- Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
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Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.
- Chien, Wei-Jynn,Gupta, Sachin,Liu, Bin,Lou, Da Wei,Shen, Yu-Jhe,Syu, Kun-Jie,Tseng, Jui-Chang,Zhang, Yuan-Xin
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- Preparation method of rice borer pheromone component
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The invention provides a preparation method of a rice borer pheromone component, and belongs to the technical field of organic synthesis. The preparation method uses Sodium Hexamethyldisilazane, namely sodium bis(trimethylsilyl)amide as an alkali to obtain relatively high yield, the cis-isomer content is improved, by controlling first wittig reaction at the temperature of -70 DEG C or less and limiting dropwise addition of acetate 12-oxo-dodecyl ester into the reaction system, the problem of increase of trans-type products caused by local overheating of the reaction system can be avoided, andthe reaction yield is improved. The data shows that the yield of the first wittig reaction is 72%, wherein the cis-isomer content is over 97%.
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Paragraph 0061; 0074; 0075
(2019/05/15)
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