CN88102112A - 杂环新芬烷类似物，其制备方法及其作为杀虫剂的应用 - Google Patents

杂环新芬烷类似物，其制备方法及其作为杀虫剂的应用 Download PDF

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CN88102112A
CN88102112A CN88102112.1A CN88102112A CN88102112A CN 88102112 A CN88102112 A CN 88102112A CN 88102112 A CN88102112 A CN 88102112A CN 88102112 A CN88102112 A CN 88102112A
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carbon
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CN1027448C (zh
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汉斯·赫伯特
吉哈德·萨尔贝克
汉斯-皮特·克劳斯
瓦尔特·卢德斯
威尔勒·科诺夫
安娜·瓦尔特斯多夫
曼夫来德·肯
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Hoechst AG
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明式(I)化合物及其立体异构体具有有效的防治害虫特别是昆虫和螨类的特性。此外，本发明还提出式(I)化合物的制备方法。

Description

某些苄基-新芬醚（neophylether）化合物及其烃类似物的杀虫作用已见于DE-A-3117510和DE-A-3317908。
现已发现具有优异的杀虫，杀螨和杀线虫特性的新杂环新芬烷（neophan）化合物，其应用性能远远超出各种现有制剂。
因此本发明的目的是提出式（Ⅰ）化合物及其立体异构体。
式中
A、B、C′、D＝互不关联的CH或N且其中之一必须为N，
X＝CH2或O，
R1＝碳原子连接基，H，1-4碳烷基，三（1-4）碳烷基甲硅烷基，囟素，硝基，氰基，2-6碳烯基，2-6碳炔基，氨基，3-7碳环烷基，苯基，苯氧基，1-5碳烷氧基，2-4碳烯氧基，2-4碳炔氧基，羟基羰基，1-4碳烷硫基，3-7环碳烷氧基，1-6碳烷基羰基，1-4碳烷氧羰基，2-4碳烯氧羰基，3-5碳炔氧羰基，1-4碳囟代烷基，1-4碳烷氧基（1-4）碳烷基，1-3碳囟代烷氧基，1-3碳囟代烷硫基，囟代（1-4）碳烷氧基（1-4）碳烷基，1-4碳烷硫基（1-4）碳烷基，1-4碳烷氧基（1-4）碳烷氧基，囟代（1-4）碳烷氧基（1-4）碳烷氧基，2-4碳烯氧基（1-4）碳烷氧基，囟代（2-4）碳烯氧基，1-4碳烷氧基（1-4）碳烷硫基，1-4碳烷硫基（1-4）碳烷氧基，1-4碳烷硫基（1-4）碳烷硫基，囟代（1-4）碳烷氧羰基，囟代（2-4）碳烯氧羰基或二（1-6碳烷基）氨基或两个R1一起在邻位形成亚甲二氧基，亚乙二氧基或3-5碳亚烷基，
R2，R3＝互不关联的1-3碳烷基，2-8碳烯基，苯基或R2和R3为亚烷基链段，与季碳原子一起构成未取代或氟取代的3-6员环，R4＝-H，F，-CN，-CCl3，-C≡CH，1-4碳烷基，
Figure 88102112_IMG12
R5＝吡啶基，呋喃基，噻吩基并均可被取代，邻苯二甲酰亚氨基，二（1-4）碳烷基马来酰亚氨基，硫代邻苯二甲酰亚氨基，二氢邻苯二甲酰亚氨基，四氢邻苯二甲酰亚氨基，取代的苯基或R4和R5与其连接的碳原子一起形成必要时被取代的2，3-二氢化茚基，环戊烯酰基或环戊烯基，
n＝0，1或2。
R1优选为氢，囟素，1-4碳烷基，2-6碳烯基，3-7碳环烷基，1-5碳烷氧基，2-4碳烯氧基，1-4碳烷硫基，1-4碳囟代烷基，1-3碳囟代烷氧基或2个R1一起形成亚甲二氧基，其中R1特别是位于杂环基的3和4位。
R2和R3优选为1-3碳烷基如甲基，乙基，异丙基和正丙基或与其连接的碳原子一起形成未取代或一或二氟丙环。
R4优选为氢，氟，氰基或1-4碳烷基特别优选为氢。
取代的苯基R5优选为式（A）苯基，
Figure 88102112_IMG13
其中R6互不关联地为H，囟素，1-4碳烷基，1-4碳烷氧基，1-4碳囟代烷基，苯基或N-吡咯基或式（B）的基，
Figure 88102112_IMG14
其中R7互不关联地为H，囟素，1-4碳烷基，1-4碳烷氧基或1-4碳囟代烷基;U＝-CH2-，C＝O，-O-或-S-优选为-O-;V，W＝CH或N，其中V为N时，W必须为CH，反之亦然，
p＝1-5的整数，特别是1，2或在R6＝氟时为5并且R6为式（B）基团时特别为1或2，q＝1或2。
R5的这些基团中特别重要的是式（A）的基团中R6＝H或4-氟，此外还有式（B）的基团并且位于式（A）苯基中的3位上。
必要时取代的吡啶基R5特别是一或二取代式（C）的吡啶基
Figure 88102112_IMG15
其中R8为囟素特别是氟或H，而R9＝氢，囟素（碘除外），1-4碳烷基，1-4碳烷氧基或1-4碳囟代烷基。
必要时取代的噻吩基R5或呋喃基R5特别是式（D）的杂环
Figure 88102112_IMG16
其中Z＝O，S，
R10＝H，囟素，1-4碳烷基，1-4碳烷氧基，1-4碳囟代烷基，CN或NO2，
R11＝必要时取代的苄基，炔丙基，烯丙基或苯氧基，
r＝1或2。
取代的苯基R5对本发明特别重要。
作为R5基典型例子给出以下基团：
五氟苯基，5-苄基-3-呋喃基，4-苯氧基苯基，3-苯氧基苯基，3-（4-氟苯氧基）苯基，3-（4-氯苯氧基）苯基，3-（4-溴苯氧基）苯基，3-（3-氟苯氧基）苯基，3-（3-氯苯氧基）苯基，3-（3-溴苯氧基）苯基，3-（2-氟苯氧基）苯基，3-（2-氯苯氧基）苯基，3-（2-溴苯氧基）苯基，3-（4-甲基苯氧基）苯基，3-（3-甲基苯氧基）苯基，3-（2-甲基苯氧基）苯基，3-（4-甲氧基苯氧基）苯基，3-（3-甲氧基苯氧基）苯基，3-（2-甲氧基苯氧基）苯基，3-（4-乙氧基苯氧基）苯基，3-（苯硫基）苯基，3-（4-氟苯硫基）苯基，3-（3-氟苯硫基）苯基，3-苯甲酰基苯基，3-苄基苯基，3-（4-氟苄基）苯基，3-（4-氯苄基）苯基，3-（3，5-二氯苯氧基）苯基，3-（3，4-二氯苯氧基）苯基，3-（4-氯-2-甲基苯氧基）苯基，3-（2-氧-5-甲基苯氧基）苯基，3-（4-氯-5-甲基苯氧基）苯基，3-（4-乙基苯氧基）苯基，3-（3-氯-5-甲氧基苯氧基）苯基，3-（2，5-二氯苯氧基）苯基，3-（3，5-二氯苯甲酰基）苯基，3-（3，4-二氯苯甲酰基）苯基，3-（4-甲基苄基）苯基，3-（4-异丙氧基苯氧基）苯基，4-氟-3-苯氧基苯基，4-氯-3-苯氧基苯基，4-溴-3-苯氧基苯基，4-氟-3-（4-氟苯氧基）苯基，4-氟-3-（4-氯苯氧基，4-氟-3-（4-溴苯氧基）苯基，4-氟-3-（4-甲基苯氧基）苯基，4-氟-3-（4-甲氧基苯氧基）苯基，4-氟-3-（3-氟苯氧基）苯基，4-氟-3-（3-氯苯氧基）苯基，4-氟-3（3-溴苯氧基）苯基，4-氟-3-（3-甲氧基苯氧基）苯基，4-氟-3-（4-乙氧基苯氧基）苯基，4-氟-3-（2-氟苯氧基）苯基，3-甲氧基-5-苯氧基苯基，2-氟-3-苯氧基苯基，2-氟-3-（4-氟苯氧基）苯基，2-氟-3-（3-氟苯氧基）苯基，2-氟-3-（2-氟苯氧基）苯基，3-氟-5-（4-氟苯氧基）苯基，3-氟-5-（3-氟苯氧基）苯基，3-氟-5-（2-氟苯氧基）苯基，4-甲基-3-苯氧基苯基，3-氟-5-（4-甲基苯氧基）苯基，3-氟-5-（3-甲氧基苯氧基）苯基，2-氟-5-（4-氟苯氧基）苯基，2-氟-5-（3-氟苯氧基）苯基，2-氟-5-（2-氟苯氧基）苯基，2-氯-3-苯氧基苯基，3-氟-5-苯氧基苯基，2-氟-5-苯氧基苯基，2-氯-5-苯氧基苯基，2-溴-5-苯氧基苯基，4-氯-3-（3-甲基苯氧基）苯基，4-氯-3-（4-氟苯氧基）苯基，3-氯-5-苯氧基苯基，3-溴-5-苯氧基苯基，4-溴-3-苯氧基苯基，4-三氟甲基-3-苯氧基苯基，4-氟-3-苯硫基苯基，4-氟-3-苄基苯基，3-（2-吡啶氧基）苯基，3-（3-吡啶氧基）苯基，4-氟-3-（2-吡啶氧基）苯基，4-氯-3-（2-吡啶氧基）苯基，4-溴-3（2-吡啶氧基）苯基，4-甲基-3-（2-吡啶氧基）苯基，4-氟-3-（3-吡啶氧基）苯基，4-氯-3-（3-吡啶氧基）苯基，4-溴-3-（3-吡啶氧基）苯基，4-甲基-3-（3-吡啶氧基）苯基，2-甲基-3-苯基苯基，2-甲基-3-（N-吡咯基）苯基，6-苯氧基-2-吡啶基，6-（4-氟苯氧基）-2-吡啶基，6-（4-氯苯氧基）-2-吡啶基，6-（4-溴苯氧基）-2-吡啶基，6-（4-甲基苯氧基）-2-吡啶基，6-（4-甲氧基苯氧基）-2-吡啶基，6-（4-乙氧基苯氧基）-2-吡啶基、6-（3-氟苯氧基）-2-吡啶基，6-（3-氯苯氧基）-2-吡啶基，6-（3-溴苯氧基-2-吡啶基，6-（3-甲氧基苯氧基）-2-吡啶基，6-（2-氟苯氧基）-2-吡啶基，6-（2-氯苯氧基）-2-吡啶基，6-（2-溴苯氧基）-2-吡啶基，5-炔丙基-3-呋喃基，N-苯邻二甲酰亚胺基，N-3，4，5，6-苯邻二甲酰亚胺基，2-甲基-5-炔丙基-3-呋喃基，4-叔丁基苯基，4-甲基苯基，4-异丙苯基，4-（2-氯-4-三氟甲基-2-吡啶氧基）苯基，4-环己基苯基，4-二氟甲氧苯基，4-联苯基及4-三甲基甲硅烷基苯基以及4-苯氧基-2-噻吩基。
作为
Figure 88102112_IMG17
基的其它典型例子是：
2-烯丙基-3-甲基环戊-2-烯-1-酮-4-基，4-苯基-1，2-二氢化茚-2-基。
本发明还提出了通式（Ⅰ）化合物的制法，其特征是，
a）对于X＝O的化合物，将式（Ⅱ）或（Ⅲ）的化合物必要时在碱存在下与式（Ⅳ）的烷基化剂反应而成：
Figure 88102112_IMG18
式中Y为离核基团如囟素或磺酸根，M相当于当量碱金属或碱土金属特别是Li，Na，K，Mg，
或者
b）对于X＝O的化合物，在碱存在下将式（Ⅴ）的化合物与式（Ⅵ）的XH酸化合物或与式（Ⅶ）的金属有机化合物反应而成：
Figure 88102112_IMG19
其中R4′＝H或1-4碳烷基，
或者
c）对于X＝CH2的化合物，将式（Ⅷ）化合物与式（Ⅸ）化合物反应而成：
Figure 88102112_IMG20
其中X′＝CH，
或者
d）将式（Ⅹ）的化合物与式（Ⅺ）的金属有机试剂反应而成：
Figure 88102112_IMG21
或者
e）对于R4＝H和X＝CH2的化合物，将式（Ⅻ）的醛与式（ⅩⅢ）的酮缩合成式（ⅩⅣ）的中间产物，并遂后按常规方式进行还原而成：
Figure 88102112_IMG22
或者
f）对于X＝CH2的化合物，将式（ⅩⅤ）的醛与式（ⅩⅥ）的内盐或式（ⅩⅦ）的膦酸酯缩合成式（ⅩⅧ）的中间产物，并遂后与还原剂反应得X＝CH2的终产品（Ⅰ）
作为起始化合物用于方法a）的物质（Ⅱ）和（Ⅲ）可用杂环（ⅩⅨ）经多步合成制得：
Figure 88102112_IMG24
其中先逐步用强碱如氢化钠和烷基化剂如烷基碘或二烷基硫酸酯引入R2和R3两个基团，从而得到中间产物（ⅩⅩ），之后先皂化成相应的羧酸，然后用强还原剂如Li Al H4还原成所需醇（Ⅱ）
Figure 88102112_IMG25
作为起始化合物用于方法b）的杂环（Ⅴ）可按普通方法囟化醇（Ⅱ）（Ⅹ＝O）而制得：
Figure 88102112_IMG26
作为起始化合物用于方法e）所需的通式（Ⅻ）的醛可用氧化剂吡啶x    SO按简单方法氧化相应醇（Ⅱ）（X＝O）而制得（后续制备过程如上述）。
Figure 88102112_IMG27
作为起始化合物用于方法f）所需的通式（ⅩⅤ）的醛可用例如N，N-二甲基甲酰胺使从相应囟化剂（Ⅴ）得到的金属化合物（Ⅷ）羰基化而制得
Figure 88102112_IMG28
上面谈到的初产物和中间产物可按常规的普通方法制得，因此各方法中提到的所有金属有机产物均可通过常规金属化反应如氢/金属交换或优选为囟素/金属交换而制得。
已讲到的合成方案c）和d）最好均在稀释剂中进行，稀释剂的性能取决于所用的金属有机物的种类。作为稀释剂尤以脂肪烃和芳烃为宜，诸如戊烷，己烷，庚烷，环己烷，石油醚，汽油，石油英，苯，甲苯及二甲苯，醚类如二乙醇，二丁醚，乙二醇二甲醚，二甘醇二甲醚，四氢呋喃，二恶烷，并包括由前述溶剂组成的各种可能的混合物。
在上述合成方案中，反应温度在-75℃和+150℃之间，尤其是在-75℃和+105℃之间为宜。起始原料通常当量加入，但也可能有一种组分或其它组分过量。
对于上述其它合成方案a），b），e）和f）来说，基本上同方案c）和d）。但在采用类型（Ⅱ）及（Ⅵ）离析物以及类型（Ⅻ）和（ⅩⅢ）的羰基化合物时，还允许采用其它稀释剂。在这种情况下适于采用下列稀释剂，酮类如丙酮，甲乙酮，甲基异丙基酮及甲基异丁基酮，酯类如乙酸甲酯及乙酸乙酯，腈类如乙腈及丙腈，酰胺类如二甲基甲酰胺，二甲基乙酰胺，以及N-甲基吡咯烷酮，二甲基亚砜，四亚甲基砜（环丁砜）和六甲基磷酸三酰胺。作为碱可用无机碱，诸如碱金属或碱土金属的氢氧化物，氢化物，碳酸盐或碳酸氢盐，但也可用有机碱，诸如吡啶，三乙胺，N，N-二异丙基乙胺或者二氮二环辛烷。
通式（Ⅰ）所示化合物的分离及必需时的精制可按通用方法进行。例如采用溶剂蒸发法（必要时在减压下进行）及随后的连续蒸馏法或色谱柱提纯法，或采用两相间粗产品分配以及随后的普通加工方法。
通式（1）化合物均能很好的溶解在绝大多数有机溶剂中。
这类生物活性化合物具有良好的植物相容性以及优良的热血动物致毒性，适于防治动物侵害，特别适于防治在农业，森林，仓库及物料保存以及公共卫生领域中常出现的昆虫、蛛形纲动物和线虫。这类化合物对一般具有知觉性及具有抵抗力的生物种以及在全部或个别发育阶段的生物种均有防治效果。上述各类害虫包括：
属于等足目，例如潮虫（球鼠妇），鼠妇（Armadillidium    Vulgare），Porcellio    scaber。
属于倍员目：例如Blaniulus    guttulatus。
属于唇足亚纲，例如地蜈蚣（Geophilus    carpophagus），蚰蜒（Scutigera    spec.）
属于综合纲，例如庭园么蚰。
属于缨尾目，例如西洋衣鱼。
属于弹尾目，例如刺跳虫（Onychiurus    armatus）。
属于直翅目，例如东方蠊，美洲大蠊，马德拉
Figure 88102112_IMG29
蠊，德国蠊（茶婆虫），家蟋，蝼蛄属，非洲飞蝗，异黑蝗，沙漠蝗。
属于革翅目，例如欧洲球螋。
属于等翅目，例如散白蚁属。
属于虱目，例如葡萄根瘤蚜，瘿绵蚜属，体虱，盲虱属，长鄂虱属。
属于食毛目，例如羽虱属，畜虱属。
属于缨翅目，例如温室条篱蓟马，烟蓟马。
属于异翅亚目，例如扁盾蝽属，红蝽（Dysdercus    intermedius），方背皮蝽，温带臭虫，长江猪蝽，猪蝽属。
属于同翅目，例如甘兰粉虱，木薯粉虱，温室粉虱，棉蚜，甘蓝蚜，茶藨隐瘤蚜，敌伏蚜，敌普蚜，苹果绵蚜，梅大尾蚜，麦长管蚜，瘤额蚜属，忽布疣蚜，缢管属，小叶蝉，诱贝蚜，艾辛蚜，水木竖蚧，乌盔蚧，灰飞虱，褐飞虱，红肾圆盾蚧，常春藤圆盾蚧，粉蚧属，木虱属。
属于鳞翅目，例如：红玲麦蛾，松尺蠖，Cheimatobia    brumata蛾，苹细蛾，苹果巢蛾，菜蛾，黄褐天幕毛虫，黄毒蛾，毒蛾，棉潜蛾，桔潜蛾，夜蛾属，切根虫属，地虎属，埃及金刚钻，夜蛾属，甜菜夜蛾，甘蓝夜蛾，松夜蛾，斜纹夜蛾，夜蛾属，粉纹夜蛾，苹果小卷蛾，菜粉蝶属，螟类，玉米螟，地中海粉斑螟，六蜡螟，亚麻黄卷蛾，烟卷蛾，枞色卷蛾，葡萄果蠹蛾，茶长卷蛾，栎绿卷蛾。
属于鞘翅目，例如：家具窃蠹，谷蠹，菜锥胸豆象，菜豆象，北美家天牛，杨树萤叶甲，马玲薯叶甲，辣根猿叶，叶甲属，油菜金头跳甲，大豆瓢虫，锯谷盗，花象属，谷象属，黑葡萄耳象，香蕉根颈象，白菜籽龟象，紫苜蓿叶象，皮蠹属，斑皮蠹属，圆皮蠹属，毛皮蠹属，粉蠹属，菜花露尾甲，蛛甲属，黄蛛甲，裸蛛甲，拟谷盗属，黄粉虫，叩头虫属，宽胸叩头虫属，西方五月鳃鱼角金龟，马玲薯鳃角金龟，褐新西兰助翅鳃角金龟。
属于膜翅目，例如：据角叶蜂属，叶蜂属，地蚁属，法老蚁，胡蜂属。
属于双翅目，例如，伊蚊属，按蚊属，库蚊属，黑尾果蝇，象蝇属，厕蝇属，红头丽蝇，绿蝇属，金蝇属，疽蝇科，胃蝇属，赭虱属，厩螯蝇属，狂蝇属，皮蝇属，虻属，螗蜩属，毛蚊属，瑞典麦杆蝇，草种蝇属，甜菜泉蝇，地中海蜡实蝇，橄榄大实蝇，欧洲大蚊。
属于蚤目，例如：印鼠客蚤，角叶蚤属。
属于科，例如.蝎蛉，黑寡妇球腹蛛。
属于蜱螨目，例如：粗脚粉螨，锐绿蜱属，钝缘蜱属，鸡皮刺螨，茶藨瘿螨，桔芸锈螨，牛蜱属，扁头蜱科，花蜱属，卉乐蜱属，硬蜱属，痒螨属，皮痒螨属，疥螨属，线螨属，苜蓿苔螨，全爪螨属，叶螨属。
此外，本发明提出的化合物对损害植物的线虫具有优异的抵抗作用，如防治根结线虫属，狭佈叩头虫，茎线虫，叶线虫，内侵线虫，球线虫，草地垫刃线虫属，长囊线虫，剑尾线虫。
本发明也提出一种制剂，它除含有适宜的配方助剂外还含有通式（Ⅰ）化合物。
根据本发明提出的制剂一般含有1～95%（重量）的通式（Ⅰ）生物活性物质。一般可将它们配制成可湿性粉剂，乳油，喷撒溶液，粉剂或颗粒剂加以利用。
可湿性粉剂可制成均匀分散在水中的制剂，这种制剂除含有生物活性物质及稀释剂，或惰性物质，还含有润湿剂，例如含有聚氧乙基化烷基酚，聚氧乙基化脂肪醇，烷基磺酸盐或烷基苯酚磺酸盐以及分散剂，例如木质素磺酸钠，2，2′-二萘基甲烷-6，6′-二磺酸钠，二丁基萘磺酸钠或者油酰基甲基牛磺酸钠。
乳油可在加入一种或多种乳化剂下将生物活性物质溶解在有机溶剂中制成，例如溶解在丁醇，环己酮，二甲基甲酰胺，二甲苯中，也可溶解在高沸点芳烃或烃类中。作为乳化剂可采用：烷基芳基磺酸钙盐，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，脱水山梨（糖）醇脂肪酸酯，聚氧乙烯脱水山梨（糖）醇脂肪酸酯或聚氧乙烯山梨酸酯。
粉剂可通过生物活性物质与细分散固体材料，例如与滑石，天然粘土，如高岭土，膨润土，斑岩或硅藻土共同研磨而制得。颗粒剂可将生物活性物质喷涂在吸附性的颗粒状惰性材料上而制得，或者借助粘合剂，例如聚乙烯醇、聚丙烯酸钠，也可借助矿物油将生物活性物质浓缩物敷在载体材料如砂，高岭土的表面上，或者敷在颗粒状惰性材料的表面上而制得。也可采用生产肥料颗粒用的普通方式，根据需要将适当的生物活性物质与肥料混合而制得。
基于本发明的生物活性物质可采用一般市售品制剂形式以及采用将这些配方与其它生物活性物质互相混合并进一步加工成的其它应用形式，例如与杀虫剂，诱饵，杀菌剂，杀螨剂，杀线虫剂，防霉剂，生长调节剂或除草剂互相混合。例如，所用杀虫剂特别是磷酸酯，氨基甲酸酯，碳酸酯，甲脒，锡化合物，由微生物制得的物料，昆虫生长调节剂。优选的混合组分包括：
1.选自磷酸酯类
乙基谷硫磷（益棉磷，乙基保棉磷），甲基保棉磷，1-（4-氯苯基）-4-（O-乙基，S-丙基）磷酰氧吡唑（T    IA-230），氯蜱硫磷（毒死蜱），蝇毒磷，内吸磷（一0五九），S-甲基内吸磷，二嗪农，乙嘧硫磷，杀螟松，倍硫磷，甲基对硫磷，伏杀硫磷，乙基虫螨磷，甲基虫螨磷，朴吩磷（Profenfos），低毒硫磷，硫普磷（Sulprofos），三唑磷，敌百虫;
2.选自氨基甲酸酯类
涕灭威，噁虫威，BPMC（2-（-甲基丙基）苯基甲基氨基甲酸酯），甲硫基丁酮甲氨基羰基肟（Butocarboxim），丁酮肟威，西维因，虫螨威，硫泛威（Carbosulfan），氯乙威（Cloethocarb），异丙威，甲肟威，草肟威，普米威（Primicarb），甲丙威，普洛赛（Propoxur），硫双威（Thiodicarb）;
3.选自羧酸酯类
丙烯菊酯，α型甲除虫菊（Alphamethrin），右旋反丙烯菊酯，右旋反苄呋菊酯，环丙除虫菊（Cycloprothrin），环氟除虫菊（Cyfluthrin），环囟除虫菊（Cyhalothrin），腈二氯苯醚菊酯，δ型甲除虫菊（Deltamethrin），2，2-二甲基-3-（2-氯-2-三氟甲基乙烯基）环丙酸（α-氰基-3-苯基-2-甲基苄基）酯（FMC54800），伐丙除虫菊（Fenpropathrin），伐氟除虫菊（Fenfluthrin），腈氯苯苯醚菊酯，氟氰除虫菊酯（Flucythrinate），氟甲除虫菊（Flumethrin），氟缬氨酸酯（Fluvalinate），全甲除虫菊，苄呋喃酯，Tralo型甲除虫菊（Tralomethrin）;
4.选自甲脒类
氨山氮螨，杀虫脒基;
5.选自铝化合物类偶氮环锡（Azocyclotin），三环锡，螨完锡;
6.选自生长调节剂类
Fenoxycarb，Flufenoxuron，Buprofezin，Cyromazine，Flubenzimin，Diflubenzuron，Triflumuron，N-（（（3，5-二氯-4-（1，1，2，2-四氟乙氧基）苯基）氨基羰基）-2，6-二氟苯甲酰胺（XRD    473），Tetraflubenzuron，Chlorfluazuron，Flucyclooxuron，Hydroprene，Methoprene，N-（2-氟苯甲酰基）-N′-（4-（2-氯-4-三氟甲基-1-苯基巯基）苯基）尿素，N-（2-氯苯甲酰基）-N′-（4-（2-氯-4-三氟甲基-1-苯基巯基）苯基）尿素，N-（2，6-二氟苯甲酰基）-N′-（4-（2-氯-4-三氟甲基-1-苯基巯基）苯基）尿素，N-（N-（2-氯-4-三氟甲基-1-苯基巯基）苯基）氨基甲酰基）-2-氟苯并碳化酰亚氨基酸乙酯，N-（N-（2-氯-4-三氟甲基-1-苯基巯基）苯基）氨基甲酰基）-2-氯苯并碳化酰亚氨基酸乙酯，N-（N-（2-氯-4-三氟甲基-1-苯基巯基）苯基）氨基甲酰基）-2，6-二氟苯并碳化酰亚氨基酸乙酯。
7.其它类
α-和β-阿威麦克汀（α-和β-Acemectine），苏云金杆菌，苄硫丹，乐杀螨，双氯芬芹（Bisclofentezin），布洛非辛（Buprofecin），巴丹，曲洛麦芹（Cyromecin），开乐散，硫丹，乙氧丙氧芬，伐氧威（Fenoxycarb），六噻斯（Hexythiazox），3-〔2-（4-乙氧苯基）-2-甲基-丙氧甲基〕-1，3-二苯醚（MTI-500），5-〔4-（4-乙氧苯基）-4-甲苯基〕-2-氟-1，3-二苯醚（MTI-800），3-（2-氯苯基）-3-羟基-2-（2-苯基-4-噻唑基）丙烯腈（SN    72129），硫环拉姆（Thiocyclam），开朴敌（Kernpolyederen）及克拉灵（Granuloseviren）。
在一般市售品制剂基础上加工过的应用形式中，生物活性物质的含量可在宽范围内变化。在这种应用形式中生物活性物质浓度可达0.0000001至100%（重量），最好在0.00001和1%（重量）之间。
施用要采用与使用形式相适应的方式。
本发明提出的生物活性物质也适宜于防治外寄生虫和内寄生虫，特别适用于防治兽医领域及家畜领域的外寄生害虫。
使用本发明提出的生物活性物质时可采用通常的使用方式，例如采用片剂、胶囊，饮料及粒剂等口服形式，也可采用经皮肤使用的方式，例如浸泡（浸渍），喷射（喷洒），灌浇（灌淋），撒粉。
A.配方实例
a）粉剂由10份（重量）生物活性物质和90份（重量）滑石作为惰性材料进行混合而制得，并经锤磨机粉碎。
b）易在水中分散的可湿性粉剂由25份（重量）生物活性物质，65份（重量）含高岭土的石英作为惰性材料，10份（重量）木质素磺酸钾及1份（重量）油酰甲牛磺酸钠作为润湿剂和分散剂进行混合而制得，并经棒磨机研磨。
c）易分散于水中的分散体浓缩物由20份（重量）生物活性物质与6份（重量）烷基苯酚聚乙二醇醚（Triton    X    207），3份（重量）异十三烷醇聚乙二醇醚（8Aeo）及71份（重量）烷（属）烃矿物油（例如，沸程约从225至377℃以上）进行混合而制得，并经球磨机研磨至粒度低于5微米。
d）乳油由15份（重量）生物活性物质，75份（重量）环己酮作为溶剂以及10份（重量）氧乙基化壬基苯酚（10Aeo）作为乳化剂而制得。
e）颗粒剂由2至15份（重量）生物活性物质及惰性粒状载体材料，如绿坡缕石，浮石粒料及/或石英砂而制得。
B.化学实施例
实施例1
2-甲基-2-（6-氯-3-吡啶基）-丙基-（3-丙氧苄基）醚（表1中化合物18）
1.1）6-氯吡啶-3-甲醇
室温下将69.5g（0.5mol）6-羟基烟酸加入200g（1mol）五氯化磷和233g（1.5mol）三氯氧化磷中，于95℃搅拌5h并在此之后真空分出过量磷酰氯。将晶体残余物加入75g（1.98mol）硼氢化钠的1000ml水溶液，其中将温度保持在最高30℃下。再于室温下搅拌直至发泡结束，吸滤出固体并用乙醚萃取滤液。有机相分出溶剂后得44.5g（理论值的62%）油状粗产物。0.4毫巴（Kp110-115℃）下蒸馏得到36.6g（理论值的51%）产物。
1.2）2-氯-5-氯甲基吡啶
小心地于14.4g（0.1mol）6-氯吡啶-3-甲醇中加入85ml亚硫酰（二）氯。之后滴入8.1g（0.1mol）吡啶并回流加热，直至发泡结束。真空除去过量亚硫酰（二）氯并将残余物倒入冰中。吸滤出沉淀物并干燥，收率10.6g（理论值的65.5%），Fp.38-40℃。该粗产物无需再提纯即可进一步使用。
1.3）6-氯吡啶-3-乙腈
将25.6g（0.522mol）氰化钠溶于123g二甲亚砜，加热到90℃并逐渐引入68.9g（0.43mol）2-氯-5-氯甲基吡啶，其间将温度升至90℃。冷却到室温后倒入水中并用乙醚萃取。分出溶剂并于1.0毫巴（130-150℃）下蒸馏粗产物。Fp：80℃，收率41.1g（理论值的63%）。
1.4）2-（6-氯-3-吡啶基）-2-甲基丙腈
将24g（0.8mol）80%氢化钠（于轻油中）悬浮在640ml四氢呋喃中并滴入56g（0.37mol）6-氯吡啶-3-丙腈的160ml四氢呋喃溶液。待发泡完毕再于0-20℃滴入105.3g（0.74mol）甲基碘的160ml四氢呋喃溶液。室温下再搅拌3小时后倒入860ml水中。用乙醚萃取出粗产物并分出溶剂后于0.3毫巴（Kp110-120℃）下蒸馏。得到49.1g（理论值的73.5%）黄色油状产物并静置结晶。Fp63-65℃。
1.5）2-（6-氯-3-吡啶基）-2-甲基丙醇
将3.6g（20mmol）2-（6-氯-3-吡啶基）-2-甲基丙腈溶于50ml甲苯中并于无冷却条件下滴入25ml氢化二异丁基铝溶液（甲苯中1M），其中内部温度升至45℃。室温下搅拌2小时后小心地依次加入10ml甲醇，50ml水和90ml    2N硫酸，并再于室温下搅拌2小时后于50℃搅拌2小时。分出甲苯相后再从中分出溶剂。残余物溶于10ml甲醇中并将其与0.1g钠和0.4g（10.6mmol）硼氢化钠的10ml甲醇溶液掺混起来。室温下搅拌1小时，用0.7g乙酸酸化并分出溶剂。残余物在乙酸乙酯中熬煮，分出酯相后再从中真空分出溶剂。油状粗产物于0.15毫巴且装置温度170℃的球形管中蒸馏。收率2.5g（理论值的67%），产品呈无色油状。
1.6）2-（6-氯-3-吡啶基）-2-甲基丙基-（3-苯氧苄基）醚
将1.9g（10.2mmol）2-（6-氯-3-吡啶基）-2-甲基丙醇溶于15ml甲苯中，加入2.7g（10.3mmol）3-苯氧苄基溴之后再与0.6g（1.8mmol）四正丁基硫酸氢铵的5g50%苛性钠溶液混合。70-80℃搅拌2小时后再拌入2ml甲醇和2ml浓氨水混合物并在此后将水和甲苯完全分开。有机相用氯化铵溶液洗涤，分出溶剂后的粗产物用硅胶柱提纯。得2.4g（理论值的62.9%）浅黄色油状物。然后于0.03毫巴且装置温度230-240℃的球形管中进行蒸馏。
实施例2
1-（6-氯-3-吡啶基）环丙基）-甲基-（3-苯氧苄基）醚（表2中化合物513）
2.1）1-（6-氯-3-吡啶基）环丙烷-1-腈（相当于实施例1中的1.4化合物）
将6.5g（0.217mol）80%的轻油中氢化钠悬浮于170ml四氢呋喃中，并滴入15.3g（0.1mol）6-氯吡啶-3-腈的60ml四氢呋喃溶液。搅拌至发泡结束，冷却后于5-20℃滴入14.3g（0.1mol）1-溴-2-氯-乙烷的15ml四氢呋喃溶液。室温搅拌2小时后倒入浓食盐水中并用乙醚萃取。从溶剂中分出的粗产物用乙酸乙酯提取后通过200g硅胶中过滤。得到14.3g棕色半晶体物质并进行球形管蒸馏提纯。于130-140℃装置温度和0.08毫巴下蒸馏得5.8g（理论值的32.5%）冷凝油状物。
该物质再按实施例1中所述方法1.5）和1.6）处理而得化合物513（表2）。
实施例3
（2-（6-乙氧基-3-哒嗪基）-2-甲基丙基）-（3-苯氧苄基）醚（表1中化合物343）
3.1）2-（6-羟基-3-哒嗪基）丙腈
将60.4g（2.02mol）80%轻油中氢化钠悬浮于21四氢呋喃并于20-30℃逐滴与311.8g（2.02mol）2-氰丙酸叔丁酯掺混。于45分钟内将该透明液滴入298g（2.0mol）3，6-二氯哒嗪并一起回流加热2小时。然后加入317ml乙酸并真空分出溶剂。残余物用6400ml乙酸，250ml乙酸酐和32g对甲苯磺酸一水合物的混合物提取，回流加热3小时后进行真空干燥。悬浮在少量水中，用苛性钠溶液调至pH5并蒸出水。残余物用乙酸乙酯热萃取。得到99.7g（理论值的33%）粗产物，该产物无需进一步处理即可用于以下反应。
3.2）2-（6-氯-3-哒嗪基）丙腈
将1.5g（10mmol）2-（6-羟基-3-哒嗪基）丙腈与5g三氯氧化磷混合并于80-90℃搅拌45分钟。倒入30g冰中，用2N    NaOH调至pH6并用乙醚萃取。分出溶剂后余下油状物，静置后凝固下来。收率1g（理论值的59.7%）;Fp：己烷中65℃。
3.3）2-（6-氯-3-哒嗪基）-2-甲基丙腈
将3.9g（0.131mol）80%轻油中氢化钠悬浮于380ml四氢呋喃中并于15-20℃与18.9g（0.113mol）2-（6-氯-3-哒嗪基）丙腈的80ml四氢呋喃溶液掺混。待发泡完毕再滴入16.3g（0.115mol）甲基碘的50ml四氢呋喃溶液并于室温下搅拌1小时。倒入1.41浓食盐水溶液并用乙醚萃取。分出溶剂后余下的粗产物于球形管中蒸馏提纯，其中装置温度180-190℃，压力0.1毫巴。收率8.4g（理论值的41%），为油状物，静置后凝固下来，Fp.：107-111℃。
这种腈再按实施例1中所述方法1.5）处理而得2-（6-氯-3-哒嗪基）-2-甲基丙醇。
3.4）2-（6-乙氧基-3-哒嗪基）-2-甲基丙醇
将1.6g（0.053mol）80%轻油中氢化钠悬浮于50ml二甲亚砜中并于15-20℃滴入2.5g（0.055mol）乙醇。待发泡完毕后再引入1.0g（0.005mol）2-（6-氯-3-哒嗪基）-2-甲基丙醇的20ml二甲亚砜溶液并于1.5小时内加热到90-100℃。冷却后倒入浓食盐水溶液中并用乙醚萃取。分出溶剂后余下黄色油状粗产物。收率0.6g（理论值的61%）。
该粗产物可直接按实施例1中所述方法1.6处理而得表1中化合物343。
以下表1和2的续表中各代号意思为：
Fortsetzung    Tabelle：续表
Verbdg.Nr.：化合物号
physik    Daten：物理数据
blassgelbes    Oel：浅黄色油状
Figure 88102112_IMG30
以类似于上述实施例的方法可制得X＝O的下列式（Ⅰ）化合物（表1和2）。X＝CH的化合物优选按方法e）和f）制备。
Figure 88102112_IMG31
表1 R2，R3＝CH3，A＝N，CH或C-R1
化合物号 A R1B C′ D X R4R5物理数据
1 N EtO CH CH CH CH2H Kp0.01＝225-230℃
2 N EtO CH CH CH CH2H Kp0.05＝240-245℃
3 N EtO CH CH CH CH2H
4 N EtO CH CH CH CH2H
5 N EtO CH CH CH CH2H Kp0.02＝230-240℃
6 N EtO CH CH CH CH2CN
Figure 88102112_IMG32
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
7 N EtO CH CH CH CH2CN
8    N    EtO    CH    CH    CH    O    H
9    N    EtO    CH    CH    CH    O    H
10    N    EtO    CH    CH    CH    O    H
11    N    EtO    CH    CH    CH    O    CN
12 N Cl CH CH CH CH2H
13 N Cl CH CH CH CH2H
14 N Cl CH CH CH CH2H
15 N Cl CH CH CH CH2H
Figure 88102112_IMG33
30
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
16 N Cl CH CH CH CH2CN
17 N Cl CH CH CH CH2CN
18 N Cl CH CH CH O H Kp0.03＝230-240℃
19 N Cl CH CH CH O H Kp0.01＝225-230℃
20    N    Cl    CH    CH    CH    O    H
21    N    Cl    CH    CH    CH    O    CN
22 N Cl CH CH CH O CH3
23 N H3CO CH CH CH CH2H
24 N H3CO CH CH CH CH2H
25 N H3CO CH CH CH CH2H
31
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
26 N H3CO CH CH CH CH2H
27 N H3CO CH CH CH CH2CN
28 N H3CO CH CH CH CH2CN
29 N H3CO CH CH CH O H
30 N H3CO CH CH CH O H Kp0.07＝220-240℃
31 N H3CO CH CH CH O H
32 N H3CO CH CH CH O CN
33 N H3CO CH CH CH O CH3
34 N EtS CH CH CH CH2H
35 N EtS CH CH CH CH2H
32
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
36 N EtS CH CH CH CH2H
37 N EtS CH CH CH CH2H
38 N EtS CH CH CH CH2CN
39 N EtS CH CH CH CH2CN
40    N    EtS    CH    CH    CH    O    H
41 N EtS CH CH CH O H Kp0.01＝220-230℃
42    N    EtS    CH    CH    CH    O    H
43    N    EtS    CH    CH    CH    O    CN
44 N EtS CH CH CH O CH3
45 N H3CS CH CH CH CH2H
Figure 88102112_IMG36
33
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
46 N H3CS CH CH CH CH2H
47 N H3CS CH CH CH CH2H
48 N H3CS CH CH CH CH2H
49 N H3CS CH CH CH CH2CN
50 N H3CS CH CH CH CH2CN
51 N H3CS CH CH CH O H
52 N H3CS CH CH CH O H
53 N H3CS CH CH CH O H
54 N H3CS CH CH CH O CN
55 N H3CS CH CH CH O CH3
34
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
56 CCl Cl CH N CH CH2H
57 CCl Cl CH N CH CH2H
58 CCl Cl CH N CH CH2H
59 CCl Cl CH N CH CH2H
60 CCl Cl CH N CH CH2CN
61 CCl Cl CH N CH CH2CN
62    CCl    Cl    CH    N    CH    O    H
63    CCl    Cl    CH    N    CH    O    H
64    CCl    Cl    CH    N    CH    O    H
65    CCl    Cl    CH    N    CH    O    CN
Figure 88102112_IMG38
35
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
66 CCl Cl CH N CH O CH3
67 CCl EtO CH N CH CH2H
68 CCl EtO CH N CH CH2H
69 CCl EtO CH N CH CH2H
70 CCl EtO CH N CH CH2H
71 CCl EtO CH N CH CH2CN
72 CCl EtO CH N CH CH2CN
73    CCl    EtO    CH    N    CH    O    H
74    CCl    EtO    CH    N    CH    O    H
75    CCl    EtO    CH    N    CH    O    H
Figure 88102112_IMG39
36
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
76    CCl    EtO    CH    N    CH    O    CN
77 CCl EtO CH N CH O CH3
78 CF EtO CH N CH CH2H
79 CF EtO CH N CH CH2H
80 CF EtO CH N CH CH2H
81 CF EtO CH N CH CH2H
82 CF EtO CH N CH CH2CN
83 CF EtO CH N CH CH2CN
84    CF    EtO    CH    N    CH    O    H
85    CF    EtO    CH    N    CH    O    H
Figure 88102112_IMG40
37
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
86    CF    EtO    CH    N    CH    O    H
87    CF    EtO    CH    N    CH    O    CN
88 CF EtO CH N CH O CH3
89 C-O-CH2-O CH N CH CH2H
90 C-O-CH2-O CH N CH CH2H
91 C-O-CH2-O CH N CH CH2H
92 C-O-CH2-O CH N CH CH2H
93 C-O-CH2-O CH N CH CH2CN
94 C-O-CH2-O CH N CH CH2CN
95 C-O-CH2-O CH N CH O H
Figure 88102112_IMG41
38
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
96 C-O-CH2-O CH N CH O H
97 C-O-CH2-O CH N CH O H
98 C-O-CH2-O CH N CH O CN
99 C-O-CH2-O CH N CH O CH3
100 CH EtO N CH CH CH2H Kp0.04＝230-245℃
101 CH EtO N CH CH CH2H
102 CH EtO N CH CH CH2H
103 CH EtO N CH CH CH2H
104 CH EtO N CH CH CH2CN
105 CH EtO N CH CH CH2CN
Figure 88102112_IMG42
39
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
106    CH    EtO    N    CH    CH    O    H
107    CH    EtO    N    CH    CH    O    H
108    CH    EtO    N    CH    CH    O    H
109    CH    EtO    N    CH    CH    O    CN
110 CH EtO N CH CH O CH3
111 CH Cl N CH CH CH2H
112 CH Cl N CH CH CH2H
113 CH Cl N CH CH CH2H
114 CH Cl N CH CH CH2H
115 CH Cl N CH CH CH2CN
40
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
116 CH Cl N CH CH CH2CN
117    CH    Cl    N    CH    CH    O    H
118    CH    Cl    N    CH    CH    O    H
119    CH    Cl    N    CH    CH    O    H
120    CH    Cl    N    CH    CH    O    CN
121 CH Cl N CH CH O CH3
122 CH H3CO N CH CH CH2H
123 CH H3CO N CH CH CH2 H
124 CH H3CO N CH CH CH2H
125 CH H3CO N CH CH CH2H
Figure 88102112_IMG44
41
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
126 CH H3CO N CH CH CH2CN
127 CH H3CO N CH CH CH2CN
128 CH H3CO N CH CH O H
129 CH H3CO N CH CH O H
130 CH H3CO N CH CH O H
131 CH H3CO N CH CH O CN
132 CH H3CO N CH CH O CH3
133 CH EtS N CH CH CH2H
134 CH EtS N CH CH CH2H
135 CH EtS N CH CH CH2H
Figure 88102112_IMG45
42
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
136 CH EtS N CH CH CH2H
137 CH EtS N CH CH CH2CN
138 CH EtS N CH CH CH2CN
139    CH    EtS    N    CH    CH    O    H
140    CH    EtS    N    CH    CH    O    H
141    CH    EtS    N    CH    CH    O    H
142    CH    EtS    N    CH    CH    O    CN
143 CH EtS N CH CH O CH3
144 CH F2CHO N CH CH CH2H
145 CH F2CHO N CH CH CH2H
Figure 88102112_IMG46
43
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
146 CH F2CHO N CH CH CH2H
147 CH F2CHO N CH CH CH2H
148 CH F2CHO N CH CH CH2CN
149 CH F2CHO N CH CH CH2CN
150 CH F2CHO N CH CH O H
151 CH F2CHO N CH CH O H
152 CH F2CHO N CH CH O H
153 CH F2CHO N CH CH O CN
154 CH F2CHO N CH CH O CH3
155 CCl CL N CH CH CH2H
Figure 88102112_IMG47
44
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
156 CCl Cl N CH CH CH2H
157 CCl Cl N CH CH CH2H
158 CCl Cl N CH CH CH2H
159 CCl Cl N CH CH CH2CN
160 CCl Cl N CH CH CH2CN
161    CCl    Cl    N    CH    CH    O    H
162    CCl    Cl    N    CH    CH    O    H
163    CCl    Cl    N    CH    CH    O    H
164    CCl    Cl    N    CH    CH    O    CN
165 CCl Cl N CH CH O CH3
Figure 88102112_IMG48
45
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
166 CCl EtO N CH CH CH2H
167 CCl EtO N CH CH CH2H
168 CCl EtO N CH CH CH2H
169 CCl EtO N CH CH CH2H
170 CCl EtO N CH CH CH2CN
171 CCl EtO N CH CH CH2CN
172    CCl    EtO    N    CH    CH    O    H
173    CCl    EtO    N    CH    CH    O    H
174    CCl    EtO    N    CH    CH    O    H
175    CCl    EtO    N    CH    CH    O    CN
Figure 88102112_IMG49
46
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
176 CCl EtO N CH CH O CH3
177 C-O-CH2-O N CH CH CH2H
178 C-O-CH2-O N CH CH CH2H
179 C-O-CH2-O N CH CH CH2H
180 C-O-CH2-O N CH CH CH2H
181 C-O-CH2-O N CH CH CH2CN
182 C-O-CH2-O N CH CH CH2CN
183 C-O-CH2-O N CH CH O H
184 C-O-CH2-O N CH CH O H
185 C-O-CH2-O N CH CH O H
Figure 88102112_IMG50
47
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
186 C-O-CH2-O N CH CH O CN
187 C-O-CH2-O N CH CH O CH3
188 C-O-CH2-O CH CH N CH2H
189 C-O-CH2-O CH CH N CH2H
190 C-O-CH2-O CH CH N CH2H
191 C-O-CH2-O CH CH N CH2H
192 C-O-CH2-O CH CH N CH2CN
193 C-O-CH2-O CH CH N CH2CN
194 C-O-CH2-O CH CH N O H
195 C-O-CH2-O CH CH N O H
48
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
196 C-O-CH2-O CH CH N O H
197 C-O-CH2-O CH CH N O CN
198 C-O-CH2-O CH CH N O CH3
199 N EtO CH N CH CH2H Kp0.005＝230-245℃
200 N EtO CH N CH CH2H Kp0.01＝230-240℃
201 N EtO CH N CH CH2H
202 N EtO CH N CH CH2H
203 N EtO CH N CH CH2CN
204 N EtO CH N CH CH2CN
205 N EtO CH N CH O H Kp0.05＝230-240℃
49
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
206    N    EtO    CH    N    CH    O    H
207    N    EtO    CH    N    CH    O    H
208    N    EtO    CH    N    CH    O    CN
209 N EtO CH N CH O CH3
210 N Cl CH N CH CH2H
211 N Cl CH N CH CH2H
212 N Cl CH N CH CH2H
213 N Cl CH N CH CH2H
214 N Cl CH N CH CH2CN
215 N Cl CH N CH CH2CN
50
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
216    N    Cl    CH    N    CH    O    H
217    N    Cl    CH    N    CH    O    H
218    N    Cl    CH    N    CH    O    H
219    N    Cl    CH    N    CH    O    CN
220 N Cl CH N CH O CH3
221 N H3CO CH N CH CH2H
222 N H3CO CH N CH CH3H
223 N H3CO CH N CH CH2H
224 N H3CO CH N CH CH2H
225 N H3CO CH N CH CH2CN
Figure 88102112_IMG54
51
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
226 N H3CO CH N CH CH2CN
227 N H3CO CH N CH O H
228 N H3CO CH N CH O H
229 N H3CO CH N CH O H
230 N H3CO CH N CH O CN
231 N H3CO CH N CH O CH3
232 N EtS CH N CH CH2H blaβ-gelbesoel
233 N EtS CH N CH CH2H blaβ-gelbesoel
234 N EtS CH N CH CH2H
235 N EtS CH N CH CH2H
Figure 88102112_IMG55
52
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
236 N EtS CH N CH CH2CN
237 N EtS CH N CH CH2CN
238    N    EtS    CH    N    CH    O    H        blaβ-gelbesoel
239    N    EtS    CH    N    CH    O    H        blaβ-gelbesoel
240    N    EtS    CH    N    CH    O    H
241    N    EtS    CH    N    CH    O    CN
242 N EtS CH N CH O CH3
243 N n-C3H7CH N CH CH2H
244 N n-C3H7CH N CH CH2H
245 N n-C3H7CH N CH CH2H
Figure 88102112_IMG56
53
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
247 N n-C3H7CH N CH CH2CN
248 N n-C3H7CH N CH CH2CN
249 N n-C3H7CH N CH O H
250 N n-C3H7CH N CH O H
251 N n-C3H7 CH N CH O H
252 N n-C3H7CH N CH O CN
253 N n-C3H7CH N CH O CH3
254 CH EtO N CH N CH2H Kp0.05＝225-245℃
255 CH EtO N CH N CH2H
256 CH EtO N CH N CH2H
54
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
257 CH EtO N CH N CH2H
258 CH EtO N CH N CH2CN
259 CH EtO N CH N CH2CN
260 CH EtO N CH N O H Kp0.03＝230℃
261    CH    EtO    N    CH    N    O    H
262    CH    EtO    N    CH    N    O    H
263    CH    EtO    N    CH    N    O    CN
264 CH EtO N CH N O CH3
265 CH Cl N CH N CH2H
266 CH Cl N CH N CH2H
Figure 88102112_IMG58
55
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
267 CH Cl N CH N CH2H
268 CH Cl N CH N CH2H
269 CH Cl N CH N CH2CN
270 CH Cl N CH N CH2CN
271    CH    Cl    N    CH    N    O    H
272    CH    Cl    N    CH    N    O    H
273    CH    Cl    N    CH    N    O    H
274    CH    Cl    N    CH    N    O    CN
275 CH Cl N CH N O CH3
276 CH H3CO N CH N CH2H
Figure 88102112_IMG59
56
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
277 CH H3CO N CH N CH2H
278 CH H3CO N CH N CH2H
279 CH H3CO N CH N CH2H
280 CH H3CO N CH N CH2CN
281 CH H3CO N CH N CH2CN
282 CH H3CO N CH N O H
283 CH H3CO N CH N O H
284 CH H3CO N CH N O H
285 CH H3CO N CH N O CN
286 CH H3CO N CH N O CH3
Figure 88102112_IMG60
57
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
287 CH F2CHO N CH N CH2H
288 CH F2CHO N CH N CH2H
289 CH F2CHO N CH N CH2H
290 CH F2CHO N CH N CH2H
291 CH F2CHO N CH N CH2CN
292 CH F2CHO N CH N CH2CN
293 CH F2CHO N CH N O H
294 CH F2CHO N CH N O H
295 CH F2CHO N CH N O H
296 CH F2CHO N CH N O CN
Figure 88102112_IMG61
58
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
297 CH F2CHO N CH N O CH3
298 CH EtS N CH N CH2H
299 CH EtS N CH N CH2H
300 CH EtS N CH N CH2H
301 CH EtS N CH N CH2H
302 CH EtS N CH N CH2CN
303 CH EtS N CH N CH2CN
304    CH    EtS    N    CH    N    O    H
305    CH    EtS    N    CH    N    O    H
306    CH    EtS    N    CH    N    O    H
59
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
307    CH    EtS    N    CH    N    O    CN
308 CH EtS N CH N O CH3
309 N EtO CH CH N CH2H
310 N EtO CH CH N CH2H
311 N EtO CH CH N CH2H
312    N    EtO    CH    CH    N    O    H        blaβ-gelbesoel
313    N    EtO    CH    CH    N    O    H        blaβ-gelbesoel
314 N Cl CH CH N CH2H
315 N Cl CH CH N CH2H
60
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
316 N Cl CH CH N CH2H
317    N    Cl    CH    CH    N    O    H
318    N    Cl    CH    CH    N    O    H
319 N CH3O CH CH N CH2H
320 N CH3O CH CH N CH2H
321 N CH3O CH CH N CH2H
322 N CH3O CH CH N O H
323 N CH3O CH CH N O H
324 N EtS CH CH N CH2H
325 N EtS CH CH N CH2H
Figure 88102112_IMG64
61
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
326 N EtS CH CH N CH2H
327    N    EtS    CH    CH    N    O    H
328    N    EtS    CH    CH    N    O    H
329 CCl EtO N N CH CH2H
330 CCl EtO N N CH CH2H
331 CCl EtO N N CH CH2H
332    CCl    EtO    N    N    CH    O    H
333    CCl    EtO    N    N    CH    O    H
334 CCl Cl N N CH CH2H
335 CCl Cl N N CH CH2H
Figure 88102112_IMG65
62
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
336 CCl Cl N N CH CH2H
337    CCl    Cl    N    N    CH    O    H
338    CCl    Cl    N    N    CH    O    H
339 CH EtO CH N N CH2H
340 CH EtO CH N N CH2H
341 CH EtO CH N N CH2H
342    CH    EtO    CH    N    N    O    H        blaβ-gelbesoel
343    CH    EtO    CH    N    N    O    H        blaβ-gelbesoel
344 CH CH3O CH N N CH2H
345 CH CH3O CH N N CH2H
Figure 88102112_IMG66
63
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
346 CH CH3O CH N N CH2H
347 CH CH3O CH N N O H
348 CH CH3O CH N N O H
349 CH Cl CH N N CH2H
350 CH Cl CH N N CH2H
351 CH Cl CH N N CH2H
352    CH    Cl    CH    N    N    O    H
353    CH    Cl    CH    N    N    O    H
354 CH EtS CH N N CH2H
355 CH EtS CH N N CH2H
64
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
356 CH EtS CH N N CH2H
357 CH EtS CH N N O H blaβ-gelbes
Figure 88102112_IMG68
l
358 CH EtS CH N N O H blaβ-gelbes
Figure 88102112_IMG69
l
359 CCl Cl CH N N CH2H
360 CCl Cl CH N N CH2H
361 CCl Cl CH N N CH2H
362    CCl    Cl    CH    N    N    O    H
363    CCl    Cl    CH    N    N    O    H
364 CH EtO N N N CH2H
365 CH EtO N N N CH2H
65
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
366 CH EtO N N N CH2H
367    CH    EtO    N    N    N    O    H
368    CH    EtO    N    N    N    O    H
369 CH CH3O N N N CH2H
370 CH CH3O N N N CH2H
371 CH CH3O N N N CH2H
372 CH CH3O N N N O H
373 CH CH3O N N N O H
374 CH Cl N N N CH2H
375 CH Cl N N N CH2H
Figure 88102112_IMG71
66
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
376 CH Cl N N N CH2H
377    CH    Cl    N    N    N    O    H
378    CH    Cl    N    N    N    O    H
379 CH EtS N N N CH2H
380 CH EtS N N N CH2H
381 CH EtS N N N CH2H
382    CH    EtS    N    N    N    O    H
383    CH    EtS    N    N    N    O    H
384 N EtS N N N CH2H
385 N EtO N N CH CH2H
67
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
386 N EtO N N CH CH2H
387    N    EtO    N    N    N    O    H
388    N    EtO    N    N    CH    O    H
389 N CH3O N N CH CH2H
390 N CH3O N N CH CH2H
391 N CH3O N N CH CH2H
392 N CH3O N CH O H
393 N CH3O N N CH O H
394 N Cl N N CH CH2H
395 N Cl N N CH CH2H
Figure 88102112_IMG73
68
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
396 N Cl N N CH CH2H
397    N    Cl    N    N    CH    O    H
398    N    Cl    N    N    CH    O    H
399 N EtS N N CH CH2H
400 N EtS N N CH CH2H
401 N EtS N N CH CH2H
402    N    EtS    N    N    CH    O    H
403    N    EtS    N    N    CH    O    H
404 N EtO N N N CH2H
405 N EtO N N N CH2H
69
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
406 N EtO N N N CH2H
407    N    EtO    N    N    N    O    H
408    N    EtO    N    N    N    O    H
409 N CH3O N N N CH2H
410 N CH3O N N N CH2H
411 N CH3O N N N CH2H
412 N CH3O N N N O H
413 N CH3O N N N O H
414 N Cl N N N CH2H
415 N Cl N N N CH2H
Figure 88102112_IMG75
70
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
416 N Cl N N N CH2H
417    N    Cl    N    N    N    O    H
418    N    Cl    N    N    N    O    H
419 N EtS N N N CH2H
420 N EtS N N N CH2H
421 N EtS N N N CH2H
422    N    EtS    N    N    N    O    H
423    N    EtS    N    N    N    O    H
71
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
424 N F3C-CH2-O- CH CH CH CH2H Kp0.01＝225-235℃
425 N F3C-CH2-O- CH CH CH CH2H Kp0.01＝230-235℃
426 N F3C-CH2-O- CH CH CH CH2H
427 N F3C-CH2-O- CH CH CH CH2H
428 N F3C-CH2-O- CH CH CH CH2H
429 N F3C-CH2-O- CH CH CH O H Kp0.02＝230-240℃
430 N F3C-CH2-O- CH CH CH O H Kp0.04＝230-240℃
431 N F3C-CH2-O- CH CH CH O H
Figure 88102112_IMG77
72
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
432 CH F3C-CH2-O- N CH CH CH2H
433 CH F3C-CH2-O- N CH CH CH2H
434 CH F3C-CH2-O- N CH CH CH2H
435 CH F3C-CH2-O- N CH CH CH2H
436 CH F3C-CH2-O- N CH CH CH2H
437 CH F3C-CH2-O- N CH CH O H
438 CH F3C-CH2-O- N CH CH O H
439 CH F3C-CH2-O- N CH CH O H
Figure 88102112_IMG78
73
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
440 N F3C-CH2-O- CH N CH CH2H Kp0.01＝240-245℃
441 N F3C-CH2-O- CH N CH CH2H Kp0.01＝240-245℃
442 N F3C-CH2-O- CH N CH CH2H
443 N F3C-CH2-O- CH N CH CH2H
444 N F3C-CH2-O- CH N CH CH2H
445 N F3C-CH2-O- CH N CH O H blaβgelbes
Figure 88102112_IMG79
l
446 N F3C-CH2-O- CH N CH O H blaβgelbes
Figure 88102112_IMG80
l
447 N F3C-CH2-O- CH N CH O H
Figure 88102112_IMG81
74
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
448 CH F3C-CH2-O- N CH N CH2H
449 CH F3C-CH2-O- N CH N CH2H
450 CH F3C-CH2-O- N CH N CH2H
451 CH F3C-CH2-O- N CH N CH2H
452 CH F3C-CH2-O- N CH N CH2H
453 CH F3C-CH2-O- N CH N O H
454 CH F3C-CH2-O- N CH N O H
455 CH F3C-CH2-O- N CH N O H
Figure 88102112_IMG82
75
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
456 N F3C-CH2-O- N CH CH CH2H blaβgelbes
Figure 88102112_IMG83
l
457 N F3C-CH2-O- N CH CH CH2H blaβgelbes l
458 N F3C-CH2-O- N CH CH CH2H
459 N F3C-CH2-O- N CH CH CH2H
460 N F3C-CH2-O- N CH CH CH2H
461 N F3C-CH2-O- N CH CH O H blaβgelbes
Figure 88102112_IMG85
l
462 N F3C-CH2-O- N CH CH O H blaβgelbes
Figure 88102112_IMG86
l
463 N F3C-CH2-O- N CH CH O H
Figure 88102112_IMG87
76
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
464 N F3C-CH2-O- CH CH N CH2H blaβgelbes
Figure 88102112_IMG88
l
465 N F3C-CH2-O- CH CH N CH2H blaβgelbes
Figure 88102112_IMG89
l
466 N F3C-CH2-O- CH CH N CH2H
467 N F3C-CH2-O- CH CH N CH2H
468 N F3C-CH2-O- CH CH N CH2H
469 N F3C-CH2-O- CH CH N O H blaβgelbes
Figure 88102112_IMG90
l
470 N F3C-CH2-O- CH CH N O H blaβgelbes
Figure 88102112_IMG91
l
471 N F3C-CH2-O- CH CH N O H
Figure 88102112_IMG92
77
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
472 N F3C-CH2-O- N N CH CH2H
473 N F3C-CH2-O- N N CH CH2H
474 N F3C-CH2-O- N N CH CH2H
475 N F3C-CH2-O- N N CH CH2H
476 N F3C-CH2-O- N N CH CH2H
477 N F3C-CH2-O- N N CH O H
478 N F3C-CH2-O- N N CH O H
479 N F3C-CH2-O- N N CH O H
Figure 88102112_IMG93
Figure 88102112_IMG94
78
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
480 N F3C-CH2-O- N CH N CH2H
481 N F3C-CH2-O- N CH N CH2H
482 N F3C-CH2-O- N CH N CH2H
483 N F3C-CH2-O- N CH N CH2H
484 N F3C-CH2-O- N CH N CH2H
485 N F3C-CH2-O- N CH N O H
486 N F3C-CH2-O- N CH N O H
487 N F3C-CH2-O- N CH N O H
79
Fortsetzung    Tabelle    1
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
488 N F3C-CH2-O- N N N CH2H
489 N F3C-CH2-O- N N N CH2H
490 N F3C-CH2-O- N N N CH2H
491 N F3C-CH2-O- N N N CH2H
492 N F3C-CH2-O- N N N CH2H
493 N F3C-CH2-O- N N N O H
494 N F3C-CH2-O- N N N O H
495 N F3C-CH2-O- N N N O H
Figure 88102112_IMG96
表2
R    R＝CH-CH;A＝N，CH或CR的式（Ⅰ）化合物
化合物号 A R1B C′ D X R4R5物理数据
496 N EtO CH CH CH CH2H
497 N EtO CH CH CH CH2H
498 N EtO CH CH CH CH2H
499 N EtO CH CH CH CH2H
500 N EtO CH CH CH CH2H
501 N EtO CH CH CH CH2CN
81
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
502 N EtO CH CH CH CH2CN
503    N    EtO    CH    CH    CH    O    H
504    N    EtO    CH    CH    CH    O    H
505    N    EtO    CH    CH    CH    O    H
506    N    EtO    CH    CH    CH    O    CN
507 N Cl CH CH CH CH2H
508 N Cl CH CH CH CH2H
509 N Cl CH CH CH CH2H
510 N Cl CH CH CH CH2H
Figure 88102112_IMG98
82
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
511 N Cl CH CH CH CH2CN
512 N Cl CH CH CH CH2CN
513    N    Cl    CH    CH    CH    O    H        blaβ-glbes    oel
514    N    Cl    CH    CH    CH    O    H
515    N    Cl    CH    CH    CH    O    H
516    N    Cl    CH    CH    CH    O    CN
517 N Cl CH CH CH O CH3
518 N H3CO CH CH CH CH2H
519 N H3CO CH CH CH CH2H
520 N H3CO CH CH CH CH2H
Figure 88102112_IMG99
83
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
521 N H3CO CH CH CH CH2H
522 N H3CO CH CH CH CH2CN
523 N H3CO CH CH CH CH2CN
524 N H3CO CH CH CH O H
525 N H3CO CH CH CH O H
526 N H3CO CH CH CH O H
527 N H3CO CH CH CH O CN
528 N H3CO CH CH CH O CH3
529 N EtS CH CH CH CH2H
530 N EtS CH CH CH CH2H
Figure 88102112_IMG100
84
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
531 N EtS CH CH CH CH2H
532 N EtS CH CH CH CH2H
533 N EtS CH CH CH CH2CN
534 N EtS CH CH CH CH2CN
535    N    EtS    CH    CH    CH    O    H
536    N    EtS    CH    CH    CH    O    H
537    N    EtS    CH    CH    CH    O    H
538    N    EtS    CH    CH    CH    O    CN
539 N EtS CH CH CH O CH3
540 N H3CS CH CH CH CH2H
Figure 88102112_IMG101
85
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
541 N H3CS CH CH CH CH2H
542 N H3CS CH CH CH CH2H
543 N H3CS CH CH CH CH2H
544 N H3CS CH CH CH CH2CN
545 N H3CS CH CH CH CH2CN
546 N H3CS CH CH CH O H
547 N H3CS CH CH CH O H
548 N H3CS CH CH CH O H
549 N H3CS CH CH CH O CN
550 N H3CS CH CH CH O CH3
Figure 88102112_IMG102
86
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
551 CCl Cl CH N CH CH2H
552 CCl Cl CH N CH CH2H
553 CCl Cl CH N CH CH2H
554 CCl Cl CH N CH CH2H
555 CCl Cl CH N CH CH2CN
556 CCl Cl CH N CH CH2CN
557    CCl    Cl    CH    N    CH    O    H
558    CCl    Cl    CH    N    CH    O    H
559    CCl    Cl    CH    N    CH    O    H
560    CCl    Cl    CH    N    CH    O    CN
Figure 88102112_IMG103
87
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
561 CCl Cl CH N CH O CH3
562 CCl EtO CH N CH CH2H
563 CCl EtO CH N CH CH2H
564 CCl EtO CH N CH CH2H
565 CCl EtO CH N CH CH2H
566 CCl EtO CH N CH CH2CN
567 CCl EtO CH N CH CH2CN
568    CCl    EtO    CH    N    CH    O    H
569    CCl    EtO    CH    N    CH    O    H
570    CCl    EtO    CH    N    CH    O    H
88
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
571    CCl    EtO    CH    N    CH    O    CN
572 CCl EtO CH N CH O CH3
573 CF EtO CH N CH CH2H
574 CF EtO CH N CH CH2H
575 CF EtO CH N CH CH2H
576 CF EtO CH N CH CH2H
577 CF EtO CH N CH CH2CN
578 CF EtO CH N CH CH2CN
579    CF    EtO    CH    N    CH    O    H
580    CF    EtO    CH    N    CH    O    H
Figure 88102112_IMG105
89
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
581    CF    EtO    CH    N    CH    O    H
582    CF    EtO    CH    N    CH    O    CN
583 CF EtO CH N CH O CH3
584 C-O-CH2-O CH N CH CH2H
585 C-O-CH2-O CH N CH CH2H
586 C-O-CH2-O CH N CH CH2H
587 C-O-CH2-O CH N CH CH2H
588 C-O-CH2-O CH N CH CH2CN
589 C-O-CH2-O CH N CH CH2CN
590 C-O-CH2-O CH N CH O H
Figure 88102112_IMG106
90
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
591 C-O-CH2-O CH N CH O H
592 C-O-CH2-O CH N CH O H
593 C-O-CH2-O CH N CH O CN
594 C-O-CH2-O CH N CH O CH3
595 CH EtO N CH CH CH2H
596 CH EtO N CH CH CH2H
597 CH EtO N CH CH CH2H
598 CH EtO N CH CH CH2H
599 CH EtO N CH CH CH2CN
600 CH EtO N CH CH CH2CN
Figure 88102112_IMG107
91
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
601    CH    EtO    N    CH    CH    O    H
602    CH    EtO    N    CH    CH    O    H
603    CH    EtO    N    CH    CH    O    H
604    CH    EtO    N    CH    CH    O    CN
605 CH EtO N CH CH O CH3
606 CH Cl N CH CH CH2H
607 CH Cl N CH CH CH2H
608 CH Cl N CH CH CH2H
609 CH Cl N CH CH CH2H
610 CH Cl N CH CH CH2CN
Figure 88102112_IMG108
92
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
611 CH Cl N CH CH CH2CN
612    CH    Cl    N    CH    CH    O    H
613    CH    Cl    N    CH    CH    O    H
614    CH    Cl    N    CH    CH    O    H
615    CH    Cl    N    CH    CH    O    CN
616 CH Cl N CH CH O CH3
617 CH H3CO N CH CH CH2H
618 CH H3CO N CH CH CH2 H
619 CH H3CO N CH CH CH2H
620 CH H3CO N CH CH CH2H
Figure 88102112_IMG109
93
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
621 CH H3CO N CH CH CH2CN
622 CH H3CO N CH CH CH2CN
623 CH H3CO N CH CH O H
624 CH H3CO N CH CH O H
625 CH H3CO N CH CH O H
626 CH H3CO N CH CH O CN
627 CH H3CO N CH CH O CH3
628 CH EtS N CH CH CH2H
629 CH EtS N CH CH CH2H
630 CH EtS N CH CH CH2H
Figure 88102112_IMG110
94
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
631 CH EtS N CH CH CH2H
632 CH EtS N CH CH CH2CN
633 CH EtS N CH CH CH2CN
634    CH    EtS    N    CH    CH    O    H
635    CH    EtS    N    CH    CH    O    H
636    CH    EtS    N    CH    CH    O    H
637    CH    EtS    N    CH    CH    O    CN
638 CH EtS N CH CH O CH3
639 CH F2CHO N CH CH CH2H
640 CH F2CHO N CH CH CH2H
Figure 88102112_IMG111
95
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
641 CH F2CHO N CH CH CH2H
642 CH F2CHO N CH CH CH2H
643 CH F2CHO N CH CH CH2CN
644 CH F2CHO N CH CH CH2CN
645 CH F2CHO N CH CH O H
646 CH F2CHO N CH CH O H
647 CH F2CHO N CH CH O H
648 CH F2CHO N CH CH O CN
649 CH F2CHO N CH CH O CH3
650 CCl CL N CH CH CH2H
96
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
651 CCl Cl N CH CH CH2H
652 CCl Cl N CH CH CH2H
653 CCl Cl N CH CH CH2H
654 CCl Cl N CH CH CH2CN
655 CCl Cl N CH CH CH2CN
656    CCl    Cl    N    CH    CH    O    H
657    CCl    Cl    N    CH    CH    O    H
658    CCl    Cl    N    CH    CH    O    H
659    CCl    Cl    N    CH    CH    O    CN
660 CCl Cl N CH CH O CH3
97
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
661 CCl EtO N CH CH CH2H
662 CCl EtO N CH CH CH2H
663 CCl EtO N CH CH CH2H
664 CCl EtO N CH CH CH2H
665 CCl EtO N CH CH CH2CN
666 CCl EtO N CH CH CH2CN
667    CCl    EtO    N    CH    CH    O    H
668    CCl    EtO    N    CH    CH    O    H
669    CCl    EtO    N    CH    CH    O    H
670    CCl    EtO    N    CH    CH    O    CN
Figure 88102112_IMG114
98
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
671 CCl EtO N CH CH O CH3
672 C-O-CH2-O N CH CH CH2H
673 C-O-CH2-O N CH CH CH2H
674 C-O-CH2-O N CH CH CH2H
675 C-O-CH2-O N CH CH CH2H
676 C-O-CH2-O N CH CH CH2CN
677 C-O-CH2-O N CH CH CH2CN
678 C-O-CH2-O N CH CH O H
679 C-O-CH2-O N CH CH O H
680 C-O-CH2-O N CH CH O H
99
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
681 C-O-CH2-O N CH CH O CN
682 C-O-CH2-O N CH CH O CH3
683 C-O-CH2-O CH CH N CH2H
684 C-O-CH2-O CH CH N CH2H
685 C-O-CH2-O CH CH N CH2H
686 C-O-CH2-O CH CH N CH2H
687 C-O-CH2-O CH CH N CH2CN
688 C-O-CH2-O CH CH N CH2CN
689 C-O-CH2-O CH CH N O H
690 C-O-CH2-O CH CH N O H
Figure 88102112_IMG116
100
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
691 C-O-CH2-O CH CH N O H
692 C-O-CH2-O CH CH N O CN
693 C-O-CH2-O CH CH N O CH3
694 N EtO CH N CH CH2H
695 N EtO CH N CH CH2H
696 N EtO CH N CH CH2H
697 N EtO CH N CH CH2H
698 N EtO CH N CH CH2CN
699 N EtO CH N CH CH2CN
700    N    EtO    CH    N    CH    O    H
Figure 88102112_IMG117
101
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
701    N    EtO    CH    N    CH    O    H
702    N    EtO    CH    N    CH    O    H
703    N    EtO    CH    N    CH    O    CN
704 N EtO CH N CH O CH3
705 N Cl CH N CH CH2H
706 N Cl CH N CH CH2H
707 N Cl CH N CH CH2H
708 N Cl CH N CH CH2H
709 N Cl CH N CH CH2CN
710 N Cl CH N CH CH2CN
Figure 88102112_IMG118
102
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
711    N    Cl    CH    N    CH    O    H
712    N    Cl    CH    N    CH    O    H
713    N    Cl    CH    N    CH    O    H
714    N    Cl    CH    N    CH    O    CN
715 N Cl CH N CH O CH3
716 N H3CO CH N CH CH2H
717 N H3CO CH N CH CH3H
718 N H3CO CH N CH CH2H
719 N H3CO CH N CH CH2H
720 N H3CO CH N CH CH2CN
Figure 88102112_IMG119
103
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
721 N H3CO CH N CH CH2CN
722 N H3CO CH N CH O H
723 N H3CO CH N CH O H
724 N H3CO CH N CH O H
725 N H3CO CH N CH O CN
726 N H3CO CH N CH O CH3
727 N EtS CH N CH CH2H
728 N EtS CH N CH CH2H
729 N EtS CH N CH CH2H
730 N EtS CH N CH CH2H
104
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
731 N EtS CH N CH CH2CN
732 N EtS CH N CH CH2CN
733    N    EtS    CH    N    CH    O    H
734    N    EtS    CH    N    CH    O    H
735    N    EtS    CH    N    CH    O    H
736    N    EtS    CH    N    CH    O    CN
737 N EtS CH N CH O CH3
738 N n-C3H7CH N CH CH2H
739 N n-C3H7CH N CH CH2H
740 N n-C3H7CH N CH CH2H
Figure 88102112_IMG121
105
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
741 N n-C3H7CH N CH CH2CN
742 N n-C3H7CH N CH CH2CN
743 N n-C3H7CH N CH O H
744 N n-C3H7CH N CH O H
745 N n-C3H7 CH N CH O H
746 N n-C3H7CH N CH O CN
747 N n-C3H7CH N CH O CH3
748 CH EtO N CH N CH2H
749 CH EtO N CH N CH2H
750 CH EtO N CH N CH2H
Figure 88102112_IMG122
106
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
751 CH EtO N CH N CH2H
752 CH EtO N CH N CH2CN
753 CH EtO N CH N CH2CN
754    CH    EtO    N    CH    N    O    H
755    CH    EtO    N    CH    N    O    H
756    CH    EtO    N    CH    N    O    H
757    CH    EtO    N    CH    N    O    CN
758 CH EtO N CH N O CH3
759 CH Cl N CH N CH2H
760 CH Cl N CH N CH2H
Figure 88102112_IMG123
107
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
761 CH Cl N CH N CH2H
762 CH Cl N CH N CH2H
763 CH Cl N CH N CH2CN
764 CH Cl N CH N CH2CN
765    CH    Cl    N    CH    N    O    H
776    CH    Cl    N    CH    N    O    H
777    CH    Cl    N    CH    N    O    H
778    CH    Cl    N    CH    N    O    CN
779 CH Cl N CH N O CH3
780 CH H3CO N CH N CH2H
Figure 88102112_IMG124
108
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
781 CH H3CO N CH N CH2H
782 CH H3CO N CH N CH2H
783 CH H3CO N CH N CH2H
784 CH H3CO N CH N CH2CN
785 CH H3CO N CH N CH2CN
786 CH H3CO N CH N O H
787 CH H3CO N CH N O H
788 CH H3CO N CH N O H
789 CH H3CO N CH N O CN
790 CH H3CO N CH N O CH3
Figure 88102112_IMG125
109
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
791 CH F2CHO N CH N CH2H
792 CH F2CHO N CH N CH2H
793 CH F2CHO N CH N CH2H
794 CH F2CHO N CH N CH2H
795 CH F2CHO N CH N CH2CN
796 CH F2CHO N CH N CH2CN
797 CH F2CHO N CH N O H
798 CH F2CHO N CH N O H
799 CH F2CHO N CH N O H
800 CH F2CHO N CH N O CN
110
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
801 CH F2CHO N CH N O CH3
802 CH EtS N CH N CH2H
803 CH EtS N CH N CH2H
804 CH EtS N CH N CH2H
805 CH EtS N CH N CH2H
806 CH EtS N CH N CH2H
807 CH EtS N CH N CH2CN
808    CH    EtS    N    CH    N    O    H
809    CH    EtS    N    CH    N    O    H
810    CH    EtS    N    CH    N    O    H
Figure 88102112_IMG127
111
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
811    CH    EtS    N    CH    N    O    CN
812 CH EtS N CH N O CH3
813 N EtO CH CH N CH2H
814 N EtO CH CH N CH2H
815 N EtO CH CH N CH2H
816    N    EtO    CH    CH    N    O    H
817    N    EtO    CH    CH    N    O    H
818 N Cl CH CH N CH2H
819 N Cl CH CH N CH2H
Figure 88102112_IMG128
112
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
820 N Cl CH CH N CH2H
821    N    Cl    CH    CH    N    O    H
822    N    Cl    CH    CH    N    O    H
823 N CH3O CH CH N CH2H
824 N CH3O CH CH N CH2H
825 N CH3O CH CH N CH2H
826 N CH3O CH CH N O H
827 N CH3O CH CH N O H
828 N EtS CH CH N CH2H
829 N EtS CH CH N CH2H
Figure 88102112_IMG129
113
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
830 N EtS CH CH N CH2H
831    N    EtS    CH    CH    N    O    H
832    N    EtS    CH    CH    N    O    H
833 CCl EtO N N CH CH2H
834 CCl EtO N N CH CH2H
835 CCl EtO N N CH CH2H
836    CCl    EtO    N    N    CH    O    H
837    CCl    EtO    N    N    CH    O    H
838 CCl Cl N N CH CH2H
839 CCl Cl N N CH CH2H
Figure 88102112_IMG130
114
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
840 CCl Cl N N CH CH2H
841    CCl    Cl    N    N    CH    O    H
842    CCl    Cl    N    N    CH    O    H
843 CH EtO CH N N CH2H
844 CH EtO CH N N CH2H
845 CH EtO CH N N CH2H
846    CH    EtO    CH    N    N    O    H
847    CH    EtO    CH    N    N    O    H
848 CH CH3O CH N N CH2H
849 CH CH3O CH N N CH2H
Figure 88102112_IMG131
115
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
850 CH CH3O CH N N CH2H
851 CH CH3O CH N N O H
852 CH CH3O CH N N O H
853 CH Cl CH N N CH2H
854 CH Cl CH N N CH2H
855 CH Cl CH N N CH2H
856    CH    Cl    CH    N    N    O    H
857    CH    Cl    CH    N    N    O    H
858 CH EtS CH N N CH2H
859 CH EtS CH N N CH2H
Figure 88102112_IMG132
116
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
860 CH EtS CH N N CH2H
861    CH    EtS    CH    N    N    O    H
862    CH    EtS    CH    N    N    O    H
863 CCl Cl CH N N CH2H
864 CCl Cl CH N N CH2H
865 CCl Cl CH N N CH2H
866    CCl    Cl    CH    N    N    O    H
867    CCl    Cl    CH    N    N    O    H
868 CH EtO N N N CH2H
869 CH EtO N N N CH2H
Figure 88102112_IMG133
117
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
870 CH EtO N N N CH2H
871    CH    EtO    N    N    N    O    H
872    CH    EtO    N    N    N    O    H
873 CH CH3O N N N CH2H
874 CH CH3O N N N CH2H
875 CH CH3O N N N CH2H
876 CH CH3O N N N O H
877 CH CH3O N N N O H
878 CH Cl N N N CH2H
879 CH Cl N N N CH2H
Figure 88102112_IMG134
118
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
880 CH Cl N N N CH2H
881    CH    Cl    N    N    N    O    H
882    CH    Cl    N    N    N    O    H
883 CH EtS N N N CH2H
884 CH EtS N N N CH2H
885 CH EtS N N N CH2H
886    CH    EtS    N    N    N    O    H
887    CH    EtS    N    N    N    O    H
888 N EtS N N N CH2H
889 N EtO N N CH CH2H
Figure 88102112_IMG135
119
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
890 N EtO N N CH CH2H
891    N    EtO    N    N    N    O    H
892    N    EtO    N    N    CH    O    H
893 N CH3O N N CH CH2H
894 N CH3O N N CH CH2H
895 N CH3O N N CH CH2H
896 N CH3O N N CH O H
897 N CH3O N N CH O H
898 N Cl N N CH CH2H
899 N Cl N N CH CH2H
Figure 88102112_IMG136
120
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
900 N Cl N N CH CH2H
901    N    Cl    N    N    CH    O    H
902    N    Cl    N    N    CH    O    H
903 N EtS N N CH CH2H
904 N EtS N N CH CH2H
905 N EtS N N CH CH2H
906    N    EtS    N    N    CH    O    H
907    N    EtS    N    N    CH    O    H
908 N EtO N N N CH2H
909 N EtO N N N CH2H
Figure 88102112_IMG137
121
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
910 N EtO N N N CH2H
911    N    EtO    N    N    N    O    H
912    N    EtO    N    N    N    O    H
913 N CH3O N N N CH2H
914 N CH3O N N N CH2H
915 N CH3O N N N CH2H
916 N CH3O N N N O H
917 N CH3O N N N O H
918 N Cl N N N CH2H
919 N Cl N N N CH2H
Figure 88102112_IMG138
122
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
920 N Cl N N N CH2H
921    N    Cl    N    N    N    O    H
923    N    Cl    N    N    N    O    H
924 N EtS N N N CH2H
925 N EtS N N N CH2H
926 N EtS N N N CH2H
927    N    EtS    N    N    N    O    H
928    N    EtS    N    N    N    O    H
123
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
929 N F3C-CH2-O- CH CH CH CH2H
930 N F3C-CH2-O- CH CH CH CH2H
931 N F3C-CH2-O- CH CH CH CH2H
932 N F3C-CH2-O- CH CH CH CH2H
933 N F3C-CH2-O- CH CH CH CH2H
934 N F3C-CH2-O- CH CH CH O H
935 N F3C-CH2-O- CH CH CH O H
936 N F3C-CH2-O- CH CH CH O H
124
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
937 CH F3C-CH2-O- N CH CH CH2H
938 CH F3C-CH2-O- N CH CH CH2H
939 CH F3C-CH2-O- N CH CH CH2H
940 CH F3C-CH2-O- N CH CH CH2H
941 CH F3C-CH2-O- N CH CH CH2H
942 CH F3C-CH2-O- N CH CH O H
943 CH F3C-CH2-O- N CH CH O H
944 CH F3C-CH2-O- N CH CH O H
Figure 88102112_IMG141
125
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
945 N F3C-CH2-O- CH N CH CH2H
946 N F3C-CH2-O- CH N CH CH2H
947 N F3C-CH2-O- CH N CH CH2H
948 N F3C-CH2-O- CH N CH CH2H
949 N F3C-CH2-O- CH N CH CH2H
950 N F3C-CH2-O- CH N CH O H
951 N F3C-CH2-O- CH N CH O H
952 N F3C-CH2-O- CH N CH O H
126
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
953 CH F3C-CH2-O- N CH N CH2H
954 CH F3C-CH2-O- N CH N CH2H
955 CH F3C-CH2-O- N CH N CH2H
956 CH F3C-CH2-O- N CH N CH2H
957 CH F3C-CH2-O- N CH N CH2H
958 CH F3C-CH2-O- N CH N O H
959 CH F3C-CH2-O- N CH N O H
960 CH F3C-CH2-O- N CH N O H
Figure 88102112_IMG143
127
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
961 N F3C-CH2-O- N CH CH CH2H
962 N F3C-CH2-O- N CH CH CH2H
963 N F3C-CH2-O- N CH CH CH2H
964 N F3C-CH2-O- N CH CH CH2H
965 N F3C-CH2-O- N CH CH CH2H
966 N F3C-CH2-O- N CH CH O H
967 N F3C-CH2-O- N CH CH O H
968 N F3C-CH2-O- N CH CH O H
Figure 88102112_IMG144
128
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
969 N F3C-CH2-O- CH CH N CH2H
970 N F3C-CH2-O- CH CH N CH2H
971 N F3C-CH2-O- CH CH N CH2H
972 N F3C-CH2-O- CH CH N CH2H
973 N F3C-CH2-O- CH CH N CH2H
974 N F3C-CH2-O- CH CH N O H
975 N F3C-CH2-O- CH CH N O H
976 N F3C-CH2-O- CH CH N O H
Figure 88102112_IMG145
129
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
977 N F3C-CH2-O- N N CH CH2H
978 N F3C-CH2-O- N N CH CH2H
979 N F3C-CH2-O- N N CH CH2H
980 N F3C-CH2-O- N N CH CH2H
981 N F3C-CH2-O- N N CH CH2H
982 N F3C-CH2-O- N N CH O H
983 N F3C-CH2-O- N N CH O H
984 N F3C-CH2-O- N N CH O H
130
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
985 N F3C-CH2-O- N CH N CH2H
986 N F3C-CH2-O- N CH N CH2H
987 N F3C-CH2-O- N CH N CH2H
988 N F3C-CH2-O- N CH N CH2H
989 N F3C-CH2-O- N CH N CH2H
990 N F3C-CH2-O- N CH N O H
991 N F3C-CH2-O- N CH N O H
992 N F3C-CH2-O- N CH N O H
Figure 88102112_IMG147
131
Fortsetzung    Tabelle    2
Verbdg. A R1B C′ D X R4R5physik.
Nr.    Daten
993 N F3C-CH2-O- N N N CH2H
994 N F3C-CH2-O- N N N CH2H
995 N F3C-CH2-O- N N N CH2H
996 N F3C-CH2-O- N N N CH2H
997 N F3C-CH2-O- N N N CH2H
998 N F3C-CH2-O- N N N O H
999 N F3C-CH2-O- N N N O H
1000 N F3C-CH2-O- N N N O H
C.生物活性试验实例
实例1
将含有1000ppm生物活性物质的用水稀释的乳液喷洒在具有大量菜豆蚜虫（豆蚜-Aphis    craccivora）的农田植物菜豆（蚕豆-Vicia    faba）上，喷洒量直至开始滴落为止。三天后，当采用实例1，2，5，8，18，19，41，199，200，205，206，232，238，239，312，342，343，357，424，425，429，430，440，441，445，446，462，497，503，504和513的生物活性物质药剂时，死亡率分别达到100%。
实例2
将用水稀释的乳液（含1000ppm生物活性物质）喷淋在具有大量粉虱（温室白粉虱-Trialeurodes    vaporarium）的豆科植物（普通菜豆-Phaseolus    vulgaris）上，喷淋量直至开始滴落为止。将植物置于培植室后，用显微镜观查，当采用实例2，8，9，18，206，239，424，425，429，430，440，441，445，446和503的生物活性物质药剂时，十四天后的结果是，死亡率分别达到100%。
实例3
试验过程：类似实例2
试验用动物：棉叶螨（Tetronychus    urticae）
试验植物：普通菜豆
药剂用量：喷淋液中含1000ppm生物活性物质
八天后测试药效表明，当采用实例425，429，430，445和446化合物时，死亡率达到100%。
实例4
将用水稀释的乳液（喷淋液中含1000ppm生物活性物质）喷洒在具有大量桔蚜（桔粉蚧-Pseudococcus    citri）的豆科植物（普通菜豆）上，喷洒量直至开始滴落为止。
在20～25℃培植室放置七天时间后检查发现：
采用实例2，5，8，9，18，19，41，200，205，206，238，342，424，429，430，446，503和504化合物时，死亡率达到100%。
实例5
用水稀释的乳液（喷淋液中含生物活性物质1000ppm）处理棉（臭）虫（美洲脊胸长蝽-Oncopeltus    fasciatus），所用生物活性物质选自实例2，9，19，206，425，430，441，446和504。然后将棉虫在室温下放置在带有通气盖的容器中。
处理后五天发现棉虫死亡，使用每种上述生物活性物质时死亡率均达100%。
实例6
每次用3毫升含2000ppm生物活性物质的水乳液在饲料糊凝固后喷洒在用合成营养介质涂层的佩特里（Petri）培养皿的底部内侧。喷洒层干燥后，加入10只普通棉
Figure 88102112_IMG148
虫（斜纹液蛾-Prodenia litura），将培养皿在21℃下保存七天，然后测定每种化合物效能（用%死亡率表示）。在该试验中，化合物1，2，5，8，9，18，19，41，200，205，206，239，424，425，430，445，446，503和504的效能分别为100%。
实例7
用浓度为1000ppm（以生物活性物质计）的实例1化合物的水乳液处理豆科植物（普通菜豆）的叶子，并同时在观察笼中放入墨西哥豆科甲虫（Epilachna    varivestis）幼虫。48小时后评价;被试验的动物100%死亡。用实例2，8，9，18，19，41，200，206，239，342，424，425，429，430，441，445，446，497，503和504化合物所做的试验均显示出相同的效能。
实例8
用吸移管取出1毫升浓度为1000ppm的溶于丙酮中的实例1化合物作为生物活性物质，将其均匀涂敷在佩特里培养皿顶盖及底部内侧，并且敞开培养皿直到溶剂完全蒸发。然后将10只舍蝇（家蝇-Musca    domestica）放入加盖的佩特里培养皿中。3小时后，被试验的动物100%死亡。采用实例2，8，9，18，19，41，200，206，238，312，424，425，429，430，440，441，445，446，503，504和513化合物也显示出相同效能。
实例9
用吸移管每次取出1毫升浓度为2000ppm的溶于丙酮中的生物活性物质溶液，将其均匀涂敷在佩特里培养皿顶盖及底部内侧。溶剂完全蒸发后，向每个佩特里培养皿加入10只德国小蠊（Blatella    germanica）幼虫（L4），并用盖关上培养皿。72小时后评断效能（用%死亡率表示）。在该试验中，化合物1，2，8，9，18，19，41，200，206，239，312，424，425，429，430，441，446，503，504和513的效能均为100%。

Claims (4)

1、式(I)化合物及其立体异构体的制法，
Figure 88102112_IMG2
式中
A、B、C′、D=互不关联的CH或N且其中之一必须为N，
X=CH2或O，
R1=碳原子连接基，H，1-4碳烷基，三(1-4)碳烷基甲硅烷基，囟素，硝基，氰基，2-6碳烯基，2-6碳炔基，氨基，3-7碳环烷基，苯基，苯氧基，1-5碳烷氧基，2-4碳烯氧基，2-4碳炔氧基，羟基羰基，1-4碳烷硫基，3-7环碳烷氧基，1-6碳烷基羰基，1-4碳烷氧羰基，2-4碳烯氧羰基，3-5碳炔氧羰基，1-4碳囟代烷基，1-4碳烷氧基(1-4)碳烷基，1-3碳囟代烷氧基，1-3碳囟代烷硫基，囟代(1-4)碳烷氧基(1-4)碳烷基，1-4碳烷硫基(1-4)碳烷基，1-4碳烷氧基(1-4)碳烷氧基，囟代(1-4)碳烷氧基(1-4)碳烷氧基，2-4碳烯氧基(1-4)碳烷氧基，囟代(2-4)碳烯氧基，1-4碳烷氧基(1-4)碳烷硫基，1-4碳烷硫基(1-4)碳烷氧基，1-4碳烷硫基(1-4)碳烷硫基，囟代(1-4)碳烷氧羰基，囟代(2-4)碳烯氧羰基或二(1-6碳烷基)氨基或两个R′一起在邻位形成亚甲二氧基，亚乙二氧基或3-5碳亚烷基，
R2，R3=互不关联的1-3碳烷基，2-8碳烯基，苯基或R2和R3为亚烷基链段，与季碳原子一起构成未取代或氟取代的3-6员环，R4=-H，F，-CN，-CCl3，-C≡CH，1-4碳烷基，
Figure 88102112_IMG3
R5=吡啶基，呋喃基，噻吩基并均可被取代，邻苯二甲酰亚氨基，二(1-4)碳烷基马来酰亚氨基，硫代邻苯二甲酰亚氨基，二氢邻苯二甲酰亚氨基，四氢邻苯二甲酰亚氨基，取代的苯基或R和R与其连接的碳原子一起形成必要时被取代的2，3-二氢化茚基，环戊烯酰基或环戊烯基，
n=0，1或2，
其特征是，
a)对于X=O的化合物，将式(Ⅱ)或(Ⅲ)的化合物必要时在碱存在下与式(Ⅳ)的烷基化剂反应而成：
Figure 88102112_IMG4
式中Y为离核基团如囟素或磺酸根，M相当于当量碱金属或碱土金属特别是Li，Na，K，Mg，
或者
b)对于X=O的化合物，在碱存在下将式(V)的化合物与式(Ⅵ)的XH酸化合物或与式(Ⅶ)的金属有机化合物反应而成：
Figure 88102112_IMG5
其中R4′=H或1-4碳烷基，
或者
c)对于X=CH2的化合物，将式(Ⅷ)化合物与式(IX)化合物反应而成：
Figure 88102112_IMG7
其中X′=CH2，
或者
d)将式(X)的化合物与式(XI)的金属有机试剂反应面成：
或者
e)对于R4=H和X=CH2的化合物，将式(XII)的醛与式(XIII)的酮缩合成式(XVI)的中间产物，并遂后按常规方式进行还原而成：
Figure 88102112_IMG9
或者
f)对于X=CH2的化合物，将式(XV)的醛与式(XVI)的内盐或式(XVII)的膦酸酯缩合成式(XVIII)的中间产物，并遂后与还原剂反应得X=CH2的终产品(Ⅰ)
Figure 88102112_IMG10
2、杀虫或杀螨剂，其特征是，其中含有效量的式（Ⅰ）化合物和常用配方助剂。
3、采用式（Ⅰ）化合物防治害虫或螨类。
4、防治害虫或螨类的方法，其特征是，用有效量的式（Ⅰ）化合物处理其生存环境。
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