CN1309897A - 不饱和肟醚类杀菌剂 - Google Patents

不饱和肟醚类杀菌剂 Download PDF

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CN1309897A
CN1309897A CN 00110143 CN00110143A CN1309897A CN 1309897 A CN1309897 A CN 1309897A CN 00110143 CN00110143 CN 00110143 CN 00110143 A CN00110143 A CN 00110143A CN 1309897 A CN1309897 A CN 1309897A
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CN1114590C (zh
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张立新
刘冬青
史蒂夫·H·塞伯
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
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Abstract

本发明涉及通式(Ⅰ)的不饱和肟醚结构及其立体异构体的杀菌化合物。式中X1-X5选自氢,卤素,烷基,烷氧基,硝基,卤烷基。与现有的不饱和肟醚类杀菌剂相比,它们具有更优良的杀菌活性。

Description

不饱和肟醚类杀菌剂
本发明属农用杀菌剂。
在中国专利公开CN1191670A中报导了具有不饱和肟醚结构的杀菌剂。这些不饱和肟醚结构的化合物具有广谱活性——可用于防治在各种作物上的由藻菌纲、卵菌纲、子囊菌纲和半知菌纲等多种真菌引起的病害。但是,现代农业和园艺上的发展要求我们不断创新,开发出使用剂量更小、药效更突出的农用杀菌剂。
为了获得在更小的剂量下就可以控制各种真菌病害的有效化合物,本发明者们在前述发明的基础上继续进行了大量的研究工作,合成、筛选出具有通式(Ⅰ)的不饱和肟醚结构的化合物。这些化合物具有广谱的杀菌活性,与现有技术中所公开的化合物相比,它们具有更高的杀菌活性,在更低的剂量下具有良好的防效,从而完成了本发明。
本发明涉及可用作杀菌剂的不饱和肟醚的衍生物、它们的制备方法和含有这些化合物的组合物。
本发明提供具有通式(Ⅰ)的不饱和肟醚化合物及其立体异构体:
式中X1-X5选自氢,卤素,烷基,烷氧基,硝基,卤烷基。
卤素包括氟、氯、溴和碘。
在本发明的化合物中,由于碳-碳双键和碳-氮双键连接不同的取代基而可以形成几何异构体(分别以E和Z来表示不同的构型),本发明包括E型异构体和Z型异构体及其任何比例的混合物。
可以用下面表(Ⅰ)中的化合物来说明本发明,但并不限定本发明。
表(Ⅰ)
    编号     X1     X2     X3     X4     X5
    1     2-Cl     3-H     4-H     5H     6-Cl
    2     2-Cl     3-Cl     4-H     5H     6-H
    3     2-Cl     3-H     4-Cl     5-H     6-H
    4     2-Cl     3-H     4-H     5-Cl     6-H
    5     2-H     3-Cl     4-Cl     5-H     6-H
    6     2-H     3-Cl     4-H     5-Cl     6-H
    7     2-Cl     3-Cl     4-Cl     5-H     6-H
    8     2-Cl     3-Cl     4-H     5-Cl     6-H
    9     2-Cl     3-Cl     4-H     5-H     6-Cl
    10     2-Cl     3-H     4-Cl     5-Cl     6-H
    11     2-Cl     3-H     4-Cl     5-H     6-Cl
    12     2-H     3-Cl     4-Cl     5-Cl     6-H
    13     2-Cl     3-Cl     4-Cl     5-Cl     6-H
    14     2-Cl     3-Cl     4-Cl     5-H     6-Cl
    15     2-Cl     3-Cl     4-H     5-Cl     6-Cl
    16     2-Cl     3-Cl     4-Cl     5-Cl     6-Cl
    17     2-F     3-H     4-H     5H     6-F
    18     2-F     3-F     4-H     5H     6-H
    19     2-F     3-H     4-F     5-H     6-H
    20     2-F     3-H     4-H     5-F     6-H
    21     2-H     3-F     4-F     5-H     6-H
    22     2-H     3-F     4-H     5-F     6-H
    23     2-Br     3-H     4-H     5H     6-Br
    24     2-Br     3-Br     4-H     5H     6-H
    25     2-Br     3-H     4-Br     5-H     6-H
    26     2-Br     3-H     4-H     5-Br     6-H
    27     2-H     3-Br     4-Br     5-H     6-H
    28     2-H     3-Br     4-H     5-Br     6-H
    29     2-Br     3-Br     4-Br     5-H     6-H
    30     2-Br     3-Br     4-H     5-Br     6-H
    31     2-Br     3-Br     4-H     5-H     6-Br
    32     2-Br     3-H     4-Br     5-Br     6-H
    33     2-Br     3-H     4-Br     5-H     6-Br
    34     2-H     3-Br     4-Br     5-Br     6-H
    35     2-Br     3-Br     4-Br     5-Br     6-H
    36     2-Br     3-Br     4-Br     5-H     6-Br
    37     2-Br     3-Br     4-H     5-Br     6-Br
    38     2-Br     3-Br     4-Br     5-Br     6-Br
    39     2-Cl     3-H     4-H     5H     6-F
    40     2-Cl      3-F      4-H     5H     6-H
    41     2-F      3-Cl      4-H     5H     6-H
    42     2-Cl      3-H      4-F     5-H     6-H
    43     2-F      3-H      4-Cl     5-H     6-H
    44     2-F      3-H      4-H     5-Cl     6-H
    45     2-Cl      3-H      4-H     5-F     6-H
    46     2-H      3-Cl      4-F     5-H     6-H
    47     2-H      3-F      4-Cl     5-H     6-H
    48     2-H      3-Cl      4-H     5-F     6-H
    49     2-F      3-Cl      4-Cl     5-H     6-H
    50     2-Cl      3-F      4-Cl     5-H     6-H
    51     2-Cl      3-Cl      4-F     5-H     6-H
    52     2-F      3-F      4-Cl     5-H     6-H
    53     2-Cl      3-F      4-F     5-H     6-H
    54     2-F      3-Cl      4-F     5-H     6-H
    55     2-F      3-F      4-F     5-H     6-H
    56     2-F      3-Cl      4-H     5-Cl     6-H
    57     2-Cl      3-F      4-H     5-Cl     6-H
    58     2-Cl      3-Cl      4-H     5-F     6-H
    59     2-F      3-F      4-H     5-Cl     6-H
    60     2-Cl      3-F      4-H     5-F     6-H
    61     2-F      3-Cl      4-H     5-F     6-H
    62     2-F      3-F      4-H     5-F     6-H
    63     2-F      3-Cl      4-H     5-H     6-Cl
    64     2-Cl      3-F      4-H     5-H     6-Cl
    65     2-Cl      3-Cl      4-H     5-H     6-F
    66     2-F      3-F      4-H     5-H     6-Cl
    67     2-F      3-Cl      4-H     5-H     6-F
    68     2-Cl      3-F      4-H     5-H     6-F
    69     2-F      3-F      4-H     5-H     6-F
    70     2-F      3-H      4-Cl     5-Cl     6-H
    71     2-Cl      3-H      4-F     5-Cl     6-H
    72     2-Cl      3-H      4-Cl     5-F     6-H
    73     2-F      3-H      4-F     5-Cl     6-H
    74     2-F      3-H      4-Cl     5-F     6-H
    75     2-Cl      3-H      4-F     5-F     6-H
    76     2-F      3-H      4-F     5-F     6-H
    77     2-F      3-H      4-Cl     5-H     6-Cl
    78     2-Cl      3-H      4-F     5-H     6-Cl
    79     2-F      3-H      4-F     5-H     6-Cl
    80     2-F      3-H      4-Cl     5-H     6-F
    81     2-F      3-H      4-F     5-H     6-F
    82     2-F     3-F      4-H     5-F     6-F
    83     2-F     3-F      4-F     5-F     6-F
    84     2-Cl     3-H      4-H     5H     6-CH3
    85     2-CH3     3-H      4-Cl     5-H     6-Cl
    86     2-Cl     3-H      4-CH3     5-H     6-Cl
    87     2-CH3     3-H      4-CH3     5-H     6-Cl
    88     2-CH3     3-H      4-Cl     5-H     6-CH3
    89     2-CH3     3-H      4-CH3     5-H     6-CH3
    90     2-Br     3-H      4-Cl     5-H     6-Cl
    91     2-Cl     3-H      4-Br     5-H     6-Cl
    92     2-Br     3-H      4-Br     5-H     6-Cl
    93     2-Br     3-H      4-Cl     5-H     6-Br
    94     2-Br     3-H      4-H     5H     6-F
    95     2-F     3-H      4-Br     5-H     6-Br
    96     2-Br     3-H      4-F     5-H     6-Br
    97     2-F     3-H      4-F     5-H     6-Br
    98     2-F     3-H      4-Br     5-H     6-F
    99     2-Cl     3-H      4-H     5H     6-OCH3
    100     2-OCH3     3-H      4-Cl     5-H     6-Cl
    101     2-Cl     3-H      4-OCH3     5-H     6-Cl
    102     2-OCH3     3-H      4-OCH3     5-H     6-Cl
    103     2-OCH3     3-H      4-Cl     5-H     6-OCH3
    104     2-Cl     3-H      4-H     5H     6-NO2
    105     2-NO2     3-H      4-Cl     5-H     6-Cl
    106     2-Cl     3-H      4-NO2     5-H     6-Cl
    107     2-NO2     3-H      4-Cl     5-H     6-NO2
    108     2-Cl     3-H      4-H     5H     6-CF3
109 2-Cl 3-H 4-CF3 5-H 6-Cl
110 2-Cl 3-Cl 4-CF3 5-H 6-CF3
    111     2-F     3-H      4-H     5H     6-CF3
    112     2-Cl     3-H      4-H     5H     6-I
本发明通式(Ⅰ)的化合物可以通过下述反应式所示的步骤来制备。其中X的定义同上,Z是离去基团,如卤素(氯、溴或碘)。
Figure A0011014300071
Figure A0011014300081
通式(Ⅳ)的化合物可以这样来制备:在适当的溶剂中如二甲基甲酰胺、四氢呋喃、丙酮或丁酮,用适当的碱如氢氧化钠、甲醇钠或氢化钠处理通式(Ⅲ)所示的肟,然后加入通式(Ⅱ)的化合物。
通式(Ⅲ)的肟可以由相应的α、β不饱和酮与盐酸羟胺在适当的溶剂(如甲醇或乙醇)中,并有适当的碱(如氢氧化钠或碳酸钾)存在下反应来获得。
欧洲专利申请EP254426中叙述了Z是溴的(E)构型的通式(Ⅱ)的化合物。
通式(Ⅰ)的化合物可以由通式(Ⅳ)的化合物与甲胺水溶液反应很容易的获得。
本发明的化合物是更有效的杀菌剂。它们具有内吸活性并可用作叶面和土壤杀菌剂。特别适合于防治下列植物病害:
水稻稻瘟病(Pyricularia oryzae);小麦条锈病(Puccinia striiformis)、叶锈病(Puccinia recondita)和其它锈病;大麦条锈病(Puccinia striiformis)、叶锈病(Puccinia recandita)和其它锈病;大麦和小麦白粉病、黄瓜白粉病、苹果白粉病和葡萄白粉病。
小麦纹枯病和颖枯病(Septoria nodorum)。谷物上的长蠕孢、嘴孢霉、壳针孢属病、核球壳菌属病、Pseudocercosporella herpotrichoides和Gaeumannomyces graminis。花生Cercospora arachidicola和Cercosporidiumpersonata甜菜、大豆和稻谷上的其它尾孢霉属病。番茄、黄瓜、葡萄灰霉病(Botrytic cinerea)。蔬菜(如黄瓜)上的铰链孢属病。黄瓜上的炭疽病,苹果黑星病,黄瓜霜霉病,葡萄霜霉病,马铃薯和番茄上的疫霉,稻谷上的Thanatephorus cucumeris以及其它宿主如小麦和大麦、蔬菜上的其它丝核菌。
本发明还提供了如上所定义的组合物的制备方法,方法是将通式(Ⅰ)的化合物和至少一种载体混合。这种组合物可以含本发明的单一化合物或几种化合物的混合物。
按照本发明的组合物,优选含从1-99%重量的活性成分。本发明的载体为满足下述条件的物质:它与活性成分配制后便于施用于待处理的位点,例如可以是植物、种子或土壤;或者有利于贮存、运输或操作。载体可以是固体或液体,包括通常为气体但已压缩成液体的物质和可使用任何通常在配制杀虫、杀菌组合物中所用的载体。
合适的固体载体包括天然和合成的黏土和硅酸盐,例如硅藻土、滑石、硅镁土、硅酸铝(高岭土)、蒙脱石和云母、碳酸钙、硫酸钙、硫酸铵;合成的氧化硅和合成硅酸钙或硅酸铝;元素如碳和硫;天然的和合成的树脂如苯并呋喃树脂,聚氯乙烯和苯乙烯聚合物和共聚物;固体多氯苯酚;沥青;蜡如蜂蜡,石蜡。
合适的液体载体包括水;醇如异丙醇和乙醇;酮如丙酮、甲基乙基酮、甲基异丁基酮和环己基酮;醚;芳烃如苯、甲苯和二甲苯;石油馏分如煤油和矿物油;氯代烃如四氯化碳、全氯乙烯和三氯乙烷。通常,这些液体的混合物也是合适的。
杀虫、杀菌组合物通常在施用之前将其稀释。少量的表面活性剂载体的存在有助于稀释过程。在本发明的组合物中,至少含有一种载体,优选以表面活性剂作载体。例如组合物可含有至少两种载体,其中至少一种是表面活性剂。
表面活性剂可以是乳化剂、分散剂或润湿剂;它可以是非离子的或离子的表面活性剂。合适的表面活性剂包括聚丙烯酸和木质素磺酸的钠盐或钙盐;分子中含至少12个碳原子的脂肪酸或脂肪胺或酰胺与环氧乙烷和/或环氧丙烷的缩合物;甘醇,山梨醇,蔗糖或季戊四醇脂肪酸酯及这些酯与环氧乙烷和/或环氧丙烷的缩合物;脂肪醇或烷基苯酚如对辛基苯酚或对辛基甲苯酚与环氧乙烷和/或环氧丙烷的缩合物;这些缩合产物的硫酸盐或磺酸盐;在分子中含有至少10个碳原子的硫酸或磺酸酯的碱金属或碱土金属盐,优选钠盐;例如硫酸月桂酯钠,硫酸仲烷基酯钠,磺化蓖麻油钠盐,磺酸烷基芳基酯钠如十二烷基苯磺酸钠盐。
本发明的组合物的实例是可湿性粉剂、粉剂、颗粒剂和溶液,可乳化的浓缩剂、乳剂、悬浮浓缩剂、气雾剂和烟雾剂。可湿性粉剂通常含25,50或75%(重量)活性成分,且通常除固体惰性载体之外,还含有3-10%(重量)的分散剂,且若需要可加入0-10%(重量)稳定剂和/或其它添加剂如渗透剂或粘着剂。粉剂通常可成型为具有与可湿性粉剂相似的组成但没有分散剂的粉剂浓缩剂,在地里进一步用固体载体稀释,得到通常含0.5-10%(重量)活性成分的组合物。粒剂通常制备成具有10和100目(1.676-0.152mm)大小,且可用成团或注入技术制备。通常,粒剂含0.5-75%(重量)的活性成分和0-10%(重量)添加剂如稳定剂、表面活性剂、缓释改良剂。所谓的“可流动干粉”由具有相对高浓度活性成分的相对小的颗粒组成。可乳化浓缩剂除溶剂外,当需要时通常含有共溶剂,1-50%W/V活性成分,2-20%W/V乳化剂和0-20%W/V其它添加剂如稳定剂、渗透剂和腐蚀抑制剂,悬浮浓缩剂通常含有10-75%(重量)的活性成分、0.5-15%(重量)的分散剂、0.1-10%(重量)的其它添加剂如消泡剂、腐蚀抑制剂、稳定剂、渗透剂和粘着剂。
水分散剂和乳剂,例如通过用水稀释按照本发明的可湿性粉剂或浓缩物得到的组合物,也列入本发明范围。所说的乳剂可具有油包水或水包油两个类型。
通过在组合物中加入其它的一种或多种杀菌剂,使其能比单独的通式(Ⅰ)化合物具有更广谱的活性。此外,其它杀菌剂可对通式(Ⅰ)化合物的杀菌活性具有增效作用。可以包含在本发明组合物中的杀菌剂化合物的实例有:腈菌唑、粉锈宁、苯菌灵、多菌灵、百菌清、王铜、波尔多液、麦穗宁、双胍辛盐、土菌消、富士一号、春雷霉素、代森锰锌、代森锰、代森锌、多氧霉素、甲基代森锌、甲基托布津、福美双、十三吗啉、烯酰吗啉等。
可以与本发明的化合物混合形成组合物的合适杀虫剂包括乐果、氧化乐果、毒死蜱、甲基毒死蜱、甲胺磷、久效磷、倍硫磷、辛硫磷、唑蚜威、吡虫啉和拟除虫菊酯类如氰戊菊酯、甲氰菊酯、氟胺氰菊酯、氯氟氰菊酯等。
本发明的化合物与现有技术中所公开的不饱和肟醚类杀菌剂相比具有更好的杀菌活性。中国专利公开CN1191670A中的化合物对各种真菌病害的防效试验其待测化合物浓度为100mg/L时是有效的;而本发明所提供的化合物当其浓度降为对照化合物的1/4甚至1/16时,其杀菌活性仍大大优于对照化合物。这种优异的杀菌效果使本发明的发明者达到了发明一种在更小的剂量下就可以控制各种真菌病害的有效化合物的目的,在不饱和肟醚类杀菌剂领域中完成了又一项重要发明。
下面以具体的实施例来说明本发明,但并不限定本发明。
合成实施例
实例1  化合物1的合成
17.5克(0.1摩尔)2,6-二氯苯甲醛溶于100毫升丙酮中,向其中滴加5克10%的氢氧化钠水溶液,滴加过程中保持温度不超过40℃。滴加完继续搅拌一小时。混合物倒入水中,用乙酸乙酯提取,再用水洗涤提取物三次,干燥浓缩得浅黄色油状物即2,6-二氯苯乙烯基甲基酮20.4克,收率94.9%。
将10克(0.0465摩尔)2,6-二氯苯乙烯基甲基酮、7.77克盐酸羟胺(0.093摩尔)和12.9克(0.093摩尔)碳酸钾在150毫升乙醇中回流3小时。将反应混合物浓缩,用水稀释并用乙酸乙酯提取。合并的提取液干燥浓缩,得2,6-二氯苯乙烯基甲基酮肟9.3克,为浅黄色固体。收率86.93%。
在室温下将2.3克(0.01摩尔)2,6-二氯苯乙烯基甲基酮肟的N,N-二甲基甲酰胺溶液(10毫升)滴加到含有0.4克(0.01摩尔)氢氧化钠的N,N-二甲基甲酰胺悬浮液(10毫升)中。半小时后,将2.86克(0.01摩尔)(E)-2-(溴甲基)苯酰基甲酸甲酯-O-甲基肟的N,N-二甲基甲酰胺溶液(10毫升)加到反应混合物中,在室温下继续搅拌2小时。将混合物倒入水中,用乙酸乙酯提取2次。合并的提取液用水洗涤3次,然后干燥、浓缩,得粗产品。用乙酸乙酯和石油醚的混合液(1∶5)为洗脱液进行柱层析得到浅黄色油状物1.28克,收率29.43%。
将0.75克(0.00172摩尔)上述化合物与3倍摩尔比的甲胺40%水溶液在50毫升甲醇中加热回流过夜,浓缩后用乙酸乙酯提取2次,合并的提取物用水洗涤3次,然后干燥,浓缩,得到标题化合物0.55克,为白色固体,收率73.3%。熔点131-133℃
核磁共振数据:2.03(3H单峰)2.82-2.87(3H双峰)3.87(3H单峰)4.97(2H单峰)6.5-6.6(1H多峰)6.71(2H单峰)6.80-7.50(7H多峰)
实例2    化合物2的合成
17.5克(0.1摩尔)2,3-二氯苯甲醛溶在100毫升丙酮中,向内滴加5克10%的氢氧化钠水溶液,在滴加过程中保持温度不超过40℃,之后继续搅拌一小时。混合物倒入水中,加入乙酸乙酯提取,用水洗涤三次,干燥浓缩得浅黄色油状物2,3-二氯苯乙烯基甲基酮20.2克,收率93.9%。
将10克(0.0465摩尔)2,3-二氯苯乙烯基甲基酮、7.77克盐酸羟胺(0.093摩尔)和12.9克(0.093摩尔)碳酸钾在150毫升乙醇中回流3小时。将反应混合物浓缩,用水稀释并用乙酸乙酯提取。合并的提取液干燥浓缩,得2,3-二氯苯乙烯基甲基酮肟9.5克,为浅黄色固体,收率88.8%。
在室温下将2.3克(0.01摩尔)2,3-二氯苯乙烯基甲基酮肟的N,N-二甲基甲酰胺溶液(10毫升)滴加到含有0.4克(0.01摩尔)氢氧化钠的N,N-二甲基甲酰胺悬浮液(10毫升)中。半小时后,将2.86克(0.01摩尔)(E)-2-(溴甲基)苯酰基甲酸甲酯-O-甲基肟的N,N-二甲基甲酰胺溶液(10毫升)加到反应混合物中,在室温下继续搅拌2小时。将混合物倒入水中,用乙酸乙酯提取2次。合并的提取液用水洗涤3次,然后干燥、浓缩,得粗产品。用乙酸乙酯和石油醚的混合液(1∶5)为洗脱液进行柱层析得到浅黄色油状物1.38克,收率31.73%。
将0.75克(0.00172摩尔)上述化合物与3倍摩尔比的甲胺40%水溶液于50毫升甲醇中加热回流过夜,浓缩后用乙酸乙酯提取2次,合并的提取物用水洗涤3次,然后干燥、浓缩,得到标题化合物0.65克,为粘稠油状物,收率86.63%。
核磁共振数据:2.04(3H单峰)2.82-2.87(3H双峰)3.89(3H单峰)5.01(2H单峰)6.5-6.6(1H多峰)6.70(2H单峰)6.80-7.50(7H多峰)
实例3    化合物3的合成
17.5克(0.1摩尔)2,4-二氯苯甲醛溶于100毫升丙酮中,向其中滴加5克10%的氢氧化钠水溶液,滴加过程中保持温度不超过40℃,之后继续搅拌一小时。混合物倒入水中,加入乙酸乙酯提取,再用水洗涤三次,干燥浓缩得浅黄色油状物2,4-二氯苯乙烯基甲基酮20.6克,收率95.8%。
将10克(0.0465摩尔)2,4-二氯苯乙烯基甲基酮、7.77克盐酸羟胺(0.093摩尔)和12.9克(0.093摩尔)碳酸钾在150毫升乙醇中回流3小时。将反应混合物浓缩,用水稀释并用乙酸乙酯提取。合并的提取液干燥浓缩,得2,4-二氯苯乙烯基甲基酮肟9.1克,为浅黄色固体,收率85.06%。
在室温下将2.3克(0.01摩尔)2,4-二氯苯乙烯基甲基酮肟的N,N-二甲基甲酰胺溶液(10毫升)滴加到含有0.4克(0.01摩尔)氢氧化钠的N,N-二甲基甲酰胺悬浮液(10毫升)中。半小时后,将2.86克(0.01摩尔)(E)-2-(溴甲基)苯酰基甲酸甲酯-O-甲基肟的N,N-二甲基甲酰胺溶液(10毫升)加到反应混合物中,在室温下继续搅拌2小时。将混合物倒入水中,用乙酸乙酯提取2次。合并的提取液用水洗涤3次,然后干燥、浓缩,得粗产品。用乙酸乙酯和石油醚的混合液(1∶5)为洗脱液进行柱层析得到浅黄色油状物1.35克,收率31.04%。
将0.75克(0.00172摩尔)上述化合物与3倍摩尔比的甲胺40%水溶液在50毫升甲醇中加热回流过夜,浓缩后用乙酸乙酯提取2次,合并的提取物用水洗涤3次,然后干燥、浓缩,得到标题化合物0.63克,为粘稠油状物,收率83.96%。
核磁共振数据:2.03(3H单峰)2.82-2.87(3H双峰)3.88(3H单峰)5.01(2H单峰)6.4-6.6(1H多峰)6.68(2H单峰)6.75-7.50(7H多峰)
实例4    化合物17的合成
14.2克(0.1摩尔)2,6-二氟苯甲醛溶在100毫升丙酮中,向内滴加5克10%的氢氧化钠水溶液,在滴加过程中要保持温度不超过40℃,继续搅拌一小时。混合物倒入水中,加入乙酸乙酯提取,用水洗涤三次,干燥浓缩得浅黄色油状物2,6-二氟苯乙烯基甲基酮15.7克,收率86.26%。
将8.46克(0.0465摩尔)2,6-二氟苯乙烯基甲基酮、7.77克盐酸羟胺(0.093摩尔)和12.9克(0.093摩尔)碳酸钾在150毫升乙醇中回流3小时。将反应混合物浓缩,用水稀释并用乙酸乙酯提取。合并的提取液干燥浓缩,得2,6-二氟苯乙烯基甲基酮肟7.91克,为浅黄色固体。收率86.37%。
在室温下将1.97克(0.01摩尔)2,6-二氟苯乙烯基甲基酮肟的N,N-二甲基甲酰胺溶液(10毫升)滴加到含有0.4克(0.01摩尔)氢氧化钠的N,N-二甲基甲酰胺悬浮液(10毫升)中。半小时后,将2.86克(0.01摩尔)(E)-2-(溴甲基)苯酰基甲酸甲酯-O-甲基肟的N,N-二甲基甲酰胺溶液(10毫升)加到反应混合物中,在室温下继续搅拌2小时。将混合物倒入水中,用乙酸乙酯提取2次。合并的提取液用水洗涤3次,然后干燥,浓缩,得粗产品。用乙酸乙酯和石油醚的混合液(1∶5)为洗脱液进行柱层析得到浅黄色油状物1.18克,收率29.35%。
将0.75克(0.00186摩尔)上述化合物与3倍摩尔比的甲胺40%水溶液在50毫升甲醇中加热回流过夜,浓缩后用乙酸乙酯提取2次,合并的提取物用水洗涤3次,然后干燥、浓缩,得到标题化合物0.51克,为粘稠油状物,收率68.17%。
核磁共振数据:2.01(3H单峰)2.82-2.88(3H双峰)3.87(3H单峰)4.97(2H单峰)6.6-7.40(10H多峰)
实例5    化合物39的合成
15.8克(0.1摩尔)2-氯-6-氟苯甲醛溶于100毫升丙酮中,向其中滴加5克10%的氢氧化钠水溶液,滴加过程中保持温度不超过40℃,之后继续搅拌一小时。混合物倒入水中,加入乙酸乙酯提取,用水洗涤三次,干燥、浓缩得浅黄色油状物2-氯-6-氟苯乙烯基甲基酮15.7克,收率79.34%。
将9.23克(0.0465摩尔)2-氯-6-氟苯乙烯基甲基酮、7.77克盐酸羟胺(0.093摩尔)和12.9克(0.093摩尔)碳酸钾在150毫升乙醇中回流3小时。将反应混合物浓缩,用水稀释并用乙酸乙酯提取。合并的提取液干燥浓缩,得2-氯-6-氟苯乙烯基甲基酮肟8.38克,为浅黄色固体。收率84.41%。
在室温下将2.14克(0.01摩尔)2-氯-6-氟苯乙烯基甲基酮肟的N,N-二甲基甲酰胺溶液(10毫升)滴加到含有0.4克(0.01摩尔)氢氧化钠的N,N-二甲基甲酰胺悬浮液(10毫升)中。半小时后,将2.86克(0.01摩尔)(E)-2-(溴甲基)苯酰基甲酸甲酯-O-甲基肟的N,N-二甲基甲酰胺溶液(10毫升)加到反应混合物中,室温下继续搅拌2小时。将混合物倒入水中,用乙酸乙酯提取2次。合并的提取液用水洗涤3次,然后干燥、浓缩,得粗产品。用乙酸乙酯和石油醚的混合液(1∶5)为洗脱液进行柱层析得到浅黄色油状物1.24克,收率29.63%。
将0.75克(0.00179摩尔)上述化合物与3倍摩尔比的甲胺40%水溶液在50毫升甲醇中加热回流过夜,浓缩后用乙酸乙酯提取2次,合并的提取物用水洗涤3次,然后干燥、浓缩,得到标题化合物0.59克,为粘稠油状物,收率78.85%。
核磁共振数据:2.02(3H单峰)2.83-2.88(3H双峰)3.87(3H单峰)4.97(2H单峰)6.4-7.40(10H多峰)
配方实施例
实例6
将10份(重量)的化合物1溶解在下述混合物中,该混合物含90份(重量)二甲苯、6份(重量)的壬基酚聚氧乙烯醚、2份(重量)的十二烷基苯磺酸钙和2份(重量)的40摩尔环氧乙烷与1摩尔蓖麻油的加成产物来制备乳油(活性化合物含量为9%)。
生测实施例
实例7
部分化合物进行了杀菌活性试验。方法如下:待测化合物溶于1∶1丙酮和甲醇混合物,再以2∶1∶1水、丙酮和甲醇混合物(体积比)稀释至所需浓度。此溶液喷到待测植物上晾干2小时,一天后进行病菌接种。活性相对于空白对照以百分比计,分为A、B、C、D四级,控制率90%-100%为A级,控制率75%-90%为B级,控制率50%-75%为C级,控制率0%-50%为D级
黄瓜白粉病
施药一天后接种。接种后在温室中放置7天左右调查。测试结果见表(2)
                                               表(2)
       化合物  浓度(mg/l)    活性  浓度(mg/l)    活性
         1     25     A     6     A
         17     25     A     6     A
         39     25     A     6     A
    对照化合物1(4)     25     D     6     D
    对照化合物2(5)     25     D     6     D
    对照化合物3(6)     25     D     6     D
   对照化合物4(10)     25     D     6     D
   对照化合物5(2)     25     C     6     D
   对照化合物6(7)     25     D     6     D
   对照化合物7(9)     25     D     6     D
   对照化合物8(11)     25     D     6     D
   对照化合物9(12)     25     D     6     D
   对照化合物10(13)     25     D     6     D
   对照化合物11(19)     25     D     6     D
   对照化合物12(23)     25     D     6     D
   对照化合物13(40)     25     D     6     D
   对照化合物14(42)     25     D     6     D
   对照化合物15(45)     25     D     6     D
        CK     -     O     -      -
*对照化合物为CN1191670A中的化合物,括号内为该专利化合物表中的编号。
在25mg/l浓度下,本发明的化合物控制率为A级,而对照化合物中只有化合物5的控制率为C级,其余都为D级;在6mg/l浓度下,本发明的化合物控制率为A级,所有的对照化合物基本无效。从测试结果可以看出,本发明的化合物对黄瓜白粉病具有良好的防效,明显优于对照化合物。
水稻稻瘟病
施药一天后接种。接种后在保湿箱中保湿36小时以利于侵染,移入温室,7天左右后调查。测试结果见表(3)
                                               表(3)
      化合物  浓度(mg/l)    活性  浓度(mg/l)    活性
        1     25     A     6     A
        17     25     A     6     A
        39     25     A     6     A
    对照化合物1(4)     25     B     6     D
    对照化合物2(5)     25     C     6     D
    对照化合物3(6)     25     D     6     D
    对照化合物4(10)     25     D     6     D
    对照化合物5(2)     25     C     6     D
    对照化合物6(7)     25     D     6     D
    对照化合物7(9)     25     D     6     D
    对照化合物8(11)     25     D     6     D
    对照化合物9(12)     25     B     6     C
    对照化合物10(13)     25     B     6     D
    对照化合物11(19)     25     D     6     D
    对照化合物12(23)     25     C     6     C
    对照化合物13(40)     25     B     6     D
    对照化合物14(42)     25     D     6     D
    对照化合物15(45)     25     D     6     D
        CK     -     O
*对照化合物为CN1191670A中的化合物,括号内为该专利化合物表中的编号。
在25mg/l浓度下,本发明的化合物控制率为A级,而所有的对照化合物控制率都在B级以下;在6mg/l浓度下,本发明的化合物控制率为A级,所有的对照化合物基本无效。从测试结果可以看出,本发明的化合物对水稻稻瘟病具有良好的防效,明显优于对照化合物。
黄瓜灰霉病
施药一天后接种。接种后在恒温恒湿箱中放置5天左右后调查。测试结果见表(4)
                                              表(4)
    化合物  浓度(mg/l)    活性  浓度(mg/l)    活性
    1     25     A     6     A
    17     25     A     6     A
        39     25     A     6     A
    对照化合物1(4)     25     D     6     D
    对照化合物2(5)     25     B     6     D
    对照化合物3(6)     25     D     6     D
    对照化合物4(10)     25     D     6     D
    对照化合物5(2)     25     D     6     D
    对照化合物6(7)     25     C     6     D
    对照化合物7(9)     25     D     6     D
    对照化合物8(11)     25     D     6     D
    对照化合物9(12)     25     D     6     D
    对照化合物10(13)     25     B     6     C
    对照化合物11(19)     25     D     6     D
    对照化合物12(23)     25     D     6     D
    对照化合物13(40)     25     C     6     C
    对照化合物14(42)     25     B     6     D
    对照化合物15(45)     25     B     6     C
        CK     25     D     6     D
*对照化合物为CN1191670A中的化合物,括号内为该专利化合物表中的编号。
在25mg/l浓度下,本发明的化合物控制率为A级,而所有的对照化合物控制率都在B级以下;在6mg/l浓度下,本发明的化合物控制率为A级,所有的对照化合物都在C级以下。从测试结果可以看出,本发明的化合物对黄瓜灰霉病的防效明显优于对照化合物。小麦叶锈病
施药一天后接种。接种后在温室中放置10天左右后调查。测试结果见表(5)
                                             表(5)
       化合物  浓度(mg/l)    活性  浓度(mg/l)    活性
         1     25     A     6     A
        17     25     A     6     A
        39     25     A     6     A
    对照化合物1(4)     25     B     6     C
    对照化合物2(5)     25     C     6     D
    对照化合物3(6)     25     D     6     D
    对照化合物4(10)     25     D     6     D
    对照化合物5(2)     25     C     6     D
对照化合物6(7)     25     D     6     D
对照化合物7(9)     25     D     6     D
对照化合物8(11)     25     D     6     D
对照化合物9(12)     25     B     6     D
对照化合物10(13)     25     B     6     D
对照化合物11(19)     25     D     6     D
对照化合物12(23)     25     B     6     D
对照化合物13(40)     25     B     6     D
对照化合物14(42)     25     B     6     D
对照化合物15(45)     25     D     6     D
    CK     -     O
*对照化合物为CN1191670A中的化合物,括号内为该专利化合物表中的编号。
在25mg/l浓度下,本发明的化合物控制率为A级,而所有的对照化合物控制率都在B级以下;在6mg/l浓度下,本发明的化合物控制率为A级,所有的对照化合物基本无效。从测试结果可以看出,本发明的化合物对小麦叶锈病的防效明显优于对照化合物。小麦白粉病
施药一天后接种。接种后在温室中放置7天左右后调查。测试结果见表(6)
                                               表(6)
       化合物 浓度(mg/l)    活性  浓度(mg/l)   活性
          1     25     A     6     A
          17     25     A     6     A
          39     25     A     6     A
    对照化合物1(4)     25     C     6     D
    对照化合物2(5)     25     C     6     D
    对照化合物3(6)     25     D     6     D
    对照化合物4(10)     25     D     6     D
    对照化合物5(2)     25     B     6     D
    对照化合物6(7)     25     D     6     D
    对照化合物7(9)     25     D     6     D
    对照化合物8(11)     25     D     6     D
    对照化合物9(12)     25     B     6     C
    对照化合物10(13)     25     B     6     D
    对照化合物11(19)     25     D     6     D
对照化合物12(23)     25     C     6     D
对照化合物13(40)     25     B     6     D
对照化合物14(42)     25     D     6     D
对照化合物15(45)     25     D     6     D
    CK     -     O
*对照化合物为CN1191670A中的化合物,括号内为该专利化合物表中的编号。
在25mg/l浓度下,本发明的化合物控制率为A级,而所有的对照化合物控制率都在B级以下;在6mg/l浓度下,本发明的化合物控制率为A级,所有的对照化合物基本无效。从测试结果可以看出,本发明的化合物对小麦白粉病具有良好的防效,明显优于对照化合物。黄瓜炭疽病
施药一天后接种。接种后在温室中放置7天左右后调查。测试结果见表(7)
                                  表(7)
        化合物  浓度(mg/l)    活性 浓度(mg/l)    活性
         1     25     A     6     A
         17     25     A     6     A
         39     25     A     6     A
    对照化合物1(4)     25     B     6     C
    对照化合物2(5)     25     C     6     D
    对照化合物3(6)     25     D     6     D
    对照化合物4(10)     25     D     6     D
    对照化合物5(2)     25     C     6     C
    对照化合物6(7)     25     D     6     D
    对照化合物7(9)     25     D     6     D
    对照化合物8(11)     25     D     6     D
    对照化合物9(12)     25     B     6     D
    对照化合物10(13)     25     B     6     D
    对照化合物11(19)     25     D     6     D
    对照化合物12(23)     25     B     6     D
    对照化合物13(40)     25     B     6     D
    对照化合物14(42)     25     B     6     B
    对照化合物15(45)     25     D     6     D
         CK     -     O
*对照化合物为CN1191670A中的化合物,括号内为该专利化合物表中的编号。
在25mg/l浓度下,本发明的化合物控制率为A级,而所有的对照化合物控制率都在B级以下;在6mg/l浓度下,本发明的化合物控制率为A级,只有对照化合物14的控制率为B级,其它所有的对照化合物基本无效。从测试结果可以看出,本发明的化合物对黄瓜炭疽病具有良好的防效,明显优于对照化合物。

Claims (9)

1、不饱和肟醚类杀菌剂,其特征在于本发明具有通式(Ⅰ)的不饱和肟醚结构及其立体异构体:
Figure A0011014300021
式中X1-X5选自氢,卤素,烷基,烷氧基,硝基,卤烷基。
卤素包括氟、氯、溴和碘。
2、根据权利要求1所述的化合物,其特征在于:式(Ⅰ)中X1-X5至少有二个选自卤素,烷基,烷氧基,硝基,卤烷基。
3、根据权利要求1或2所述的化合物,其特征在于:式(Ⅰ)中X1、X5选自卤素,X2-X4选自氢,卤素,烷基,烷氧基,硝基,卤烷基。
4、根据权利要求1或2所述的化合物,其特征在于:式(Ⅰ)中X1、X5选自卤素,X2-X4为氢。
5、根据权利要求4所述的化合物,其特征在于:当式(Ⅰ)中X1、X5为氯,X2-X4为氢时,所述化合物为N-甲基2-[2-((((1-甲基-3-(2’,6’-二氯苯基)-2-丙烯基)氨基)氧基)甲基)苯基]-2-甲氧基亚胺基乙酰胺,结构式为:
6、根据权利要求4所述的化合物,其特征在于:当式(Ⅰ)中X1为氯,X2-X4为氢,X5为氟时,所述化合物为N-甲基2-[2-((((1-甲基-3-(2’-氯-6’-氟苯基)-2-丙烯基)氨基)氧基)甲基)苯基]-2-甲氧基亚胺基乙酰胺,结构式为:
Figure A0011014300031
7、根据权利要求4所述的化合物,其特征在于:当式(Ⅰ)中X1、X5为氟,X2-X4为氢时,所述化合物为N-甲基2-[2-((((1-甲基-3-(2’,6’-二氟苯基)-2-丙烯基)氨基)氧基)甲基)苯基]-2-甲氧基亚胺基乙酰胺,结构式为:
8、一种杀菌剂组合物,其特征在于:该组合物含有权利要求1中所述的化合物为活性成分和其它农业上可以接受的载体或稀释剂。
9、本发明通式(Ⅰ)的化合物或其制剂可用于防治在各种作物上由藻菌纲、卵菌纲、子囊菌纲和半知菌纲等多种真菌引起的病害。
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