Department of Biological Chemistry and Molecular Modelling , Institute of Advanced Chemistry of Catalonia (CSIC) , 08034 Barcelona , Spain.
Plant Health Department , Centro de Investigación y Tecnología Agroalimentaria de Aragón and Instituto Agroalimentario de Aragón-IA2, CITA-Zaragoza University , 50059 Zaragoza , Spain.
J Agric Food Chem. 2019 Jan 9;67(1):72-80. doi: 10.1021/acs.jafc.8b06346. Epub 2018 Dec 28.
The Moroccan locust, Dociostaurus maroccanus (Thunberg, 1815) (Orthoptera: Acrididae), is a polyphagous pest capable of inflicting large losses in agriculture under favorable environmental and climatic conditions. Currently, control of the pest relies solely on the application of conventional insecticides that have negative effects on the environment and human safety. In the search for a more rational, environmentally acceptable approach for locust control, we have previously reported that ( Z/ E)-phytal (1) is a male-produced candidate sex pheromone of this acridid. This molecule, with two stereogenic centers at C-7 and C-11, has four different diastereomers along with the Z/ E stereochemistry of the double bond at C-2. In this paper, we present for the first time the enantioselective synthesis of the four diastereomers of ( E)-phytal and their electrophysiological and behavioral activity on males and females. Our results demonstrate that the ( R, R)-phytal is the most active diastereomer in both assays, significantly attracting females in a double-choice Y olfactometer, and confirming the previous chromatographic assignment as component of the sex pheromone of the Moroccan locust.
摩洛哥飞蝗，Dociostaurus maroccanus（Thunberg，1815）（直翅目：蝗科），是一种多食性害虫，在有利的环境和气候条件下，能对农业造成巨大损失。目前，对该害虫的控制仅依赖于使用传统杀虫剂，这对环境和人类安全有负面影响。为了寻找一种更合理、更环保的蝗虫控制方法，我们之前曾报道过（ Z/ E）-phytal（1）是这种蝗科雄性产生的候选性信息素。该分子在 C-7 和 C-11 处具有两个手性中心，具有 C-2 处双键的 Z/ E 立体化学和四个不同的非对映异构体。在本文中，我们首次报道了（ E）-phytal 的四个非对映异构体的对映选择性合成及其对雄性和雌性的电生理和行为活性。我们的结果表明，（ R，R）-phytal 在两种测定中都是最活跃的非对映异构体，在双选择 Y 嗅觉计中显著吸引雌性，并证实了之前的色谱分配作为摩洛哥飞蝗性信息素的组成部分。
