CN100438865C - 有杀真菌活性的化合物及其制备和使用方法 - Google Patents
有杀真菌活性的化合物及其制备和使用方法 Download PDFInfo
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- CN100438865C CN100438865C CNB018213022A CN01821302A CN100438865C CN 100438865 C CN100438865 C CN 100438865C CN B018213022 A CNB018213022 A CN B018213022A CN 01821302 A CN01821302 A CN 01821302A CN 100438865 C CN100438865 C CN 100438865C
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- aryl
- heteroaryl
- chemical compound
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- alkyl
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- Environmental Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
Abstract
本发明提供了一种根据式一的化合物，该化合物作为杀真菌剂有用。此外，本发明提供了制备和使用该化合物的方法。
Description
优先权
本申请要求在2000年11月17日提交的美国临时申请60/249,653的优先权。
发明领域
本发明涉及有杀真菌活性的化合物及其制备和使用该化合物的方法的领域。
发明背景
我们的历史充满了真菌疾病的爆发，这些疾病已经引起大范围的人类痛苦。只要看看发生于1845-1860年爱尔兰的土豆饥荒，估计有1,000,000人死亡，估计有1,500,000人移居外国，就可以看出真菌疾病的影响。杀真菌剂是天然的或合成的化合物，其作用是保护植物免遭真菌引起的伤害。现有的农业方法极为依赖杀真菌剂。实际上，有些作物不使用杀真菌剂不能有效地生长。使用杀真菌剂使种植者增加作物的产量和质量，并且随之增加作物的价值。在大多数情况下，作物价值的增加至少是使用杀真菌剂成本的三倍。然而，没有一个杀真菌剂是在所有的状况都有用的。因此，进行研究以生产杀真菌剂，该杀真菌剂更安全，有更好的性能，更容易使用，并且成本更低。根据上面所述，本发明人提供了这个发明。
发明概述
本发明的一个目的是提供有杀真菌活性的化合物。本发明的一个目的是提供生产有杀真菌活性的化合物的方法。本发明的一个目的是提供使用有杀真菌活性的化合物的方法。根据本发明，提供了制备和使用具有根据式一通式的化合物的方法，和所述的化合物。尽管本发明的所有化合物都有杀真菌的活性，但某些种类的化合物是优选的，这是出于这样的原因，例如更高的效力或容易合成。
在该文件自始至终，除非另外说明，所有的温度是以摄氏温度给出，所有的百分比是重量百分比，除了产量百分比是摩尔百分比之外。术语“烷基”，“烯基”，“炔基”指非支链的，或支链碳基。术语“烷氧基”指非支链的，或支链的烷氧基。术语“卤代烷基”指非支链的，或支链的被一个或多个卤原子取代的烷基，卤原子限定为F，Cl，Br，和I。术语“卤代烷氧基”指非支链的，或支链的被一个或多个卤原子取代的烷氧基。术语“烷氧烷基”指非支链的，或支链的被一个或多个烷氧基取代的烷基。术语“烷氧烷氧基”指非支链的，或支链的被一个或多个烷氧基取代的烷氧基。术语“芳基”指苯基或萘基。术语“Me”指甲基。术语“Et”指乙基。术语“Pr”指丙基。术语“Bu”指丁基。术语“EtOAc”指乙酸乙酯。术语“ppm”指百万分之一。术语“psi”指磅每平方英寸。
杂芳基定义为如下的式二
式二
其中2A代表5-或6-元的环和2B代表9-或10-元稠合的二环，其中X1-X5中每一个独立地是一个键，O，S，NR7，N或CR，其中R选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，C1-4烷氧烷氧基，CN，NO2，OH，SCN，C(＝O)R6，C(＝NR6)R6，S(On)R6，其中n＝0，1或2，芳基，芳氧基，杂芳基，和杂芳氧基，并且其中X1-X5中不超过一个是O，S，或NR7，X1-X5中不超过一个是一个键，当X1-X5中任意一个是O，S，或NR7时，X1-X5中相邻的一个必须代表一个键；并且X1-X5中至少一个必须是O，S，NR7或N。
这样的杂芳基的例子是吡啶基，哒嗪基，嘧啶基，吡嗪基，吡咯基，吡唑基，咪唑基，喹啉基，异喹啉基，2，3-二氮杂萘基，喹唑啉基，喹喔啉基，噌啉基，吲哚基，异吲哚基，吲唑基，噻吩基，苯并噻吩基，呋喃基，苯并呋喃基，噻唑基，苯并噻唑基，异噻唑基，苯并异噻唑基，噁唑基，苯并噁唑基，异噁唑基，和苯并异噁唑基。
发明详述
本发明的化合物有式一的结构
式一
在式一中：
R1选自F，Cl，Br，CN，C1-4烷基，C2-4烯基，C2-4炔基，C1-4卤代烷基，C1-4烷氧基烷基，C3-C6环烷基，C3-C6环烯基，CH2(C＝O)R5，和CH2CN；
R2和R3选自H，CH3，F，和Cl；
R4选自C1-6烷基，C2-6烯基，C2-6炔基，C3-6环烷基，C3-6环烯基，芳基，和杂芳基，其中所述的烷基，烯基，炔基，环烷基和环烯基可以被一个或多个取代基取代，取代基选自卤素，C1-4烷氧基，C3-6环烷基，芳基和杂芳基，其中所述的芳基和杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，C1-4烷氧烷氧基，CN，NO2，OH，SCN，C(＝O)R6，C(＝NR6)R6，S(On)R6，其中n＝0，1或2，芳基，芳氧基，杂芳基，和杂芳氧基；
R5选自H，OR7，和C1-4烷基；
R6选自H，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，芳基，和杂芳基，OR7，N(R7)2，SR7，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，CN，和NO2；
R7选自H，C1-4烷基，C2-4烯基，和C2-4炔基，C1-4卤代烷基，芳基，和杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，CN，和NO2；
A选自芳基或杂芳基，其中所述芳基和杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，C1-4烷氧烷氧基，CN，NO2，OH，SCN，C(＝O)R6，C(＝NR6)R6，S(On)R6，其中n＝0，1或2，芳基，芳氧基，取代的芳氧基，杂芳基，和杂芳氧基；和
Z选自C(＝O)R6，C(＝S)R6，P(＝O)(R6)2，和P(＝S)(R6)2。
在本发明的一个优选实施方案中，本发明的化合物有式一的结构，其中R1选自Cl，C1-4烷基，和C2-4烯基；
R2和R3选自H，CH3；
R4选自C1-6烷基，其中所述的烷基能被一个或多个C1-4烷氧基取代基取代；
R5是H；
R6选自H，C1-4烷氧基，OR7，N(R7)2，和SR7；
R7选自H，C1-4烷基，C2-4烯基，C2-4炔基，C1-4卤代烷基，芳基，和杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，CN，C1-4烷基，和C1-4烷氧基；
A选自芳基或杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，CN，C1-4烷氧基，C1-4卤代烷氧基，芳基，取代的芳氧基，C2-4烯基，C(＝NR6)R6，NO2，和C(＝O)R6；和
Z选自C(＝O)R6和C(＝S)R6。
更优选A选自芳基或杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自Br和CN；和
Z选自异丙基和C(＝O)R6，其中所述的R6是OR7，并且所述的R7选自芳基和杂芳基，其中所述的芳基或杂芳基被一个取代基取代，取代基选自卤素和甲基。
最优选(i)其中A是取代的苯基，其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位；和
(ii)其中Z是C(＝O)R6，其中所述的R6是OR7，并且所述的R7是取代的苯基，并且其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位。
在本发明的另一个优选实施方案中，本发明的化合物有式一的结构，R1选自Cl和甲基；
R2和R3是H；
R4是C1-6烷基；
R5是H；
R6选自H，甲氧基，和OR7；
R7选自C1-4烷基，C2-4炔基，芳基，其中所述的芳基能被一个或多个取代基取代，取代基选自卤素和甲基；
A选自芳基或杂芳基，其中所述的芳基和杂芳基能被一个或多个取代基取代，取代基选自卤素，CN，C1-4烷氧基，C1-4卤代烷氧基，芳基，取代的芳氧基，C2-4炔基，C(＝NR6)R6，NO2，和C(＝O)R6；和
Z是C(＝O)R6其中所述的R6是OR7。
优选A选自芳基或杂芳基，其中所述的芳基和杂芳基能被一个取代基取代，取代基选自Br和CN；和
Z选自异丙基和C(＝O)R6，其中所述的R6是OR7，并且所述的R7选自芳基和杂芳基，其中所述的芳基或杂芳基被一个取代基取代，取代基选自卤素和甲基。
更优选(i)其中A是取代的苯基，其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位；并且
(ii)其中Z是C(＝O)R6，其中所述的R6是OR7，并且所述的R7是取代的苯基，并且其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位。
式一化合物有两个手性中心，因此能以对映异构体和非对映异构体的混合物存在。其中立体化学是公知的，它在结构中标明。本发明要求保护纯的对映异构体和非对映异构体及其混合物。通常，该化合物能用于各种途径。该化合物优选以包含一种或多种化合物和植物学上可接受载体的剂型的形式被使用。浓缩的剂型能分散在水中，或其它的液体中来运用，或者剂型可以是粉末状的或颗粒状的，然后它们能不经进一步的处理就可使用。剂型可以制备根据农业化学领域常规的程序制备，但它是新颖的和重要的，这是因为其中有一种或多种这些化合物。
最常使用的剂型是水悬浮剂或乳状液。这种水溶性的，水悬浮性的，或者可乳化的剂型的任何一个是固体，通常已知为可湿的粉末，或液体，通常已知为可乳化的浓缩物，水悬浮液，或悬浮浓缩物。本发明预见了所有的载体，一种或多种化合物可以通过它们配制，用于分送并用作杀真菌剂。
容易理解的，其中可以加入这些化合物的任何材料都可以使用，只要他们产生期望的用途，而不显著干扰这些化合物作为抗真菌剂的活性。
可湿性粉末，其可以压缩形成水分散性颗粒，包含一种或多种这些化合物的紧密混合物，惰性载体和表面活性剂。在可湿性粉末中化合物的浓度通常是从大约10％到大约90％W/W，更优选的是从大约25％到大约75％W/W。在可湿性粉末剂型的制备中，这些化合物能混合任何微细固体，例如，prophyllite，滑石粉，白垩，石膏，漂白土，皂土，绿坡缕石，淀粉，酪蛋白，麦麸，蒙脱石，粘土，硅藻土，纯化的硅胶或类似物。在这种操作中，微细载体是研磨或混合在挥发性有机溶剂中的化合物。包含从大约0.5％到大约10％的可湿性粉末的有效的表面活性剂包括磺化木质素，萘磺酸盐，烷基苯磺酸盐，烷基硫酸盐，和非离子表面活性剂，例如烷基酚的环氧乙烷加成物。
这些化合物的可乳化的浓缩物包括适宜的液体中的合适浓度，例如从大约10％到大约50％w/w。这些化合物溶于惰性载体，所述惰性载体或者是水混溶性溶剂，或者是水不混溶性有机溶剂的混合物，和乳化剂的混合物。浓缩物可以用水和油稀释，以形成水包油乳状液形式的喷雾混合物。有用的有机溶剂包括芳香族化合物，特别是高沸点的石油的萘基和烯基部分，例如重芳香族石脑油。其他的有机溶剂也可以使用，例如，萜烯溶剂，包括松香衍生物；脂族酮，如环己酮；和复合的醇，如2-乙氧乙醇。
此处可有利使用的乳化剂能容易的被本领域的熟练技术人员决定，且包括各种非离子的、阴离子的、阳离子的和两性乳化剂，或两种或更多的乳化剂的混合物。用于制备乳化剂浓缩物的非离子乳化剂的例子包括聚烷撑二醇醚和烷基和芳基苯酚的浓缩产品，脂族醇，脂族胺或脂肪酸和环氧乙烷，环氧丙烷例如乙氧基化烷基苯酚和溶于多元醇或聚氧化烯的羧酸酯。阳离子乳化剂包括季铵盐化合物和脂族胺盐。阴离子活化剂包括烷基芳基硫酸的油溶性盐(例如钙)，油溶性盐或硫酸化聚乙二醇醚和磷酸化聚乙二醇醚的适当的盐。
能用于制备本发明可乳化浓缩物的代表性的有机液体是芳香族液体，例如二甲苯，丙苯部分；或混合的萘部分，矿物油，取代的芳香族有机液体例如邻苯二甲酸二辛酯；煤油；各种脂肪酸的二烷基酰胺，特别是脂肪乙二醇和乙二醇衍生物的二甲基酰胺，例如正丁基醚，乙醚或二甘醇的甲醚，和三甘醇的甲醚。两种或更多有机液体的混合物在制备可乳化浓缩物中也是经常适宜使用的。优选的有机液体是二甲苯，和丙苯部分，其中二甲苯是最优选的。表面活性的分散剂是通常以液体剂型的形式使用，并且其量为分散剂和一种或多种化合物的联合重量的0.1到20wt％。制剂也能含有其他适宜的添加剂，例如，植物生长调节剂和其他的农业上使用的生物活性化合物。
水悬浮液含有一种或多种水溶性化合物的悬浮液，以从大约5％到50％W/W范围的浓度分散在水性载体中。悬浮液是通过精细磨碎一种或多种化合物，并且将研磨后的材料剧烈混合到载体中而制备的，其中载体包含水和选自上面讨论的同样类型的表面活性剂。也可以加入其他的成分，例如无机盐和合成或天然树胶，以增加水性载体的密度和粘度。通常在同样的时间内最有效的磨细和混合是通过制备水性混合物并在一个工具例如砂磨机，球磨机，或活塞式均化器内均匀化。
这些化合物也可以以颗粒剂型使用，这是对于土壤使用特别有用的。颗粒剂型通常含有从大约0.5％到大约10％w/w的化合物，分散在惰性载体中，其中惰性载体含有全部的或大部分的粗糙分散的绿坡缕石、皂土、硅藻土、粘土或相似的不昂贵的物质。这种剂型通常通过把化合物溶解在适宜的溶剂中并把它用于粒状载体而制备，其中粒状载体已经被预先制成适宜的粒径，在大约0.5到大约3mm的范围内。这种剂型也可以通过制成载体和化合物的面团或糊来制备，并粉碎和干燥以获得需要的粒状颗粒。
包含这些化合物的粉末的制备仅仅通过密切混合一种或多种粉状化合物和适宜的粉状农业载体，例如，高岭土，磨碎的火山岩，和类似物。粉末能适宜地含有从大约1％到大约10％w/w的化合物。
剂型可以含有辅助用的表面活性剂来增加这些化合物对于目标作物和有机体的沉积作用，可湿性和穿透性。这种辅助的表面活性剂可以任意被用作一种制剂成分或用作桶混制剂。辅助表面活性剂的量可以在0.01％到1.0％v/v之间变化，优选的在0.05％到0.5％之间，基于水的喷雾体积。适宜的辅助表面活性剂包括乙氧基化壬基酚，乙氧基化合成或天然醇，酯或硫基琥珀酸的盐，乙氧基化有机硅，乙氧基化脂肪胺，和表面活性剂和矿物油或植物油的混合物。
制剂可以任选地包括这样的组合，所述组合可以包括至少1％的一种或多种本发明的化合物和另外的杀虫化合物。这种附加的杀虫化合物可以是杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂，杀菌剂或其组合，它们和本发明的化合物在为应用选择的媒介中能相容，并且不对抗本发明化合物的活性。因此，在这种实施例中另外的杀虫化合物被用作补足毒素，用于相同或不同杀虫用途。在组合中本发明的化合物和杀虫化合物通常能以1∶100到100∶1的重量比例存在。
本发明在它的范围中包括用于控制或预防真菌发病的方法。这些方法包括将一种或多种本发明化合物的杀真菌量运用于真菌存在的位点，或感染将被控制的位点(例如，用于谷类或葡萄植物)。本发明化合物在杀真菌水平适用于各种植物的治疗，而表现低的植物毒性。本发明化合物以保护剂或铲除剂方式有用。本发明化合物通过各种公知技术中任意一种应用，或者作为化合物或作为含有这些化合物的制剂。例如，这些化合物可以用于根，种子，或植物的叶子来控制各种真菌，不会损害植物的商业价值。材料以任一种通常所用剂型的形式使用，例如，作为溶液，粉末，可湿性粉末，易流动的浓缩液，或可乳化的浓缩液。这些材料以各种公知方式常规使用。
已经发现本发明化合物有显著的杀真菌效果，特别是用于农业运用。这些化合物中许多对用于农业作物和园艺植物是尤其有效的，或用于木材，涂料，叶子或地毯背衬。
特别是，本发明的化合物有效地控制各种感染有用植物作物的不需要的真菌。对于各种真菌的活性已经被证明，例如包括下列有代表性的真菌种类：葡萄霜霉病(plasmopara viticola-PLASVI)；土豆和西红柿晚疫病(phytophthora infestans-PHYTIN)；小麦褐锈病(Pucciniarecondita-PUCCRT)；小麦白粉病(Erysiphe graminis-ERYSGT)；小麦叶斑枯病(Septorla tritici-SEPTTR)；稻纹枯病(Rhizoctoniasolani-RHIZSO)，和小麦颖斑病(Septoria nodorum-LEPTNO)。本领域技术人员可理解的，该化合物对于前述真菌的效力确立了本化合物作为杀真菌剂的普遍用途。
本发明的化合物作为杀真菌剂的效能是大范围的。使用的活性材料的精确的量不但依赖使用的特定化合物，而且依赖期望的特定活性，被控制的真菌种类，和其生长的阶段，以及和化合物相关的植物或其它产品的部分。因此，所有的化合物以及含有这些化合物的制剂，在相似的浓度下或对抗同样的真菌种类时，可能不是同等有效的。
本发明的化合物以植物疾病拟制和植物可接受的量使用于时是有效的。术语“疾病抑制和植物可接受的量”指杀死或抑制希望控制的植物疾病的化合物的量，但是对植物没有显著的毒性。这个量通常是从1到1000ppm，从10到500ppm是优选的。需要化合物的精确的浓度随着需要控制的真菌疾病，使用的剂型形式，应用方法，特定的植物种类，气候条件等等而变化。适宜的应用率通常是从大约0.10到大约0.4磅/英亩(大约0.1到0.45克每平方米g/m2)。
实施例
提供这些实施例以对本发明进一步说明。它们并不意味着解释为限制本发明。
本发明化合物的制备
权利要求请求保护的材料通过下面描述的几种方法制备。通常，期望的最终产物是通过亲电子试剂和硫亲核试剂的偶合，接着把硫氧化成砜来制备。硫可以在分子的胺的半侧或在芳烷基的半侧，如在下面的图1中所示。亲电子和亲核反应物可以如图1中所示通过本领域熟练技术人员公知的常规方法制备。(a.Carlson，R.M.；Lee，S.Y.Tetrahedron Lett.1969，4001.b.Rosenthal，D.等人J.Org.Chem.1965，30，3689.c.Mezo，G.；Mihala，N.；Koczan，B.；Hudecz，F.Tetrahedron1998，54，6757，d.Boemer，A.；Voss，G.Synthesis 1990，573.)
这两半被偶合，如果有必要胺可以被酰化，并且硫如在图2中所示被氧化。
制备化合物21
通过使用硫醇亲核试剂和苯基亲电子试剂
1.55g(S)-2-缬氨酸硫醇亲核试剂在10ml干燥的二甲基甲酰胺(DMF)中的溶液用氮气吹扫10分钟。向其中加入20ml 1M的叔丁氧化钾的四氢呋喃(THF)溶液，接着马上加入2.20g的1-(4-溴苯基)氯乙烷亲电子试剂。将该混合物搅拌20分钟，然后在水和乙醚/己烷(1∶1)中分配。水相提取两次或更多，并且有机相用盐水洗涤，干燥，并在旋转蒸发仪(rotovap)上除去溶剂得苍色油。该油可以通过蒸发蒸镏纯化，但是通常就这样使用。1.21g上述的粗产品在30ml二氯甲烷中的溶液用冰浴冷却，然后加入20mol％过量的3-丁基卡因-1-基氯甲酸酯(通过3当量的光气以20％的甲苯溶液在乙醇上作用3-4小时，再蒸发除去甲苯制备)，接着加入10ml的饱和的碳酸氢钠水溶液。将两相混合物剧烈搅拌30分钟，然后相分离，有机相干燥并用二氯甲烷稀释到40ml的体积。用冰浴冷却，然后在搅拌的同时分批加入1.73g m-氯过苯甲酸，在低于5℃的温度下将该混合物搅拌4-5小时。加入足量的1.5M硫代硫酸钠溶液以瘁灭过量氧化剂，然后将该混合物用2N氢氧化钠碱化(basicified)。相分离，有机相干燥，并旋转蒸发，且将粗产品通过色谱纯化得到砜21，为1.42g白色泡沫，通过气液色谱法(GLC)测定纯度96％。
制备化合物4
通过使用硫醇亲核试剂和甲苯磺酸酯亲电子试剂
354mg的1-(4-三氟甲氧苯基)乙硫醇溶液加入到氮气净化的1当量的氯化钠在20ml的干燥四氢呋喃(THF)的悬浮液中并搅拌得到干净的溶液。向其中加入500mg的(S)-异丙氧基羰基缬氨酸醇甲苯磺酸酯，该混合物在室温下搅拌过夜。采用与上面化合物21使用的方法相同的方式进行反应并氧化，通过色谱纯化得到269mg的白色固体。熔点(MP)为50-60℃。
通过上面的两种方法，能制备权利要求请求保护的大多数类型的化合物，包括化合物1-43，除了化合物11，12，和15之外，这几种化合物是从化合物1制备运用下面描述的方法制备的，并且化合物22的制备也在下面描述。第一个描述的方法通常是最有用的。
所用的苯基亲电子试剂能如图3所示制备。
乙酰苯还原成乙醇，并且通过使用纯的浓盐酸或二氯甲烷中的亚硫酰氯进行的这些乙醇的转化是本领域熟练人员所公知的。(Larock，R.C.Comprehensive Organic Transformations：a Guide toFunctonal Group Preparation；VCH Publishers，Inc.：New York，New York，1989；529，354-355页。)用于制备化合物1-43(除了化合物8，10-12，15，和26)的亲电子试剂是通过该方法制备的。
用N-溴化琥珀酰亚胺的芳基乙烷取代基的溴化和UV光来制备1-溴-1-芳基乙烷也是公知的，(Djerassi，C；Chem.Rev.1948，43，271)并且这种方法用于制备用于化合物8和10的亲电子试剂。
上面讨论的苯基亲电子试剂能通过图4所示黄原酸盐的详细描述的使用转变成硫醇亲核试剂。(Degani，L；Fochi，R.Synthesis 1978，365)这些亲核试剂能用甲苯磺酸酯亲电子试剂制备本发明的许多材料。
化合物1转变成化合物11，并且该材料用于制备化合物15和22，如图5所示。图5中所示的所有步骤对于本领域的技术人员是公知的。(Morris，J.；Wishka，D.G.J.Org.Chem.1991，56，3549.)
化合物22的制备如图6所示，并在下面的制备中描述。
异丙基1-({[氯(4-氯苯基)甲基]磺酰基}甲基)-2-
甲基丙基氨基甲酸酯(化合物22)
在氮气下将88mg干燥THF∶DMF(4∶1)中的60％氢化钠加入到350mg 4-氯苯硫醇中，并且搅拌该混合物得澄清溶液。向该澄清溶液中加入686mg的甲苯磺酸盐亲电子试剂，并且反应物在室温下搅拌3小时。反应在0.1N HCl和醚之间分配，水相用醚提取两次，并且用盐水将合并的有机相洗涤两次。干燥并蒸镏醚相，并且通过快速色谱纯化粗产品。于-78℃向385mg的在10ml干燥THF中的这种材料中在5分钟内加入500μl的2.5M正丁基锂己烷溶液，在5分钟后接着加入281mg的2ml THF中的二叔丁基碳酸氢盐。将反应加热到室温并搅拌4小时，然后如上面结束并且通过快速色谱纯化粗的硫化物产品，得到245mg的几乎无色的粘性油，通过TLC和氢谱核磁共振(1H NMR)纯化。在5分钟内，在用冰浴冷却的上述硫化物在10ml二氯甲烷中的溶液中加入3ml二氯甲烷中的83mg N-氯代琥珀酰亚胺的溶液。当溶液加热到室温时搅拌4小时。向该溶液中加入300mg的MCPBA，并且反应再次搅拌2小时。过量的氧化物用硫代硫酸钠溶液反应掉，然后用2N的氢氧化钠碱化。相分离，有机相干燥，并且在旋转蒸发仪上除去溶剂。剩余物溶于5ml的二氯甲烷中并且冷却到10℃，然后加入2ml的三氟乙酸(TFA)，接着搅拌过夜。在旋转蒸发仪上除去溶剂并且剩余物用闪柱纯化，得到80mg的白色固体。
化合物26是使用砜上的选择性烷化条件制备的，图7中所示。(Wada，A.；Tode，C.；Hiraishi，S.；Tanaka，Y.；Ohfusa，T.；Ito，M.Synthesis 1995，1107.)BOC基离去并且用芳族氨基甲酸酯代替，使用前面描述的方法。
化合物32-34是通过异氰酸酯和适宜的芳香醇的反应制备的，如图8所示。(Blahak，J.Ann.Chem.1978，1353.)
同样地，化合物37是从胺盐和适宜的取代的苯基异氰酸酯制备，如图9所示。(Gaudry，R.CanJ.Chem.1951，29，544)
化合物44是用8步从缬氨酸甲酯制备的，使用了氨基酸化学(a.Overhand，M.；Hecht，S.M.J.Org.Chem.1994，59，4721.B.Son，Y.C.；Park，C.H.；Koh，J.S.；Choy，N.Y.；Lee，C.S.；Choi，H.；Kim，S.C.；Yoon，H.S.Totrahedron Lett.1994，35，3745.C.Nacci，V.；Campianl，G.；Garofalo，A.Synth.Commun.1990，20，3019)结合上面描述的偶合和氧化化学。
在表1中，“EA”代表元素分析。
生物试验
这些化合物以100ppm在10vol％丙酮加90vol％的Triton X水(去离子水99.99wt％+0.01wt％Triton X100)中制备。在一天保护性试验(1DP)中试验化合物以整株水平控制植物疾病的能力。将化合物喷洒在安装有两个相反的空气雾化喷嘴的转盘式喷雾器上，其中所述喷嘴释放大约1500L/ha的喷射体积。植物第二天接种真菌的孢子，然后在诱导疾病发展的环境中孵育。依据疾病的发展速度，4到19天后评价疾病的严重程度。
下面的实验是在试验室中实施来确定本发明化合物的杀真菌效能。
土豆晚疫病(phytophthora infestans-PHYTIN)：土豆(Rutgers品种)在无土的泥炭罐装混合物(Metromix)中从种子生长直到秧苗长到1-2片叶子(BBCH 12)。然后以100ppm的比率对这些植物喷洒配制的实验化合物，喷洒到这些化合物流下来。24小时后实验化合物接种phytophthora infestans的孢子水悬浮液并在露室中孵育过夜。然后将植物转入温室中直到疾病在未经处理的对照组植物上产生。
葡萄霜霉病(plasmopara viticola-PLASVI)：葡萄植物(‘Carignane’品种)在无土的罐装混合物中从种子开始在温室中生长六个星期，直到秧苗长到2-3片叶子的阶段。然后以100ppm的比率对这些植物喷洒配制的实验化合物，喷洒到这些化合物流下来。24小时后在叶子的下方接种plasmopara viticola的孢子水悬浮液并在高湿度中保持过夜。然后将植物转入温室中直到疾病在未经处理的对照组植物上产生。
小麦叶斑枯病(Septoria tritici-SEPTTR)：小麦植物(Monon品种)在温室中在50％用巴氏法灭菌的土壤/50％无土混合物中从种子开始生长，直到最初的真叶完全展开，每罐6-8植株。然后以100ppm的比率对这些植物喷洒配制的实验化合物，喷洒到这些化合物流下来。24小时后在叶子上接种Septoria tritici的孢子水悬浮液并在高湿度中保持过夜。然后将植物转入温室中直到疾病在未经处理的对照组植物上产生。
下面的表格给出了当在这些实验中评价时，本发明典型化合物的活性。试验化合物在控制疾病上的效果是通过给出与未经处理的，接种的植物相比控制植物疾病的百分比进行评价的。
Claims (23)
1.根据通式一的化合物，
式一
其中：
R1选自F，Cl，Br，CN，C1-4烷基，C2-4烯基，C2-4炔基，C1-4卤代烷基，C1-4烷氧基烷基，C3-C6环烷基，C3-C6环烯基，CH2(C＝O)R5，和CH2CN；
R2和R3选自H，CH3，F，和Cl；
R4选自C1-6烷基，C2-6烯基，C2-6炔基，C3-6环烷基，C3-6环烯基，芳基，和杂芳基，其中所述的烷基，烯基，炔基，环烷基和环烯基，能被一个或多个取代基取代，取代基选自卤素，C1-4烷氧基，C3-6环烷基，芳基和杂芳基，其中所述的芳基和杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，C1-4烷氧烷氧基，CN，NO2，OH，SCN，C(＝O)R6，C(＝NR6)R6，S(On)R6其中n＝0，1或2，芳基，芳氧基，杂芳基，和杂芳氧基；
R5选自H，OR7，和C1-4烷基；
R6选自H，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，芳基，和杂芳基，OR7，N(R7)2，和SR7，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，CN，和NO2；
R7选自H，C1-4烷基，C2-4烯基，C2-4炔基，C1-4卤代烷基，芳基，和杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，CN，和NO2；
A选自芳基或杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，C1-4烷基，C2-4烯基，C2-4炔基，C1-4烷氧基，C1-4卤代烷基，C1-4卤代烷氧基，C1-4烷氧基烷基，C1-4烷氧烷氧基，CN，NO2，OH，SCN，C(＝O)R6，C(＝NR6)R6，S(On)R6，其中，n＝0，1，或2，芳基，芳氧基，取代的芳氧基，杂芳基，和杂芳氧基；和
Z选自C(＝O)R6，C(＝S)R6，P(＝O)(R6)2，和P(＝S)(R6)2。
2.根据权利要求1的化合物，其中：
R1选自Cl，C1-4烷基，和C2-4烯基；
R2和R3选自H，CH3；
R4选自C1-6烷基，其中所述的烷基能被一个或多个C1-4烷氧基取代基取代；
R5是H；
R6选自H，C1-4烷氧基，OR7，N(R7)2，和SR7；
R7选自H，C1-4烷基，C2-4烯基，C2-4炔基，C1-4卤代烷基，芳基，和杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，CN，C1-4烷基，和C1-4烷氧基；
A选自芳基或杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自卤素，CN，C1-4烷氧基，C1-4卤代烷氧基，芳基，取代的芳氧基，C2-4烯基，C(＝NR6)R6，NO2，和C(＝O)R6；和
Z选自C(＝O)R6和C(＝S)R6。
3.根据权利要求2的化合物，其中：
A选自芳基或杂芳基，其中所述的芳基或杂芳基能被一个或多个取代基取代，取代基选自Br和CN；和
Z选自异丙基和C(＝O)R6，其中所述的R6是OR7，并且所述的R7选自芳基和杂芳基，其中所述的芳基或杂芳基被一个取代基取代，取代基选自卤素和甲基。
4.根据权利要求3的化合物：
(i)其中A是取代的苯基，其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位；和
(ii)其中Z是C(＝O)R6，其中所述的R6是OR7，并且所述的R7是取代的苯基，并且其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位。
5.根据权利要求1的化合物，其中：
R1选自Cl和甲基；
R2和R3是H；
R4是C1-6烷基；
R5是H；
R6选自H，甲氧基，和OR7；
R7选自C1-4烷基，C2-4炔基，芳基，其中所述的芳基能被一个或多个取代基取代，取代基选自卤素和甲基；
A选自芳基或杂芳基，其中所述的芳基和杂芳基能被一个或多个取代基取代，取代基选自卤素，CN，C1-4烷氧基，C1-4卤代烷氧基，芳基，取代的芳氧基，C2-4炔基，C(＝NR6)R6，NO2，和C(＝O)R6；和
Z是C(＝O)R6其中所述的R6是OR7。
6.根据权利要求5的化合物，其中：
A选自芳基或杂芳基，其中所述的芳基和杂芳基能被一个取代基取代，取代基选自Br和CN；和
Z选自异丙基和C(＝O)R6，其中所述的R6是OR7，并且所述的R7选自芳基和杂芳基，其中所述的芳基或杂芳基被一个取代基取代，取代基选自卤素和甲基。
7.根据权利要求6的化合物，
(i)其中A是取代的苯基，其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位；并且
(ii)其中Z是C(＝O)R6，其中所述的R6是OR7，并且所述的R7是取代的苯基，并且其中所述的取代的苯基有一个取代基，并且所述的取代基是在对位。
8.根据权利要求1所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
9.根据权利要求2所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
10.根据权利要求3所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
11.根据权利要求4所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
12.根据权利要求5所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
13.根据权利要求6所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
14.根据权利要求7所述的化合物在制备控制或预防真菌侵袭的剂型中的用途。
15.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求1的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
16.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求2的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
17.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求3的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
18.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求4的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
19.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求5的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
20.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求6的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
21.一种组合物，所述组合物含有一种能抑制疾病量的和生理上可接受量的根据权利要求7的化合物和至少一种附加的杀虫化合物，其中杀虫化合物选自杀真菌剂，杀虫剂，杀线虫剂，杀螨剂，杀节肢动物剂和杀菌剂。
22.化合物4-氟苯基-(1S)-1-({[1-(4-氰基苯基)乙基]磺酰基}甲基)丙基氨基甲酸酯
23.化合物4-氟苯基-(1S)-1-({[(1S)-(4-氰基苯基)乙基]磺酰基}甲基)丙基氨基甲酸酯
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| IL117940A (en) * | 1995-04-19 | 2003-06-24 | Kumiai Chemical Industry Co | Benzylsulfide derivatives, process for their production and insecticide compositions containing them |
-
2001
- 2001-11-16 CN CNB018213022A patent/CN100438865C/zh not_active Expired - Fee Related
- 2001-11-16 PL PL01362137A patent/PL362137A1/xx not_active Application Discontinuation
- 2001-11-16 JP JP2002542761A patent/JP4280495B2/ja not_active Expired - Fee Related
- 2001-11-16 HU HU0303859A patent/HUP0303859A3/hu unknown
- 2001-11-16 EP EP01989756A patent/EP1341534B1/en not_active Expired - Lifetime
- 2001-11-16 AT AT01989756T patent/ATE462429T1/de not_active IP Right Cessation
- 2001-11-16 AU AU2002228640A patent/AU2002228640B2/en not_active Ceased
- 2001-11-16 AU AU2864002A patent/AU2864002A/xx active Pending
- 2001-11-16 WO PCT/US2001/044032 patent/WO2002040431A2/en active IP Right Grant
- 2001-11-16 PT PT01989756T patent/PT1341534E/pt unknown
- 2001-11-16 ZA ZA200303819A patent/ZA200303819B/en unknown
- 2001-11-16 NZ NZ525744A patent/NZ525744A/en unknown
- 2001-11-16 US US10/415,722 patent/US6815556B2/en not_active Expired - Fee Related
- 2001-11-16 MX MXPA03004357A patent/MXPA03004357A/es active IP Right Grant
- 2001-11-16 ES ES01989756T patent/ES2339532T3/es not_active Expired - Lifetime
- 2001-11-16 DE DE60141706T patent/DE60141706D1/de not_active Expired - Lifetime
- 2001-11-16 BR BR0115452-4A patent/BR0115452A/pt not_active IP Right Cessation
- 2001-11-16 KR KR1020037006634A patent/KR100796182B1/ko not_active IP Right Cessation
- 2001-11-16 CA CA002428733A patent/CA2428733A1/en not_active Abandoned
- 2001-11-16 CZ CZ20031300A patent/CZ20031300A3/cs unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5346907A (en) * | 1988-04-05 | 1994-09-13 | Abbott Laboratories | Amino acid analog CCK antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0303859A2 (hu) | 2004-03-29 |
| EP1341534A2 (en) | 2003-09-10 |
| EP1341534B1 (en) | 2010-03-31 |
| JP2004513930A (ja) | 2004-05-13 |
| PL362137A1 (en) | 2004-10-18 |
| WO2002040431A2 (en) | 2002-05-23 |
| EP1341534A4 (en) | 2005-09-28 |
| DE60141706D1 (de) | 2010-05-12 |
| ATE462429T1 (de) | 2010-04-15 |
| KR100796182B1 (ko) | 2008-01-21 |
| US20040030189A1 (en) | 2004-02-12 |
| PT1341534E (pt) | 2010-04-14 |
| JP4280495B2 (ja) | 2009-06-17 |
| NZ525744A (en) | 2004-10-29 |
| HUP0303859A3 (en) | 2004-06-28 |
| AU2002228640B2 (en) | 2005-11-10 |
| ES2339532T3 (es) | 2010-05-21 |
| US6815556B2 (en) | 2004-11-09 |
| CN1482907A (zh) | 2004-03-17 |
| CZ20031300A3 (cs) | 2003-10-15 |
| WO2002040431B1 (en) | 2003-03-20 |
| BR0115452A (pt) | 2003-12-23 |
| CA2428733A1 (en) | 2002-05-23 |
| KR20030051832A (ko) | 2003-06-25 |
| ZA200303819B (en) | 2004-05-17 |
| WO2002040431A3 (en) | 2002-08-01 |
| MXPA03004357A (es) | 2005-06-30 |
| AU2864002A (en) | 2002-05-27 |
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