(CH3)2 H OC2H5 OC2H5 CH 092 CH(CH3)2 H C2H5 OCH3 CH 093 CH(CH3)2 H CF3 OCH3 CH 094 CH(CH3)2 H OCH2CF3 CH3 CH 095 CH(CH3)2 H OCH2CF3 OCH3 CH 096 CH(CH3)2 H OCH2CF3 OCH2CF3 CH 0实例序号 R1 R2 R3 R5 R6 E n 熔点97 CH(CH3)2 H OCH3 OCH3 N 098 CH(CH3)2 H OCH2CF3 OCH3 N 099 CH(CH3)2 H OCH2CF3 NHCH3 N 0100 CH(CH3)2 H OCH3 NHC2H5 CH 0101 CH(CH3)2 H OCH2CF3 NHC2H5 CH 0102 CH(CH3)2 H OCH3 N(CH3)2 CH 0103 CH(CH3)2 H OCH3 CH(OCH3)2CH 0104 CH2CH3 6-Cl H OCH3 OCH3 CH 1 162-163105 CH2CH3 6-Cl H OCH3 CH3 CH 1 151-152106 CH2CH3 6-Cl H OCH3 CH3 N 1 128-129107 CH2CH3 6-Cl H OCH3 Cl CH 1108 CH2CH3 6-F H OCH3 OCH3 CH 1 149-150℃109 CH2CH3 6-F H OCH3 CH3 CH 1 130-131℃110 CH2CH3 6-F H OCH3 CH3 N 1 116-117℃112 CH2CH3 6-F H OCH3 Cl CH 1113 CH2CH3 6-Br H OCH3 OCH3 CH 1114 CH2CH3 5-F H OCH3 CH3 CH 1115 CH2CH3 5-Br H OCH3 CH3 N 1116 CH2CH3 5-Cl H OCH3 Cl CH 1 146-147℃117 CH2CH3 5-Cl H OCH3 OCH3 CH 1 182-183℃118 CH2CH3 4-Cl H OCH3 CH3 CH 1 136-137℃119 CH2CH3 4-F H OCH3 CH3 N 1 163-164℃120 CH2CH3 4-Br H OCH3 Cl CH 1121 CH2CH3 3-Cl H OCH3 OCH3 CH 1 148-149122 CH2CH3 3-F H OCH3 CH3 CH 1123 CH2CH3 6-OCH3 H OCH3 CH3 N 1 153-154℃(分解)124 CH2CH3 6-OCH3 H OCH3 Cl CH 1125 CH2CH3 6-OCH3 H OCH3 OCH3 CH 1 188-189℃126 CH2CH3 6-OCH3 H OCH3 CH3 CH 1 151-152℃127 CH2CH3 5-OCH3 H OCH3 CH3 N 1128 CH2CH3 5-OCH3 H OCH3 Cl CH 1129 CH2CH3 4-OCH3 H OCH3 OCH3 CH 1130 CH2CH3 4-OCH3 H OCH3 CH3 CH 1131 CH2CH3 3-OCH3 H OCH3 CH3 N 1132 CH2CH3 3-OCH3 H OCH3 Cl CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点133 CH2CH3 6-OC2H5 H OCH3 OCH3 CH 1 194-195134 CH2CH3 6-OC3H7 H OCH3 CH3 CH 1135 CH2CH3 6-OC4H9 H OCH3 CH3 N 1136 CH2CH3 6-SCH3 H OCH3 Cl CH 1137 CH2CH3 6-COOCH3 H OCH3 OCH3 CH 1 163138 CH2CH3 6-COOCH3 H OCH3 CH3 CH 1 148139 CH2CH3 6-COOCH3 H OCH3 CH3 N 1140 CH2CH3 6-COOCH3 H OCH3 Cl CH 1 154-156141 CH2CH3 6-COOC2H5 H OCH3 OCH3 CH 1 124-125142 CH2CH3 6-COOC2H5 H OCH3 CH3 CH 1 128-129143 CH2CH3 5-COOCH3 H OCH3 CH3 N 1144 CH2CH3 5-COOCH3 H OCH3 Cl CH 1145 CH2CH3 4-COOCH3 H OCH3 OCH3 CH 1146 CH2CH3 4-COOCH3 H OCH3 CH3 CH 1147 CH2CH3 3-COOCH3 H OCH3 CH3 N 1148 CH2CH3 3-COOCH3 H OCH3 Cl CH 1149 CH2CH3 6-COOC3H7 H OCH3 OCH3 CH 1150 CH2CH3 6-COOC4H9 H OCH3 CH3 CH 1151 CH2CH3 6-CH3 H OCH3 CH3 N 1 139-140152 CH2CH3 6-CH3 H OCH3 Cl CH 1153 CH2CH3 6-CH3 H OCH3 OCH3 CH 1 177-178154 CH2CH3 6-CH3 H OCH3 CH3 CH 1 155-156(分解)155 CH2CH3 5-CH3 H OCH3 CH3 N 1156 CH2CH3 5-CH3 H OCH3 Cl CH 1 82(分解)157 CH2CH3 4-CH3 H OCH3 OCH3 CH 1 149-150℃158 CH2CH3 3-CH3 H OCH3 CH3 CH 1 118-120159 CH2CH3 6-C2H5 H OCH3 CH3 N 1 139-141160 CH2CH3 6-C3H7 H OCH3 Cl CH 1 122-124161 CH2CH3 6-C4H9 H OCH3 OCH3 CH 1162 CH2CH3 6-NO2 H OCH3 CH3 CH 1163 CH2CH3 6-CF3 H OCH3 CH3 N 1 155-156164 CH2CH3 6-CN H OCH3 Cl CH 1165 CH2CH3 6-SCH3 H OCH3 OCH3 CH 1166 CH2CH3 6-SC2H5 H OCH3 CH3 CH 1167 CH2CH3 6-SC5H9 H OCH3 CH3 N 1168 CH2CH3 6-SCH3 H OCH3 Cl CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点169 CH2CH2CH3 6-Cl H OCH3 OCH3 CH 1170 CH2CH2CH3 6-Cl H OCH3 CH3 CH 1171 CH2CH2CH3 6-Cl H OCH3 CH3 N 1172 CH2CH2CH3 6-Cl H OCH3 Cl CH 1173 CH2CH2CH3 6-F H OCH3 OCH3 CH 1174 CH2CH2CH3 6-F H OCH3 CH3 CH 1175 CH2CH2CH3 6-F H OCH3 CH3 N 1176 CH2CH2CH3 6-F H OCH3 Cl CH 1177 CH2CH2CH3 6-Br H OCH3 OCH3 CH 1178 CH2CH2CH3 5-F H OCH3 CH3 CH 1179 CH2CH2CH3 5-Br H OCH3 CH3 N 1180 CH2CH2CH3 5-Cl H OCH3 Cl CH 1181 CH2CH2CH3 5-Cl H OCH3 OCH3 CH 1182 CH2CH2CH3 4-Cl H OCH3 CH3 CH 1183 CH2CH2CH3 4-F H OCH3 CH3 N 1184 CH2CH2CH3 4-Br H OCH3 Cl CH 1185 CH2CH2CH3 3-Cl H OCH3 OCH3 CH 1186 CH2CH2CH3 3-F H OCH3 CH3 CH l187 CH2CH2CH3 6-OCH3 H OCH3 CH3 N 1188 CH2CH2CH3 6-OCH3 H OCH3 Cl CH 1189 CH2CH2CH3 6-OCH3 H OCH3 OCH3 CH 1190 CH2CH2CH3 6-OCH3 H OCH3 CH3 CH 1191 CH2CH2CH3 5-OCH3 H OCH3 CH3 N 1192 CH2CH2CH3 5-OCH3 H OCH3 Cl CH 1193 CH2CH2CH3 4-OCH3 H OCH3 OCH3 CH 1194 CH2CH2CH3 4-OCH3 H OCH3 CH3 CH 1195 CH2CH2CH3 3-OCH3 H OCH3 CH3 N 1196 CH2CH2CH3 3-OCH3 H OCH3 Cl CH 1197 CH2CH2CH3 6-OC2H5 H OCH3 OCH3 CH 1198 CH2CH2CH3 6-OC3H7 H OCH3 CH3 CH 1199 CH2CH2CH3 6-OC4H9 H OCH3 CH3 N 1200 CH2CH2CH3 6-SCH3 H OCH3 Cl CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点201 CH2CH2CH3 6-COOCH3 H OCH3 OCH3 CH 1202 CH2CH2CH3 6-COOCH3 H OCH3 CH3 CH 1203 CH2CH2CH3 6-COOCH3 H OCH3 CH3 N 1203a CH2CH2CH3 6-COOCH3 H OCH3 Cl CH 1204 CH2CH2CH3 6-COOC2H5 H OCH3 OCH3 CH 1205 CH2CH2CH3 6-COOC2H5 H OCH3 CH3 CH 1206 CH2CH2CH3 5-COOCH3 H OCH3 CH3 N 1207 CH2CH2CH3 5-COOCH3 H OCH3 Cl CH 1208 CH2CH2CH3 4-COOCH3 H OCH3 OCH3 CH 1209 CH2CH2CH3 4-COOCH3 H OCH3 CH3 CH 1210 CH2CH2CH3 3-COOCH3 H OCH3 CH3 N 1211 CH2CH2CH3 3-COOCH3 H OCH3 Cl CH 1212 CH2CH2CH3 6-COOC3H7 H OCH3 OCH3 CH 1213 CH2CH2CH3 6-COOC4H9 H OCH3 CH3 CH 1214 CH2CH2CH3 6-CH3 H OCH3 CH3 N 1215 CH2CH2CH3 6-CH3 H OCH3 Cl CH 1216 CH2CH2CH3 6-CH3 H OCH3 OCH3 CH 1217 CH2CH2CH3 6-CH3 H OCH3 CH3 CH 1218 CH2CH2CH3 5-CH3 H OCH3 CH3 N 1219 CH2CH2CH3 5-CH3 H OCH3 Cl CH 1220 CH2CH2CH3 4-CH3 H OCH3 OCH3 CH 1221 CH2CH2CH3 3-CH3 H OCH3 CH3 CH 1222 CH2CH2CH3 6-C2H5 H OCH3 CH3 N 1223 CH2CH2CH3 6-C3H7 H OCH3 Cl CH 1224 CH2CH2CH3 6-C4H9 H OCH3 OCH3 CH 1225 CH2CH2CH3 6-NO2 H OCH3 CH3 CH 1226 CH2CH2CH3 6-CF3 H OCH3 CH3 N 1227 CH2CH2CH3 6-CN H OCH3 Cl CH 1228 CH2CH2CH3 6-SCH3 H OCH3 OCH3 CH 1229 CH2CH2CH3 6-SC2H5 H OCH3 CH3 CH 1230 CH2CH2CH3 6-SC5H9 H OCH3 CH3 N 1231 CH2CH2CH3 6-SCH3 H OCH3 Cl CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点232 CH(CH3)2 6-Cl H OCH3 OCH3 CH 1233 CH(CH3)2 6-Cl H OCH3 CH3 CH 1234 CH(CH3)2 6-Cl H OCH3 CH3 N 1235 CH(CH3)2 6-Cl H OCH3 Cl CH 1236 CH(CH3)2 6-F H OCH3 OCH3 CH 1237 CH(CH3)2 6-F H OCH3 CH3 CH 1238 CH(CH3)2 6-F H OCH3 CH3 N 1239 CH(CH3)2 6-F H OCH3 Cl CH 1240 CH(CH3)2 6-Br H OCH3 OCH3 CH 1241 CH(CH3)2 5-F H OCH3 CH3 CH 1242 CH(CH3)2 5-Br H OCH3 CH3 N 1243 CH(CH3)2 5-Cl H OCH3 Cl CH 1244 CH(CH3)2 5-Cl H OCH3 OCH3 CH 1245 CH(CH3)2 4-Cl H OCH3 CH3 CH 1246 CH(CH3)2 4-F H OCH3 CH3 N 1247 CH(CH3)2 4-Br H OCH3 Cl CH 1248 CH(CH3)2 3-Cl H OCH3 OCH3 CH 1249 CH(CH3)2 3-F H OCH3 CH3 CH 1250 CH(CH3)2 6-OCH3 H OCH3 CH3 N 1251 CH(CH3)2 6-OCH3 H OCH3 Cl CH 1252 CH(CH3)2 6-OCH3 H OCH3 OCH3 CH 1 1766-177℃253 CH(CH3)2 6-OCH3 H OCH3 CH3 CH 1 156-157℃254 CH(CH3)2 5-OCH3 H OCH3 CH3 N 1255 CH(CH3)2 5-OCH3 H OCH3 Cl CH 1256 CH(CH3)2 4-OCH3 H OCH3 OCH3 CH 1257 CH(CH3)2 4-OCH3 H OCH3 CH3 CH 1258 CH(CH3)2 3-OCH3 H OCH3 CH3 N 1259 CH(CH3)2 3-OCH3 H OCH3 Cl CH 1260 CH(CH3)2 6-OC2H5 H OCH3 OCH3 CH 1261 CH(CH3)2 6-OC3H7 H OCH3 CH3 CH 1262 CH(CH3)2 6-OC4H9 H OCH3 CH3 N 1263 CH(CH3)2 6-SCH3 H OCH3 Cl CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点264 CH(CH3)2 6-COOCH3 H OCH3 OCH3 CH 1265 CH(CH3)2 6-COOCH3 H OCH3 CH3 CH 1266 CH(CH3)2 6-COOCH3 H OCH3 CH3 N 1267 CH(CH3)2 6-COOCH3 H OCH3 Cl CH 1268 CH(CH3)2 6-COOC2H5 H OCH3 OCH3 CH 1269 CH(CH3)2 6-COOC2H5 H OCH3 CH3 CH 1270 CH(CH3)2 5-COOCH3 H OCH3 CH3 N 1271 CH(CH3)2 5-COOCH3 H OCH3 Cl CH 1272 CH(CH3)2 4-COOCH3 H OCH3 OCH3 CH 1273 CH(CH3)2 4-COOCH3 H OCH3 CH3 CH 1274 CH(CH3)2 3-COOCH3 H OCH3 CH3 N 1275 CH(CH3)2 3-COOCH3 H OCH3 Cl CH 1276 CH(CH3)2 6-COOC3H7 H OCH3 OCH3 CH 1277 CH(CH3)2 6-COOC4H9 H OCH3 CH3 CH 1278 CH(CH3)2 6-CH3 H OCH3 CH3 N 1279 CH(CH3)2 6-CH3 H OCH3 Cl CH 1280 CH(CH3)2 6-CH3 H OCH3 OCH3 CH 1281 CH(CH3)2 6-CH3 H OCH3 CH3 CH 1282 CH(CH3)2 5-CH3 H OCH3 CH3 N 1283 CH(CH3)2 5-CH3 H OCH3 Cl CH 1284 CH(CH3)2 4-CH3 H OCH3 OCH3 CH 1285 CH(CH3)2 3-CH3 H OCH3 CH3 CH 1286 CH(CH3)2 6-C2H5 H OCH3 CH3 N 1287 CH(CH3)2 6-C3H7 H OCH3 Cl CH 1288 CH(CH3)2 6-C4H9 H OCH3 OCH3 CH 1289 CH(CH3)2 6-NO2 H OCH3 CH3 CH 1290 CH(CH3)2 6-CF3 H OCH3 CH3 N 129l CH(CH3)2 6-CN H OCH3 Cl H 1292 CH(CH3)2 6-SCH3 H OCH3 OCH3 CH 1293 CH(CH3)2 6-SC2H5 H OCH3 CH3 CH 1294 CH(CH3)2 6-SC5H9 H OCH3 CH3 N 1295 CH(CH3)2 6-SCH3 H OCH3 Cl CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点296 CH2CH3 4，6-Cl2 H OCH3 Cl CH 2297 CH2CH3 4，6-Cl2 H OCH3 OCH3 CH 2298 CH2CH3 4，6-Cl2 H OCH3 CH3 N 2299 CH2CH3 3，5-Cl2 H OCH3 OCH3 CH 2300 CH2CH2CH3 4，6-Cl2 H OCH3 Cl CH 2301 CH2CH2CH3 4，6-Cl2 H OCH3 OCH3 CH 2302 CH2CH2CH3 4，6-Cl2 H OCH3 CH3 CH 2303 CH2CH2CH3 3，5-Cl2 H OCH3 OCH3 CH 2304 CH(CH3)2 4，6-Cl2 H OCH3 CH3 N 2305 CH(CH3)2 4，6-Cl2 H OCH3 OCH3 CH 2306 CH(CH3)2 4，6-Cl2 H OCH3 Cl CH 2307 CH(CH3)2 3，5-Cl2 H OCH3 OCH3 CH 2308 CH2CH3 4，6-F2 H OCF2H CH3 CH 2309 CH2CH3 4，6-F2 H OCH3 OCH3 CH 2310 CH2CH3 4，6-F2 H OCH3 CH3 N 2311 CH2CH3 3，5-F2 H OCH3 OCH3 CH 2312 CH2CH2CH3 4，6-F2 H OCH3 Cl CH 2313 CH2CH2CH3 4，6-F2 H OCH3 OCH3 CH 2314 CH2CH2CH3 4，6-F2 H OCF2H OCF2H CH 2315 CH2CH2CH3 3，5-F2 H OCH3 OCH3 CH 2316 CH(CH3)2 4，6-F2 H OCH3 CH3 N 2317 CH(CH3)2 4，6-F2 H OCH3 OCH3 CH 2318 CH2CH3 4，6-(CH3)2H OCH3 Cl CH 2319 CH2CH3 4，6-(CH3)2H OCH3 OCH3 CH 2320 CH2CH3 3，5-(NO2)2H OCH2CF3OCH3 CH 2321 CH2CH3 H CH3 OCH3 OCH3 CH O 119-120322 CH2CH3 H CH3 OCH3 CH3 N 0 101-102323 CH2CH3 H CH2CH＝CH2 OCH3 OCH3 CH 0324 CH2CH3 H CH2CH＝CH2 OCH3 Cl CH 0325 CH2CH2CH3 H CH3 OCH3 OCH3 CH 0326 CH2CH2CH3 H CH3 OCH3 CH3 CH 0327 CH2CH2CH3 H CH2CH＝CH2 OCH3 OCH3 CH 0328 CH2CH2CH3 H CH2CH＝CH2 OCH3 CH3 N 0实例序号 R1 R2 R3 R5 R6 E n 熔点329 CH(CH3)2 H CH3 OCH3 OCH3 CH 0 127-130330 CH(CH3)2 H CH3 OCH3 Cl CH 0331 CH(CH3)2 H CH2CH＝CH2 OCH3 OCH3 CH 0332 CH(CH3)2 H CH2CH＝CH2 OCF2H CH3 CH 0333 CH2CH3 H C2H5 OCH3 OCH3 CH 0334 CH2CH2CH3 H C2H5 OCH3 Cl CH 0335 CH(CH3)2 H C2H5 OCH3 OCH3 CH 0336 CH2CH3 H C2H5 OCH2CF3OCH3 CH 0337 CH2CH2CH3 H C2H5 OCH3 OCH3 CH 0338 CH2CH3 6-CH3 CH3 OCH3 CH3 N 1339 CH2CH2CH3 6-OCH3 CH3 OCH3 OCH3 CH 1340 CH(CH3)2 6-Cl CH2CH＝CH2 OCH3 Cl CH 1341 CH2CH3 6-F CH2CH＝CH2 OCH3 OCH3 CH 1342 CH2CH2CH3 6-CF3 CH3 OCH2CF3OCH3 N 1343 CH(CH3)2 6-COOCH3 CH3 OCH3 OCH3 CH 1 166-167344 CH2CH3 6-C2H5 H OCH3 OCH3 CH 1 166-167345 ″ ″ H OCH3 CH3 CH 1 155-156346 ″ ″ H OCH3 Cl CH 1347 ″ ″ H CH3 CH3 CH 1348 ″ ″ H OCH3 OCH2CF3N 1349 ″ ″ CH3 OCH3 OCH3 CH 1350 ″ ″ CH3 OCH3 CH3 N 1351 ″ ″ H OCF2H OCF2H CH 1352 ″ ″ H OCH3 OCH3 N 1353 ″ 6-C3H7 H OCH3 OCH3 CH 1 158354 ″ ″ H OCH3 CH3 CH 1 148355 ″ ″ H OCH3 CH3 N 1 124-126356 ″ ″ H OC2H5 NHCH3 N 1 167-169357 ″ ″ H OCH3 OCH2CF3N 1 115-117358 ″ ″ H CH3 Cl CH 1 90(分解)359 ″ 6-OC2H5 H OCH3 CH3 CH 1 157-158360 ″ ″ H OCH3 Cl CH 1 158-159实例序号 R1 R2 R3 R5 R6 E n 熔点361 CH2CH3 6-OC2H5 H OCH3 CH3 N 1 166-167362 ″ ″ H CH3 CH3 CH 1 139-140363 ″ ″ H OCH3 OCH2CF3 N 1 124364 ″ ″ CH3 OCH3 OCH3 CH 1 112-115365 ″ ″ CH3 OCH3 CH3 N 1366 ″ ″ H OCF2H OCF2H CH 1367 ″ ″ H OCH3 OCH3 N 1 150-151(分解)368 ″ 6-CF3 H OCH3 OCH3 CH 1 181369 ″ ″ H OCH3 CH3 CH 1 151-153370 ″ ″ H OCH3 Cl CH 1371 ″ ″ H CH3 CH3 CH 1372 ″ ″ H OCH3 OCH2CF3 N 1373 ″ ″ CH3 OCH3 OCH3 CH 1374 ″ ″ CH3 OCH3 CH3 N 1375 ″ ″ H OCF2H OCF2H CH 1376 ″ ″ H OCH3 OCH3 N 1377 ″ 6-CH3 CH3 OCH3 OCH3 CH 1 88(分解)378 ″ 5-CH3 H OCH3 OCH3 CH 1 158-61379 ″ ″ H OCH3 CH3 CH 1 113(分解)380 ″ 5-C2H5 H OCH3 OCH3 CH 1 132-133℃381 ″ ″ H OCH3 CH3 CH 1 117-118℃382 ″ 5-Cl H OCH3 OCH3 CH 1 182-183℃383 ″ ″ H OCH3 CH3 CH 1 138-139℃384 ″ 5-OCH3 H OCH3 OCH3 CH 1385 ″ ″ H OCH3 CH3 CH 1386 ″ 6-CO2CH3CH3 OCH3 OCH3 CH 1 102-105(分解)387 ″ ″ H OCH3 OCH3 N 1 154-155388 CH2CH2CH3 6-C2H5 H OCH3 OCH3 CH 1389 ″ ″ H OCH3 CH3 CH 1390 ″ ″ H OCH2 Cl CH 1391 ″ ″ H CH3 CH3 CH 1392 ″ ″ CH3 OCH3 OCH3 CH 1393 ″ ″ CH3 OCH3 CH3 N 1394 ″ ″ H OCF2H OCF2H CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点395 ″ 6-C3H7 H OCH3 OCH3 CH 1 143-145396 ″ ″ H OCH3 CH3 CH 1397 ″ ″ H OCH3 CH3 N 1398 ″ 6-OC2H5 H OCH3 OCH3 CH 1 138-139399 ″ ″ H OCH3 Cl CH 1400 ″ ″ H OCH3 CH3 N 1401 ″ ″ H CH3 CH3 CH 1402 ″ ″ CH3 OCH3 OCH3 CH 1 111-113403 ″ ″ CH3 OCH3 CH3 N 1404 ″ ″ H OCF2H OCF2H CH 1405 ″ 6-CF3 H OCH3 OCH3 CH 1 165-166406 ″ ″ H OCH3 CH3 CH 1407 ″ ″ H OCH3 Cl CH 1408 ″ ″ H CH3 CH3 CH 1409 ″ ″ CH3 OCH3 OCH3 CH 1410 ″ ″ H OCF2H OCF2H CH 1 121-122411 ″ 6-CH3 CH3 OCH3 OCH3 CH 1412 ″ 6-CO2CH3CH3 OCH3 OCH3 CH 1413 CH(CH3)26-C2H5 H OCH3 OCH3 CH 1414 ″ ″ H OCH3 CH3 CH 1415 ″ ″ H OCH3 Cl CH 1416 ″ ″ H CH3 CH3 CH 1417 ″ ″ CH3 OCH3 OCH3 CH 1418 ″ ″ CH3 OCH3 CH3 N 1419 ″ ″ H OCF2H OCF2H CH 1420 ″ 6-C3H7 H OCH3 OCH3 CH 1 137421 ″ ″ H OCH3 CH3 CH 1 131-133422 ″ ″ H OCH3 CH3 N 1423 ″ 6-OC2H5 H OCH3 OCH3 CH 1 129-130424 ″ ″ H OCH3 CH3 CH 1425 ″ ″ H OCH3 Cl CH 1426 ″ ″ H OCH3 CH3 N 1427 ″ ″ H CH3 CH3 CH 1428 ″ ″ CH3 OCH3 OCH3 CH 1实例序号 R1 R2 R3 R5 R6 E n 熔点429 ″ ″ CH3 OCH3 CH3 N 1430 ″ ″ H OCF2H OCF2H CH 1431 ″ 6-CF3 H OCH3 OCH3 CH 1 157-159432 ″ ″ H OCH3 CH3 CH 1433 ″ ″ H OCH3 Cl CH 1434 ″ ″ H CH3 CH3 CH 1435 ″ ″ CH3 OCH3 OCH3 CH 1436 ″ ″ H OCF2H OCF2H CH 1437 ″ 6-CH3 CH3 OCH3 OCH3 CH 1438 ″ 6-CO2CH3 CH3 OCH3 OCH3 CH 1439 CH2CH3 3，4，6-F3 H OCH3 OCH3 CH 3440 ″ 6-Cl C2H5 OCH3 OCH3 CH 1441 ″ 6-OCH3 C2H5 OCH3 OCH3 CH 1442 ″ ″ C2H5 OCH3 OCH3 N 1443 CH2CH2CH2″ C2H5 OCH3 OCH3 N 1
表2实例序号 R1 R2 R5 n 熔点[℃]444 CH2CH3 H CH3 0445 CH2CH3 H H 0446 CH2CH3 H OCH3 0447 CH2CH2CH3 H CH3 0448 CH2CH2CH3 H H 0449 CH2CH2CH3 H OCH3 0450 CH(CH3)2 H CH3 0451 CH(CH3)2 H H 0452 CH(CH3)2 H OCH3 0453 CH2CH3 6-CH3 OCH3 1454 CH2CH2CH3 6-OCH3 OCH3 1455 CH(CH3)2 6-Cl OCH3 1456 CH2CH3 6-CF3 OCH3 1457 CH2CH2CH3 6-F OCH3 1458 CH(CH3)2 6-OCF2H OCH3 1
表3
实例序号 R1 R2 R5 G n 熔点[℃]459 CH2CH3 H CH3 CH2 0460 CH2CH3 H H CH2 0461 CH2CH3 H OCH3 CH2 0462 CH2CH2CH3 H CH3 CH2 0463 CH2CH2CH3 H H CH2 0464 CH2CH2CH3 H OCH3 CH2 0465 CH(CH3)2 H CH3 CH2 0466 CH(CH3)2 H H CH2 0467 CH(CH3)2 H OCH3 CH2 0468 CH2CH3 H CH3 O 0469 CH2CH3 H H O 0470 CH2CH3 H OCH3 O 0471 CH2CH2CH3 H CH3 O 0472 CH2CH2CH3 H H O 0473 CH2CH2CH3 H OCH3 O O474 CH(CH3)2 H CH3 O 0475 CH(CH3)2 H H O 0476 CH(CH3)2 H OCH3 O 0477 CH2CH3 6-CH3 CH3 CH2 1478 CH2CH2CH3 6-OCH3 CH3 O 1479 CH(CH3)2 6-Cl CH3 CH2 1480 CH2CH3 6-CF3 CH3 O 1481 CH2CH2CH3 6-F CH3 CH2 1482 CH(CH3)2 6-OCF2H CH3 O 1
表4
实例序号 R1 R2 R5 n 熔点483 CH2CH3 H CH3 0484 CH2CH3 H H 0485 CH2CH3 H OCH3 0486 CH2CH2CH3 H CH3 0487 CH2CH2CH3 H H 0488 CH2CH2CH3 H OCH3 0489 CH(CH3)2 H CH3 0490 CH(CH3)2 H H 0491 CH(CH3)2 H OCH3 0492 CH2CH3 6-CH3 OCH3 1493 CH2CH2CH3 6-OCH3 OCH3 1494 CH(CH3)2 6-Cl OCH3 1495 CH2CH3 6-CF3 OCH3 1496 CH2CH2CH3 6-F OCH3 1497 CH(CH3)2 6-OCF2H OCH3 1
表5
实例序号 R1 R2 R5 R7 n 熔点498 CH2CH3 H CH3 CH3 0499 CH2CH3 H H CH3 0500 CH2CH3 H OCH3 CH3 0501 CH2CH3 H CH3 H 0502 CH2CH2CH3 H CH3 CH3 0503 CH2CH2CH3 H H CH3 0504 CH2CH2CH3 H OCH3 CH3 0505 CH2CH2CH3 H CH3 H 0506 CH(CH3)2 H CH3 CH3 0507 CH(CH3)2 H H CH3 0508 CH(CH3)2 H OCH3 CH3 0509 CH(CH3)2 H CH3 H 0510 CH2CH3 6-CH3 CH3 H 1511 CH2CH2CH3 6-OCH3 CH3 CH3 1512 CH(CH3)2 6-Cl CH3 H 1513 CH2CH3 6-CF3 CH3 CH3 1514 CH2CH2CH3 6-F CH3 H 1515 CH(CH3)2 6-OCF2H CH3 CH3 1
表6实例序号 R1 R2 R5 R6 E n 熔点516 CH2CH3 H OCH3 OCH3 CH 0517 CH2CH3 H OCH3 CH3 CH 0518 CH2CH3 H OCH3 CH3 N 0519 CH2CH2CH3 H OCH3 OCH3 CH 0520 CH2CH2CH3 H OCH3 CH3 CH 0521 CH2CH2CH3 H OCH3 CH3 N 0522 CH(CH3)2 H OCH3 OCH3 CH 0523 CH(CH3)2 H OCH3 CH3 CH 0524 CH(CH3)2 H OCH3 CH3 N 1525 CH2CH3 6-CH3 OCH3 CH3 N 1526 CH2CH2CH3 6-OCH3 OCH3 OCH3 CH 1527 CH(CH3)2 6-Cl OCH3 OCH3 N 1528 CH2CH3 6-CF3 OCH3 CH3 CH 1529 CH2CH2CH3 6-F OCH3 OCH3 N 1530 CH(CH3)2 6-OCF2H OCH3 CH3 CH 1
表7实例序号 R1 R2 R8 n 熔点531 CH2CH3 H OCH3 0532 CH2CH3 H CH3 0533 CH2CH2CH3 H OCH3 0534 CH2CH2CH3 H CH3 0535 CH(CH3)2 H OCH3 0536 CH(CH3)2 H CH3 0537 CH2CH3 6-CH3 CH3 1538 CH2CH2CH3 6-OCH3 CH3 1539 CH(CH3)2 6-Cl OCH3 1540 CH2CH3 6-CF3 CH3 1541 CH2CH2CH3 6-F OCH3 1542 CH(CH3)2 6-OCF2H CH3 1
表8实例序号 R1 R2 R7 R8 R11 n 熔点543 CH2CH3 H H OCH3 H 0544 CH2CH3 H H CH3 CH3 0545 CH2CH3 H CH3 CH3 CH3 0546 CH2CH2CH3 H H OCH3 H 0547 CH2CH2CH3 H H CH3 CH3 0548 CH2CH2CH3 H CH3 CH3 CH3 0549 CH(CH3)2 H H OCH3 H 0550 CH(CH3)2 H H CH3 CH3 0551 CH(CH3)2 H CH3 CH3 CH3 0552 CH2CH3 6-CH3 H CH3 H 1553 CH2CH2CH3 6-OCH3 H CH3 CH3 1554 CH(CH3)2 6-Cl CH3 OCH3 CH3 1555 CH2CH3 6-CF3 H CH3 H 1556 CH2CH3 6-F H OCH3 CH3 1557 CH(CH3)2 6-Cl CH3 CH3 CH3 1生物活性实例
对杂草的药效及作物的耐药性用0-5的数值来分级，以表示其活性程度。其中，
0代表无作用
1代表0-20％药效或药害
2代表20-40％药效或药害
3代表40-60％药效或药害
4代表60-80％药效或药害
5代表80-100％药效或药害1.芽前除草作用
将单子叶和双子叶杂草种子或根茎片段放置在装沙壤土的塑料盆中，并覆土。然后以不同剂量施用本发明化合物的可湿性粉剂或乳油的水悬浊液或乳浊液于覆盖土表面。药液量为600-800升/公顷(经换算)。
药剂处理后，将这些盆置于温室中，并保持适于杂草生长的良好条件。经3-4星期试验时间并且供试植物萌芽后，对杂草或其芽的药效进行目测分级，将它们与未经处理的对照进行对比。如表9中的分级数据所示，本发明的化合物对许多禾本科杂草和阔叶杂草具有很好的芽前除草效果。
芽后除草作用
将单子叶或双子叶杂草的种子或根茎片段放置在装有沙壤土的塑料盆中并覆土，将这些盆子放在温室中并使杂草获得良好的生长条件，下种三周后，对供试试植物在三叶期进行药剂处理。
制成可湿性粉剂或乳油的本发明化合物以不同剂量兑水喷洒在这些植物的绿色部分。药液用量为600-800升/公顷(已换算)。当供试植物在温室中以最佳生长条件经过3-4周后，对这些制剂的作用目测分级，把它们与未经处理的对照植物进行对比。
依本发明的制剂对许多经济上重要的禾本科杂草和阔叶杂草显示了很好的除草活性(表10)。3.作物的耐药性
在另一个温室实验中，相对较大量的作物种子和杂草种子放置在沙壤土中，并覆土。
一些盆子被立即进行1.中所述的处理，其余这些盆子放在温室中，直至植物发育到其第二或第三真叶时，喷洒不同剂量的依本发明的化合物(如2.中所述)。
施用后四至五周，目测温室中的植物，结果表明，本发明的化合物对双子叶作物无任何药害，例如大豆、棉花、产籽油菜、甜菜和马铃薯，不论是芽前或芽后处理，即使是使用高剂量有效成分也没有药害。此外，禾本科作物如大麦、小麦、黑麦、粟、玉米或稻，也不受某些化合物影响。因此化合物(I)施用于作物田块中，具有很高的选择性，能控制杂草的生长。
表9：本发明化合物的芽前除草作用
| 实 例序 号 | 有效成分剂量(kg/ha) | 除草作用 | |||||
| SIA | CRS | STM | AS | ECG | LOM | ||
| 2345775104133137138153163321 | 0.60.60.60.60.60.60.30.30.30.30.30.30.3 | 5555555555555 | 5554555555555 | 5544355555555 | 1242221425341 | 3342223544342 | 4311221525451 |
表10
本发明化合物的芽后除草作用
缩写：SIA＝欧白芥 ECG＝稗
| 实例序号 | 有效成分剂量(kg/ha) | 除草作用 | |||||
| SIA | CRS | STM | AS | ECG | LOM | ||
| 2345775104133137138153163321 | 0.60.60.60.60.60.60.30.30.30.30.30.30.3 | 5555555555554 | 5545555545455 | 5544555555555 | 0132103324241 | 4442354545443 | 5423233524251 |
CRS＝南蒿 LOM＝多花黑麦草
STM＝繁缕
AS＝燕麦
Claims (15)
1.一种制备式(I)化合物或其盐的方法，
其中，R1是乙基、正丙基或异丙基，R2是CH3、C2H5、C3H7、OCH3、OC2H5、CF3、Cl、CN、CO2CH3或CH2CH＝CH2，n是0或1，y是O，R3是氢或CH3，R4是下式表示的杂环基团
E是CH或N，R5是OCH3或CH3和R6是OCH3或CH3，该制备方法包括(a)使式(II)表示的一种化合物与式(III)表示的一种化合物反应或，(b)使式(IV)表示的一种化合物
与式(V)表示的一种氯磺酰脲反应，
或
(c)使式(VI)表示的一种化合物
与式(VII)表示的一种氨基甲酸酯反应，
其中z是苯基或(C1-C6)烷基，
必要时，把所得化合物转化成它们的盐。
2.根据权利要求1所述的方法，其中
n为0，
R3为H，
E是CH，
R5是OCH3和
R6是OCH3。
3.根据权利要求1所述的方法，其中，
n是0；R3是H；R5是CH3或OCH3；R6是CH3或OCH3。
4.根据权利要求1所述的方法，其中
R1是乙基；n是0；R3是H；R5是OCH3；R6是OCH3；E是CH。
5.根据权利要求1-4中任一项所述的方法，其中，反应是在一种惰性非质子溶剂中、按方法的变通方案a)、b)或c)中任一项进行的。
6.根据权利要求5所述的方法，其中，反应是在0℃至溶剂的沸点之间的温度下、按方法的变通方案a)进行的。
7.根据权利要求5所述的方法，其中，反应是在-10℃至80℃之间，在一种碱存在下、按方法的变通方案b)进行的。
8.根据权利要求5所述的方法，其中，反应是在20℃至溶剂的沸点之间、在一种叔式有机碱的存在下、按方法的变通方案c)进行的。
9.一种除草组合物，含有有效量的一种或多种式(I)化合物或其盐、以及惰性助剂
其中，
R1是乙基、正丙基或异丙基，
R2是CH3、C2H5、C3H7、OCH3、OC2H5、CF3、Cl、CN、
CO2CH3或CH2CH＝CH2，
n是0或1，
y是O，
R3是氢或CH3，
R4是下式表示的杂环基团
E是CH或N，
R5是OCH3或CH3和
R6是OCH3或CH3。
10.根据权利要求9所述的组合物，其中
n为0，
R3为H，
E是CH，
R5是OCH3和
R6是OCH3。
11.根据权利要求9所述的组合物，其中n是0；R3是H；R5是CH3或OCH3；R6是CH3或OCH3。
12.根据权利要求9所述的组合物，其中
R1是乙基；n是0；R3是H；R5是OCH3；R6是OCH3；E是CH。
13.根据权利要求9-12中任一项所述的组合物，其中有效成分式(I)化合物的含量为2-90％(重量)。
14.根据权利要求9或13中任一项所述的组合物，其中，组合物以以下制剂形式存在：可湿性粉剂、乳油、乳液、喷洒药液、粉剂、种子包衣剂、分散剂、粒剂和微粒剂。
15.根据权利要求9或14中任一项所述的组合物，其中，所说的助剂选自润湿剂、稀释剂、惰性固体或液体物质、惰性有机溶剂、乳化剂、分散剂、粘着剂、渗透剂、填料和载体。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3816704A DE3816704A1 (de) | 1988-05-17 | 1988-05-17 | Heterocyclische 2-alkoxyphenoxysulfonylharnstoffe und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
| DEP3816704.2 | 1988-05-17 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89103342A Division CN1044427C (zh) | 1988-05-17 | 1989-05-15 | 用带杂环的2－烷氧苯氧基硫酰脲类除草剂除灭杂草的方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1190651A true CN1190651A (zh) | 1998-08-19 |
| CN1068593C CN1068593C (zh) | 2001-07-18 |
Family
ID=6354502
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89103342A Expired - Lifetime CN1044427C (zh) | 1988-05-17 | 1989-05-15 | 用带杂环的2－烷氧苯氧基硫酰脲类除草剂除灭杂草的方法 |
| CN97108749A Expired - Lifetime CN1068593C (zh) | 1988-05-17 | 1997-12-19 | 带杂环的2－烷氧苯氧基硫酰脲的制备方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89103342A Expired - Lifetime CN1044427C (zh) | 1988-05-17 | 1989-05-15 | 用带杂环的2－烷氧苯氧基硫酰脲类除草剂除灭杂草的方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5104443A (zh) |
| EP (1) | EP0342569B1 (zh) |
| JP (1) | JPH0774206B2 (zh) |
| KR (1) | KR100215617B1 (zh) |
| CN (2) | CN1044427C (zh) |
| AU (1) | AU634473B2 (zh) |
| BR (1) | BR8902278A (zh) |
| CA (1) | CA1341034C (zh) |
| DD (1) | DD283760A5 (zh) |
| DE (2) | DE3816704A1 (zh) |
| ES (1) | ES2057015T3 (zh) |
| HU (1) | HU206439B (zh) |
| IL (1) | IL90299A (zh) |
| RU (1) | RU1829896C (zh) |
| ZA (1) | ZA893643B (zh) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3811777A1 (de) * | 1988-04-08 | 1989-10-19 | Hoechst Ag | Heterocyclisch substituierte alkyl- und alkenylsulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
| DE3816703A1 (de) * | 1988-05-17 | 1989-11-30 | Hoechst Ag | Heterocyclisch substituierte phenoxysulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
| US5272129A (en) * | 1989-03-18 | 1993-12-21 | Hoechst Aktiengesellschaft | Phenoxysulfonylureas based on 3-substituted alkyl salicylates, and their use as herbicides and plant growth regulators |
| DE3933543A1 (de) * | 1989-10-07 | 1991-04-11 | Hoechst Ag | Synergistische herbizide mittel |
| US5599769A (en) * | 1990-11-13 | 1997-02-04 | Hoechst Aktiengesellschaft | Synergistic herbicidal compositions comprising glyphosate or glufosinate in combination with a sulfonylurea herbicide |
| US5294741A (en) * | 1991-02-25 | 1994-03-15 | Hoechst Aktiengesellschaft | Continuous process for the preparation of sulfonylisocyanates |
| DE59206592D1 (de) * | 1991-03-07 | 1996-07-25 | Hoechst Schering Agrevo Gmbh | Verfahren zur Herstellung von Sulfonylharnstoffen |
| DE4110636A1 (de) * | 1991-04-02 | 1992-10-08 | Hoechst Ag | Verfahren zur herstellung von sulfonylharnstoffen |
| ES2096786T3 (es) * | 1992-03-07 | 1997-03-16 | Hoechst Schering Agrevo Gmbh | Procedimiento para preparar sulfonil-ureas. |
| DE4337847A1 (de) * | 1993-11-05 | 1995-05-11 | Bayer Ag | Substituierte Phenylaminosulfonylharnstoffe |
| KR100415595B1 (ko) * | 1995-07-25 | 2004-05-12 | 가부시키가이샤 에스디에스 바이오테크 | 수전용제초제조성물 |
| MY116568A (en) * | 1995-10-13 | 2004-02-28 | Syngenta Participations Ag | Herbicidal synergistic composition, and method controlling weeds |
| US6114283A (en) * | 1998-07-28 | 2000-09-05 | E. I. Du Pont De Nemours And Company | Herbicidal mixtures |
| DE19963383A1 (de) | 1999-12-28 | 2001-07-05 | Aventis Cropscience Gmbh | Formulierung von Herbiziden und Pflanzenwachstumsregulatoren |
| DE19903064A1 (de) * | 1999-01-27 | 2000-10-05 | Aventis Cropscience Gmbh | Formulierung von Herbiziden und Pflanzenwachstumsregulatoren |
| WO2001030155A2 (de) * | 1999-10-26 | 2001-05-03 | Aventis Cropscience Gmbh | Herbizide mittel |
| EP1844654A1 (de) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Penetrationsförderer für agrochemische Wirkstoffe |
| DE102007013362A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Penetrationsförderer für herbizide Wirkstoffe |
| JP5322308B2 (ja) | 2006-09-22 | 2013-10-23 | ダニスコ・ユーエス・インク、ジェネンコー・ディビジョン | トリコデルマ・レセイ（ＴｒｉｃｈｏｄｅｒｍａＲｅｓｓｅｉ）由来のアセトラクテートシンターゼ（ＡＬＳ）選択マーカー |
| WO2011076731A1 (de) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid |
| EP2654433B1 (en) | 2010-12-21 | 2017-08-30 | Bayer Cropscience LP | Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests |
| EP2755485A1 (en) | 2011-09-12 | 2014-07-23 | Bayer Cropscience LP | Methods of enhancing health and/or promoting growth of a plant and/or of improving fruit ripening |
| CN103719127B (zh) * | 2013-12-18 | 2016-08-24 | 山东先达农化股份有限公司 | 针对玉米安全的除草剂组合物 |
| CN105360149A (zh) * | 2015-07-22 | 2016-03-02 | 南京华洲药业有限公司 | 一种含炔草酯与乙氧嘧磺隆的复合除草组合物及其应用 |
| CN107698525B (zh) * | 2017-09-27 | 2020-04-21 | 南开大学 | 一类取代苯氧磺酰脲类化合物及其制备方法和用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191553A (en) * | 1978-03-02 | 1980-03-04 | E. I. Du Pont De Nemours And Company | Herbicidal sulfamates |
| BR8102529A (pt) * | 1980-04-29 | 1982-01-05 | Du Pont | Compostos e composicoes herbicidas ou adequados ao controle do crescimento de vegetacao indesejavel e seus processos de preparacao;processo para o controle do crescimento de vegetacao indesejavel |
| US4480101A (en) * | 1981-07-16 | 1984-10-30 | Ciba-Geigy Corporation | Fluoroalkoxy-aminopyrimidines |
| JPS5815962A (ja) * | 1981-07-21 | 1983-01-29 | Mitsui Toatsu Chem Inc | 新規スルホニルウレイド誘導体 |
| DE3151450A1 (de) * | 1981-12-24 | 1983-07-14 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | N-phenoxysulfonylharnstoffe, ihre herstellung und verwendung |
| ZA838238B (en) * | 1982-11-05 | 1985-06-26 | Du Pont | Herbicidal phenoxy esters of n-((heterocyclic)aminocarbonyl)sulfamic acid |
| US4562210A (en) * | 1983-01-17 | 1985-12-31 | Ciba-Geigy Corporation | Bactericides |
| JPH0660084B2 (ja) * | 1985-12-27 | 1994-08-10 | クミアイ化学工業株式会社 | 除草粒剤組成物 |
| DE3816703A1 (de) * | 1988-05-17 | 1989-11-30 | Hoechst Ag | Heterocyclisch substituierte phenoxysulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
-
1988
- 1988-05-17 DE DE3816704A patent/DE3816704A1/de not_active Withdrawn
-
1989
- 1989-05-15 IL IL9029989A patent/IL90299A/en unknown
- 1989-05-15 US US07/352,167 patent/US5104443A/en not_active Expired - Lifetime
- 1989-05-15 CN CN89103342A patent/CN1044427C/zh not_active Expired - Lifetime
- 1989-05-16 CA CA000599834A patent/CA1341034C/en not_active Expired - Fee Related
- 1989-05-16 DD DD89328637A patent/DD283760A5/de not_active IP Right Cessation
- 1989-05-16 JP JP1120567A patent/JPH0774206B2/ja not_active Expired - Lifetime
- 1989-05-16 BR BR898902278A patent/BR8902278A/pt not_active IP Right Cessation
- 1989-05-16 ZA ZA893643A patent/ZA893643B/xx unknown
- 1989-05-16 DE DE58907927T patent/DE58907927D1/de not_active Expired - Lifetime
- 1989-05-16 EP EP89108702A patent/EP0342569B1/de not_active Expired - Lifetime
- 1989-05-16 AU AU34784/89A patent/AU634473B2/en not_active Expired
- 1989-05-16 ES ES89108702T patent/ES2057015T3/es not_active Expired - Lifetime
- 1989-05-16 RU SU894614074A patent/RU1829896C/ru active
- 1989-05-17 HU HU892458A patent/HU206439B/hu unknown
- 1989-05-17 KR KR1019890006562A patent/KR100215617B1/ko not_active IP Right Cessation
-
1997
- 1997-12-19 CN CN97108749A patent/CN1068593C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RU1829896C (ru) | 1993-07-23 |
| EP0342569A1 (de) | 1989-11-23 |
| CN1068593C (zh) | 2001-07-18 |
| KR900018107A (ko) | 1990-12-20 |
| KR100215617B1 (ko) | 1999-08-16 |
| CN1044427C (zh) | 1999-08-04 |
| IL90299A (en) | 1994-11-28 |
| DE3816704A1 (de) | 1989-11-30 |
| IL90299A0 (en) | 1989-12-15 |
| AU3478489A (en) | 1989-11-23 |
| HUT50136A (en) | 1989-12-28 |
| CA1341034C (en) | 2000-06-20 |
| JPH0774206B2 (ja) | 1995-08-09 |
| JPH0228159A (ja) | 1990-01-30 |
| DD283760A5 (de) | 1990-10-24 |
| DE58907927D1 (de) | 1994-07-28 |
| CN1038643A (zh) | 1990-01-10 |
| AU634473B2 (en) | 1993-02-25 |
| ES2057015T3 (es) | 1994-10-16 |
| EP0342569B1 (de) | 1994-06-22 |
| HU206439B (en) | 1992-11-30 |
| US5104443A (en) | 1992-04-14 |
| ZA893643B (en) | 1989-12-27 |
| BR8902278A (pt) | 1990-01-09 |
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