Mozaina Kobaisy, Cantrell Charles L, Mims Amelia B, Lax Alan R, Tellez Maria R, Osbrink Weste L A
National Products Utilization Research Unit, Agricultural Research Service, U.S. Department of Agriculture, Mississippi 38677, USA.
J Agric Food Chem. 2008 Jun 11;56(11):4021-6. doi: 10.1021/jf800331r. Epub 2008 May 8.
A large number of naturally occurring and synthetic benzoquinones were evaluated for activity against the Formosan subterranean termite, Coptotermes formosanus, with potential use in termite control. Among these bioactive naturally occurring benzoquinones are 2-methyl-5-isopropyl-1,4-benzoquinone, 2-methoxy-6-pentyl-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone, 2,3-dimethoxy-5,6-dimethyl-1,4-benzoquinone, and 2,3-dichloro-5,6-dimethyl-1,4-benzoquinone. All five of these compounds demonstrated 100% mortality against C. formosanus by day 11 at a concentration of 1% (wt/wt) or less. In general, benzoquinones with one or two hydrophobic groups on the 5 and/or 6 positions of the quinone ring along with one or two group(s) on the opposite side of the ring, at the 2 and/or 3 position, led to high rates of mortality against C. formosanus. Quantitative structure-activity relationship (QSAR) studies showed no correlation between lipophilicity (calculated log P) and mortality for the entire group of nonhalogenated benzoquinones. A correlation was observed between C-6 chain length and day 3 percent mortality for 2,3-dimethoxy-5-methyl-6-substituted aliphatic benzoquinones where short chain lengths resulted in higher mortality.
对大量天然存在的和合成的苯醌进行了评估,以确定其对台湾地下白蚁(台湾乳白蚁)的活性,这些苯醌具有用于白蚁防治的潜力。这些具有生物活性的天然苯醌包括2-甲基-5-异丙基-1,4-苯醌、2-甲氧基-6-戊基-1,4-苯醌、2,3-二甲氧基-5-甲基-6-(3-甲基-2-丁烯基)-1,4-苯醌、2,3-二甲氧基-5,6-二甲基-1,4-苯醌和2,3-二氯-5,6-二甲基-1,4-苯醌。所有这五种化合物在浓度为1%(重量/重量)或更低时,到第11天对台湾乳白蚁的死亡率均达到100%。一般来说,醌环5和/或6位带有一个或两个疏水基团,同时在环的另一侧2和/或3位带有一个或两个基团的苯醌,对白蚁的死亡率较高。定量构效关系(QSAR)研究表明,对于整个非卤代苯醌组,亲脂性(计算的log P)与死亡率之间没有相关性。观察到2,3-二甲氧基-5-甲基-6-取代脂肪族苯醌的C-6链长度与第3天的死亡率百分比之间存在相关性,其中短链长度导致较高的死亡率。