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CN1044765C - 吡啶磺酰脲类除草剂及其用途 - Google Patents

吡啶磺酰脲类除草剂及其用途 Download PDF

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CN1044765C
CN1044765C CN91100184A CN91100184A CN1044765C CN 1044765 C CN1044765 C CN 1044765C CN 91100184 A CN91100184 A CN 91100184A CN 91100184 A CN91100184 A CN 91100184A CN 1044765 C CN1044765 C CN 1044765C
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汗斯·凯恩
罗萨·微廉母斯
奥斯华德·沃特
克老斯·布尔
海尔曼·比尔凌格
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Hechester Jsc
Hoechst AG
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Abstract

式(Ⅰ)所示化合物可作为除草剂和植物生长调节剂，式中R1，R2，n，w，R3和A含义详见权利要求1。式(Ⅰ)所示化合物可用与已知方法相类似的方法制备，也可以用式(Ⅱ)所示的新化合物与式R*-O-CO-NR3A(式中R3代表苯基或烷基)所示的一个氨基甲酸酯化合物反应制备。式(Ⅱ)所示的化合物可由相应的磺酰氯制备。

Description

吡啶磺酰脲类除草剂及其用途
本发明涉及吡啶磺酰脲类除草剂及其防除杂草的用途。
已知有些2-吡啶磺酰脲类化合物具有除草和植物生长调节性能；参见EP-A-13480,EP-A-272855,EP-A-84224,US-PS4421550、EP-A-103543(US-A-4579583),US-PS4487626,EP-A-125864,WO88/04297。
已发现，在吡啶基3位上带有某些特定基团的2-吡啶基磺酰脲类化合物特别适于作为除草剂和植物生长调节剂。
本发明的对象是式(Ⅰ)所示的化合物或它们的盐：
Figure C9110018400061
式中R1代表-OSO2NR4R5,-NR6R7或碘，R2代表H,(C1-C4)烷基，优选(C1-C3)烷基，
(C1-C3)卤代烷基，卤素，硝基、氰基、(C1-
C3)烷氧基、(C1-C3)卤代烷氧基，(C1-C3)
烷硫基，(C1-C3)烷氧基-
(C1-C3)烷基，(C1-C3)烷氧基羰基，(C1
-C3)烷基氨基，二((C1-C3)烷基)氨基，
(C1-C3)-烷基亚磺酰基，(C1-C3)烷基磺
酰基，SO2NRaRb或C(O)NRaRb,Ra,Rb分别代表H,(C1-C3)烷基，(C3-C4)
烯基、炔丙基，或共同代表
-(CH2)4-,-(CH2)5-或-CH2CH2OCH2-CH2-R3代表H或CH3,R4代表H,(C1-C3)烷基，(C3-C4)烯基，
(C1-C3)烷氧基或(C3-C4)炔基，优选炔丙
基，和R5代表H,(C1-C3)烷基，((C3-C4)烯基或
(C3-C4)炔基，优选炔丙基，或R4和R5合在一起为-(CH2)4-,-(CH2)5-或
-CH2CH2OCH2CH2-,R6代表H，未被取代或被一个或多个选自卤素，(C1-C4)
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-
烷氧基)羰基和CN的基团取代的(C1-C8)烷基，
未被取代或被一个或多个卤素原子取代的(C3-C6)
烯基、未被取代或被一个或多个卤素原子取代的(C3-
C6)-炔基，未被取代或被一个或多个卤素原子取代的
(C1-C4)烷基磺酰基，苯基磺酰基，其中苯基未被
取代或被选自-个或多个卤素原子，(C1-C4)烷
基，和(C1-C4)烷氧基取代，未被取代或被一个或
多个卤素原子取代的(C1-C4)烷氧基或(C1-C4
-烷基)羰基、R7代表未被取代或被一个或多个卤素原子取代的
(C1-C4)烷基磺酰基、苯基磺酰基，其中苯基未被
取代或被选自一个或多个卤素原子，(C1-C4)烷基和
(C1-C4)烷氧基取代，或二-[(C1-C4)烷
基]氨基磺酰基或R6和R7合在一起代表式-(CH2)m-SO2-所示的一
个链，此链可被1至4个(C1-C3)烷基取代，m是
3或4，n    代表0或1,W    代表O或S,A    代表下式中一个基团
Figure C9110018400081
X代表H，卤素，(C1-C3)烷基，(C1-C3)烷氧
基，这些基团中的最后两个基团未被取代或者被卤素取代一
次或多次，或被(C1-C3)-烷氧基取代一次、Y代表H，(C1-C3)烷基，(C1-C3)烷氧基或
(C1-C3烷硫基，在上述这些基团中含有烷基的基团未
被取代或者被卤素取代一次或多次，或者被(C1-C3)
烷氧基或(C1-C3)烷硫基取代一次或两次，此外还代
表如式NR8R9所示的一个基团，(C3-C6)-环烷
基，(C2-C4)烯基，(C2-C4)炔基，(C3-
C4)-烯氧基或(C3-C4)炔氧基，Z代表CH或N,R8和R9分别为H,(C1-C3)烷基或(C3-C4)-
烯基，X1代表CH3,OCH3,OC2H5或OCF2H1Y1代表-O-或-CH2-,X2代表CH3,C2H5或CH2CF3,Y2代表OCH3,OC2H5,SCH3,SC2H5,CH3
或C2H5,X3代表CH3或OCH3,Y3代表H或CH3,X4代表CH3、OCH3,OC2H5,CH2OCH3或Cl,Y4代表CH3,OCH3,OC2H5或Cl,Y5代表CH3,C2H5,OCH3或Cl，式(Ⅰ)中的烷基，烷氧基，卤代烷基，烷基氨基和烷硫基以及相应的不饱和的和/或取代的基团可以是直链或支链。烷基以及在烷氧基，卤代烷基中的烷基指的是甲基，乙基，正丙基或异丙基。烯基和炔基同烷基的情景一样可能含有相应的不饱和基团如2-丙烯基、2-丁烯基或3-丁烯基、2-丙炔基、2-丁炔基或3-丁炔基。卤素指的是氟、氯、溴或碘。
式(Ⅰ)所示的化合物可以形成盐，化合物中-SO2-NH-基团的氢原子可由对于农业适宜的阳离子所取代。这些盐指的是金属盐，特别是碱金属盐或碱土金属盐，也可是铝盐或有机胺盐。式(Ⅰ)化合物中的吡啶部分与强酸反应也可以形成盐，这些酸以HCl,HBr,H2SO4或HNO3为宜。
优选的通式(Ⅰ)所示的化合物或它们的盐为这样的化合物，其中n为零，W为O,A为下式所示的一个基团
Figure C9110018400101
式中X、Y和Z具有上述含义。式(Ⅰ)所示的化合物及它们的盐以选择下列基团较佳。R2、Ra、Rb、n、W和A具有上述含义，和R4、R5分别代表(C1-C3)烷基、烯丙基或炔丙基或R4、R5合在一起为-(CH2)4-,-(CH2)5-或
-CH2CH2OCH2CH2-,R6代表H，未被取代或被一个或多个卤素原子取代，或被选自
(C1-C3)烷氧基，(C1-C3)烷硫基，(C1-
C3)烷基磺酰基，(C1-C4)-烷氧基羰基和CN的
基团取代的(C1-C4)烷基，(C3-C4)烯基，
(C3-C4)炔基，(C1-C4)烷基磺酰基，苯基磺
酰基，被选自一至三个卤素，(C1-C3)烷基和(C1
-C3)烷氧基取代的苯基磺酰基、(C1-C3)烷氧基
或(C1-C4)烷基羰基、
R7代表(C1-C4)烷基磺酰基，苯基磺酰基或被选自一至
三个卤素，(C1-C3)烷基和(C1-C3)烷氧基取
代的苯基磺酰基，或二-(C1-C4-烷基)-氨基磺酰
基或
R6和R7合在一起为式-(CH2)mSO2-所示的一个链，
其中m是3或4，
式(Ⅰ)所示的化合物和它们的盐以选择下列基团为最佳，其中R2为H,(C1-C3)烷基、(C1-C3)-烷氧基，卤素或(C1-C3)烷硫基，R4和R5分别为(C1-C3)烷基，R6为氢，(C1-C4)烷基或(C1-C3)烷基磺酰基，R7为(C1-C3)烷基磺酰基，A为下式所示的一个基团
Figure C9110018400111
其中Z代表CH或N,X代表卤素，(C1-C2)-烷基，(C1-C2)烷氧基，OCF2H,CF3或OCH2CF3,Y代表(C1-C2)烷基，(C1-C2)烷氧基或OCF2H,具有上述含义的化合物特别优选n为零，W为一氧原子。
此外本发明的对象还是通式(Ⅰ)所示化合物及其盐的制备方法，其特征在于：
(a)使式(Ⅱ)化合物与一个式(Ⅲ)所示的杂环氨基甲酸酯反应
Figure C9110018400122
在式(Ⅲ)中R*代表苯基或(C1-C4)烷基，或者(b)式(Ⅳ)所示的吡啶基磺酰基氨基甲酸酯与式(Ⅴ)所示的氨基杂环化合物反应
Figure C9110018400124
(C)式(Ⅵ)所示的磺酰基异氰酸酯与式(Ⅴ)R3-NH-A所示的一个氨基杂环化合物反应
(d)在一单釜反应中，在一碱性物质如三乙基胺的存在下，先用式(Ⅴ)R3-NH-A所示的氨基杂环化合物与碳酰氯(光气)反应，再将上述反应生成的中间产物与式(Ⅱ)所示的-个吡啶磺酰胺反应(例如类似于EP-A-232067)。
式(Ⅱ)与式(Ⅲ)化合物的反应最好在惰性有机溶剂如二氯甲烷，乙腈，二氧六环或四氢呋喃中，用碱催化进行，反应温度控制在0℃和溶剂沸点温度之间作为碱优选1.8-重氮二环[5,4,0]十-碳烯-7(DBU)或三甲基铝或三乙基铝。
磺酰胺(Ⅱ)是一个新化合物。它们及其制备方法同样是本发明的对象。它可以通过一个合适的取代的2-卤代吡啶与一个S-亲核试剂如苄基硫醇或硫代脲反应制备。得到的反应产物与次氯酸钠或氯反应转化为磺酰氯(类似于EP-A-272855)，磺酰氯再直接与氨反应生成磺酰胺或者与叔丁基胺反应生成带叔丁基酰胺基团的产物，继之其保护基团断裂而形成式(Ⅱ)所示的磺酰胺。
式(Ⅲ)所示的氨基甲酸酯类化合物可用南非专利申请82/55671和82/5045以及EP-A-70804(US-A-4480101)或RD275056中所提供的方法制备。
式(Ⅳ)所示化合物与式Ⅴ所示氨基杂环化合物的反应优选在惰性的非质子性溶剂如二氧六环，乙腈或四氢呋喃中进行反应温度控制在0℃与溶剂沸点温度之间。反应所需式Ⅴ所示的原料在文献中是已知的或者按文献所提供的方法制备。式(Ⅳ)所示的吡啶磺酰基氨基甲酸酯可用类似于EP-A-44808或EP-A-237292中介绍的方法制备。
式(Ⅵ)所示的吡啶基磺酰基异氰酸酯可用类似于EP-A-184385的方法制备。再与式(Ⅴ)所示的氨基杂环化合物反应。
式(Ⅰ)所示化合物的盐最好在水，甲醇或丙酮这些惰性溶剂中制备。反应温度控制在0～100℃。用于制备本发明盐的合适的碱为碱金属碳酸盐如碳酸钾、碱金属氧氧化物、碱土金属氢氧化物，氨或乙醇胺。制备盐所需的酸以HCl,HBr,H2SO4或HNo3最合适。
上述不同制备方法中所提到的惰性有机溶剂指的是某一溶剂在某一特定的反应条件下呈惰性，而並非要求其在任何条件下都必须呈惰性。
已证实本发明通式(Ⅰ)所示的化合物对那些有重要经济意义的单子叶和双子叶杂草具有优良的广谱的除草性能。它们的有效成分对于那些依靠块根，地下根茎或其它生命力很强的植物器官发芽生长而难以防治的多年生杂草具有良好的防治效果。而且无论是播种前，苗前或苗后都可以使用这种化合物。作为例子下面列举了可用本发明化合物防治的一些有代表性的单子叶和双子叶杂草群的名称，但是其防治对象並不仅限于所列举的种类。
单子叶的杂草如野燕麦属、毒麦属、看麦娘属、虉草属、稗属、马唐属、狗尾草属以及一年生莎草属、以及单子叶多年生杂草如冰草属、狗牙根、白茅属、蜀黍属、以及多年生的莎草类。
本发明的化合物可以防治的双子叶一年生杂草种类有猪殃
Figure C9110018400151
，紫花地丁，婆 纳属，野芝麻属，繁缕属，苋属，欧白芥属，牵牛属，母菊属，苘麻属，黄花稔属，以及多年生的田旋花，蓟属，酸模属和蒿属。
在水稻田特殊的栽培条件下出现的一些杂革如慈菇属，泽泻属，荸荠属，扁杆藨草属及莎草属也可用本发明的化合物有效地防除。
本发明的化合物也可以在发芽前作土壤表面处理以完全阻止杂草发芽或者控制杂草只能生长至子叶阶段便停止继续生长，三至四周后完全死亡。
如果在杂草出苗之后用药剂的有效成分处理植物的绿色部分，施药后杂草迅速停止生长並使之停留在施药时的生长阶段或者在施药后经历一段时间死亡。用这种方式可使那些对农作物有害的杂草尽早或永久失去竞争力。
本发明的化合物虽已被证实对单子叶和双子叶杂草具有优良的除草活性。但它们对那些具有重要经济意义的农作物如小麦，大麦，黑麦，水稻，玉米，甜菜，棉花和大豆影响很小或完全无害。正因为如此本发明的化合物适合于在农作物中进行选择性除草。
此外还证实本发明的化合物对农作物具有显著的生长调节作用。它能影响植物自身的物质转化。因此可以通过使用本发明的化合物有目的影响植物的内含物质，也可以用它控制植物的株型和脱水干燥使之更易于收获。它还可以调节和抑制植物疯长，而不会使植物致死。这种生长抑制作用对许多单子叶和双子叶农作物十分重要，因为借此可以减少或完全阻止倒伏。
本发明的化合物可以制备成可湿性粉剂，乳油，可喷洒的溶液，粉剂或常规剂型的颗粒剂供使用。所以本发明的对象还包括用式(Ⅰ)化合物或它们的盐制备的具有除草和植物生长调节性能的制剂。
通式(Ⅰ)所示的化合物可以根据其有关生物学和(或)化学-物理学参数加工成不同的剂型。比如可以加工成下列剂型：可湿性粉剂(WP)，水溶性粉剂(SP)，水溶性浓缩物，乳油(EC)，水包油和油包水的乳化液(EW)，可喷洒的溶液，悬浮浓缩物(SC)，以油或水为基物的分散剂，可与油相混的溶液，胶悬液(CS)，粉剂(DP)，浸渍剂，撒播和土壤中施用的颗粒剂，微型颗粒剂，喷洒颗粒剂，沉降颗粒剂和吸附颗粒剂(GR)，在水中可分散的颗粒剂(WG)，水溶性颗粒剂(SG)，超低容量剂型，微胶囊剂和蜡剂。
上述剂型基本上是已知的，在有些著述中已有介绍，如Winnacker-Kiichler，“化学技术”第七卷，C,Hauser出版社，慕尼黑、第四版，1986；Wade Van Valkenburg,“农药剂型”，Marcel Dekker纽约，1973；K.Martens，“喷雾干燥手册”，第三版，1979,G.Goodwin股份有限公司、伦敦。
一些必要的助剂物质如惰性物质，表面活性剂，溶剂以及其它一些添加剂都是常用的助剂材料。在下述著作中都有介绍：如Watkins，“杀虫剂粉状稀释剂和载体手册”第二版，DarlandBooks,Caldwell新泽西州；H.V.Olphen，“粘土胶体化学入门”；第二版，J.Wiley&Sons，纽约；c.Marsden，“溶剂指南”，第二版，Interscience，纽约，1963；Mccutcheon＇s“洗涤剂和乳化剂年鉴”，MC出版公司，Ridgewood，纽约；Sisley和Wood，“表面活性剂百科全书”，化学出版公司，纽约，1964；Schonfeldt，“有表面活性作用的环氧乙烷加成物”，科学出版社，斯图加特，1976；Winnacker-Kchler，“化学技术”，第七卷，C.Hauser出版社，慕尼黑，第四版。
在这些剂型的基础上，它们可与其它具有农药效能的物质，肥料和/或植物生长调节剂混配。例如它可以加工成一种成品制剂形式或是加工成罐装混合物形式。
在水中可均匀分散的可湿性粉剂除了含有有效成分和一种稀释剂或惰性物质外、还含有湿润剂、如聚氧乙基化烷基酚类、聚氧乙基化脂肪醇类、聚氧乙基化脂肪胺类，脂肪醇聚乙二醇醚硫酸酯、烷烃磺酸酯或烷基苯磺酸酯类、还含有分散剂如木质素磺酸钠，2,2＇-二萘基甲烷-6,6＇-二磺酸钠，二丁基萘-磺酸钠或油酰甲基牛磺酸钠。
乳油是将有效成分溶解在如丁醇，环己酮，二甲基甲酰胺，二甲苯或高沸点的芳香族或烃类中的某一种溶剂中，再添加一种或多种乳化剂制备而成。作为乳化剂的化合物例如可采用烷基磺酸钙盐如十二烷基苯磺酸钙或非离子型乳化剂如脂肪酸聚乙二醇酯，烷基芳基聚乙二醇醚，脂肪醇聚乙二醇醚，环氧丙烷-环氧乙烷缩合产物，烷基聚醚，山梨烷脂肪酸酯，聚氧乙烯山梨烷脂肪酸酯或聚氧乙烯山梨酯。
粉剂是将有效成分与细颗粒的呈分散状固体物质如滑石，自然界粘土如高岭土，皂土，叶蜡石土或硅藻土经磨粉加工而制得。
颗粒剂的制备是将有效成分喷洒在具有吸附性能的颗粒状惰性物质表面或是将有效成分用聚乙烯醇，聚丙烯酸钠这些粘合剂或矿物油粘附到砂子，高岭土等载体物质表面或颗粒状惰性物质的表面。也可以用通常制造颗粒肥料的方法将某些合适的有效成分加工成颗粒剂。需要时也可以与肥料混在一起加工。
式(Ⅰ)化合物的农业化学制剂通常含有效成分0.1～99％(重量)，又以含有效成分0.1～95％(重量)为佳。
可湿性粉剂含有效成分大约在10～90％(重量)，其余部分由常用的一些剂型助剂物质组成。乳油中有效成分含量大约为1～85％(重量)，通常含有效成分5～80％(重量)。粉状剂型含有效成分大约为1～25％(重量)，通常为5～20％(重量)。可喷洒的溶液含有效成分大约为0.2～20％(重量)，通常为2～20％(重量)。颗粒剂中有效成分含量部分取决于有效成分是呈液态或固态。通常在水中可分散的颗粒剂其有效成分含量为10-90％(重量)之间。
此外，所列举的有效成分加工剂型中有时还含有常规使用的粘合剂，润湿剂，分散剂，乳化剂，渗透剂，溶剂，填料和载体。
通常以商品形式提供的剂型在使用时有时需要采用常规方法稀释，例如可湿性粉剂，乳油，分散剂及水中可分散的颗粒剂可用水稀释。而粉剂，撒播或在土壤中施用的颗粒剂以及可喷洒的溶液使用前则无需用惰性物质进一步稀释。
式(Ⅰ)化合物的用量因温度、湿度这些外部条件以及所用除草剂的种类不同而变化。其用量变动范围很大。在0.001和10.0公斤/公顷之间或者活性物质用量更多一些。但其用量以0.005-5kg/公顷之间为好。
必要时本发明的化合物可与其它一些有效成分如杀虫剂、杀螨剂、除草剂、安全剂、肥料、生长调节剂或杀菌剂混用或加工成混合剂型。
A．化学制备例实施例12-苄硫基-3-碘吡啶
34.0g(0.15摩尔)2-氟-3-碘吡啶和18.6g(0.15摩尔)苄硫醇溶在250ml乙腈溶剂中的溶液与22.8g(0.165摩尔)碳酸钾一起加热回流8小时，冷却，用旋转蒸发器蒸去溶剂、用二氯甲烷溶解残渣、用水洗有机相，有机相用无水硫酸钠干燥后蒸去溶剂並减压蒸馏油状残留物得到37.3g(理论量的76％)2-苄硫基-3-碘吡啶，在0.1mbar时其沸点150-153℃。实施例23-碘-2-吡啶磺酰胺
在℃下向含有25.0g(76.5毫摩尔)2-苄硫基-3-碘吡啶，125ml二氯甲烷，60ml水和38ml浓盐酸的混合溶液中滴加入510ml 5％的次氯酸钠(0.34摩尔)溶液，在0℃下搅拌30分钟，反应物用3×100ml二氯甲烷萃取，有机相用无水硫酸钠干燥将所得到的有机相冷却至-20℃。维持此温度在20分钟内加入6.8g(0.4摩尔)氨，在-20℃下搅拌2小时，然后使其升至室温。用水洗反应混合物，有机相干燥后蒸去有机溶剂，残渣用二异丙基醚研磨成细粉得到15.5g(理论量的71％)3-碘-2-吡啶磺酰胺，熔点247-250℃(分解)。实施例33-(4,6-二甲氧基嘧啶-2-基)-1-(3-碘-2-吡啶基磺酰基)-脲
向含有2.1g(7.4毫摩尔)3-碘-2-吡啶磺酰胺和2.2g(8.1毫摩尔)N-(4,6-二甲氧基-嘧啶-2-基)-苯基氨基甲酸酯的30ml乙腈悬浮液中加入1.2g(0.081摩尔)1,8-重氮二环[5.4.0]十-碳烯-7(DBU)。在室温下搅拌45分钟后加入20ml水。用盐酸将溶液调至PH4，抽滤沉淀产物，得到3.2g(理论量的93％)3-(4,6-二甲氧基嘧啶-2-基)-1-(3-碘-2-吡啶基磺酰基)-脲，熔点161-162℃(分解)。实施例43-二甲基氨磺酰基氧基-2-吡啶磺酰胺
在℃下向含有5.7g(17.6毫摩尔)2-苄硫基-3-二甲基-氨磺酰基氧基吡啶，30ml二氯甲烷，15ml水及8.5ml浓盐酸混合物中滴加入107ml(72毫摩尔)5％次氯酸钠溶液。在℃下搅拌30分钟后用3×20ml二氯甲烷萃取，有机相用无水硫酸钠干燥。将得到的溶液冷却到-70℃。在此温度下向溶液内加入氨至反应混合物明显地与碱反应。在-70℃搅拌3小时后使之升至室温，用水洗。有机相经干燥並蒸去溶剂后得到3.0g(理论量的61％)3-二甲基氨磺酰基氧基-2-吡啶磺酰胺；NMR(CDCl3):δ(ppm)=3.06(S,6H,
                N(CH3)2),5.80
                (S,2H,NH2),
                7.48(dd,1H),
                7.98(dd,1H),
                8.38(dd,1H)。实施例53-(4,6-二甲氧基嘧啶-2-基)-1-(3-二甲基氨磺酰基氧基-2-吡啶基磺酰基)-脲
向含有3.0g(10.6毫摩尔)3-二甲基氨磺酰基氧基-2-吡啶磺酰胺和3.4g(12.7毫摩尔)N-(4,6-二甲氧基嘧啶-2-基)-苯基氨基甲酸酯的40ml乙腈悬浮液中加入1.9g(12.7毫摩尔)1.8-重氮二环-〔5.4.0〕十-碳烯-7(DBU)。将上述溶液在室温下搅拌1小时后加入30ml水。用盐酸将溶液调至PH4，抽滤沉淀物，用乙醚研磨后得到2.1g(理论量的42％)3-(4,6-二甲氧基嘧啶-2-基)-1-(3-二甲基氨磺酰基氧基-2-吡啶基磺酰基)-脲熔点155-157℃。实施例63-(4,6-二甲氧基-1,3,5-三嗪-2-基)-1-(3-碘-2-吡啶基磺酰基)-脲
在室温下向含有4.3g(15毫摩尔)3-碘-2-吡啶磺酰胺的150ml二氯甲烷中滴加入浓度为2M的三甲基铝甲苯溶液9.0ml(18毫摩尔)。至气体产生完毕，滴加入20ml含有3.85g(18毫摩尔)4,6-二甲氧基-1,3,5-三嗪-2-基氨基甲酸甲基酯的二氯甲烷溶液，加热回流24小时。冷却后加入用冰致冷的1N盐酸150ml。分去有机相，水相用二氯甲烷萃取2次后，有机相经干燥並蒸去溶剂。粗产物用乙醚研磨后得到3.1g(理论量的44％)3-(4,6-二甲氧基-1,3,5-三嗪-2-基)-1-(3-碘-2-吡啶基磺酰基)-脲，熔点：155℃(分解)。
下面表1至表4中所列的化合物是按与实施例1-6类似的方法制备的。
                表1化合物编号R1  R2  R3  X         Y        Z     熔点[℃]1          I    H    H    OCH3     OCH3    CH    161-162(Z.)2          ＂   H    CH3 OCH3     OCH3    CH3          ＂   H    CH3 OCH3     CH3     N4          ＂   H    H    CH3      CH3     CH    186(Z.)5          ＂   H    H    OCH3     CH3     CH    177-1786          ＂   H    H    CH3      CH3     N7          ＂   H    H    OCH3     CH3     N     156-157(分解)8          ＂   H    H    OCH3     OCH3    N     155(分解)9          ＂   H    H    OCH3     Cl       CH10          ＂   H    H    OCF2H    CH3     CH11          ＂   H    H    OCF2H    OCF2H   CH12          ＂   H    H    OCH3     Br       CH13          ＂   H    H    OCH3     OC3H5  CH14          ＂   H    H    OCH3     OCH3    CH15          ＂   H    H    OCH3     OC3H5  N16          ＂   H    H    OCH3     OC3H7  CH17          ＂   H    H    OCH3     Cl       N18          ＂   H    H    Cl        OC2H5  CH19          ＂   H    H    OC2H5   OC2H5  CH20          ＂   H    H    C2H5    OCH3    CH21          ＂   H    H    CF3      OCH3    CH22          ＂   H    H    OCH2CF3 CH3     CH23          ＂   H    H    OCH2CF3 OCH3    CH
表1(续)化合物编号
        R1  R2    R3   X         Y             Z    熔点[℃]24          ＂   H      H    OCH2CF3 OCH3CF3     CH25          ＂   H      H    OCH2CF3 OCH3         N26          ＂   H      H    OCH3     CH(OCH3)2   CH27          ＂   4-CH3 H    OCH3     OCH3         CH28          ＂   ＂     H    OCH3     CH3          CH29          ＂   ＂     H    OCH3     Cl            CH30          ＂   ＂     H    CH3      CH3          CH31          ＂   ＂     HO   CH3      OCH3         N32          ＂   ＂     H    OCH3     CH3          N33          ＂   ＂     H    OC2H5   NHCH3        N34          ＂   ＂     CH3 OCH3     CH3          N35          ＂   5-CH3 H    OCH3     OCH3         CH36          ＂   ＂     H    OCH3     CH3          CH37          ＂   ＂     H    OCH3     Cl            CH38          ＂   ＂     H    CH3      CH3          CH39          ＂   ＂     H    OCH3     OCH3         N40          ＂   ＂     H    OCH3     CH3          N41          ＂   ＂     H    OC2H5   NHCH3        N42          ＂   ＂     CH3 OCH3     CH3          N43          ＂   6-CH3 H    OCH3     OCH3         CH44          ＂   ＂     H    OCH3     CH3          CH45          ＂   ＂     H    OCH3     Cl            CH46          ＂   ＂     H    CH3      CH3          CH47          ＂   ＂     H    OCH3     OCH3         N48          ＂   ＂     H    OCH3     CH3          N49          ＂   ＂     H    OC2H5   NHCH3        N50          ＂   ＂     CH3 OCH3     CH3          N51          ＂   4-Cl   H    OCH3     OCH3         CH52          ＂   ＂     H    OCH3     CH3          CH53          ＂   ＂     H    OCH3     Cl            CH54          ＂   ＂     H    CH3      CH3          CH55          ＂   ＂     H    OCH3     OCH3         N56          ＂   ＂     H    OCH3     CH3          N
表1(续)化合物编号
        R1   R2  R3    X        Y       Z     熔点[℃]57          ＂   ＂    H    OC2H5   NHCH3   N58          ＂   ＂    CH3 OCH3     CH3     N59          ＂   5-Cl  H    OCH3     OCH3    CH60          ＂   ＂    H    OCH3     CH3     CH61          ＂   ＂    H    OCH3     Cl       CH62          ＂   ＂    H    CH3      CH3     CH63          ＂   ＂    H    OCH3     OCH3    N64          ＂   ＂    H    OCH3     CH3     N65          ＂   ＂    H    OC2H5   NHCH3   N66          ＂   ＂    CH3 OCH3     CH3     N67          ＂   6-Cl  H    OCH3     OCH3    CH68          ＂   ＂    H    OCH3     CH3     CH69          ＂   ＂    H    OCH3     Cl       CH70          ＂   ＂    H    CH3      CH3     CH71          ＂   ＂    H    OCH3     OCH3    N72          ＂   ＂    H    OCH3     CH3     N73          ＂   ＂    H    OC2H5   NHCH3   N74          ＂   ＂    CH3 OCH3     CH3     N75          ＂   4-CF3H    OCH3     OCH3    CH76          ＂   ＂    H    OCH3     CH3     CH77          ＂   ＂    H    OCH3     Cl       CH78          ＂   ＂    H    CH3      CH3     CH79          ＂   ＂    H    OCH3     OCH3    N80          ＂   ＂    H    OCH3     CH3     N81          ＂   4-F   H    OC2H5   NHCH3   N82          ＂   ＂    CH3 OCH3     CH3     N83          ＂   5-CF3H    OCH3     OCH3    CH84          ＂   ＂    H    OCH3     CH3     CH85          ＂   ＂    H    OCH3     Cl       CH86          ＂   ＂    H    CH3      CH3     CH87          ＂   ＂    H    OCH3     OCH3    N88          ＂   ＂    H    OCH3     CH3     N89          ＂   5-F   H    OC2H5   NHCH3   N
表1(续)化合物编号
         R1    R2    R3   X       Y        Z   熔点[℃]90          ＂    ＂      CH3 OCH3    CH3     N91          ＂    6-F     H    OCH3    OCH3    CH92          ＂    ＂      H    OCH3    CH3     CH93          ＂    ＂      H    OCH3    Cl       CH94          ＂    ＂      H    CH3     CH3     CH95          ＂    ＂      H    OCH3    OCH3    N96          ＂    ＂      H    OCH3    CH3     N97          ＂    ＂      H    OC2H5  NHCH3   N98          ＂    ＂      CH3 OCH3    CH3     N99          ＂    4-OCH3 H    OCH3    OCH3    CH100          ＂    ＂      H    OCH3    CH3     CH101          ＂    ＂      H    OCH3    Cl       CH102          ＂    ＂      H    CH3     CH3     CH103          ＂    ＂      H    OCH3    OCH3    N104          ＂    ＂      H    OCH3    CH3     N105          ＂    ＂      H    OC2H5  NHCH3   N106          ＂    ＂      CH3 OCH3    CH3     N107          ＂    5-OCH3 H    OCH3    OCH3    CH108          ＂    ＂      H    OCH3    CH3     CH109          ＂    ＂      H    OCH3    Cl       CH110          ＂    ＂      H    CH3     CH3     CH111          ＂    ＂      H    OCH3    OCH3    N112          ＂    ＂      H    OCH3    CH3     N113          ＂    ＂      H    OC2H5  NHCH3   N114          ＂    ＂      CH3 OCH3    CH3     N115          ＂    6-OCH3 H    OCH3    OCH3    CH116          ＂    ＂      H    OCH3    CH3     CH117          ＂    ＂      H    OCH3    Cl       CH118          ＂    ＂      H    CH3     CH3     CH119          ＂    ＂      H    OCH3    OCH3    N120          ＂    ＂      H    OCH3    CH3     N121          ＂    ＂      H    OC2H5  NHCH3   N122          ＂    ＂     CH3  OCH3    CH3     N
表1(续)化合物编号
         R1       R2       R3   X        Y       Z   熔点[℃]123          ＂       6-C2H5   H    OCH3    OCH3    CH124          ＂       6-C4H3   H    OCH3    OCH3    CH125          ＂       6-OC2H5  H    OCH3    OCH3    CH127          ＂       6-OCH2CF3H    OCH3    OCH3    CH128          ＂       6-SCH3    H    OCH3    OCH3    CH129          ＂       6-SO2CH3 H    OCH3    OCH3    CH130          ＂       6-NO2     H    OCH3    OCH3    CH131          ＂       6-CO2CH3 H    OCH3    OCH3    CH132          ＂       6-Br       H    OCH3    OCH3    CH133          ＂       6-CF3     H    OCH3    OCH3    CH134          ＂       6-OCF3    H    OCH3    OCH3    CH135          ＂       6-OCF2H   H    OCH3    OCH3    CH136  -OSO2N(CH3)2 H          H    OCH3    OCH3    CH  155-157137          ＂       H          CH3 OCH3    OCH3    CH138          ＂       H          CH3 OCH3    CH3     N139          ＂       H          H    CH3     CH3     CH140          ＂       H          H    OCH3    CH3     CH141          ＂       H          H    CH3     CH3     N142          ＂       H          H    OCH3    CH3     N 137-138(分解)143          ＂       H          H    OCH3    OCH3    N144          ＂       H          H    OCH3    Cl       CH145          ＂       H          H    OCF3H   CH3     CH146          ＂       H          H    OCF3H   OCF3H   CH147          ＂       H          H    OCH3    Br       CH148          ＂       H          H    OCH3    OC2H5  CH149          ＂       H          H    OCH3    SCH3    CH150          ＂       H          H    OCH3    OC2H5  N151          ＂       H          H    OCH3    OC3H7  CH152          ＂       H          H    OCH3    Cl       N153          ＂       H          H    Cl       OC2H5  CH154          ＂       H          H    OC2H5  OC2H5  CH155          ＂       H          H    C2H5   OCH3    CH156          ＂       H          H    CF3     OCH3    CH
表1(续)化合物编号
         R1   R2   R3    X        Y         Z    熔点[℃]157          ＂    H     H    OCH2CF3 CH3       CH158          ＂    H     H    OCH2CF3 OCH3      CH159          ＂    H     H    OCH2CF3 OCH2CF3  CH160          ＂    H     H    OCH2CF3 OCH3      N161          ＂    H     H    OCH3     CH(OCH3)2CH162          ＂    4-CH3H    OCH3     OCH3      CH163          ＂    ＂    H    OCH3     CH3       CH164          ＂    ＂    H    OCH3     Cl         CH165          ＂    ＂    H    CH3      CH3       CH166          ＂    ＂    H    OCH3     OCH3      N167          ＂    ＂    H    OCH3     CH3       N168          ＂    ＂    H    OC2H5   NHCH3     N169          ＂    ＂    CH3 OCH3     CH3       N170          ＂    5-CH3H    OCH3     OCH3      CH171          ＂    ＂    H    OCH3     CH3       CH172          ＂    ＂    H    OCH3     Cl         CH173          ＂    ＂    H    CH3      CH3       CH174          ＂    ＂    H    OCH3     OCH3      N175          ＂    ＂    H    OCH3     CH3       N176          ＂    ＂    H    OC2H5   NHCH3     N177          ＂    ＂    CH3 OCH3     CH3       N178          ＂    6-CH3H    OCH3     OCH3      CH179          ＂    ＂    H    OCH3     CH3       CH180          ＂    ＂    H    OCH3     Cl         CH181          ＂    ＂    H    CH3      CH3       CH182          ＂    ＂    H    OCH3     OCH3      N183          ＂    ＂    H    OCH3     CH3       N184          ＂    ＂    H    OC2H5   NHCH3     N185          ＂    ＂    CH3 OCH3     CH3       N186          ＂    4-Cl  H    OCH3     OCH3      CH187          ＂    ＂    H    OCH3     CH3       CH
表1(续)化合物编号
         R1    R2 R3     X        Y        Z    熔点[℃]188          ＂    ＂    H      OCH3    Cl       CH189          ＂    ＂    R      CH3     CH3     CH190          ＂    ＂    H      OCH3    OCH3    N191          ＂    ＂    H      OCH3    CH3     N192          ＂    ＂    H      OC3H5  NHCH3   N193          ＂    ＂    C      H3OCH3 CH3     N194          ＂    5-Cl  H      OCH3    OCH3    CH195          ＂    ＂    H      OCH3    CH3     CH196          ＂    ＂    H      OCH3    Cl       CH197          ＂    ＂    H      CH3     CH3     CH198          ＂    ＂    H      OCH3    OCH3    N199          ＂    ＂    H      OCH3    CH3     N200          ＂    ＂    H      OC2H5  NHCH3   N201          ＂    ＂    CH3   OCH3    CH3     N202          ＂    6-Cl  H      OCH3    OCH3    CH203          ＂    ＂    H      OCH3    CH3     CH204          ＂    ＂    H      OCH3    Cl       CH205          ＂    ＂    H      CH3     CH3     CH206          ＂    ＂    H      OCH3    OCH3    N207          ＂    ＂    H      OCH3    CH3     N208          ＂    ＂    H      OC2H5  NHCH3   N209          ＂    ＂    CH3   OCH3    CH3     N210          ＂    4-F   H      OCH3    OCH3C   H211          ＂    ＂    H      OCH3    CH3     CH212          ＂    ＂    H      OCH3    Cl       CH213          ＂    ＂    H      CH3     CH3     CH214          ＂    ＂    H      OCH3    OCH3    N215          ＂    ＂    H      OCH3    CH3     N216          ＂    ＂    H      OC2H5  NHCH3   N217          ＂    ＂    CH3   OCH3    CH3     N218          ＂    5-F   H      OCH3    OCH3    CH
表1(续)化合物编号
         R1    R2  R3       X        Y        Z    熔点[℃]219          ＂    ＂     H        OCH3    CH3     CH220          ＂    ＂     H        OCH3    Cl       CH221          ＂    ＂     H        CH3     CH3     CH222          ＂    ＂     H        OCH3    OCH3    N223          ＂    ＂     R        OCH3    CH3     N224          ＂    ＂     H        OC2H5  NHCH3   N225          ＂    ＂     CH3     OCH3    CH3     N226          ＂    6-F    H        OCH3    OCH3    CH227          ＂    ＂     H        OCH3    CH3     CH228          ＂    ＂     H        OCH3    Cl       CH229          ＂    ＂     H        CH3     CH3     CH230          ＂    ＂     H        OCH3    OCH3    N231          ＂    ＂     H        OCH3    CH3     N232          ＂    ＂     H        OC2H5  NHCH3   N233          ＂    ＂     CH3     OCH3    CH3     N234          ＂    4-OCH3H        OCH3    OCH3    CH235          ＂    ＂     H        OCH3    CH3     CH236          ＂    ＂     H        OCH3    Cl       CH237          ＂    ＂     H        CH3     CH3     CH238          ＂    ＂     H        OCH3    OCH3    N239          ＂    ＂     H        OCH3    CH3     N240          ＂    ＂     H        OC2H5  NHCH3   N241          ＂    ＂     CH3     OCH3    CH3     N242          ＂    5-OCH3H        OCH3    OCH3    CH243          ＂    ＂     H        OCH3    CH3     CH244          ＂    ＂     H        OCH3    Cl       CH245          ＂    ＂     H        CH3     CH3     CH246          ＂    ＂     H        OCH3    OCH3    N247          ＂    ＂     H        OCH3    CH3     N248          ＂    ＂     H        OC2H5  NHCH3   N249          ＂    ＂     CH3     OCH3    CH3     N250          ＂    6-OCH3H        OCH3    OCH3    CH
表1(续)化合物编号
         R1    R2        R3   X       Y        Z    熔点[℃]251          ＂    ＂          H    OCH3    CH3     CH252          ＂    ＂          H    OCH3    Cl       CH253          ＂    ＂          H    CH3     CH3     CH254          ＂    ＂          H    OCH3    OCH3    N255          ＂    ＂          H    OCH3    CH3     N256          ＂    ＂          H    OC2H5  NHCH3   N257          ＂    ＂          CH3 OCH3    CH3     N258          ＂    6-C2H5    H    OCH3    OCH3    CH259          ＂    6-C4H8    H    OCH3    OCH3    CH260          ＂    6-OC2H5   H    OCH3    OCH3    CH261          ＂    6-OCH2CF3 H    OCH3    OCH3    CH262          ＂    6-SCH3     H    OCH3    OCH3    CH263          ＂    6-SO2CH3  H    OCH3    OCH3    CH264          ＂    6-NO2      H    OCH3    OCH3    CH265          ＂    6-CO2CH3  H    OCH3    OCH3    CH266          ＂    6-Br        H    OCH3    OCH3    CH267          ＂    6-CF3      H    OCH3    OCH3    CH268          ＂    6-OCF3     H    OCH3    OCH3    CH269          ＂    6-OCF2H    H    OCH3    OCH3    CH270  H         H    OCH3    OCH3    CH271          ＂    H           H    OCH3    CH3     CH272          ＂    H           H    OCH3    Cl       CH273          ＂    H           H    CH3     CH3     CH274          ＂    H           H    OCH3    OCH3    N275          ＂    H           H    OCH3    CH3     N276          ＂    H           H    OC2H5  NHCH3   N277          ＂    H           CH3 OCH3    CH3     N278          ＂    4-CH3      H    OCH3    OCH3    CH279          ＂    4-Cl        H    OCH3    OCH3    CH280          ＂    6-CH3      H    OCH3    OCH3    CH281          ＂    6-OCH3     H    OCH3    OCH3    CH
表1(续)化合物编号
         R1        R2    R3  X         Y        Z    熔点[℃]282          ＂         6-Cl   H    OCH3     OCH3    CH283 -OSO2N(CH3)OCH3 H      H    OCH3     OCH3    CH284    H      H    OCH3     OCH3    CH285          ＂         H      H    OCH3     CH3     CH286          ＂         H      H    OCH3     Cl       CH287          ＂         H      H    CH3      CH3     CH288          ＂         H      H    OCH3     OCH3    N289          ＂         H      H    OCH3     CH3     N290          ＂         H      H    OC2H5   NHCH3   N291          ＂         H      CH3 OCH3     CH3     N292          ＂         4-CH3 H    OCH3     OCH3    CH293          ＂         4-Cl   H    OCH3     OCH3    CH294          ＂         6-CH3 H    OCH3     OCH3    CH295          ＂         6-OCH3H    OCH3     OCH3    CH296          ＂         6-Cl   H    OCH3     OCH3    CH297   -OSO2N(Allyl)2  H      H    OCH3     OCH3    CH298   
Figure C9110018400322
H      H    OCH3     OCH3    CH   157-158299          ＂         H      H    OCH3     CH3     CH   151-153[分解)300          ＂         H      H    OCH3     Cl       CH301          ＂         H      H    CH3      CH3     CH   159-160(分解)302          ＂         H      H    OCH3     OCH3    N303          ＂         H      H    OCH3     CH3     N    146-19(分解)304          ＂         H      H    OC2H5   NHCH3   N305          ＂         H      CH3 OCH3     CH2     N306          ＂         4-CH3 H    OCH3     OCH3    CH307          ＂         4-Cl   H    OCH3     OCH3    CH308          ＂         6-CH3 H    OCH3     OCH3    CH309          ＂         6-OCH3H    OCH3     OCH3    CH
表1(续)化合物编号
           R1   R2     R3   X       Y        Z     熔点[℃]310            ＂    6-Cl    H    OCH3    OCH3    CH311            ＂    6-F     H    OCH3    OCH3    CH312 
Figure C9110018400331
H       H    OCH3    OCH3    CH    158-159313            ＂    H       H    OCH3    CH3     CH    170-171314            ＂    H       H    OCH3    Cl       CH315            ＂    H       H    CH3     CH3     CH    169-170316            ＂    H       H    OCH3    OCH3    N317            ＂    H       H    OCH3    CH3     N     155318            ＂    H       H    OC2H5  NHCH3   N319            ＂    H       CH3 OCH3    CH3     N320            ＂    4-CH3  H    OCH3    OCH3    CH321            ＂    4-Cl    H    OCH3    OCH3    CH322            ＂    6-CH3  H    OCH3    OCH3    CH323            ＂    6-OCH3 H    OCH3    OCH3    CH324            ＂    6-Cl    H    OCH3    OCH3    CH325            ＂    6-F     H    OCH3    OCH3    CH326 
Figure C9110018400332
H       H    OCH3    OCH3    CH    173-174(分解)327            ＂    H       H    OCH3    CH3     CH328            ＂    H       H    OCH3    Cl       CH    185-186(分解)329            ＂    H       H    CH3     CH3     CH330            ＂    H       H    OCH3    OCH3    N331            ＂    H       H    OCH3    CH3     N332            ＂    H       H    OC2H5  NHCH3   N333            ＂    H       CH3 OCH3    CH3     N334            ＂    4-CH3  H    OCH3    OCH3    CH335            ＂    4-Cl    H    OCH3    OCH3    CH336            ＂    6-CH3  H    OCH3    OCH3    CH337            ＂    6-OCH3 H    OCH3    OCH3    CH338            ＂    6-Cl    H    OCH3    OCH3    CH
表1(续)化合物编号
       R1     R2    R3   X       Y        Z     熔点[℃]339        ＂      6-F    H    OCH3    OCH3    CH340 H    H    OCH3    OCH3    CH    141-142(分解)341        ＂      H      H    OCH3    CH3     CH342        ＂      H      H    OCH3    Cl       CH343        ＂      H      H    CH3     CH3     CH344        ＂      H      H    OCH3    OCH3    N345        ＂      H      H    OCH3    CH3     N346        ＂      H      H    OC2H5  NHCH3   N347        ＂      H      CH3 OCH3    CH3     N348        ＂      4-CH3 H    OCH3    OCH3    CH349        ＂      4-Cl   H    OCH3    OCH3    CH350        ＂      6-CH3 H    OCH3    OCH3    CH351        ＂      6-OCH3H    OCH3    OCH3    CH352        ＂      6-Cl   H    OCH3    OCH3    CH353        ＂      6-F    H    OCH3    OCH3    CH354  -NHSO2CH3  H      H    OCH3    OCH3    CH   191-192(分解)355        ＂      H      H    OCH3    CH3     CH356        ＂      H      H    OCH3    Cl       CH357        ＂      H      H    CH3     CH3     CH358        ＂      H      H    OCH3    OCH3    N359        ＂      H      H    OCH3    CH3     N360        ＂      H      H    OC2H5  NHCH3   N361        ＂      H      CH3 OCH3    CH3     N362        ＂      4-CH3 H    OCH3    OCH3    CH363        ＂      4-Cl   H    OCH3    OCH3    CH364        ＂      6-CH3 H    OCH3    OCH3    CH365        ＂      6-OCH3H    OCH3    OCH3    CH366        ＂      6-Cl   H    OCH3    OCH3    CH367        ＂      6-F    H    OCH3    OCH3    CH368 -NHSO2C2H5 H      H    OCH3    OCH3    CH
表1(续)化合物编号
       R1     R2     R3   X          Y       Z     熔点[℃]369        ＂      H       H    OCH3       CH2    CH370        ＂      H       H    OCH3       Cl      CH371        ＂      H       H    CH3        CH3    CH372        ＂      H       H    OCH3       OCH3   N373        ＂      H       H    OCH3       CH3    N374        ＂      H       H    OC2H5     NHCH3  N375        ＂      H       CH3 OCH3       CH3    N376        ＂      4-CH3  H    OCH3       OCH3   CH377        ＂      4-Cl    H    OCH3       OCH3   CH378        ＂      6-CH3  H    OCH3       OCH3   CH379        ＂      6-OCH3 H    OCH3       OCH3   CH380        ＂      6-Cl    H    OCH3       OCH3   CH381        ＂      6-F     H    OCH3       OCH3   CH382 -NHSO2C3H7 H       H    OCH3       OCH3   CH383        ＂      H       H    OCH3       CH3    CH384        ＂      H       H    OCH3       Cl      CH385        ＂      H       H    CH3        CH3    CH386        ＂      H       H    OCH3       OCH3   N387        ＂      H       H    OCH3       CH3    N388        ＂      H       H    OC2H5     NHCH3  N389        ＂      H       CH3 OCH3       CH3    N390        ＂      4-CH3  H    OCH3       OCH3   CH391        ＂      4-Cl    H    OCH3       OCH3   CH392        ＂      6-CH3  H    OCH3       OCH3   CH393        ＂      6-OCH3 H    OCH3       OCH3   CH394        ＂      6-Cl    H    OCH3       OCH3   CH395        ＂      6-F     R    OCH3       OCH3   CH396 -NHSO2C3H5 H       H    OCH3       OCH3   CH397        ＂      H       H    OCH3       CH3    CH398        ＂      H       H    OCH3       Cl      CH399        ＂      H       H    CH3        CH3    CH401        ＂      H       H    OCH3       OCH3   N402        ＂      H       H    OCH3       CH3    N
表1(续)化合物编号
         R1      R2    R3   X       Y        Z     熔点[℃]403          ＂       H      H    OC2H5  NHCH3   N404          ＂       H      CH3 OCH3    CH3     N405          ＂       4-CH3 H    OCH3    OCH3    CH406          ＂       4-Cl   H    OCH3    OCH3    CH407          ＂       6-CH3 H    OCH3    OCH3    CH408          ＂       6-OCH3H    OCH3    OCH3    CH409          ＂       6-Cl   H    OCH3    OCH3    CH410          ＂       6-F    H    OCH3    OCH3    CH411  -N(SO2CH3)2  H      H    OCH3    OCH3    CH    219-220(分解)412          ＂       H      H    OCH3    CH3     CH413          ＂       H      H    OCH3    Cl       CH414          ＂       H      H    CH3     CH3     CH415          ＂       H      H    OCH3    OCH3    N416          ＂       H      H    OCH3    CH3     N417          ＂       H      H    OC2H5  NHCH3   N418          ＂       H      CH3 OCH3    CH3     N419          ＂       4-CH3 H    OCH3    OCH3    CH420          ＂       4-Cl   H    OCH3    OCH3    CH421          ＂       6-CH3 H    OCH3    OCH3    CH422          ＂       6-OCH3H    OCH3    OCH3    CH423          ＂       6-Cl   H    OCH3    OCH3    CH424          ＂       6-F    H    OCH3    OCH3    CH425 -N(SO2C2H5)2 H      H    OCH3    OCH3    CH426          ＂       H      H    OCH3    CH3     CH427          ＂       H      H    OCH3    Cl       CH428          ＂       H      H    CH3     CH3     CH429          ＂       H      H    OCH3    OCH3    N430          ＂       H      H    OCH3    CH3     N431          ＂       H      H    OC2H5  NHCH3   N432          ＂       H      CH3 OCH3    CH3     N433          ＂       4-CH3 H    OCH3    OCH3    CH434          ＂       4-Cl   H    OCH3    OCH3    CH435          ＂       6-CH3 H    OCH3    OCH3    CH436          ＂       6-OCH3H    OCH3    OCH3    CH
表1(续)化合物编号
         R1       R2  R3    X       Y           Z     熔点[℃]437          ＂        6-Cl H    OCH3      OCH3      CH438          ＂        6-F  H    OCH3      OCH3      CH439  -N(CH3)SO2CH3 H    H    OCH3      OCH3      CH    177-178440          ＂        H    CH3 OCH3      OCH3      CH    152-153441          ＂        H    CH3 OCH3      CH3       N442          ＂        H    H    CH3       CH3       CH    185-186(分解)443          ＂        H    H    OCH3      CH3       CH    169-170(分解)444          ＂        H    H    CH3       OC2H5    CH445          ＂        H    H    OCH3      CH3       N     158-159(解)446          ＂        H    H    OCH3      OCH3      N     173-174(分解)447          ＂        H    H    OCH3      Cl         CH    167-169448          ＂        H    H    OCF2H     CH3       CH449          ＂        H    H    OCF2H     OCF2H     CH450          ＂        H    H    OCH3      Br         CH451          ＂        H    H    OCH3      OC2H5    CH452          ＂        H    H    OCH3      SCH3      CH453          ＂        H    H    OCH3      OC2H5    N454          ＂        H    H    OCH3      OC3H7    CH455          ＂        H    H    CH3       Cl         CH    168-169(分解)456          ＂        H    H    Cl         OC2H5    CH457          ＂        H    H    OC2H5    OC2H5    CH458          ＂        H    H    C2H5     OCH3      CH459          ＂        H    H    CF3       OCH3      CH460          ＂        H    H    OCH2CF3  CH3       CH461          ＂        H    H    OCH2CF3  OCH3      CH462          ＂        H    H    OCH2CF3  OCH2CF3  CH463          ＂        H    H    OCH2CF3  OCH3      N464          ＂        H    H    OCH3      CH(OCH3)2CH
表1(续)化合物编号
         R1   R2   R3   X        Y         Z     熔点[℃]465          ＂    4-CH3H    OCH3     OCH3    CH466          ＂    ＂    H    OCH3     CH3     CH467          ＂    ＂    H    OCH3     Cl       CH468          ＂    ＂    H    CH3      CH3     CH469          ＂    ＂    H    OCH3     OCH3    N470          ＂    ＂    H    OCH3     CH3     N471          ＂    ＂    H    OC2H5   NHCH3   N472          ＂    ＂    CH3 OCH3     OCH3    CH473          ＂    5-CH3H    OCH3     OCH3    CH474          ＂    ＂    H    OCH3     CH3     CH475          ＂    ＂    H    OCH3     Cl       CH476          ＂    ＂    H    CH3      CH3     CH477          ＂    ＂    H    OCH3     OCH3    N478          ＂    ＂    H    OCH3     CH3     N479          ＂    ＂    H    OC2H5   NHCH3   N480          ＂    ＂    CH3 OCH3     OCH3    CH481          ＂    6-CH3H    OCH3     OCH3    CH    185482          ＂    ＂    H    OCH3     CH3     CH483          ＂    ＂    H    OCH3     Cl       CH484          ＂    ＂    H    CH3      CH3     CH485          ＂    ＂    H    OCH3     OCH3    N486          ＂    ＂    H    OCH3     CH3     N487          ＂    ＂    H    OC2H5   NHCH3   N488          ＂    ＂    CH3 OCH3     OCH3    CH489          ＂    4-Cl  H    OCH3     OCH3    CH490          ＂    ＂    H    OCH3     CH3     CH491          ＂    ＂    H    OCH3     Cl       CH492          ＂    ＂    H    CH3      CH3     CH493          ＂    ＂    H    OCH3     OCH3    N494          ＂    ＂    H    OCH3     CH3     N495          ＂    ＂    H    OC2H5   NHCH3   N496          ＂    ＂    CH3 OCH3     OCH3    CH
表1(续)化合物编号
         R1   R2   R3    X       Y        Z     熔点[℃]497          ＂    5-Cl  H    OCH3     OCH3    CH498          ＂    ＂    H    OCH3     CH3     CH499          ＂    ＂    H    OCH3     Cl       CH500          ＂    ＂    H    CH3      CH3     CH501          ＂    ＂    H    OCH3     OCH3    N502          ＂    ＂    H    OCH3     CH3     N503          ＂    ＂    H    OC2H5   NHCH3   N504          ＂    ＂    CH3 OCH3     OCH3    CH505          ＂    6-Cl  H    OCH3     OCH3    CH506          ＂    ＂    H    OCH3     CH3     CH507          ＂    ＂    H    OCH3     Cl       CH508          ＂    ＂    H    CH3      CH3     CH509          ＂    ＂    H    OCH3     OCH3    N510          ＂    ＂    H    OCH3     CH3     N511          ＂    ＂    H    OC2H5   NHCH3   N512          ＂    ＂    CH3 OCH3     OCH3    CH513          ＂    4-CF3H    OCH3     OCH3    CH514          ＂    ＂    H    OCH3     CH3     CH515          ＂    ＂    H    OCH3     Cl       CH516          ＂    ＂    H    CH3      CH3     CH517          ＂    ＂    H    OCH3     OCH3    N518          ＂    ＂    H    OCH3     CH3     N519          ＂    4-F   H    OC2H5   NHCH3   N520          ＂    ＂    CH3 OCH3     OCH3    CH521          ＂    5-CF3H    OCH3     OCH3    CH522          ＂    ＂    H    OCH3     CH3     CH523          ＂    ＂    H    OCH3     Cl       CH524          ＂    ＂    H    CH3      CH3     CH525          ＂    ＂    H    OCH3     OCH3    N526          ＂    ＂    H    OCH3     CH3     N527          ＂    5-F   H    OC2H5   NHCH3   N528          ＂    ＂    CH3 OCH3     OCH3    CH
表1(续)化合物编号
         R1   R2    R3   X       Y         Z     熔点[℃]529          ＂    6-F    H    OCH3    OCH3    CH530          ＂    ＂     H    OCH3    CH3     CH531          ＂    ＂     H    OCH3    Cl       CH532          ＂    ＂     H    CH3     CH3     CH533          ＂    ＂     H    OCH3    OCH3    N534          ＂    ＂     H    OCH3    CH3     N535          ＂    ＂     H    OC2H5  NHCH3   N536          ＂    ＂     CH3 OCH3    OCH3    CH537          ＂    4-OCH3H    OCH3    OCH3    CH538          ＂    ＂     H    OCH3    CH3     CH539          ＂    ＂     H    OCH3    Cl       CH540          ＂    ＂     H    CH3     CH3     CH541          ＂    ＂     H    OCH3    OCH3    N542          ＂    ＂     H    OCH3    CH3     N543          ＂    ＂     H    OC2H5  NHCH3   N544          ＂    ＂     CH3 OCH3    OCH3    CH545          ＂    5-OCH3H    OCH3    OCH3    CH546          ＂    ＂     H    OCH3    CH3     CH547          ＂    ＂     H    OCH3    Cl       CH548          ＂    ＂     H    CH3     CH3     CH549          ＂    ＂     H    OCH3    OCH3    N550          ＂    ＂     H    OCH3    CH3     N551          ＂    ＂     H    OC2H5  NHCH3   N552          ＂    ＂     CH3 OCH3    OCH3    CH553          ＂    6-OCH3H    OCH3    OCH3    CH554          ＂    ＂     H    OCH3    CH3     CH555          ＂    ＂     H    OCH3    Cl       CH556          ＂    ＂     H    CH3     CH3     CH557          ＂    ＂     H    OCH3    OCH3    N558          ＂    ＂     H    OCH3    CH3     N559          ＂    ＂     H    OC2H5  NHCH3   N
表1(续)化合物编号
         R1      R2         R3    X      Y        Z     熔点[℃]560          ＂       ＂          CH3 OCH3    OCH3    CH561          ＂       6-C2H5    H    OCH3    OCH3    CH562          ＂       6-C4H9    H    OCH3    OCH3    CH563          ＂       6-OC2H5   H    OCH3    OCH3    CH564          ＂       6-OCH2CF3 H    OCH3    OCH3    CH565          ＂       6-SCH3     H    OCH3    OCH3    CH566          ＂       6-SO2CH3  H    OCH3    OCH3    CH567          ＂       6-NO2      H    OCH3    OCH3    CH568          ＂       6-CO2CH3  H    OCH3    OCH3    CH569          ＂       6-Br        H    OCH3    OCH3    CH570          ＂       6-CF3      H    OCH3    OCH3    CH571          ＂       6-OCF3     H    OCH3    OCH3    CH572          ＂       6-OCF2H    H    OCH3    OCH3    CH573    -N(Et)SO2CH3 H           H    OCH3    OCH3    CH    188(分解)574          ＂       H           H    OCH3    CH3     CH575          ＂       H           H    OCH3    Cl       CH576          ＂       H           H    CH3     CH3     CH577          ＂       H           H    OCH3    OCH3    N578          ＂       H           H    OCH3    CH3     N579          ＂       H           H    OC2H5  NHCH3   N580          ＂       H           CH3 OCH3    OCH3    CH581          ＂       4-CH3      H    OCH3    OCH3    CH582          ＂       4-Cl        H    OCH3    OCH3    CH583          ＂       6-CH3      H    OCH3    OCH3    CH584          ＂       6-OCH3     H    OCH3    OCH3    CH585          ＂       6-Cl        H    OCH3    OCH3    CH586          ＂       6-F         H    OCH3    OCH3    CH587    -N(Pr)SO2CH3 H           H    OCH3    OCH3    CH    182-183(分解)588          ＂       H           H    OCH3    CH3     CH589          ＂       H           H    OCH3    Cl       CH590          ＂       H           H    CH3     CH3     CH591          ＂       H           H    OCH3    OCH3    N592          ＂       H           H    OCH3    CH3     N
表1(续)化合物编号
         R1        R2    R3   X       Y        Z     熔点[℃]593          ＂         H      H    OC2H5  NHCH3   N594          ＂         H      CH3 OCH3    OCH3    CH595          ＂         4-CH3 H    OCH3    OCH3    CH596          ＂         4-Cl   H    OCH3    OCH3    CH597          ＂         6-CH3 H    OCH3    OCH3    CH598          ＂         6-OCH3H    OCH3    OCH3    CH599          ＂         6-Cl   H    OCH3    OCH3    CH600          ＂         6-F    H    OCH3    OCH3    CH601    -N(i-Pr)SO2CH3 H      H    OCH3    OCH3    CH    195(分解)602          ＂         H      H    OCH3    CH3     CH603          ＂         H      H    OCH3    Cl       CH604          ＂         H      H    CH3     CH3     CH605          ＂         H      H    OCH3    OCH3    N606          ＂         H      H    OCH3    CH3     N607          ＂         H      H    OC2H5  NHCH3   N608          ＂         H      CH3 OCH3    OCH3    CH609          ＂         4-CH3 H    OCH3    OCH3    CH610          ＂         4-Cl   H    OCH3    OCH3    CH611          ＂         6-CH3 H    OCH3    OCH3    CH612          ＂         6-OCH3H    OCH3    OCH3    CH613          ＂         6-Cl   H    OCH3    OCH3    CH614          ＂         6-F    H    OCH3    OCH3    CH615    -N(i-Bu)SO2CH3 H      H    OCH3    OCH3    CH 166-167616          ＂         H      H    OCH3    CH3     CH617          ＂         H      H    OCH3    Cl       CH618          ＂         H      H    CH3     CH3     CH619          ＂         H      H    OCH3    OCH3    N620          ＂         H      H    OCH3    CH3     N621          ＂         H      H    OC2H5  NHCH3   N622          ＂         H      CH3 OCH3    OCH3    CH623          ＂         4-CH3 H    OCH3    OCH3    CH624          ＂         4-Cl   H    OCH3    OCH3    CH
表1(续)化合物编号
         R1          R2      R3     X       Y        Z     熔点[℃]625          ＂           6-CH3   H      OCH3    OCH3    CH626          ＂           6-OCH3  H      OCH3    OCH3    CH627          ＂           6-Cl     H      OCH3    OCH3    CH628          ＂           6-F      H      OCH3    OCH3    CH629  -N(CF3)SO2CH3    H        H      OCH3    OCH3    CH630          ＂           H        H      OCH3    CH3     CH631          ＂           H        H      OCH3    Cl       CH632          ＂           H        H      CH3     CH3     CH633          ＂           H        H      OCH3    OCH3    N634          ＂           H        H      OCH3    CH3     N635          ＂           H        H      OC2H5  NHCH3   N636          ＂           H        CH3   OCH3    OCH3    CH637          ＂           4-CH3   H      OCH3    OCH3    CH638          ＂           4-Cl     H      OCH3    OCH3    CH639          ＂           6-CH3   H      OCH3    OCH3    CH640          ＂           6-OCH3  H      OCH3    OCH3    CH641          ＂           6-Cl     H      OCH3    OCH3    CH642          ＂           6-F      H      OCH3    OCH3    CH643  -N(CHF2)SO2CH3   H        H      OCH3    OCH3    CH644          ＂           H        H      OCH3    CH3     CH645          ＂           H        H      OCH3    Cl       CH646          ＂           H        H      CH3     CH3     CH647          ＂           H        H      OCH3    OCH3    N648          ＂           H        H      OCH3    CH3     N649          ＂           H        H      OC2H5  NHCH3   N650          ＂           H        CH3   OCH3    OCH3    CH651          ＂           4-CH3   H      OCH3    OCH3    CH652          ＂           4-Cl     H      OCH3    OCH3    CH653          ＂           6-CH3   H      OCH3    OCH3    CH654          ＂           6-OCH3  H      OCH3    OCH3    CH655          ＂           6-Cl     H      OCH3    OCH3    CH656          ＂           6-F      H      OCH3    OCH3    CH
表1(续)化合物编号
         R1   R2      R3    X      Y        Z     熔点[℃]657 
Figure C9110018400441
H        H    OCH3    OCH3    CH658          ＂    H        H    OCH3    CH3     CH659          ＂    H        H    OCH3    Cl       CH660          ＂    H        H    CH3     CH3     CH661          ＂    H        H    OCH3    OCH3    N662          ＂    H        H    OCH3    CH3     N663          ＂    H        H    OC2H5  NHCH3   N664          ＂    H        CH3 OCH3    OCH3    CH665          ＂    4-CH3   H    OCH3    OCH3    CH666          ＂    4-Cl     H    OCH3    OCH3    CH667          ＂    6-CH3   H    OCH3    OCH3    CH668          ＂    6-OCH3  H    OCH3    OCH3    CH669          ＂    6-Cl     H    OCH3    OCH3    CH670          ＂    6-F      H    OCH3    OCH3    CH671
Figure C9110018400442
H       H    OCH3    OCH3    CH672          ＂    H        H    OCH3    CH3     CH673          ＂    H        H    OCH3    Cl       CH674          ＂    H        H    CH3     CH3     CH675          ＂    H        H    OCH3    OCH3    N676          ＂    H        H    OCH3    CH3     N677          ＂    H        H    OC2H5  NHCH3   N678          ＂    H        CH3 OCH3    OCH3    CH679          ＂    4-CH3   H    OCH3    OCH3    CH680          ＂    4-Cl     H    OCH3    OCH3    CH681          ＂    6-CH3   H    OCH3    OCH3    CH682          ＂    6-OCH3  H    OCH3    OCH3    CH683          ＂    6-Cl     H    OCH3    OCH3    CH684          ＂    6-F      H    OCH3    OCH3    CH
表1(续)化合物编号
            R1   R2      R3   X       Y        Z     熔点[℃]685
Figure C9110018400451
H        H    OCH3    OCH3    CH686             ＂    H        H    OCH3    CH3     CH687             ＂    H        H    OCH3    Cl       CH688             ＂    H        H    CH3     CH3     CH689             ＂    H        H    OCH3    OCH3    N690             ＂    H        H    OCH3    CH3     N691             ＂    H        H    OC2H5  NHCH3   N692             ＂    H        CH3 OCH3    OCH3    CH693             ＂    4-CH3   H    OCH3    OCH3    CH694             ＂    4-Cl     H    OCH3    OCH3    CH695             ＂    6-CH3   H    OCH3    OCH3    CH696             ＂    6-OCH3  H    OCH3    OCH3    CH697             ＂    6-Cl     H    OCH3    OCH3    CH698             ＂    6-F      H    OCH3    OCH3    CH699  
Figure C9110018400452
 H        H    OCH3    OCH3    CH700             ＂    H        H    OCH3    CH3     CH701             ＂    H        H    OCH3    Cl       CH702             ＂    H        H    CH3     CH3     CH703             ＂    H        H    OCH3    OCH3    N704             ＂    H        H    OCH3    CH3     N706             ＂    H        H    OC2H5  NHCH3   N707             ＂    H        CH3 OCH3    OCH3    CH708             ＂    4-CH3   H    OCH3    OCH3    CH709             ＂    4-Cl     H    OCH3    OCH3    CH710             ＂    6-CH3   H    OCH3    OCH3    CH711             ＂    6-OCH3  H    OCH3    OCH3    CH712             ＂    6-Cl     H    OCH3    OCH3    CH713             ＂    6-F      H    OCH3    OCH3    CH
表1(续)化合物编号
            R1   R2     R3   X       Y        Z     熔点[℃]714 
Figure C9110018400461
H       H    OCH3    OCH3    CH715             ＂    H       H    OCH3    CH3     CH716             ＂    H       H    OCH3    Cl       CH717             ＂    H       H    CH3     CH3     CH718             ＂    H       H    OCH3    OCH3    N719             ＂    H       H    OCH3    CH3     N720             ＂    H       H    OC2H5  NHCH3   N721             ＂    H       CH3 OCH3    OCH3    CH722             ＂    4-CH3  H    OCH3    OCH3    CH723             ＂    4-Cl    H    OCH3    OCH3    CH724             ＂    6-CH3  H    OCH3    OCH3    CH725             ＂    6-OCH3 H    OCH3    OCH3    CH726             ＂    6-Cl    H    OCH3    OCH3    CH727             ＂    6-F     H    OCH3    OCH3    CH728 
Figure C9110018400462
H       H    OCH3    OCH3    CH729             ＂    H       H    OCH3    CH3     CH730             ＂    H       H    OCH3    Cl       CH731             ＂    H       H    CH3     CH3     CH732             ＂    H       H    OCH3    OCH3    N733             ＂    H       H    OCH3    CH3     N734             ＂    H       H    OC2H5  NHCH3   N735             ＂    H       CH3 OCH3    OCH3    CH736             ＂    4-CH3  H    OCH3    OCH3    CH737             ＂    4-Cl    H    OCH3    OCH3    CH738             ＂    6-CH3  H    OCH3    OCH3    CH739             ＂    6-OCH3 H    OCH3    OCH3    CH740             ＂    6-Cl    H    OCH3    OCH3    CH741             ＂    6-F     H    OCH3    OCH3    CH
表1(续)化合物编号
         R1   R2     R3   X       Y        Z     熔点[℃]742  H       H    OCH3    OCH3    CH743          ＂    H       H    OCH3    CH3     CH744          ＂    H       H    OCH3    Cl       CH745          ＂    H       H    CH3     CH3     CH746          ＂    H       H    OCH3    OCH3    N747          ＂    H       H    OCH3    CH3     N748          ＂    H       H    OC2H5  NHCH3   N749          ＂    H       CH3 OCH3    OCH3    CH750          ＂    4-CH3  H    OCH3    OCH3    CH751          ＂    4-Cl    H    OCH3    OCH3    CH752          ＂    6-CH3  H    OCH3    OCH3    CH753          ＂    6-OCH3 H    OCH3    OCH3    CH754          ＂    6-Cl    H    OCH3    OCH3    CH755          ＂    6-F     H    OCH3    OCH3    CH756  H       H    OCH3    OCH3    CH    208-210(分解)757          ＂    H       H    OCH3    CH3     CH758          ＂    H       H    OCH3    Cl       CH759          ＂    H       H    CH3     CH3     CH760          ＂    H       H    OCH3    OCH3    N761          ＂    H       H    OCH3    CH3     N762          ＂    H       H    OC2H5  NHCH3   N763          ＂    H       CH3 OCH3    OCH3    CH764          ＂    4-CH3  H    OCH3    OCH3    CH765          ＂    4-Cl    H    OCH3    OCH3    CH766          ＂    6-CH3  H    OCH3    OCH3    CH767          ＂    6-OCH3 H    OCH3    OCH3    CH768          ＂    6-Cl    H    OCH3    OCH3    CH769          ＂    6-F     H    OCH3    OCH3    CH
表1(续)化合物编号
             R1  R2     R3    X      Y        Z     熔点[℃]770 
Figure C9110018400481
H       H    OCH3    OCH3    CH    167-168(分解)771             ＂    H       H    OCH3    CH3     CH772             ＂    H       H    OCH3    Cl       CH773             ＂    H       H    CH3     CH3     CH774             ＂    H       H    OCH3    OCH3    N775             ＂    H       H    OCH3    CH3     N776             ＂    H       H    OC2H5  NHCH3   N777             ＂    H       CH3 OCH3    OCH3    CH778             ＂    4-CH3  H    OCH3    OCH3    CH779             ＂    4-Cl    H    OCH3    OCH3    CH780             ＂    6-CH3  H    OCH3    OCH3    CH781             ＂    6-OCH3 H    OCH3    OCH3    CH782             ＂    6-Cl    H    OCH3    OCH3    CH783             ＂    6-F     H    OCH3    OCH3    CH784     H       H    OCH3    OCH3    CH785             ＂    H       H    OCH3    CH3     CH786             ＂    H       H    OCH3    Cl       CH787             ＂    H       H    CH3     CH3     CH788             ＂    H       H    OCH3    OCH3    N789             ＂    H       H    OCH3    CH3     N790             ＂    H       H    OC2H5  NHCH3   N791             ＂    H       CH3 OCH3    OCH3    CH792             ＂    4-CH3  H    OCH3    OCH3    CH793             ＂    4-Cl    H    OCH3    OCH3    CH794             ＂    6-CH3  H    OCH3    OCH3    CH795             ＂    6-OCH3 H    OCH3    OCH3    CH796             ＂    6-Cl    H    OCH3    OCH3    CH797             ＂    6-F     H    OCH3    OCH3    CH
表1(续)化合物编号
         R1   R2     R3   X       Y        Z  熔点[℃]798    H       H    OCH3    OCH3    CH 195(分解)799          ＂    H       H    OCH3    CH3     CH800          ＂    H       H    OCH3    Cl       CH801          ＂    H       H    CH3     CH3     CH802          ＂    H       H    OCH3    OCH3    N803          ＂    H       H    OCH3    CH3     N804          ＂    H       H    OC2H5  NHCH3   N805          ＂    H       CH3 OCH3    OCH3    CH806          ＂    4-CH3  H    OCH3    OCH3    CH807          ＂    4-Cl    H    OCH3    OCH3    CH808          ＂    6-CH3  H    OCH3    OCH3    CH809          ＂    6-OCH3 H    OCH3    OCH3    CH810          ＂    6-Cl    H    OCH3    OCH3    CH811          ＂    6-F     H    OCH3    OCH3    CH812 
Figure C9110018400492
H       H    OCH3    OCH3    CH 192-193(分解)813          ＂    H       H    OCH3    CH3     CH814          ＂    H       H    OCH3    Cl       CH815          ＂    H       H    CH3     CH3     CH816          ＂    H       H    OCH3    OCH3    N817          ＂    H       H    OCH3    CH3     N818          ＂    H       H    OC2H5  NHCH3   N819          ＂    H       CH3 OCH3    OCH3    CH820          ＂    4-CH3  H    OCH3    OCH3    CH821          ＂    4-Cl    H    OCH3    OCH3    CH822          ＂    6-CH3  H    OCH3    OCH3    CH823          ＂    6-OCH3 H    OCH3    OCH3    CH824          ＂    6-Cl    H    OCH3    OCH3    CH825          ＂    6-F     H    OCH3    OCH3    CH
表1(续)化合物编号
         R1        R2     R3    X      Y        Z    熔点[℃]826  -N(OCH3)SO2CH3 H       H    OCH3    OCH3    CH827          ＂         H       H    OCH3    CH3     CH828          ＂         H       H    OCH3    Cl       CH829          ＂         H       H    CH3     CH3     CH830          ＂         H       H    OCH3    OCH3    N831          ＂         H       H    OCH3    CH3     N832          ＂         H       H    OC2H5  NHCH3   N833          ＂         H       CH3 OCH3    OCH3    CH834          ＂         4-CH3  H    OCH3    OCH3    CH835          ＂         4-Cl    H    OCH3    OCH3    CH836          ＂         6-CH3  H    OCH3    OCH3    CH837          ＂         6-OCH3 H    OCH3    OCH3    CH838          ＂         6-Cl    H    OCH3    OCH3    CH839          ＂         6-F     H    OCH3    OCH3    CH840  -N(CH3)SO2CF3  H       H    OCH3    OCH3    CH841          ＂         H       H    OCH3    CH3     CH842          ＂         H       H    OCH3    Cl       CH843          ＂         H       H    CH3     CH3     CH844          ＂         H       H    OCH3    OCH3    N845          ＂         H       H    OCH3    CH3     N846          ＂         H       H    OC2H5  NHCH3   N847          ＂         H       CH3 OCH3    OCH3    CH848          ＂         4-CH3  H    OCH3    OCH3    CH849          ＂         4-Cl    H    OCH3    OCH3    CH850          ＂         6-CH3  H    OCH3    OCH3    CH851          ＂         6-OCH3 H    OCH3    OCH3    CH852          ＂         6-Cl    H    OCH3    OCH3    CH853          ＂         6-F     H    OCH3    OCH3    CH
表1(续)化合物编号
         R1         R2       R3   X       Y        Z     熔点[℃]854   -N(CH3)SO2Et    H         H    OCH3    OCH3    CH    176-177855          ＂          H         H    OCH3    CH3     CH856          ＂          H         H    OCH3    Cl       CH857          ＂          H         H    CH3     CH3     CH858          ＂          H         H    OCH3    OCH3    N859          ＂          H         H    OCH3    CH3     N860          ＂          H         H    OC2H5  NHCH3   N861          ＂          H         CH3 OCH3    OCH3    CH862          ＂          4-CH3    H    OCH3    OCH3    CH863          ＂          4-Cl      H    OCH3    OCH3    CH864          ＂          6-CH3    H    OCH3    OCH3    CH    193-194(分解)865          ＂          6-OCH3   H    OCH3    OCH3    CH866          ＂          6-Cl      H    OCH3    OCH3    CH867          ＂          6-F       H    OCH3    OCH3    CH868   -N(CH3)SO2Ph    H         H    OCH3    OCH3    CH869          ＂          H         H    OCH3    CH3     CH870          ＂          H         H    OCH3    Cl       CH871          ＂          H         H    CH3     CH3     CH872          ＂          H         H    OCH3    OCH3    N873          ＂          H         H    OCH3    CH3     N874          ＂          H         H    OC2H5  NHCH3   N875          ＂          H         CH3 OCH3    OCH3    CH876          ＂          4-CH3    H    OCH3    OCH3    CH877          ＂          4-Cl      H    OCH3    OCH3    CH878          ＂          6-CH3    H    OCH3    OCH3    CH879          ＂          6-OCH3   H    OCH3    OCH3    CH880          ＂          6-Cl      H    OCH3    OCH3    CH881          ＂          6-F       H    OCH3    OCH3    CH
表1(续)化合物编号
         R1        R2     R3   X       Y        Z    熔点[℃]882  -N(CH3)SO2NMe2 H       H    OCH3    OCH3    CH883          ＂         H       H    OCH3    CH3     CH884          ＂         H       H    OCH3    Cl       CH885          ＂         H       H    CH3     CH3     CH886          ＂         H       H    OCH3    OCH3    N887          ＂         H       H    OCH3    CH3     N888          ＂         H       H    OC2H5  NHCH3   N889          ＂         H       CH3 OCH3    OCH3    CH890          ＂         4-CH3  H    OCH3    OCH3    CH891          ＂         4-Cl    H    OCH3    OCH3    CH892          ＂         6-CH3  H    OCH3    OCH3    CH893          ＂         6-OCH3 H    OCH3    OCH3    CH894          ＂         6-Cl    H    OCH3    OCH3    CH895          ＂         6-F     H    OCH3    OCH3    CH
表2
Figure C9110018400531
化合物编号      R1         R2     R3   X       Y        Z  熔点[℃]896             I           H       H    OCH3    OCH3    CH897             ＂          H       H    OCH3    CH3     CH898             ＂          H       H    OCH3    Cl       CH899             ＂          H       H    CH3     CH3     CH900             ＂          H       H    OCH3    OCH3    N901             ＂          H       H    OCH3    CH3     N902             ＂          H       H    OC2H5  NHCH3   N903             ＂          H       CH3 OCH3    OCH3    CH904             ＂          4-CH3  H    OCH3    OCH3    CH905             ＂          6-CH3  H    OCH3    OCH3    CH906             ＂          4-Cl    H    OCH3    OCH3    CH907             ＂          6-Cl    H    OCH3    OCH3    CH908             ＂          4-F     H    OCH3    OCH3    CH909             ＂          6-F     H    OCH3    OCH3    CH910             ＂          4-OCH3 H    OCH3    OCH3    CH911             ＂          6-OCH3 H    OCH3    OCH3    CH912     -OSO2N(CH3)2    H       H    OCH3    OCH3    CH913             ＂          4-CH3  H    OCH3    OCH3    CH914             ＂          6-CH3  H    OCH3    OCH3    CH915             ＂          4-Cl    H    OCH3    OCH3    CH916             ＂          6-Cl    H    OCH3    OCH3    CH917             ＂          4-F     H    OCH3    OCH3    CH
表2(续)化合物编号      R1          R2   R3   X       Y        Z  熔点[℃]918             ＂          6-F    H    OCH3    OCH3    CH919             ＂          4-OCH3H    OCH3    OCH3    CH920             ＂          6-OCH3H    OCH3    OCH3    CH921     -N(CH3)SO2CH3   H      H    OCH3    OCH3    CH922             ＂          H      H    OCH3    CH3     CH923             ＂          H      H    OCH3    Cl       CH924             ＂          H      H    CH3     CH3     CH925             ＂          H      H    OCH3    OCH3    N926             ＂          H      H    OCH3    CH3     N927             ＂          H      H    OC2H5  NHCH3   N928             ＂          H      CH3 OCH3    OCH3    CH929             ＂          4-CH3 H    OCH3    OCH3    CH930             ＂          6-CH3 H    OCH3    OCH3    CH931             ＂          4-Cl   H    OCH3    OCH3    CH932             ＂          6-Cl   H    OCH3    OCH3    CH933             ＂          4-F    H    OCH3    OCH3    CH934             ＂          6-F    H    OCH3    OCH3    CH935             ＂          4-OCH3H    OCH3    OCH3    CH936             ＂          6-OCH3H    OCH3    OCH3    CH937      -NHSO2CH3        H      H    OCH3    OCH3    CH938      -NHSO2C2H5      H      H    OCH3    OCH3    CH939      -N(SO2CH3)2     H      H    OCH3    OCH3    CH940      -N(CH3)SO2Et     H      H    OCH3    OCH3    CH941      -N(Et)SO2CH3     H      H    OCH3    OCH3    CH
表3化合物编号              R1                A
Figure C9110018400552
表3(续)化合物编号
                      R1            A
Figure C9110018400561
表3(续)化合物编号                 R1              A
Figure C9110018400571
表3(续)化合物编号
                   R1                  A
Figure C9110018400581
表3(续)化合物编号
                   R1                A
Figure C9110018400591
表4
Figure C9110018400601
化合物编号
         R1   R2        熔点[℃]968          I     H         247-250(分解)969          ＂    4-CH3970          ＂    5-CH3971          ＂    6-CH3972          ＂    4-OCH3973          ＂    5-OCH3974          ＂    6-OCH3975          ＂    4-Cl976          ＂    5-Cl977          ＂    6-Cl978          ＂    4-F979          ＂    5-F980          ＂    6-F981          ＂    6-C2H5982          ＂    6-C4H9983          ＂    6-OC2H5984          ＂    6-OCH2CF3985          ＂    6-SCH3986          ＂    6-SO2CH3987          ＂    6-NO2988          ＂    6-CO2CH3989          ＂    6-Br990          ＂    6-CF3991          ＂    6-OCF3992          ＂    6-OCF2H
表4(续)化合物编号
           R1         R2    熔点[℃]993       -OSO2N(CH3)2H        油994          ＂          4-CH3995          ＂          5-CH3996          ＂          6-CH3997          ＂          4-OCH3998          ＂          5-OCH3999          ＂          6-OCH31000          ＂          4-Cl1001          ＂          5-Cl1002          ＂          6-Cl1002          ＂          4-F1004          ＂          5-F1005          ＂          6-F1006          ＂          6-C2H51007          ＂          6-C4H91008          ＂          6-OC2H51009          ＂          6-OCH2CF31010          ＂          6-SCH31011          ＂          6-SO2CH31012          ＂          6-NO21013          ＂          6-CO2CH31014          ＂          6-Br1015          ＂          6-CF31016          ＂          6-OCF31017          ＂          6-OCF2H1018         H1019      
Figure C9110018400612
  H
表4(续)化合物编号
        R1               R2    熔点[℃]1020    
Figure C9110018400621
    H        94-971021    
Figure C9110018400622
    H        142-1431022    
Figure C9110018400623
  H        166-1671023       H        油1024    -NHSO2CH3           H        176-1781025    -NHSO2C2H5         H1026    -NHSO2C3H7         H1027    -NHSO2C6H5         H1028    -N(SO2CH3)2        H        2081029    -N(SO2C2H5)2      H1030    -N(CH3)SO2CH3      H        1751031    ＂                     4-CH31032    ＂                     5-CH31033    ＂                     6-CH3   1241034    ＂                     4-OCH31035    ＂                     5-OCH31036    ＂                     6-OCH31037    ＂                     4-Cl1038    ＂                     5-Cl1039    ＂                     6-Cl1040    ＂                     4-F1041    ＂                     5-F
表4(续)化合物编号
          R1                R2             熔点[℃]1042          ＂                6-F1043          ＂                6-C2H51044          ＂                6-C4H91045          ＂                6-OC2H51046          ＂                6-OCH2CF31047          ＂                6-SCH31048          ＂                6-SO2CH31049          ＂                6-NO21050          ＂                6-CO2CH31051          ＂                6-Br1052          ＂                6-CF31053          ＂                6-OCF31054          ＂                6-OCF2H1055          -N(Et)SO2CH3    H              178-179(分解)1056          -N(Pr)SO2CH3    H              149-1501057          -N(i-Pr)SO2CH3  H              2011058          -N(i-Bu)SO2CH3  H              非晶形1059               H1060      
Figure C9110018400632
      H1061      
Figure C9110018400633
   H1062             H
表4(续)化合物编号
         R1                   R2   熔点[℃]1063    
Figure C9110018400641
      H1064    
Figure C9110018400642
         H1065                 H1066    
Figure C9110018400644
            H    143-1441067              H    138-1411068    
Figure C9110018400646
           H1069    
Figure C9110018400647
              H    200(分解)1070    
Figure C9110018400648
           H    220-221(分解)1071    -N(OCH3)SO2CH3        H1072    -N(CH3)SO2C2H5       H    136-1371073    -N(CH3)SO2CF3         H1074    -N(CH3)SO2Ph            H    200-2031075    -N(CH3)SO2N(Me)2      HB．剂型制备例a)粉剂：10份重的式(Ⅰ)化合物与90份重的滑石粉或惰性物质混合并在锤式破碎机中磨碎。b)可湿性粉剂：25份重的式(Ⅰ)化合物和64份重充作惰性材料的含高岭土的石英粉、10份重木质素磺酸钾和1份重的油酰甲基牛磺酸钠用作润湿剂和分散剂，上述混合物在棒式破碎机中研磨加工。c)水中易分散的分散浓缩剂：20份重的式(Ⅰ)化合物，6份重的烷基酚聚乙二醇醚(Triton×207),3份重异十三烷醇聚乙二醇醚(8EO=乙烯氧基单位)和71份重石蜡矿物油(沸点范围大约在255～277℃以上)，上述混合物在球磨机内磨至粒度在5微米以下。d)乳油：15份重式(Ⅰ)化合物，75份重环己烷作为溶剂和10份重乙氧基化壬基酚作为乳化剂。e)在水中可分散的颗粒剂组成如下：
75份重式(Ⅰ)化合物
10份重木质素磺酸钙
5份重月桂基硫酸钠
3份重聚丙烯醇
7份重高岭土
将上述各组份混合并在棒式破碎机中磨碎，粉状物质在硫化床上通过用水作为颗粒状液体喷洒造粒。f)在水中可分散的颗粒剂组成如下：
25份重式(Ⅰ)化合物
5份重2,2＇-二萘基甲烷-6,6＇-二磺酸钠
2份重油酰基甲基牛磺酸钠
1份重聚丙烯醇
17份重碳酸钙和
50份重水
将上述组份在胶体磨中匀浆、预磨碎、继之在球磨机中进一步研磨，再将所得到的悬浮物在喷雾塔中通过一种单级喷头喷雾並干燥。g)挤压成形的颗粒剂组成如下：
20份重有效成份
3份重木质素磺酸钠
1份重羧甲基纤维素
76份重高岭土
将上述组分混合磨碎后加水湿润，然后挤压成形，用气流干燥。C．生物学防治实例1．苗前除草效果
单子叶和双子叶杂草的种子或块根置于盛砂质粘土的塑料盆中，上面用壤土复盖。将本发明化合物的可湿性粉剂或乳油加水稀释成悬浮液或乳化液，稀释加水至药液量相当于600～800升/公顷，然后按不同施药剂量对盆栽表层土壤进行复盖式喷洒处理。喷药处理后将塑料盆放入温室内，维持适宜于杂草生长的温室条件。3至4周后与未施药对照组比较，用目测评估方法评价供试植物发芽或发芽后植株受害情况。试验结果表明本发明化合物对于农作物出苗前的单子叶和双子叶杂草具有优良广谱的除草性能(见表5)。
表5本发明化合物的苗前除草效果
    制备例编号     剂量(公斤有效成分/公顷) 毒麦    稗     除草效果
燕麦 繁缕 珍珠菊 欧白芥
      113644113544393123267299443301298313446445756442455     0.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.3  5555554255525355553     5555554255525334552     5455552254524255552     5555554355525445553     5555554355525332553     5555555455535554555
表5(续)
    制备例编号     剂量(公斤有效成分/公顷)                        除草效果
  毒麦    稗   燕麦 繁缕  珍珠菊  欧自芥
    77085485142340573     0.30.30.30.30.30.30.3     5555555     5555555     5555535     5555555     5555555     5555555
2．苗后除草效果
单子叶和双子叶杂草的种子或块根置于盛砂质粘土的塑料盆中，上面用壤土复盖后置于有利于生长的温室中培育，播种三周后至供试植物长至3叶期时用药剂处理。
本发明化合物的可湿性粉剂或乳油用水稀释至相当于600～800升/公顷药液量。用不同剂量喷洒处理供试植株的绿色部分，然后将供试植物置于最佳生长条件的温室内约3至4周，与未施药的对照组相比较，评价制剂的效果。
已证实本发明制剂对于农作物出苗后有着重要经济意义的单子叶和双子叶杂草具有优良广谱的除草性能(见表6)。
表6
    制备例编号     剂量(公斤有效成分/公顷) 毒麦    稗            除草效果
  燕麦   繁缕  珍珠菊  欧白芥
      11364411354439729944329844575644277085485142340573     0.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.30.3  53555553533555455435     54555553552423555235     51545552522333455205     55555553543433455455     55555552334423535125  55555555553543555355
3．农作物对药剂的承受能力
在温室内还要进行下面的试验，即将大量的各种农作物和杂草的种子用盆栽方式置于盛砂质粘土的盆内，上面用壤土复盖。
其中一部分盆子立即按上面1中所述方法处理，其余部分置于温室中至供试植物长至2-3片真叶期按上面2中所述方法用不同剂量喷洒处理。
给药处理后在温室中放置4至5周通过视觉评价可以确证，本发明化合物无论作苗前或苗后处理，即使在高剂量下对两叶期的大豆，棉花，油菜，甜菜和马铃薯这些农作物没有药害。此外本发明有些化合物对禾本科农作物如大麦、小麦、黑麦、高粱、小米、玉米或水稻还有保护作用。所以式(Ⅰ)化合物被证实是可以在有农作物的农田中施用的高选择性除草剂。

Claims (5)

1．一种除草剂，其特征在于含有0.1～99％(重量)的式(Ⅰ)化合物或其盐，和99.9-1％(重量)的配方助剂：式中
R1代表-OSO2NR4R5,-NR6R7或碘，
R2代表H,(C1-C4)烷基，(C1-C3)卤代烷基，卤素，NO2,CN,(C1-C3)烷氧基，(C1-C3)-卤代烷氧基，(C1-C3)烷硫基，(C1-C3)-烷氧基-(C1-C3)烷基，(C1-C3)烷氧基羰基，(C1-C3)烷基氨基，二〔(C1-C3)烷基〕氨基，(C1-C3)-烷基亚磺酰基，(C1-C3)烷基磺酰基，SO2NRaRb或C(O)NRaRb,Ra,Rb独立地为H,(C1-C3)烷基，(C3-C4)烯基，炔丙基，或者共同为-(CH2)4-,-(CH2)5-或-CH2CH2OCH2CH2-
R3代表H或CH3,
R4代表H,(C1-C3)烷基，(C3-C4)烯基，(C1-C3)烷氧基或(C3-C4)炔基和
R5代表H,(C1-C3)烷基，(C3-C4)烯基或(C3-C4)炔基或
R4和R5一起代表-(CH2)4-,-(CH2)5-或-CH2CH2OCH2CH2-,
R6代表(C1-C8)烷基，(C3-C6)烯基，(C3-C6)炔基或(C1-C4)烷基磺酰基，
R7代表(C1-C4)烷基磺酰基，苯基磺酰基，或
R6和R7共同组成式-(CH2)m-SO2-所示的链，此链可另外被1至4个(C1-C3)烷基取代，m是3或4,
n是零或1,
W是O或S,
A是下式中的一个基团
Figure C9110018400031
X代表H，卤素，(C1-C3)烷基，(C1-C3)烷氧基，其中后两个基团未被取代或被卤素取代一次或多次或被(C1-C3)烷氧基取代一次，
Y代表H，(C1-C3)烷基，(C1-C3)烷氧基或(C1-C3)烷硫基，其中前面所列举的含烷基的基团未被取代或被卤素取代一次或多次，或被(C1-C3)烷氧基或(C1-C3)-烷硫基取代一次或两次，此外还代表一个式NR8R9所示的基团，(C3-C6)环烷基，(C2-C4)-烯基，(C2-C4)炔基，(C3-C4)烯氧基或(C3-C4)炔氧基，
Z代表CH或N,
R8和R9分别代表H,(C1-C3)烷基或(C3-C4)烯基，
X1代表CH3,OCH3,OC2H5或OCF2H,
Y1代表-O-或-CH2-,
X2代表CH3,C2H5或CH2CF3,
Y2代表OCH3,OC2H5,SCH3,SC2H5,CH3或C2H5,
X3代表CH3或OCH3,
Y3代表H或CH3,
X4代表CH3,OCH3,OC2H5,CH2OCH3或Cl、
Y4代表CH3,OCH3,OC2H5或Cl,
Y5代表CH3,C2H5,OCH3或Cl。
2．按照权利要求1的除草剂，其特征在于：
R4,R5分别代表(C1-C3)烷基，烯丙基或炔丙基或
R4,R5一起代表-(CH2)4,-(CH2)5-或-CH2CH2OCH2CH2-
R6代表(C1-C4)烷基，(C3-C4)烯基，(C3-C4)-炔基或(C1-C4)烷基磺酰基，
R7代表(C1-C4)烷基磺酰基或苯基磺酰基
R6和R7共同形成式-(CH2)mSO2-所示的一个链，其中m是3或4，
3．按照权利要求1或2的除草剂，其特征在于：W代表一个氧原子，n是零，和A代表下式所示的一个基团
Figure C9110018400051
其中X、Z和Y如权利要求1定义。
4．按照权利要求1的除草剂，其特征在于：
R2代表H,(C1-C3)烷基，(C1-C3)烷氧基，卤素或(C1-C3)烷硫基，R4和R5分别为(C1-C3)烷基，R6代表H,(C1-C4)烷基或(C1-C3)烷基磺酰基，R7代表(C1-C3)-烷基磺酰基、
A代表下式所示的一个基团
Figure C9110018400052
式中
Z代表CH或N,X代表卤素，(C1-C2)烷基，
(C1-C2)烷氧基，OCF2H,CF3或OCH2CF3、
Y代表(C1-C2)烷基，(C1-C2)烷氧基或OCF2H。
5．权利要求1-4的除草剂用于防除杂草的用途，其特征在于：按除草有效量将权利要求1至4中一项或多项所述的式(Ⅰ)所示化合物或它们的盐施用于植物，植物种子或在大田上。
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