CN1907024A - 取代甲氧基丙烯酸甲酯类化合物杀菌剂 - Google Patents

取代甲氧基丙烯酸甲酯类化合物杀菌剂 Download PDF

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CN1907024A
CN1907024A CNA2005100602717A CN200510060271A CN1907024A CN 1907024 A CN1907024 A CN 1907024A CN A2005100602717 A CNA2005100602717 A CN A2005100602717A CN 200510060271 A CN200510060271 A CN 200510060271A CN 1907024 A CN1907024 A CN 1907024A
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cooch
methyl acrylate
methyl
methoxy
phenyl
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孔小林
胡伟群
郑昀红
张晓铭
朱卫纲
窦花妮
陈定花
邢家华
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ZHEJIANG CHEM-TECH GROUP Co Ltd
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ZHEJIANG CHEM-TECH GROUP Co Ltd
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Abstract

本发明涉及一组通式I所示的甲氧基丙烯酸甲酯类化合物。其中X＝F或H；Q＝N或CH；R1、R2、R3、R4＝H、NO2、CN、Cl、C1－C9的烷基或不饱和烃基、C1－C6的烷氧亚胺甲基、C1－C6的烷氧基羰基。本发明还涉及该组化合物的制备方法，以及本发明在农用杀菌剂中的应用。生物活性评价结果表明：化合物I对防治农业上多种真菌引起的病害有很好的防效，尤其对多种植物的白粉病、霜霉病、炭疽病有特效。

Description

取代甲氧基丙烯酸甲酯类化合物杀菌剂
                        技术领域
本发明主要涉及新的甲氧基丙烯酸甲酯类化合物，该类化合物的制备方法，以及该类化合物作为农用杀菌剂的应用。
                        背景技术
甲氧基丙烯酸甲酯类杀菌剂是从天然化合物通过结构改造而来的高效农用杀真菌剂。它们特点是杀菌广、对其它生物毒性低、环境相容性好。世界上有许多农药大公司进行这方面研究，发现了几个有很好市场前景的甲氧基丙烯酸甲酯类化合物。该类杀菌剂市场占有比例越来越大，将可能取代三唑类杀菌剂成为农用杀菌剂第一大品种。
在US 4,914,128号专利申请中公开了一些甲氧基丙烯酸甲酯类化合物，并公开了其中的化合物具有杀菌活性。
在PCT/CN2004/000226号专利申请中公开了一种在侧链苯环上有2，5-二甲基取代的化合物具有杀菌活性，但未涉及其它2，5-位取代的化合物。
在PCT/EP95/03683号专利申请中公开了一组以单氟甲氧基替换原有甲氧基的氟甲氧基丙烯酸甲酯化合物具有杀菌活性，但未涉及侧链为杂环的化合物，也未涉及侧链苯环上有硝基或烷氧羰基的化合物。同时也未涉及到侧链苯环上仅有烷氧亚胺甲基取代基的化合物。
发明内容
本发明的目的之一是提供一系列作杀菌剂用的新的甲氧基丙烯酸甲酯类化合物，包括以取代吡啶基或带特殊取代基苯基为侧链的氟甲氧基丙烯酸甲酯类化合物，和以2，5-取代苯基(除2，5-二甲苯基外)为侧链的甲氧基丙烯酸甲酯类化合物，这些化合物均为未曾有任何报道的新化合物。本发明的另一目的是提供合成这一系列甲氧基丙烯酸甲酯的合成方法。
发明人通过分析、研究，合成了下述通式的系列化合物：
当X＝F，Q＝N时，R1、R2、R3、R4＝H、NO2、CN、Cl、CH3COOR6(R6为取代或未取代烷基)或CF3；当X＝F，Q＝CH，R1＝NO2时，R2，R4＝H；
当X＝F，Q＝CH，R1＝R2＝R4＝H，R3＝CH＝N-OR5或COOR5，其中R5＝CH3、C2H5、n-C3H7、i-C3H7、n-C4H9、i-C4H9、t-C4H9。
当X＝H，Q＝CH时，R2，R3＝H；R1＝OMe、CH3或N(C2H5)2；R4＝CH3，CN，COOCH3，COOC2H5，COOC3H7-n，COOCH(CH3)2，COOCH2CH(CH3)2，COOC4H9-n，COOCH2CF3，COOCH2CH2Cl，COOCH2CH＝CH2COOCH(CH2Cl)2，COOCH2CCH，COOCH(CH3)CH2CH2CH3，CONHNH2，COOPh在上述化合物中，本发明最优选的化合物为：
1，3-氟甲氧基-2-[2-(3，5，6-三氯吡啶基-2-氧基甲基)-苯基]-丙烯酸甲酯；
2，2-{2-[4-(乙氧亚胺基甲基)-苯基氧甲基]-苯基}-3-氟甲氧基丙烯酸甲酯；
3，2-[2-(4-氯-2-硝基-苯氧基甲基)-苯基]-3-氟甲氧基丙烯酸甲酯；
4，2-[2-(5-氰基-2-甲基-苯基氧甲基)-苯基]-3-甲氧基丙烯酸甲酯；
5，3-[2-(2-甲氧基-1-甲氧基羰基-乙烯基)-苯基甲氧基]-4-甲基-苯甲酸甲酯。
本发明化合物主要通过以下方法合成：
本发明2-[2-(2，3，4，5取代芳基-2-氧基甲基)-苯基]-3-取代甲氧基丙烯酸甲酯的制备方法是2，3，4，5取代芳基酚与2-(2-(溴甲基)苯基)-3-取代甲氧基丙烯酸甲酯以约1∶1的摩尔比在缚酸剂和溶剂的存在下加热反应。反应温度与反应时间视所用原料品种和介质不同而有所变化，一般反应温度控制在溶剂回流温度下，反应时间在6-48小时。反应可用如下反应式表示：
反应中适用的溶剂，可依不同底物选用：丙酮、四氢呋喃、二甲基甲酰胺、二甲亚砜、乙腈等，其中以丙酮适用范围较广。溶剂的使用量，亦视底物不同而不同，一般溶剂用量控制在原料投料量的3-6倍。
为促进反应的顺利进行，反应中需添加缚酸剂，以消除反应中产生的HBr。适用的缚酸剂为碱金属氢氧化物、碳酸盐或酸式碳酸盐，如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾或碳酸氢钠、碳酸氢钾等。缚酸剂的用量，为原料2-(2-(溴甲基)苯基)-3-取代甲氧基丙烯酸甲酯投料摩尔量的1.5-2.0倍。
反应结束后，过滤，蒸去溶剂(必要时用水洗，再用乙酸乙酯萃取，干燥，脱溶)，得到固体粗产品，再用乙醇重结晶，或以石油醚加乙酸乙酯混和液作展开剂，进行柱层析，即得本发明精制品。
发明人发现此类化合物可以与杀虫剂、不同作用机制的常规杀菌剂、杀线虫剂、植物生长调节剂、肥料或其它农用化学品混配使用。
本发明的化合物及其制剂，具有以下一些特点和优点：
1、具有高效的杀菌活性，在较低剂量下能很好地防治由真菌引起的病害，如各种植物的白粉病、锈病、霜霉病、炭疽病等均有很好的防效。
2、对试验作物如小麦、草莓、黄瓜、南瓜等各种瓜类安全，对作物生长无不良影响。
3、具有合理的毒性、生态毒性和环境相容性，属低毒环境友好型农药。
本发明所提供的结构式不仅合成方法简便，而且具有较高杀菌活性，具备开发成商品化杀菌剂的潜力。其制剂在较低剂量下能有效地防治多种植物病害。如小麦白粉病(Erysiphe graminis)、黄瓜白粉病(Sphaerotheca fuligenea)、黄瓜霜霉病(Pseudoperonospora cubensis)、黄瓜炭疽病(Colletotrichum lagenarium)等。
具体实施方式：
下面的实施例可以使本专业技术人员全面的理解本发明，但不以任何方式限制本发明。
实施例1  化合物1
2-[2-(5-氰基-2-甲基-苯基氧甲基)-苯基]-3-甲氧基丙烯酸甲酯的合成
在室温下将1.33g(0.01摩尔)2-甲基-5-氰基苯酚加到150ml盛有60ml干燥丙酮的三口瓶中，然后加入2.76g(0.02摩尔)碳酸钾，室温搅拌30分钟，然后慢慢加入2.85g(0.01摩尔)2-(2-(溴甲基)苯基)-3-甲氧基丙烯酸甲酯。然后回流反应4小时结束，过滤，浓缩，得粗品。用乙酸乙酯和石油醚的混合液(1∶4)为洗脱液进行柱层析得到化合物I 3.13g，为白色固体，收率为93％。产品并经核磁共振(1HNMR)和质谱(MS)分析以确证。分析结果如下：
1HNMR：2.324(3H，s)，3.732(3H，s)，3.885(3H，s)，5.012(2H，s)，6.917-6.920(1H，s)，7.126-7.260(3H，m)，7.313-7.361(2H，m)，7.481-7.503(1H，m)，7.640(1H，s)，MS 337
注：1HNMR谱是用CDCl3溶剂记录。在实验中所用的缩写如下：
NMR＝核磁共振  s＝单峰  d＝双重峰  t＝三重峰  q＝四重峰  m＝多重峰
实施例2化合物4
3-[2-(2-甲氧基-1-甲氧基羰基-乙烯基)-苯基甲氧基]-4-甲基-苯甲酸甲酯的合成
在室温下将3.32g(0.02摩尔)3-羟基-4-甲基苯甲酸甲酯加到250ml盛有100ml干燥丙酮的三口瓶中，然后加入5.52g(0.04摩尔)碳酸钾，室温搅拌30分钟，然后慢慢加入5.7g(0.02摩尔)2-(2-(溴甲基)苯基)-3-甲氧基丙烯酸甲酯。然后回流反应4小时结束，过滤，浓缩，得粗品。用乙酸乙酯和石油醚的混合液(1∶4)为洗脱液进行柱层析得到化合物I 6.22g，为淡黄色固体，收率为84％。熔点：97.2～101.6℃。产品并经核磁共振(1HNMR)和质谱(MS)分析以确证。分析结果如下：
1HNMR：2.316(3H，m)，3.713(3H，s)，3.849(3H，s)，3.902(3H，s)，5.019(2H，s)，7.198-7.216(2H，m)，7.271-7.483(2H，m)，7.552-7.613(1H，m)，7.687(3H，m)，MS：370
实施例3化合物5
2-{2-[4-(乙氧亚胺基甲基)-苯基氧甲基]-苯基}-3-氟甲氧基丙烯酸甲酯的合成
在室温下将4.95g(0.03摩尔)4-(乙氧亚胺-甲基)-苯酚加到250ml盛有100ml干燥丙酮的三口瓶中，然后加入8.28g(0.06摩尔)碳酸钾，室温搅拌30分钟，然后慢慢加入9.09g(0.03摩尔)2-(2-(溴甲基)苯基)-3-氟甲氧基丙烯酸甲酯。然后回流反应4小时结束，过滤，浓缩，得粗品。用乙酸乙酯和石油醚的混合液(1∶4)为洗脱液进行柱层析得到化合物I 8.94g，为白色固体，收率为77％。熔点：74.1-76.1℃。产品并经核磁共振(1HNMR)和质谱(MS)分析以确证。分析结果如下：
1HNMR：1.307(3H，t)，3.823(3H，s)，4.197(2H，q)，4.988(2H，s)，5.403-5.536(2H，d)，6.869-6.886(2H，d)，7.206-7.263(2H，m)，7.369-7.535(4H，m)，7.712(1H，s)，8.006(1H，s)
MS 387.1
实施例4化合物6
2-[2-(4-氯-2-硝基-苯氧基甲基)-苯基]-3-氟甲氧基丙烯酸甲酯的合成
在室温下将3.47g(0.02摩尔)2-硝基-4-氯苯酚加到250ml盛有100ml干燥丙酮的三口瓶中，然后加入5.52g(0.04摩尔)碳酸钾，室温搅拌30分钟，然后慢慢加入6.06g(0.02摩尔)2-(2-(溴甲基)苯基)-3-氟甲氧基丙烯酸甲酯。然后回流反应4小时结束，过滤，浓缩，得粗品。用乙酸乙酯和石油醚的混合液(1∶4)为洗脱液进行柱层析得到化合物I 7.00g，为白色固体，收率为89％。熔点：117.8～118℃。产品并经核磁共振(1HNMR)和质谱(MS)分析以确证。分析结果如下：
1HNMR：3.753(3H，s)，5.139(2H，s)，5.433-5.565(2H，d)，6.943-6.965(1H，d)，7.188-7.209(1H，d)，7.265-7.422(3H，m)，7.573-7.591(1H，d)，7.739(1H，s)，7.824(1H，s)MS 395.5
实施例5化合物7
3-氟甲氧基-2-[2-(3，5，6-三氯吡啶基-2-氧基甲基)-苯基]-丙烯酸甲酯的合成
在室温下将4g(0.02摩尔)2-羟基-3，5，6-三氯吡啶加到250ml盛有100ml干燥丙酮的三口瓶中，然后加入5.52g(0.04摩尔)碳酸钾，室温搅拌30分钟，然后慢慢加入6.1g(0.02摩尔)2-(2-(溴甲基)苯基)-3-氟甲氧基丙烯酸甲酯。然后回流反应4小时结束，过滤，浓缩，得粗品。用乙酸乙酯和石油醚的混合液(1∶4)为洗脱液进行柱层析得到化合物I 6.78g，为白色固体，收率为80％。熔点：108.3～108.8℃。产品并经核磁共振(1HNMR)和质谱(MS)分析以确证。分析结果如下：
1HNMR：3.729(3H，s)，5.332(2H，s)，5.413-5.545(2H，d)7.198-7.264(1H，m)，7.378-7.416(2H，m)，7.592-7.608(1H，d)，7.698-7.729(2H，d)
MS 420
表1中其它化合物的制备方法均实施例1进行，其结果如下表1所示：
                            表1
Figure A20051006027100081
Figure A20051006027100091
Figure A20051006027100101
实施例6生物活性测定：
下面给出使用本发明的化合物进行生物活性测定的实例，需要指出的是本发明并不仅仅局限在下述实例的范围内。
杀菌活性评价试验根据下列方法进行：
第一次活性测定(普筛)试验的化合物处理浓度为200mg/L，再次活性测定(初筛或复筛)试验的化合物处理浓度根据化合物生物活性情况确定药剂浓度，测试方法均采用活体盆栽。
1.黄瓜霜霉病菌(Pseudoperonospora cubensis)
选择两张真叶期(摘去生长点)长势一致的盆栽黄瓜苗，喷雾处理后自然晾干，处理后24h左右进行接种，取新鲜黄瓜霜霉病病叶，用毛笔蘸取10℃左右蒸馏水洗下病叶背面孢子囊，配成孢子囊悬浮液(2-3×105个/ml)，并加入＜0.1％吐温-80的实验室制剂。用接种喷雾器(压力0.1MPa)在黄瓜苗上均匀喷雾接种，接种后的试材移至人工气候室，保持相对湿度100％，温度为15-20℃，24h后保持温度15-24℃，相对湿度90％左右保湿诱发，5d后视空白对照发病情况进行分级调查，按病指计算防效。
2.灰霉病(Botrytis cinerea)
采用叶片接菌法。选择二张真叶期长势一致盆栽黄瓜苗，待药剂喷雾晾干后，接菌饼于叶片上。22-26℃暗光保湿24h后，恢复自然光照培养约4d。待对照充分发病后用卡尺计量每个接种点病斑直径，计算防效。
3.水稻纹枯病(Rhizoctonia solani)
选择二张真叶期长势一致盆栽黄瓜苗，待药剂喷雾晾干后，将菌饼有菌丝的一面接贴于叶片上。22-26℃暗光保湿24h后，恢复自然光照培养约4d。待对照充分发病后用卡尺计量每个接种点病斑直径，计算防效。
4.黄瓜白粉病菌(Sphaerotheca uliginea)
选择一片真叶期、长势一致黄瓜苗，喷雾处理后阴干24h。洗取长满白粉菌黄瓜叶片上的新鲜孢子，用双层纱布过滤，制成孢子浓度为10万个/ml左右的悬浮液，并加入＜0.1％吐温-80的实验室制剂进行喷雾接种。接种后的试材自然风干，然后移至恒温室灯光下(21-23℃)中，7-8d后视空白对照发病情况进行分级调查，按病指计算防效。
5.油菜菌核病(Sclerotinia sclerotiorum)
采用离体叶片接菌法。待药剂喷雾晾干后，接菌饼(直径5mm)于叶片上。25℃暗光保湿24h后，恢复自然光照培养约4-5d。待对照充分发病后调查实验结果，计算防效。
筛选结果详见各表，生测试验结果表明：本发明化合物具有良好的杀菌活性，而且杀菌谱较广，对试验作物安全。
附表1：化合物对各靶标普筛结果
  编号   浓度mg/L   霜霉病％   灰霉病％   纹枯病％   白粉病％
  1   200   94.5   41.70   49.08   100
  2   200   83.24   50.0   49.39   94.17
  3   200   81.23   40.0   0   99.21
  4   200   98.14   49.68   59.01   92.18
  5   200   99.87   32.90   54.93   100
  6   200   97.22   16.56   9.63   98.41
  7   200   100   2.3   0   100
  8   200   100   33.33   0   100
  9   200   12.76   14.29   0   0
  10   200   34.89   2.27   39.62   33.21
  11   200   88.89   26.73   25.54   100
  12   200   97.22   56.74   47.88   100
  13   200   94.44   54.67   52.45   98.15
  14   200   83.26   22.11   5.60   90.12
  15   200   85.24   28.08   0   100
  16   200   89.54   37.67   0   100
  17   200   94.89   0   0   49.38
  18   200   10.23   0   0   19.88
附表2：化合物对黄瓜霜霉病的复筛结果
  化合物代号   浓度mg/L   防效％
  12   200   98.30
  100   86.10
  50   71.25
  25   47.40
  12.5   26.93
  5   200   100
  100   97.78
  50   81.11
  25   60.54
  12.5   53.24
  6   200   98.15
  100   93.21
  50   84.66
  25   47.40
  12.5   25.00
  7   200   100
  100   99.31
  50   95.14
  25   95.83
  12.5   87.50
  1   200   94.44
  100   83.33
  50   75.56
  25   59.63
  12.5   50.71
  8   200   99.87
  100   97.62
  50   92.36
  25   85.71
  12.5   65.93
附表3：化合物对黄瓜白粉病的复筛结果
  化合物代号   浓度mg/L   防效％
  12   200   100
  100   98.15
  50   77.78
  25   66.67
  12.5   43.59
  5   200   100
  100   100
  50   95.24
  25   78.69
  12.5   68.97
  6   200   62.96
  100   51.85
  50   48.89
  25   29.06
  12.5   11.11
  7   200   100
  100   99.07
  50   98.89
  25   93.33
  12.5   88.89
  1   200   100
  100   94.4
  50   85.3
  25   72.6
  12.5   63.2
  8   200   98.23
  100   94.44
  50   93.83
  25   89.81
  12.5   53.54
附表4黄瓜霜霉病田间试验结果
  试验处理   有效浓度(a.i.)mg/L                  防治效果(％)
  上海农科学院(三次药后10天)   马鞍山市植保植检站(二次药后7天)
5％化合物7EC   200   91.15   88.55
  100   85.35   88.60
  50   69.45   83.93
  25   60.25   76.09
72％克露WP   1152   78.73   /
  957.6   /   90.95
5％化合物1EC   200   89.02   92.51
  100   83.43   87.75
  50   75.87   86.31
  25   62.26   80.56
72％克露WP   1152   87.38   /
  957.6   /   94.01
田间试验结果表明，在50-100mg/L浓度下，化合物1和7对黄瓜霜霉病和黄瓜白粉病均表现出很好的防效，持效期长，对作物安全，具有较好的市场应用前景。推荐剂量为50-100mg/L，首次施药时间为黄瓜霜霉病发病前或发病初期，视病害发生情况或天气情况每隔一周喷药一次。
需要在其它瓜类或果树、花卉等作物上开展田间试验，为进一步的开发提供科学依据。

Claims (11)

1，一组甲氧基丙烯酸甲酯类化合物杀菌剂，特征是如结构式(I)所示及其异构体：
Figure A2005100602710002C1
其中当X＝F，Q＝N时，R1、R2、R3、R4＝H、NO2、CN、Cl、CH3COOR6(R6为取代或未取代烷基)或CF3；
当X＝F，Q＝CH，R1＝NO2时，R2，R4＝H；
当X＝F，Q＝CH，R1＝R2＝R4＝H，R3＝CH＝N-OR5或COOR5，其中R5＝CH3、C2H5、n-C3H7、i-C3H7、n-C4H9、i-C4H9、t-C4H9。
当X＝H，Q＝CH时，R2，R3＝H；R1＝OMe、CH3或N(C2H5)2；R4＝CH3、CN，COOCH3，COOC2H5，COOC3H7-n，COOCH(CH3)2，COOCH2CH(CH3)2，COOC4H9-n，COOCH2CF3，COOCH2CH2Cl，COOCH2CH＝CH2、COOCH(CH2Cl)2COOCH2CCH、COOCH(CH3)CH2CH2CH3、CONHNH2、COOPh。
2，按照权利要求1的一组化合物，特征是如结构式(II)所示及其异构体：
Figure A2005100602710002C2
其中R1、R2、R3、R4＝H、NO2、CN、Cl、CH3、COOR6(R6为取代或未取代烷基)或CF3。
3，按照权利要求1的一组化合物，特征是如结构式(III)所示及其异构体：
Figure A2005100602710002C3
式中R＝CH＝N-OR5或COOR5；
其中R5＝CH3、C2H5、n-C3H7、i-C3H7、n-C4H9、i-C4H9、t-C4H9。
4，按照权利要求1的一组化合物，特征是如结构式(IV)所示及其异构体：
Figure A2005100602710003C1
式中R＝Cl、CH3、COOC2H5。
5，按照权利要求1的一组化合物，特征是如结构式(V)所示及其异构体：
Figure A2005100602710003C2
式中R1＝OMe、CH3或N(C2H5)2；R4＝CH3、CN，COOCH3，COOC2H5，COOC3H7-n，COOCH(CH3)2，COOCH2CH(CH3)2，COOC4H9-n，COOCH2CF3，COOCH2CH2Cl，COOCH2CH＝CH2、COOCH(CH2Cl)2、COOCH2CCH、COOCH(CH3)CH2CH2CH3、CONHNH2、COOPh。
6，一种如权利要求2所述的含氟甲氧基丙烯酸甲酯类化合物，其特征是指：3-氟甲氧基-2-[2-(3，5，6-三氯吡啶基-2-氧基甲基)-苯基]-丙烯酸甲酯。
7，一种如权利要求3所述的含氟甲氧基丙烯酸甲酯类化合物，其特征是指：2-{2-[4-(乙氧亚胺基甲基)-苯基氧甲基]-苯基}-3-氟甲氧基丙烯酸甲酯。
8，一种如权利要求4所述的含氟甲氧基丙烯酸甲酯类化合物，其特征是指：2-[2-(4-氯-2-硝基-苯氧基甲基)-苯基]-3-氟甲氧基丙烯酸甲酯。
9，一种如权利要求5所述的含氟甲氧基丙烯酸甲酯类化合物，其特征是指：2-[2-(5-氰基-2-甲基-苯基氧甲基)-苯基]-3-甲氧基丙烯酸甲酯。
10，一种如权利要求5所述的含氟甲氧基丙烯酸甲酯类化合物，其特征是指：3-[2-(2-甲氧基-1-甲氧基羰基-乙烯基)-苯基甲氧基]-4-甲基-苯甲酸甲酯。
11，一组如权利要求1、2、3、4、5所述的甲氧基丙烯酸甲酯类化合物的用途，其特征是用于农用化学杀菌剂。
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