Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae.
Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae.
复制标题
DOI：
10.1021/jf062562t
复制
发表时间：
2007-01
影响因子：
6.1
通讯作者：
M. Morimoto;Hiromi Fukumoto;T. Nozoe;A. Hagiwara;K. Komai
中科院分区：
文献类型：
--
作者：
M. Morimoto;Hiromi Fukumoto;T. Nozoe;A. Hagiwara;K. Komai
以酚类化合物为原料，通过苯氧乙酸和香豆烷酮合成了一系列橙酮化合物，并对斜纹夜蛾进行了拒食活性评价。天然存在的橙酮在ED 50为0.12 μ mol/cm 2时最具活性。合成的前体，香豆烷酮，表明甲氧基和甲基基团的苯环上的引入增加昆虫拒食活性。类似地，所测试的橙酮显示在A和/或B环上引入甲氧基增加了昆虫拒食活性，但是4，5，6-和3 '，4'，5 '-三取代的化合物在该测试中没有显示这种活性。橙酮在B环上的羟基化不利于昆虫对S.斜纹。虽然熔点与昆虫拒食活性没有很好的相关性，但几乎无活性的化合物具有高熔点。生物活性（pED 50）和氢键参数之间的显着相关性，从SiOH薄层色谱法获得的Rf值计算和亲脂性参数（log k）从ODS高效液相色谱法的保留时间计算。相关系数（r）分别为-0.83和-0.70。烷氧基和烷基基团的引入以及足够的氢键合似乎有助于测试化合物的拒食活性，沿着。
A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 micromol/cm2. The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED50) and a hydrogen-bonding parameter calculated from the Rf value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.