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CN1024662C - N-(取代的苄氧基)亚胺衍生物、它们的制备方法、它们的应用以及应用的方法 - Google Patents

N-(取代的苄氧基)亚胺衍生物、它们的制备方法、它们的应用以及应用的方法 Download PDF

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Publication number
CN1024662C
CN1024662C CN90107137A CN90107137A CN1024662C CN 1024662 C CN1024662 C CN 1024662C CN 90107137 A CN90107137 A CN 90107137A CN 90107137 A CN90107137 A CN 90107137A CN 1024662 C CN1024662 C CN 1024662C
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China
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continued
compound
substituents
independently selected
lower alkyl
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CN1049654A (zh
Inventor
津幡健治
新井野信之
远藤胜利
山本好伸
菅野英夫
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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    • C07—ORGANIC CHEMISTRY
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
    • C07C251/20—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups being part of rings other than six-membered aromatic rings
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Abstract

本发明涉及通式(I)化合物(各基团的意义详见说明书)，它适用于作为一种农用和园林杀真菌剂，含有所说化合物的农用和园林杀真菌组合物；所说组合物在控制植物病害方面的应用；制备所说化合物的方法。

Description

本发明涉及N-（取代的苄氧基）亚胺衍生物、含有它们作为有效成分的农业和园林杀真菌剂、它们的制备方法、以及控制真菌的方法。
JP，A-61-106538和JP，A-61-28045公开了在结构上与本发明化合物相似的一些化合物，据述它们适用作为农用杀真菌剂或杀虫剂。但是，它们的活性还不能说是足以令人满意的。
本发明化合物是新化合物，它有不同于已知化合物的取代基，并具有比已知化合物优越得多的杀真菌药效。
本发明涉及N-（取代的苄氧基）亚胺衍生物，其通式为
Figure 901071374_IMG5
（Ⅰ）
其中，R1和R2分别独立地代表一个低级烷基，R3和R4分别独立地代表一个氢原子;氰基;硝基;烷基;卤代烷基;环烷基;烷氧基;卤代烷氧基;烷硫基;卤代烷硫基;烷基磺酰基;烷基亚磺酰基;链烯硫基;炔硫基;烷氧烷基;烷硫烷基;环烷硫基;低级烷氧羰基烷硫烷基;具有1-5个取代基的苯基，这些取代基独立地选自氢原子、卤素原子、氰基、硝基、低级烷基、低级卤代烷基、低级烷氧基、低级卤代烷氧基、低级烷硫基、低级卤代烷硫基、具有一个或多个取代基的氨基，这些氨基上的取代基独立地选自氢原子、甲酰基、低级烷基和低级烷基羰基、低级烷氧羰基、单或双低级烷基氨基羰基、单或双低级烷基氨基羰氧基、亚甲二氧基、具有1-5个取代基的苯基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、具有1-5个取代基的苯氧基，这些取代基独立地选自氢原子、卤素原子、氰基、硝基、低级烷基和低级卤代烷基、具有一个或多个取代基的吗啉代基，这些取代基独立地选自低级烷基、具有一个或多个取代基的嘧啶氧基，这些取代基独立地选自低级烷基、以及可能具有一个或多个取代基的吗啉代羰基，这些取代基独立地选自低级烷基;具有1-5个取代基的苯氧烷基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基;具有1-5个取代基的苯硫基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基;具有1-5个取代基的苯基烷硫基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基;具有1-5个取代基的苯基磺酰基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基;具有1-5个取代基的苯基硫烷 基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基;具有1-5个取代基的苯基烷硫烷基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基，具有一个或多个取代基的氨基烷基，这些取代基独立地选自氢原子、低级烷基、低级卤代烷基、苯基和苄基;糠硫基;糠硫烷基，可以具有一个或多个取代基的吗啉代基烷基，这些取代基独立地选自低级烷基;-CO-R5基（其中，R5代表一个低级烷基;低级卤代烷基;低级烷氧基;低级卤代烷氧基;低级烷硫基;低级卤代烷硫基;具有一个或多个取代基的氨基，这些取代基独立地选自氢原子、低级烷基、低级卤代烷基和苯基;具有1-5个取代基的苯基，这些取代基独立地选自氢原子、卤素原子、氰基、硝基、低级烷基、低级卤代烷基、低级烷氧基、低级卤代烷氧基、低级烷硫基、低级卤代烷硫基、低级烷基亚磺酰基、低级卤代烷基亚磺酰基、低级烷基磺酰基、低级卤代烷基磺酰基、低级烷氧烷基、具有一个或多个取代基的氨基，这些取代基独立地选自氢原子、低级烷基、低级烷基羰基、低级卤代烷基羰基、低级烷基磺酰基、低级卤代烷基磺酰基、低级烷氧羰基和低级卤代烷氧羰基、具有一个或多个取代基的苯基，这些取代基独立地选自氢原子、卤素原子、低级烷基、低级卤代烷基，具有1-5个取代基的苯氧基，这些取代基独立地选自氢原子、卤素原子、氰基、硝基、低级烷基和低级卤代烷基、具有1-5个取代基的苄基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、具有1-5个取代基的苄氧基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、具有1-4个取代基的吡啶氧基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、亚甲二氧基、以及与一个相邻碳原子相联的具有3-4个碳原子的亚烷基;具有1-5个取代基的苄氧基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、低级烷氧基、低级卤代烷氧基、低级烷硫基和低级卤代烷硫基;萘基;具有1-3个杂原子的5-6元杂环，这些杂原子独立地选自氧、硫和氮原子，且在环上具有一个或多个取代基，这些取代基独立地选自低级烷基、低级卤代烷基、低级烷氧基和低级卤代烷氧基）;具有一个或多个取代基的氨基，这些取代基独立地选自氢原子、低级烷基、低级卤代烷基、低级链烯基、低级炔基、低级烷氧烷基、低级二烷氧烷基，一或二个烷氧基烷基、具有1-5个取代基的苯基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、吡啶烷基和吗啉代基烷基;具有1-5个取代基的苯基烷基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基、低级烷氧基、低级卤代烧氧基、低级烷硫基和低级卤代烷硫基;具有1-5个取代基的苯基链烯基，这些取代基独立地选自氢原子、卤素原子、低级烷基和低级卤代烷基;萘基;低级二烷基膦酰基;或具有1-3个杂原子的5-7元杂环，这些杂原子独立地选自氧、硫和氮原子，且具有一个或多个取代基，这些取代基独立地选自氢原子、卤素原子、氰基、硝基、低级烷基、低级烷氧基、低级卤代烷氧基、低级烷硫基、低级卤代烷硫基、低级烷氧羰基、具有1～5个取代基的苯基，这些取代基独立地选自氢原子、卤素原子苄基、吡啶基、嘧啶基和二氧戊环基;或一个稠化到苯或环烷环上的杂环，或R3和R4共同代表一个可被1-3个选自氧、硫、氮原子、羰基或具有一个取代基的氮原子等原子或基团间隔的亚烷基或亚链烯基，所说氮原子上的取代基为低级烷基或苯基，且所说基团可在亚烷基或亚链烯基链上具有一个或多个取代基，这些取代基独立地选自低级烷基、低级卤代烷基、低级烷氧基和低级卤代烷氧基，并可与一苯环稠化以形成一个稠环。
在通式（Ⅰ）所示N-（取代的苄氧基）亚胺上的优选取代基如下。甲基优选作为R1和R2。R3和R4的优选例子最好是低级烷基如甲基和乙基;低级烷氧基如甲氧基、乙氧基和丙氧基;低级烷硫基如甲硫基、乙硫基和丙硫基;低级烷氧烷基如甲氧甲基、甲氧乙基和乙氧乙基;具有一个或多个取代基的苯基，所说取代基独立地选自卤素原子如氯，溴和氟、低级烷基如甲基，乙基和丙基、以及低级卤代烷基如二氟甲基，三氟甲基和四氟乙基;在其苯环上具有一个或多个取代基的苯基羰基，所说取代基独立地选自卤素原子如氯，溴和氟、低级烷基如甲基、乙基和丙基、低级卤代烷基如二氟甲基，三氟甲基和四氟乙基、以及低级卤代烷氧基如二氟甲氧基，三氟甲氧基和四氟乙氧基;以及具有一个低级烷基如甲基或乙基取代基的吗啉。
以下给出的化合物可以作为优选的N-（取代的苄氧基）亚胺衍生物的示例。举出这样的化合物，其中R1和R2为独立的低级烷基，且R3和R4之一是低级烷基、低级卤代烷基或低级烷氧烷基，而另一个是具有1-3个杂原子的5-7元杂环，所说杂原子独立地选自氧、硫和氮原子，且杂环上有1-3个取代基，它们独立地选自氢原子、卤素原子、氰基、硝基、低级烷基、低级烷氧基、低级卤代烷氧基、低级烷硫基、低级卤代烷硫基、低级烷氧羰基、可具有1-5个取代基的苯基，这些取代基独立地选自卤素原子、苄基、吡啶基、嘧啶基和二氧戊环基、或它们的一个与苯或环烷稠化的杂环。
以下具有一个杂环的化合物可作为更为优选的化合物：这样的化合物，它的杂环或所说杂环（它与苯或环烷稠化）是吡咯烷、哌啶、吗啉、硫代吗啉、哌嗪、六亚甲基亚胺、四氢喹啉、四氢异喹啉、2，3-二氢-1，4-苯并噁嗪，且在所说杂环中的氮原子总形成R3或R4上的取代基的键。下述化合物可作为N-（取代的苄氧基）亚胺衍生物中的特别优选的化合物，其上具有作为R3或R4的吗啡基（morphino），它可用一个低级烷基所取代，而另一个是低级烷基、低级卤代烷基、低级烷氧烷基、苯基或苄基。更为优选的化合物是这样的N-（取代的苄氧基）亚胺，它具有一个低级烷基或低级卤代烷基作为上述另一个R3或R4（除吗啡基外）取代基。
在本发明中，术语“低级”限定的取代基如低级烷基通常意味着该取代基有1-6个碳原子。例如，“低级烷氧羰基烷硫烷基”应该理解为一个具有4-19个碳原子（包括羰基上的碳）的烷氧羰基烷硫烷基。
然而，本发明并不限于上述限定的取代基。
本发明的N-（取代的苄氧基）亚胺衍生物是以一种具有E-构型或Z-构型的异构体形式存在的（关于碳-氮双键或碳-碳双键），这些异构体及其混合物包括在本发明范围之内。
若R3或R4中有一个氮原子，则本发明的N-（取代的苄氧基）亚胺衍生物可以以一种季盐形式例如以一种甲苯磺酸盐的盐形式分离出来。
按照下列反应模式，可制得通式（Ⅰ）所示的N-（取代的苄氧基）亚胺衍生物
Figure 901071374_IMG6
其中，R1、R2、R3和R4的定义同上，X是卤素。
也即，在一种碱或银化合物以及在一种惰性溶剂存在下，使通式（Ⅱ）化合物与通式（Ⅲ）化合物反应，可以制得通式（Ⅰ）的N-（取代的苄氧基）亚胺衍生物。
任何不妨碍本反应的惰性溶剂都可用在本发明中。这种溶剂的例子是醇如异丙醇、叔丁醇和二甘醇;酮类如丙酮，甲乙酮和环己酮;醚类如二乙基醚、二异丙基醚、四氢呋喃、二噁烷、甘醇二甲单醚、甘醇二甲双醚;卤代烃如二氯乙烷、氯仿、四氯化碳和四氯乙烷;芳烃如苯、氯苯、硝基苯和甲苯;腈类如乙清;二甲基甲酰胺;二甲亚砜;水以及这些溶剂的混合物。
当两相反应在混合溶剂中进行时，可使用一种相转移催化剂如三乙基苄基氯化铵、三辛基甲基氯化铵等等。
无机碱和有机碱可用作反应用碱。无机碱的例子有碱金属或碱土金属的碳酸盐如碳酸钠、碳酸钾、碳酸钙和碳酸氢钠;碱金属或碱土金属的氢氧化物如氢氧化钠、氢氧化钾和氢氧化钙;还有碱金属的氢化物如氢化锂和氢化钠。有机碱的例子有碱金属原子的醇盐如甲醇钠和叔丁醇钾，二乙胺、三乙胺、吡啶、以及苄基三甲基氢氧化铵。
氧化银以及类似物可用作银化合物。
反应温度适宜地是在-70℃至溶剂的沸点之间，最好在-40℃至30℃。反应时间随反应温度和反应规模而变，通常为30分钟至12小时。
本反应是一个等摩尔反应，因此，通式（Ⅱ）化合物和通式（Ⅲ）化合物可等摩尔使用，但是，其中之一可过量使用。
完成反应后，通过通常技术分离出目的产物，并根据需要提纯，如用柱层析法或重结晶法。
通式（Ⅱ）化合物可按JP，A-61-280452中公开的方法制得。通式（Ⅲ）化合物（它涵盖了一些新化合物）可按制备已知化合物的方法制备[例如，Org·Syn·Coll·Vol·2，313（1943），ditto，363（1943），以及J·Org·Chem，1980，45，4198]。
表1示出通式（Ⅰ）的N-（取代的苄氧基）亚胺的典型例子。但是，本发明并不限于这些例子。（见表1、表1续）
＊以四甲硅烷作内标物，在次氯仿中记录的丙烯酸甲氧基酯部分的烯属质子的1H-NMR化学位移[δ值（ppm）]。
在表1所述的化合物中，组合（如化合物55和56，化合物57和58等）是Z型异构体和E型异构体的组合。
此外，表1中“高”和“低”Rf指硅胶薄层色谱（正己烷/乙酸乙酯）中高Rf值和低Rf值。
下述实例说明通式（Ⅰ）N-（取代苄氧基）亚胺衍生物的典型方案，但本发明不应限制于此。
实例1
2-（2-亚苄基氨基氧甲苯基）-3-甲氧基丙烯酸甲酯（化合物1）
Figure 901071374_IMG7
将0.57g2-（2-溴甲基苯基）-3-甲氧基丙烯酸甲酯和0.36g苯甲醛肟溶于10ml二甲亚砜，加入0.19g氢氧化钾粉末。所得混合物在室温下搅拌6小时。
静置过夜后，将混合物倾入冰水，用盐水洗涤，用乙酸乙酯萃取两次，萃取物用硫酸镁干燥，过滤并减压浓缩。剩余物经硅胶柱色谱提纯，得到0.2g目的化合物。
产率：31%，性质：nD1.5905（18.9℃）
实例2
2-｛2-（3-氧化-2-亚丁基氨基氧甲基）基苯｝-3-
甲氧基丙烯酸甲酯（化合物52）
Figure 901071374_IMG8
将0.86g2-（2-溴甲基苯基）-3-甲氧基丙烯酸甲酯和0.33g二乙酰单肟溶于20ml二甲基甲酰胺，将混合物冷却至5℃。加入0.22g氢氧化钾粉末，搅拌混合物10分钟，然后在室温下再搅拌1小时进行反应。反应结束后，将反应混合物倾入冰水，用乙酸乙酯萃取。萃取物用5%氢氧化钠水溶液和盐水洗涤，用硫酸镁干燥，过滤并减压浓缩。剩余物经硅胶柱色谱提纯，得到0.81g目的化合物。
产率：89%，性质：m·p·82.7-84.6℃
实例3
2-｛2-（α-甲硫基亚苄氨基氧甲基）苯基｝-3-甲氧基丙烯酸甲酯（化合物59）
Figure 901071374_IMG9
将0.33g氢氧化钾粉末加到含有0.85g苯氧肟基甲基硫醚的10ml二甲亚砜溶液中，搅拌混合物10分钟。然后加入1.45g2-（2-溴甲基苯基）-3-甲氧基丙烯酸甲酯，搅拌下使混合物反应4小时。
反应结束后，将反应混合物倾入冰水，用乙醚萃取，萃取物用水和盐水洗涤，硫酸钠干燥。萃取物经过滤和减压浓缩，所得剩余物经硅胶柱色谱提纯，得到1.50g目的化合物。
产率：81%，性质：nD1.5924（18.6℃）
实例4
2-｛2-（α-吗啉代亚苄基氨基氧甲基）苯基｝-3-甲氧基丙烯酸甲酯（化合物88）
Figure 901071374_IMG10
将0.44gα-吗啉代苯甲醛肟溶于5ml二甲亚砜，加入0.14g氢氧化钾粉末，搅拌30分钟，然后，加入0.55g2-（2-溴甲基苯基）-3-甲氧基丙烯酸甲酯，使混合物搅拌下反应2小时。
反应结束后，将10ml冰水加到反应混合物中，用乙酸乙酯萃取所得混合物。萃取物用水洗涤，硫酸钠干燥，过滤并减压浓缩。剩余物经硅胶柱色谱提纯，得到0.29g目的化合物。
产率：33%，性质：糊状
实例5
2-｛2-（1，3-二硫戊环-2-亚基氨基氧甲基）苯基｝-3-甲氧基丙烯酸甲酯（化合物96）
Figure 901071374_IMG12
将0.44g2-羟基亚氨基-1，3-二硫戊环溶于5ml二甲亚砜，加入0.18g氢氧化钾粉末，室温下搅拌混合物30分钟。然后加入0.86g2-（2-溴甲基苯基）-3-甲氧基丙烯酸甲酯，使混合物在搅拌下反应2小时。
反应结束后，反应混合物中加入冰水，用乙酸乙酯萃取。萃取物用水洗涤，硫酸镁干燥，过滤并减压浓缩。剩余物经硅胶柱色谱提纯，得到0.56g目的化合物。
产率：55%，性质：nD1.5917（18.6℃）
实例6
2-[2-｛1-（顺式-2，6-二甲基吗啉代）亚乙基｝亚氨基氧甲基苯基]-3-甲氧基丙烯酸甲酯（化合物357）
Figure 901071374_IMG13
将1.72g1-（顺式-2，6-二甲基吗啉代）乙醛肟溶于30ml二甲基甲酰胺，加入0.66g氢氧化钾粉末，0℃搅拌混合物10分钟。加入2.85g2-（2-溴甲基苯基）-3-甲氧基丙烯酸甲酯，所得混合物于室温下再搅拌1小时进行反应。反应结束后，将反应混合物倾入冰水，用乙酸乙酯萃取，萃取物用水洗涤、硫酸镁干燥，过滤并减压浓缩。剩余物经硅胶柱色谱提纯，得到0.4g目的化合物。
产率：10.6%，性质：107-109℃
通式（Ⅰ）的N-（取代苄氧基）亚胺衍生物是有用的农业和园林杀真菌剂，可有效控制各种植物疾病，如稻瘟病（Pyriculariaoryzae）、稻枯病（Rhizoctonia    Solani）、稻褐斑病（Cochliobolus    miyabeanus）、大麦和其它植物的霉粉病（Erysiphe    graminisf·sp·hordei）、各种植物的锈斑病以及由卵菌纲真菌导致的植物疾病，如蕃茄晚疫（Phytophthora    infestans）和黄瓜茸霉病（Pseudoperonospora    Cubensis）。
在病状出现前或出现后，通过在植物叶茎、灌溉水或土壤中施用，本发明的化合物具有优异的控制水田、旱田植物、果树、蔬菜和其它植物以及花木植物疾病的药效。然而，本发明并不局限于上述具体应用。
当通式（Ⅰ）的N-（取代苄氧基）亚胺衍生物用作农业或园林杀（真）菌剂时，通常根据制备农药的常规方法将其制成为易于使用的形式。即通过溶解、分散、悬浮、混合、浸渍、吸附或粘附等方式，使通式（Ⅰ）的N-（取代苄氧基）亚胺衍生物以及根据需要采用的辅剂掺混于适宜的惰性载体，并将其制成适宜的剂型如悬液、浓乳液、浓溶液、可湿性粉剂、颗粒、粉剂或片剂。
本发明中的惰性载体可以是固体或液体。固体载体的实例有大豆粉、谷类粉、木粉、锯末、粉碎的烟梗、粉碎的胡桃壳、麸糠、粉碎的纤维素、蔬菜提取残余物、粉碎的合成聚合物或树脂、粘土（如高岭土、膨润土和酸性粘土）、滑石（如滑石和叶蜡石）、二氧化硅粉或屑（如硅藻土、硅砂、云母和白碳，即合成的高分散硅酸，称为细分散的水合氧化硅或水合硅酸）、活性炭、硅粉、浮石粉、焙烧硅藻土、研碎的硅末、灰分、沙、碳酸钙粉末、硫酸钙粉末和其它无机物或矿物粉末、化肥（如硫酸铵、硝酸铵、尿素和氯化铵）和复合肥料，上述载体可单独使用或组合使用。
液体载体或是其自身具有溶解性，或是没有溶解性但能借助于辅剂将有效成分分散的那些物质。下述是液体载体的典型实例，可单独使用其一，也可组合使用。典型实例包括水;醇，如甲醇，乙醇，异丙醇，丁醇和乙二醇;酮，如丙酮，甲乙酮，甲基异丙基酮，二异丁基酮和环乙酮;醚，如乙醚，二噁烷，溶纤醚，二丙醚和四氢呋喃;脂族烃，如汽油和矿物油;芳烃，如苯，甲苯，二甲苯，溶剂石脑油和烷基萘;卤代烃，如二氯乙烷，氯仿，四氯化碳和氯苯;酯，如乙酸乙酯，邻苯二甲酸二异丙酯，邻苯二甲酸二丁酯和邻苯二甲酸二辛酯;酰胺，如二甲基甲酰胺和二甲基乙酰胺;腈，如乙腈;以及二甲亚砜。
下面是辅剂的典型实例，根据使用目的可以单独使用或组合使用，且在某些情况下可以完全不用。
为乳化、分散、溶解和/或润湿有效成分，使用表面活性剂。表面活性剂的实例有聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨糖醇单月桂酸酯、聚氧乙烯脱水山梨糖醇单油酸酯、烷芳基磺酸酯、萘磺酸缩合产物、木素磺酸盐和硫酸高级醇酯。
此外，为使有效成分分散稳定、使其粘合或结合，可以使用辅剂。这种辅剂的实例有酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、阿拉伯胶、聚乙烯醇、松节油、糠油、膨润土和木素磺酸盐。
为改善固体产物的流动性，可以使用辅剂。这种辅剂的实例有蜡、硬脂酸盐和磷酸烷基酯。
萘磺酸缩合产物和磷酸盐的多缩合物等辅剂可作为分散性产物的胶溶剂。
硅油一类的辅剂可被用来作消泡剂。
有效成分的含量可根据需要变化/在粉剂或颗粒中，适宜的含量为0.1-50%（重量）。在浓乳液、流动性可湿性粉剂中，其含量为0.1-90%（重量）。
含有通式（Ⅰ）N-（取代苄氧基）亚胺衍生物作为活性成分的农业或园林杀（真）菌剂以下述方式控制各种作物疾病。即以有效控制量直接或用水适当稀释或悬浮于水将其施用在预计将发生疾病的作物上或不需要出现疾病的区域。
含有通式（Ⅰ）N-（取代苄氧基）亚胺衍生物作为活性成分的农业或园林杀真菌剂的用量可依各种因素变化，如使用目的、待控制的疾病、植物的生长状态、疾病发生的趋势、气候、环境条件、剂型、使用方便、施用区域和时间。然而，根据不同用途，有效成分的用量在每10公亩用0.1g～1000g的范围内。
含有通式（Ⅰ）N-（取代苄氧基）亚胺衍生物作为有效成分的农业或园林杀（真）菌剂可以与适时可用的农药、肥料和/或植物营养素形成混合物使用，或与其组合应用。
当采用含有本发明化合物作为有效成分的农业或园林杀（真）菌剂控制作物疾病时，可将其与其它控制剂混合，从而控制与本发明杀（真）菌剂所要控制的作物疾病同时出现的其它作物病害。这时混合物可被用作为多用途控制剂。这里所指的其它控制剂的实例如下所列。
硫代磷酸0，0-二甲基0-（3-甲基-4-硝基苯基）酯（杀螟松）
硫代磷酸0，0-二甲基0-（3-甲基-4-甲硫基苯基）酯（倍硫磷）
二硫代磷酸0，0-二甲基S-（α-乙氧羰基苄基）酯（稻丰散）
硫代磷酸0，0-二乙基0-（2-异丙基-6-甲基-4-嘧啶基）酯（二嗪农）
膦酸二甲基2，2，2-三氯-1-羟基乙基酯（敌百虫）硫代磷酸0-4-氰基苯基0-乙基苯基酯（Cyanophenphos）
硫代磷酸0-乙基0-4-硝基苯基苯基酯（苯硫磷）
磷酸4-（甲硫基）苯基二异丙基酯（丙虫磷）
二硫代磷酸0，0-二甲基S-邻苯二甲酰亚胺基甲基酯（亚胺硫磷）
磷酸2，2-二氯乙烯基二甲基酯（敌敌畏）
二硫代磷酸0，0-二甲基S-甲基氨基甲酰甲基酯（乐果）
二硫代磷酸0，0-二甲基S-1，2-双（乙氧羰基）乙基酯（马拉松）
氨基甲酸1-萘基甲基酯（西维因）
氨基甲酸间甲苯基甲基酯（Metocarb）
氨基甲酸2-异丙氧苯基甲基酯（残杀威）
二硫代磷酸0，0-二乙基S-（N-乙氧羰基-N-甲基氨基甲酰甲基）酯（灭蚜磷）
氨基甲酸3，4-二甲苯基甲基酯（Xylylcarb）
氨基甲酸2-仲丁苯基甲基酯（丁苯威）
氨基甲酸2-异丙苯基甲基酯（Isoprocarb）
氨基甲酸2-氯苯基甲基酯（害扑威）
氨基甲酸3，5-二甲苯基甲基酯（二甲威）
氨基甲酸2-（1，3-二氧戊环-2-基）苯基甲基酯（二氧威）。
氨基甲酸3-叔丁苯基甲基酯（叔丁威）
氨基甲酸4-二烯丙氨基-3，5-二甲苯基甲基酯（除害威）
硫代乙酰亚胺S-甲基N-（甲基氨基甲酰氧基）酯（灭多虫）
N-（4-氯-邻甲苯基）-N，N-二甲基甲脒盐酸盐（Chlorodimeform）
1，3-双（氨基甲酰硫基）-2-二甲基氨基丙烷盐酸盐（巴丹）
丙二酸1，3-二硫戊烷-2-叉二异丙酯（富士一号）
硫代磷酸0，0-二异丙基S-苄基酯（异稻瘟净）
下面是本发明代表性配方实例和试验实例，但并不限制本发明。
在配方实例中，“份”指“重量份”。
配方实例1
化合物21    50份
主要含粘土的粘土/白碳混合物    45份
聚氧乙烯壬基苯基醚    5份
将上述组分均匀混合，粉化后得到可湿性粉末。
配方实例2
化合物44    5份
膨润土/粘土混合物    90份
木素磺酸钙    5份
将上述组分均匀混合，加适量水捏合混合物，造粒，干燥，得到颗粒。
配方实例3
化合物96    50份
二甲苯    40份
聚氧乙烯壬基苯基醚和
烷基苯磺酸钙混合物    10份
将上述组分充分混合溶解，得到浓乳液。
配方实例4
化合物201    3份
粉化粘土    82份
粉化硅藻土    15份
将上述组分均匀混合，粉化后得到粉剂。
配方实例5
化合物272    5份
聚氧乙烯（10mol）壬基苯基醚    1.4份
聚氧乙烯苯乙烯酚醚    2份
丙二醇    3份
消泡剂    0.5份
杂多糖    0.15份
水    87.95份
将上述组分均匀混合，粉化后得到流动性制剂。
试验实例1
对大麦霉粉病（Enysiphe    graminis    f·sp·hordei）的控制效果
两叶期大麦幼苗在用Erysiphe    graminis    f·sp·hordei分生孢子接种1天后，用试验化合物（200ppm）喷洒。将幼苗保持在25℃恒温室内一周，检查每片叶感染的百分率。与未处理区域相比，评价控制疾病药效。
A：控制率    100-95%
B：控制率    94-80%
C：控制率    79-60%
D：控制率    59-0%
表2示出了结果。（见表2）
注：
参比化合物A：JP-A-61-280452的化合物
Figure 901071374_IMG14
参比化合物B：JP-A-61-106538的化合物
参比化合物C：JP-A-61-106538的化合物
Figure 901071374_IMG16
试验实例2
对黄瓜茸霉病（Pesudoperonospora    cubensis）的控制效果
在用Pseudoperonospora    cubensis游动孢子接种前一天，用试验化合物（200ppm）喷洒两叶期黄瓜植株。植物在25℃潮湿室内保持一天然后在温室保持6天后，检查每片叶感染的程度。以与试验实例1相同的方式评价疾病控制药效。结果示于表3。（见表3）
试验实例3
对稻瘟病（Pyricularia    oryzae）的控制效果
在用Pyricularia    oryzae分生孢子接种前一天，用试验化合物（200ppm）喷洒五叶期水稻幼苗。幼苗在25℃潮湿室内保持一天然后在温室保持6天后，检查每片叶上出现的病灶数。以与试验实例1相同的方式评价疾病控制药效。结果示于表。（见表4）
表1
Figure 901071374_IMG18
（Ⅰ）
Figure 901071374_IMG17
表1（续）
Figure 901071374_IMG20
表1（续）
Figure 901071374_IMG21
表1（续）
Figure 901071374_IMG22
表1（续）
表1（续）
Figure 901071374_IMG24
表1（续）
Figure 901071374_IMG25
表1（续）
Figure 901071374_IMG26
表1（续）
表1（续）
Figure 901071374_IMG28
表1（续）
Figure 901071374_IMG29
表1（续）
表1（续）
Figure 901071374_IMG31
表1（续）
Figure 901071374_IMG32
表1（续）
Figure 901071374_IMG33
表1（续）
表1（续）
表1（续）
Figure 901071374_IMG36
表1（续）
Figure 901071374_IMG37
表1（续）
Figure 901071374_IMG38
表1（续）
Figure 901071374_IMG39
表1（续）
Figure 901071374_IMG40
表1（续）
Figure 901071374_IMG41
表1（续）
Figure 901071374_IMG42
表1（续）
Figure 901071374_IMG43
表1（续）
Figure 901071374_IMG44
表1（续）
表1（续）
Figure 901071374_IMG46
表1（续）
表1（续）
Figure 901071374_IMG48
表1（续）
表1（续）
Figure 901071374_IMG51
表1（续）
Figure 901071374_IMG52
表1（续）
表1（续）
Figure 901071374_IMG54
表1（续）
Figure 901071374_IMG55
表1（续）
Figure 901071374_IMG56
表1（续）
表1（续）
Figure 901071374_IMG58
表1（续）
Figure 901071374_IMG59
表1（续）
Figure 901071374_IMG60
表1（续）
Figure 901071374_IMG61
表1（续）
Figure 901071374_IMG62
表1（续）
Figure 901071374_IMG63
表1（续）
表1（续）
Figure 901071374_IMG65
表1（续）
Figure 901071374_IMG66
表1（续）
Figure 901071374_IMG67
表1（续）
Figure 901071374_IMG68
表1（续）
Figure 901071374_IMG69
表1（续）
Figure 901071374_IMG70
表1（续）
Figure 901071374_IMG71
表1（续）
Figure 901071374_IMG72
表1（续）
Figure 901071374_IMG73
表1（续）
Figure 901071374_IMG74
表1（续）
Figure 901071374_IMG75
表1（续）
Figure 901071374_IMG76
表1（续）
Figure 901071374_IMG77
表1（续）
Figure 901071374_IMG78
表1（续）
Figure 901071374_IMG79
表1（续）
表1（续）
Figure 901071374_IMG81
表1（续）
表2
化合物号    杀真菌效果    化合物号    杀真菌效果
1    A    25    A
2    C    26    A
3    B    27    A
4    A    28    A
5    C    29    A
6    A    30    A
7    A    31    A
9    A    32    A
10    A    33    A
11    A    34    A
12    A    35    A
13    A    36    A
14    A    38    A
15    A    39    A
16    A    40    A
17    A    41    A
21    A    42    A
22    A    43    A
23    A    44    A
24    A    47    A
表2（续）
48    A    80    C
49    A    81    A
50    B    82    A
51    A    83    B
52    A    84    B
55    A    87    A
56    A    88    A
57    C    89    B
59    A    91    A
60    A    92    A
61    C    93    A
65    C    94    A
66    A    95    A
67    A    96    A
68    A    97    C
69    A    98    A
70    A    102    A
71    B    103    B
72    B    105    B
74    A    106    B
75    A    107    A
78    B    108    A
79    A    109    A
表2（续）
110    A    133    A
111    B    134    A
112    B    135    A
113    A    137    A
114    A    139    A
115    A    141    B
116    A    142    A
117    A    143    A
118    A    144    A
119    A    145    C
120    A    146    A
121    A    147    A
122    A    148    A
123    A    149    A
124    A    150    A
125    A    151    A
126    A    152    A
127    A    153    B
128    B    154    A
129    A    155    A
130    A    156    B
131    A    157    A
132    A    158    A
表2（续）
159    A    182    A
160    A    183    A
161    A    184    A
162    A    185    A
163    A    186    A
164    A    187    C
165    A    188    A
166    A    189    A
167    A    190    A
168    A    191    A
169    A    192    A
170    C    193    A
171    A    194    A
172    A    197    A
173    A    198    A
174    A    199    A
175    C    200    B
176    A    201    A
177    A    202    A
178    A    203    A
179    C    204    A
180    A    205    C
181    B    206    A
表2（续）
207    B    233    A
208    A    234    A
209    B    235    A
210    A    236    A
211    A    237    B
212    A    238    A
213    A    239    A
215    B    240    A
216    B    241    A
217    A    242    A
218    A    243    A
219    A    244    A
220    B    245    A
221    C    246    A
223    A    247    A
225    A    248    C
226    A    249    A
227    A    253    A
228    A    254    A
229    A    255    A
230    A    256    A
231    A    257    A
232    A    258    A
表2（续）
259    C    290    A
260    C    291    A
265    C    292    A
268    C    293    A
271    A    294    A
272    A    295    A
273    A    296    A
274    A    297    A
275    A    298    A
276    A    299    A
277    A    300    A
278    A    301    A
279    A    302    A
280    A    303    A
281    B    304    A
282    A    305    C
283    A    306    C
284    A    307    A
285    A    308    A
286    A    309    B
287    A    310    C
288    A    311    B
289    A    312    A
表2（续）
313    A    339    A
314    A    340    A
315    A    341    A
316    A    342    A
317    B    343    A
318    A    344    C
319    C    345    A
321    A    346    A
322    B    347    A
323    A    348    A
326    C    349    A
327    A    350    A
328    C    351    B
329    A    352    A
330    A    353    A
331    A    354    A
332    A    355    A
333    A    356    A
334    A    357    A
335    A    358    A
336    A    359    A
337    C    360    A
338    A    361    A
表2（续）
362    A    391    A
363    A    392    A
365    A    393    A
366    C    394    A
368    A    396    A
369    A    397    A
370    A    398    A
371    A    399    A
372    A    400    A
374    B    401    B
379    A    402    A
380    A    403    A
381    A    400    A
382    A    404    A
383    A    405    A
384    A    406    A
385    A    407    A
386    A
387    A
388    A    参比化合物A    D
389    A    参比化合物B    D
390    A    参比化合物C    C
表3
化合物号    杀真菌效果    化合物号    杀真菌效果
1    A    27    A
2    B    28    B
3    A    29    A
5    B    30    A
6    C    31    A
9    C    32    A
10    A    33    A
11    B    34    A
12    A    35    A
13    B    40    A
14    A    41    A
15    A    42    B
16    B    43    B
17    B    44    A
20    A    45    C
21    A    47    C
22    A    48    A
23    A    49    B
24    A    52    B
25    A    53    C
表3（续）
55    A    92    A
56    C    93    A
58    C    95    B
59    A    96    B
61    B    97    A
62    C    104    C
66    A    105    A
67    A    106    A
68    A    107    B
69    B    109    A
70    A    110    A
71    B    111    A
74    C    112    B
75    B    114    A
77    C    115    B
78    B    118    A
79    A    119    A
80    C    120    A
81    A    122    A
82    A    124    A
83    A    125    A
86    B    126    A
91    B    127    A
表3（续）
128    A    156    A
129    C    157    A
131    C    158    A
132    C    159    A
133    A    160    A
134    A    161    A
135    A    162    C
137    A    163    A
139    B    164    A
142    C    165    A
143    A    167    A
144    A    168    A
145    B    169    A
146    A    170    C
147    A    172    A
148    A    174    A
149    A    175    A
150    A    176    A
151    A    177    A
152    A    178    A
153    A    179    A
154    A    181    A
155    A    185    A
表3（续）
186    A    224    A
187    B    225    A
188    A    226    A
190    A    227    A
193    C    228    A
198    A    229    A
199    A    230    A
200    A    231    A
201    A    232    A
202    C    233    A
203    A    234    A
204    A    235    A
205    B    236    A
206    A    237    A
207    A    238    A
208    A    239    A
216    B    240    A
218    C    241    A
219    A    242    C
220    A    243    A
221    A    244    A
222    A    245    A
223    A    246    A
表3（续）
247    C    278    A
248    A    279    A
249    A    281    A
250    A    282    A
255    A    283    A
256    A    284    A
257    B    285    A
258    B    286    A
259    A    287    A
260    A    288    B
261    C    289    C
262    C    290    A
263    C    291    A
264    B    292    A
266    B    293    A
269    B    294    A
271    A    295    A
272    A    296    A
273    A    298    B
274    A    299    C
275    B    300    A
276    B    301    A
277    A    302    A
表3（续）
303    A    334    A
304    A    336    A
306    C    338    A
307    A    339    A
308    C    340    A
309    B    341    A
313    A    342    A
314    A    343    B
315    A    344    A
316    A    345    A
317    B    347    A
318    A    348    A
319    A    349    A
321    A    350    A
323    A    351    A
324    A    352    A
325    B    353    A
326    A    354    A
329    B    355    A
330    A    356    A
331    B    357    A
332    A    358    A
333    C    360    A
表3（续）
361    A    385    A
363    A    386    A
364    B    387    A
365    A    388    A
366    B    389    A
367    C    391    A
368    A    392    A
370    A    393    A
371    A    394    B
372    C    396    A
374    C    397    A
379    B    399    A
380    B    400    A
381    B    401    C
384    A
表4
化合物号    杀真菌效果    化合物号    杀真菌效果
1    A    25    A
2    B    26    A
3    A    27    A
4    C    28    A
6    A    29    A
9    C    30    A
10    B    31    A
11    A    32    B
12    B    33    A
13    A    34    A
14    A    35    A
15    A    36    A
16    A    39    B
17    C    40    A
19    B    41    A
20    C    42    A
21    A    43    A
22    C    44    A
23    A    46    C
24    A    47    C
表4（续）
48    A    80    A
49    A    81    A
50    B    82    A
51    B    83    A
52    A    84    A
53    C    86    A
55    A    87    C
56    C    88    C
57    C    89    A
59    A    90    C
60    C    92    A
66    C    93    A
67    A    94    B
68    A    96    A
69    B    97    B
70    C    98    A
71    C    101    C
72    A    102    B
73    C    103    A
75    A    104    C
77    C    105    A
78    B    106    A
79    A    107    A
表4（续）
109    A    133    A
110    A    134    A
111    A    135    A
112    A    136    A
113    A    137    A
114    A    138    A
115    A    139    A
116    B    140    A
118    A    141    A
119    A    142    A
120    A    143    A
121    B    144    A
122    A    145    A
123    A    146    A
124    A    147    A
125    A    148    A
126    A    149    A
127    A    150    A
128    A    151    A
129    A    152    A
130    A    153    A
131    A    154    A
132    A    155    A
表4（续）
156    A    179    A
157    A    180    A
158    A    181    A
159    A    182    B
160    B    183    A
161    B    184    A
162    C    185    A
163    A    186    A
164    A    187    A
165    A    188    A
166    A    189    A
167    A    190    A
168    A    191    A
169    A    192    A
170    A    193    C
171    A    194    A
172    A    197    A
173    C    198    A
174    A    199    A
175    B    200    A
176    A    201    A
177    A    202    A
178    A    203    A
表4（续）
204    A    227    A
205    B    228    A
206    A    229    A
207    A    230    A
208    A    231    A
209    A    232    A
210    A    233    A
211    A    234    B
212    A    235    A
213    A    236    A
214    C    237    A
215    B    238    A
216    A    239    B
217    B    240    A
218    A    241    A
219    A    242    A
220    A    243    A
221    B    244    A
222    C    245    A
223    A    246    A
224    A    247    A
225    A    248    B
226    A    249    A
表4（续）
250    A    281    B
253    A    282    A
254    A    283    A
255    A    284    A
256    A    285    A
257    A    286    A
258    A    287    A
259    A    288    A
260    A    289    A
261    C    290    A
263    C    292    A
265    A    293    A
266    A    294    A
271    B    295    A
272    A    296    A
273    A    297    B
274    A    298    A
275    A    299    A
276    A    300    A
277    A    301    A
278    A    302    A
279    A    303    A
280    A    304    A
表4（续）
305    A    330    A
306    A    331    A
307    A    332    A
308    A    333    C
309    A    334    A
310    A    335    A
311    C    336    A
312    A    337    B
313    A    338    A
314    A    339    A
315    A    340    A
316    A    341    A
317    C    342    A
318    A    343    A
319    A    344    A
320    A    345    A
321    A    346    A
322    A    347    A
323    A    348    A
324    B    349    A
327    A    350    A
328    B    351    B
329    A    352    A
表4（续）
353    A    380    A
354    B    381    A
355    A    382    A
356    A    383    A
357    A    385    B
358    A    386    A
359    A    387    A
360    A    388    A
361    A    389    C
362    A    391    A
363    A    392    A
364    A    393    A
365    A    394    A
366    A    396    A
369    A    397    A
370    A    398    A
371    A    399    A
372    A    400    A
373    B    401    A
374    B    402    A
375    B    403    A
376    B    404    A
379    A    405    A
表4（续）
406    B    参比化合物A    D
407    A
408    C    参比化合物B    D
参比化合物C    C

Claims (1)

  1. 下列通式(Ⅰ)化合物的制备方法
    Figure 901071374_IMG2
    (Ⅰ)
    其中
    R1和R2为C- 1-3烷基、R3和R4之一为C- 1-3烷基、具有1-3个碳原子的卤代烷基、C- 1-3烷氧基-C- 1-3烷基或苄氧基，而另一个为一个含氮原子的杂环，所说杂环选自吡咯烷、哌啶、吗啉、硫代吗啉、六亚甲基亚胺、四氢喹啉和四氢异喹啉，其氮原子上有R3或R4的基团健，所说杂环是未取代的或被至少一个下述基团取代：C- 1-3烷基、苯基、苄基、吡啶基、嘧啶基、1，3-二氧戊环基和卤代的1，3-二氧戊环基，
    其特征在于，使一种通式(Ⅱ)化合物
    Figure 901071374_IMG3
    (Ⅱ)
    其中，R1和R2的定义同式(Ⅰ)所述，X代表一个卤素原子，与一种通式(Ⅲ)化合物反应，
    Figure 901071374_IMG4
    (Ⅲ)
    其中，R3和R4的定义同式(Ⅰ)所述。
CN90107137A 1989-08-22 1990-08-22 N-(取代的苄氧基)亚胺衍生物、它们的制备方法、它们的应用以及应用的方法 Expired - Fee Related CN1024662C (zh)

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US10544092B2 (en) 2015-12-25 2020-01-28 Shenyang Sinochem Agrochemicals R&D Co., Ltd. Malononitrile oxime ether compound and use thereof

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KR910004546A (ko) 1991-03-28
DE69006290T2 (de) 1994-05-05
KR950002839B1 (ko) 1995-03-27
EP0414153B1 (en) 1994-01-26
DE69006290D1 (de) 1994-03-10
JPH03169842A (ja) 1991-07-23
AU628625B2 (en) 1992-09-17
CA2023515A1 (en) 1991-02-23
EP0414153A1 (en) 1991-02-27
US5104872A (en) 1992-04-14
AU6112790A (en) 1991-02-28
CA2023515C (en) 1997-02-11
CN1088384A (zh) 1994-06-29
CN1049654A (zh) 1991-03-06

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