Carpropamid, a New Fungicide for Rice Blast Control
Carpropamid, a New Fungicide for Rice Blast Control
复制标题
卡菌酰胺，一种用于稻瘟病防治的新型杀菌剂
DOI：
10.1584/jpestics.23.145
复制
发表时间：
1998
影响因子：
2.4
通讯作者：
Y. Kurahashi
中科院分区：
文献类型：
--
作者：
S. Kagabu;Y. Kurahashi
为了有效防治植物病原体，一直需要具有新作用模式的杀真菌化合物。现在，一种新型的环丙烷甲酰胺结构的杀真菌剂，环丙酰菌胺（carpropamid）（13，图1）被添加到用于稻瘟病防治的标准工具中。我们报告的过程中，以获得carpropamid的结构和生物功效有关的立体构型的这种化合物和类似的手性分子。1972年，壳牌公司的研究人员声称，（WL28325; 1）作为水稻稻瘟病的内吸性杀菌剂1）不仅其不常见的骨架引起了我们的注意，而且其在寄主植物中诱导植物抗毒素的独特防病作用也引起了我们的兴趣2）在田间应用中，结果表明，作为一种实用的杀真菌剂，这种羧酸是相当挥发性的并且过于亲水。酯化（2和3），引入亲脂性增量（4和5），或将羧酸改变为生物电子等排基团（6和7），都没有得到令人满意的解决方案（图1，表1）。值得一提的是，在试图克服铅的物理化学缺点的变化中，保持高水平活性的醇（7）和衍生物（8和9）可以被视为基于代谢纯化的分子设计的实例。3，4）来自烷基或芳族胺的羧酰胺（10-12）也没有达到我们的期望。在这种情况下，活性似乎也随着分子大小的增加而降低。然而，在结构-活性关系研究中，逐渐清楚的是，将α-取代的2，2-二氯环丙烷羧酸与α-苯乙胺组合的特定酰胺结构对于增加活性特别有效。酰胺（13-17）显示出非常高的效力。其中，选择甲酰胺（13）与三甲基衍生物（15）及其4-溴同系物（17）一起进行进一步深入的实地研究。酰胺15和17具有两个，并且13具有三个不对称
Fungicidal compounds with novel modes of action are constantly required for effective control of plant pathogens. Now a new type of fungicide of cyclopropanecarboxamide structure, carpropamid (13, Fig. 1), was added to the standard tools for rice blast control. We report the process to attain the structure of carpropamid and the biological efficacies related to the stereo configurations of this compound and the analogous chiral molecules. In 1972 Shell researchers claimed 2, 2-dichlorocyclopropanecarboxylic acid (WL28325; 1) as a systemic fungicide for rice blast disease.1) Not only the uncommon skeleton caught our attention, but also the unique disease-control action by inducing phytoalexin in the host plants stimulated our interest.2) In field application, however, it turned out that this carboxylic acid is rather volatile and too hydrophilic as a practical fungicide. Esterification (2 and 3), introduction of lipophilic increments (4 and 5), or changing the carboxylic acid into the bioisosteric groups (6 and 7) brought no satisfactory solution (Fig. 1, Table 1). It should be worth mentioning that among the attempted variations to overcome the physicochemical drawbacks of the lead, alcohol (7) and the derivatives (8 and 9) holding the high level of activity may be counted as an example of molecular designs based on the metabolic consideration.3,4) Carboxamides from alkyl or aromatic amines (10-12) did not fulfill our expectation either. In this case also the activity seemed to decrease as the molecular size increases. In the structure-activity relationship study, however, it became gradually clear that specific amide structures combining a-substituted 2, 2-dichlorocyclopropanecarboxylic acid with a-phenethylamine were particularly effective for increasing activities. Amides (13-17) showed remarkably high potencies. Among them carboxamide (13) was selected for a further intensive field study together with trimethyl derivative (15) and its 4-bromo homologue (17). Amides 15 and 17 have two, and 13 has three asymmetric