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CN1015981B - 吡啶基亚胺酸酯的制备方法 - Google Patents

吡啶基亚胺酸酯的制备方法

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CN1015981B
CN1015981B CN87103162A CN87103162A CN1015981B CN 1015981 B CN1015981 B CN 1015981B CN 87103162 A CN87103162 A CN 87103162A CN 87103162 A CN87103162 A CN 87103162A CN 1015981 B CN1015981 B CN 1015981B
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pyridyl
inert solvent
alkyl
och
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CN87103162A (zh
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唐·罗伯特·贝克
凯瑟·哈维·布朗内尔
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Stauffer Chemical Co
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Stauffer Chemical Co
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Publication of CN1015981B publication Critical patent/CN1015981B/zh
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Abstract

制备通式如下的化合物及其适于杀真菌的盐的方法(式中R1、R2、X和R的定义见说明书)，该方法包括2位取代的5-氨基吡啶与环丙烷羰酰氯在酸结合剂存在下于惰性溶剂中反应，然后在惰性溶剂中与五氯化磷反应，再使所得亚胺酰氯与取代的硫醇在惰性溶剂中反应，得所要化合物，如果需要，该产物与路易斯酸反应得到所需的盐。这类化合物及其盐，均为高效杀真菌剂。

Description

真菌对作物如大麦，稻谷，蕃茄，小麦，豆子，玫瑰，葡萄和其它重要的农作物的侵染，会使农产品在质量和数量上均遭到严重损失。因而，急需的是防止，控制或消除真菌生长的方法。在防止真菌固定和生长于重要的农作物方面，已用喷洒市售杀真菌剂作了尝试。另外还需要一种治理性杀真菌剂，当观察到有真菌性侵染时，用它能破坏真菌，并且在作为一种侵染后的治疗性喷洒剂应用时，能消除真菌侵染的有害效应。
本文公开的是通式如下的新的杀真菌性吡啶基亚胺酸酯类化合物及其适用于杀真菌的有机或无机盐类：
Figure 87103162_IMG7
其中R选自这样一个组：C1～C16烷基，C3～C8环烷基，C2～C8链烯基，C2～C8取代链烯基，C3～C4烷氧羰烷基，芳基，具C1～C3烷基的芳烷基，取代的芳基和芳烷基（其中的取代基是-Cl，-Br，-F和-NO2），优选的芳基和芳烷基是苯基，苄基，苯乙基和萘基，糠基，吡啶基，C1～C6（优选C1～C4）烷基取代的硫代磷酰基和
Figure 87103162_IMG8
（其中R3和R4是C1～C10烷基，并且能形成一个杂环），R1是选自由下列基团组成的一个组：卤素，如氯，氟和溴，优选氯，C1～C3烷氧基，如丙氧基，乙氧基和甲氧基，优选甲氧基，以及C1～C3卤代烷氧基，R2选自由甲基和氢组成的一个组， X是S或O;它们作为预防性或治疗性杀真菌应用时，均为高效的杀真菌剂。
术语“杀真菌剂”指能防治真菌生长的化合物。“防治”包括阻止、破坏和抑制真菌的生长。术语“治理性”指在侵染后应用时，该杀真菌剂能控制真菌的侵染和防止真菌对宿主作物进一步的有害效应。
本发明的新杀真菌性化合物是通式如下的吡啶亚胺酸酯类化合物及其适用于杀真菌的有机或无机盐：
Figure 87103162_IMG9
其中R选自下面一组基团：C1～C16烷基，C3～C8环烷基，C2～C8链烯基，C2～C8取代链烯基，C3～C4烷氧羰烷基，芳基，具C1～C3烷基的芳烷基，取代的芳基和芳烷基（其中的取代基是-Cl，-Br，-F和-NO2），优选的芳基和芳烷基是苯基，苄基，苯乙基和萘基，糠基，吡啶基，C1～C6（优选C1～C4）烷基取代的硫代磷酰基，以及
Figure 87103162_IMG10
（其中R3和R4为C1～C10烷基并能与N一起形成一个杂环），R1选自下面一组基团：卤素，如氯，氟和溴，优选氯，C1～C3烷氧基，如丙氧基，乙氧基和甲氧基，优选甲氧基和C1～C3卤代烷氧基，R1选自甲基和氢，X是S或O。它们在作为预防性或治理性杀真菌剂应用时，均为高效的杀真菌剂。
本发明化合物的一般制备方法是用一种新型适当取代的N-（2-取代-5-吡啶基）环丙烷甲亚胺酰氯进行反应而得到，该化合物具有如下通式：
Figure 87103162_IMG11
其中R1和R2定义如上所述，它是由2位上有适当取代基的5-氨基吡啶与环丙烷羰酰氯在有酸结合剂存在的条件下于惰性溶剂如二氯甲烷中反应制得。再使所得到的环丙烷甲酰胺与五氯化磷在惰性溶剂如二氯甲烷中反应得到相应的亚胺酰氯，再使后者与适当取代的硫醇在一惰性溶剂如二氯甲烷中，于一适当的反应器内反应。在反应器中最好保持有酸结合剂如吡啶。该反应一般在室温下进行，但依据硫醇和亚胺酰氯则可在-20至80℃的温度范围内进行。该反应一般在1～3小时内完成。所获产物用常规方法回收，即用碱溶液如NaOH和水洗，用常规干燥剂如硫酸镁干燥，蒸发除去溶剂得到产物。各种吡啶基环丙烷甲亚胺酸酯类化合物的盐可按常规方法用至少一摩尔的路易斯酸与硫代亚胺酸酯化合物反应制成。反应最好在适于硫代亚胺酸酯类化合物的溶剂中进行。所制成的盐类用常规技术从反应混合物中回收得到。
本发明的吡啶基硫代亚胺酸酯类化合物是弱碱性化合物。吡啶环上的未质子化的氮原子可用酸予以质子化，有机酸或无机酸均可。无机酸的代表有盐酸，硝酸，氢溴酸，硫酸，氨基磺酸和磷酸。有机酸的代表有乙酸，三氟乙酸，苯甲酸，苯磺酸，对甲苯磺酸，萘磺酸，苯膦酸和有机磷酸。这样形成的盐类也是杀真菌性的。
实施例1
N-（2-甲氧基-5-吡啶基）-环丙烷甲酰胺的制备
在含有200ml二氯甲烷的反应烧瓶中将5-氨基-2-甲氧基吡啶（12.4g，0.10mole）和10ml吡啶相混合。历时2分钟将9.1ml（0.10mole）环丙烷碳酰氯加到反应混合物中。反应是放热性的，温度升到34℃。让该反应在室 温下进行一小时，然后用200ml    5%氢氧化钠和100ml水洗反应混合物。分离所获的有机相，以无水硫酸镁干燥。晶体析出后，将混合物过滤，用300ml丙酮洗，滤液经真空蒸发得到固体物，将其与己烷其研制，干燥后，得16.7克。经红外光谱和核磁共振谱鉴定，该产物确为标题化合物，熔点为130～131℃。该化合物被定为1号化合物。
实施例2
N-（2-甲氧基-5-吡啶基）环丙烷碳亚胺酰氯的制备
50ml二氯甲烷和10.4g（0.05M）五氧化磷在一反应烧瓶中混合。在氮气保护并在搅拌条件下，将9g（0.05M）实施例1的化合物分批加入到反应烧瓶中。反应为放热性，室温下搅拌1小时，然后再加热搅拌回流1小时使反应器中的固体溶解并反应。反应混合物经真空蒸发得到固状产物，用乙醚洗两次（每次用50ml），真空干燥后得12.0g固体，经核磁共振谱鉴定为标题化合物。
实施例3
N-（2-甲氧基-5-吡啶基）环丙烷硫代甲亚胺酸S-乙基酯的制备
在一个300ml单颈圆底烧瓶中，在旋摇下，将3g（0.01mole）实施例2的化合物和0.74ml（0.01mole）乙硫醇溶于150ml二氯甲烷中。加入3.0ml三乙胺。该反应混合物变为紫色，1小时后变为清澈。所获溶液在旋转蒸发器上蒸发后，将得到的油状物与50ml己烷研磨并过滤。己烷提取物经旋转蒸发后得油状物1.6g，用核磁共振谱鉴定为标题化合物。该化合物被称作1号化合物。
表1中给出于本发明的代表化合物及其性质。
表1
Figure 87103162_IMG12
11    15号化合物的盐酸盐    155.0
12    22号化合物的盐酸盐    128.0
13 -CH3-Cl -H -O
14 -CH3-OCH3-H -O
15 -CH2CH=CH2-OCH3-H -O
实施例4
等摩尔预防性喷洒剂的评价程序
叶锈病（LR）
试验前12天将7粒小麦（Anz    A    wheat）种子种入直径2英寸小盆的沙壤土中。试验化合物用50∶50的丙酮/水溶液稀释，制成一浓度在0.004M以下的溶液系列。用喷雾器将试验溶液12ml喷洒到小麦植株上。
隐匿柄锈菌（Puccinia recondita）夏孢子悬浮液由具孢子突起的小麦叶上真空吸来的孢子以105个孢子/ml悬浮于含0.5% Tween20的去离子水中而制成。用试验化合物溶液处理24小时后，以喷洒方法用孢子悬浮液接种植株至饱和状，让其在叶子上干燥，再重喷洒至饱和状，然后将植株移入到黑暗雾室中。于雾室中放置48小时后，将植株移到地下灌溉温室中。
接种10天后记录结果，根据同未处理对照株植比的病灶区域减少的百分数，将试验结果表示为叶锈病防治百分数。能达到90%疾病控制的化合物浓度（EC90）可由剂量/稀释曲线上确定。
葡萄孢芽枯病（BB）
将两片白玫瑰花瓣放入铺有湿滤纸的培养皿中。试验化合物用50∶50的丙酮/水的溶液稀释成一系列浓度在0.004M以下的溶液。将半毫升试验溶液喷雾到花瓣上，使之干燥。将从在Elliot′s    V-8琼脂上生长了2周的灰葡萄孢（Botrytis    cineria）培养物中获得的5mm孢塞加到10ml无菌蒸馏水+0.5%葡萄汁的液体中制成接种物。将这种接种悬浮液以20微升为一滴加到每片花瓣上。将载有接种过的花瓣的培养皿放入封密的塑料盒中以保持饱和湿度。
接种4天后记录结果，以与丙酮/水的对照组相比在坏死区域减少的百分数来表示。能达到90%疾病控制的化合物浓度（EC90）从剂量/稀 释曲线上确定。
表2中给出的结果是以ppm表示的EC90近似值。数字（750）表示在750ppm时的部分控制。
表2
化合物号    LR    BB
1    750    80
2    750    25
3    -    250
4    -    20
5    -    750
6    -    750
7    -    250
8    -    80
9    -    30
10    -    （750）
11    -    （750）
12    -    250
13    -    750
14    -    （750）
15    -    250
16    -    80
17    -    50
18    -    30
19    -    40
20    -    （750）
21    -    （750）
22    -    （750）
23    -    20
24    -    20
25    -    35
26    （750）    （750）
27    -    70
28    -    80
29    -    30
30    -    250
实施例5
治理性喷洒剂的评价程序
叶锈病（LR）
试验前12天将7粒小麦（Anza wheat）种子植入直径2英寸小盒的沙壤土中。隐匿柄锈菌（Puccinia recondita）夏孢子悬浮液是由具孢子突起的小麦叶上真空吸来的孢子以105个孢子/ml悬浮于去离子水+0.5% Tween20而制成。喷洒孢子悬浮液接种植株至饱和状，让其在叶子上干燥，再喷洒至饱和状，然后将植株移入雾室。雾室中放置48小时后，将植株移入地下灌溉温室中。
将试验化合物用50∶50的丙酮/水的溶液稀释以得到一由0.0075%开始降低的浓度系列。接种植株50小时后，将植株放在一个旋转盘上，并用喷雾器将试验溶液喷至近于饱和状（接种时间是从植株放入雾室时起来计算的）。
接种10天后记录结果，以同未处理对照植株相比在病灶区减少的百分数为基础得到叶锈病控制百分数。
表3
化合物号    叶锈病
1    100
2    100
本发明化合物对葡萄孢芽枯病特别有效，并且与用作葡萄孢菌的预防性和治理性的标准市售化合物相比是更为有效的预防性叶面喷洒剂和治理性叶面喷洒剂。本发明化合物对之特别有效的另一真菌是隐匿柄锈菌（Puccinia    recondita）。
本发明的化合物可用作杀真菌剂，特别是作为防护性或治理性杀真菌剂，并且可以不同方式和不同浓度应用。一般说来，这些化合物及其制剂可以直接用于作物叶片，植株生长于其中的土壤及植株或土壤的灌溉水中。实际上，鉴于一种毒素的剂型和使用方式可能影响某一应用中各种物质的活性这一事实，此处所限定的化合物是以有效杀真菌剂量与通常用于促进在农业上的活性成分更好分散的赋形剂和载体一起混合制成杀真菌性组合物。例如，这些活性的杀真菌化合物可根据所需的应用方式而制成可湿性粉剂，可乳化的浓缩液，粉尘剂，溶液或其他的已知剂型。优选的用在预防性或治疗性杀真菌方面的剂型是可湿性粉剂和可乳化的浓缩液。这些剂型所含的活性成分可少至0.5%（重量），也可多至95%（重量）或更多。有效的杀真菌剂量依据所要处理的种子及植物的性质而定，使用量可为约每英亩0.05至25磅，优选约每英亩0.1至10磅。
可湿性粉剂的型式是细颗粒状的，它能在水或其它分散剂中迅速分散。可湿性粉剂最终用于土壤和植物时，是作为干粉尘或作为分散体于水或其它液体中的悬浮体应用的。对可湿性粉剂而言，典型的载体包括漂白土 高岭土，硅石和其它易湿的有机或无机稀释剂。一般制备的可湿性粉剂含约5%至95%的活性成分，并且通常含有小量的润湿剂，分散剂或乳化剂，以促进润湿和分散。
干流动性的或水分散性的颗粒是附聚的可湿性粉剂，是由盘式粒化床或流化床制成的。干流动性颗粒最终用于土壤或植物时是作为分散物存在于水或其它液体中。这些颗粒不含粉尘，当干燥时可自由流动，当稀释于水中时，形成均一的分散剂。对干流动性颗粒而言，典型的载体包括漂白土，高岭土，粘土，硅石和其它易湿的有机或无机稀释物。常规制备的干流动性颗粒含有约5%至95%的活性成分，并且一般还含有少量的润湿剂，分散剂或乳化剂，以促进润湿和分散。
可乳化浓缩液均质液体组合物，可分散于水或其它分散剂中，它可仅由活性化合物以及液体或固体乳化剂组成，或者还可以含有液体载体，如二甲苯，重芳石脑油，异佛乐酮及其他非挥发性有机溶剂。用于杀真菌时，这些浓缩物分散于水或其它液体载体，通常以喷洒液的形式施用于被处理的地区。基本活性组分的重量百分比要依该组合物的应用方式来决定，但一般而言，活性成分的含量约为杀真菌组合物重量的0.1%至95%。
农用剂型中所用的润湿剂，分散剂和乳化剂的典型例子有磺酸烷基酯，磺酰烷芳基酯，硫酸烷基酯，硫酸烷芳基酯及其钠盐，多羟基醇，其它类型的表面活性剂，其中大多数均有市售。当使用表面活性剂时，其含量一般占杀真菌组合物重量的0.1%至15%。
粉剂是由活性成分与微细的固体如滑石，粘土，面粉和其它对该活性成分起分散剂和载体作用的有机以及无机固体形成的自由流动混合物，该粉剂是很有用的剂型。
由细微固体药物分散于液体载体如水或油中制成的均质悬浮液-糊浆，是用于特殊目的。这种剂型通常含有约5%至95%的活性成分（重量），并且还可含有少量的润湿剂，分散剂或乳化剂以促进分散。应用时，糊浆通 常经稀释作为一种喷洒剂施于作业区。
典型剂型的实例
油剂
成分    重量%
1号化合物    1
油溶剂-重芳石脑油    99
合计    100
可乳化浓缩液
2号化合物    50
煤油    45
乳化剂（长链乙氧基化的聚醚与    5
长链磺酸盐的混合物）
合计    100
可乳化浓缩液
3号化合物    90
煤油    5
乳化剂（长链乙氧基化的聚醚与    5
长链磺酸盐的混合物）
合计    100
粉尘剂和/或粉剂
成分    重量%    重量%    重量%
1号化合物    0.5    50.0    90.0
美国活性白土粉    93.5    44.0    4.0
木素磺酸钠    5.0    5.0    5.0
二辛基磺基丁二酸钠    1.0    1.0    1.0
合计    100.0    100.0    100.0
其它有用的杀真菌剂型包括活性成分以所需浓度完全溶于分散剂中而形成的简单溶液，这些分散剂有丙酮，烷基化萘，二甲苯和其它有机溶剂。借助于低沸点分散溶剂载体如氟利昂的汽化作用而使活性成分很好地分散于其中的压力喷洒液，典型的是汽溶胶，也可以使用。
本发明的杀真菌组合物按常规方法施用于植物。例如，粉剂和液剂可用动力洒粉器，臂式及手摇式喷洒器和喷粉器施于植物。这些组合物可以粉剂和喷洒剂的形式由飞机喷洒，因为在低剂量时也是有效的。

Claims (6)

1、一种制备通式如下的化合物及其适用于杀真菌的有机和无机盐的方法，
Figure 87103162_IMG2
式中R选自C1-C16烷基，C3-C8环烷基，C2-C8链烯基，C3-C4烷氧羰基烷基，取代的或未取代的苯基或苄基(其中取代基是-Cl、-Br、-F和-NO2)，糠基，吡啶基，C1-C6烷基取代的硫代磷酰基和
Figure 87103162_IMG3
(其中R3和R4是C1-C10烷基且能与N一起成杂环)；R1选自卤素和C1-C3烷氧基；R2是氢；X是S或O；所述方法包括：
使2位上有适当取代基的5-氨基吡啶与环丙烷羰酰氯在酸结合剂存在下于惰性溶剂中反应，制得下式所示的N-(2-取代-5-吡啶基)环丙烷甲亚胺酰氯：
Figure 87103162_IMG4
(其中R1和R2定义如上所述)，
使上式的环丙烷甲酰胺与五氯化磷在惰性溶剂中反应得到相应的亚胺酰氯；
使上述的亚胺酰氯与适当取代的硫醇在惰性溶剂中，在酸结合剂存在下反应，反应温度为-20℃至80℃，反应时间为1-3小时；
用常规方法，包括用碱溶液如NaOH和水洗涤，干燥和蒸除溶剂，得到上述通式所示化合物；
根据需要，可按常规方法用至少一摩尔路易斯酸与所得吡啶基亚胺酸酯化合物在适当的溶剂中反应，制备吡啶基环丙烷甲亚胺酸酯化合物的盐，得到的盐可用常规技术从反应混合物中回收。
2、根据权利要求1的方法，其中产物中R是-C（CH3）3，R1是-OCH3，R2是-H，X是-O。
3、根据权利要求1的方法，其中产物中R是
Figure 87103162_IMG5
〔OCH2CH（CH3）2〕2，R1是-OCH，R2是-H，X是-S。
4、根据权利要求1的方法，其中产物中R是
Figure 87103162_IMG6
ClR1是-OCH3，R2是-H，X是-O。
5、根据权利要求1的方法，其中所说的惰性溶剂是二氯甲烷。
6、根据权利要求1的方法，其中所说的酸结合剂是吡啶或三乙胺。
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HU205903B (en) 1992-07-28
HUT46994A (en) 1989-01-30
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