Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
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-c...
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| Format: | Article |
| Language: | English |
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Wiley
2020-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2020/5632534 |
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| author | Bin Liu Kun-Jie Syu Yuan-Xin Zhang Sachin Gupta Yu-Jhe Shen Wei-Jynn Chien Jui-Chang Tseng Da Wei Lou |
| author_facet | Bin Liu Kun-Jie Syu Yuan-Xin Zhang Sachin Gupta Yu-Jhe Shen Wei-Jynn Chien Jui-Chang Tseng Da Wei Lou |
| author_sort | Bin Liu |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-d89124db3e8843e9b0ed485b5c460583 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2020-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-d89124db3e8843e9b0ed485b5c4605832025-02-03T01:04:46ZengWileyJournal of Chemistry2090-90632090-90712020-01-01202010.1155/2020/56325345632534Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)Bin Liu0Kun-Jie Syu1Yuan-Xin Zhang2Sachin Gupta3Yu-Jhe Shen4Wei-Jynn Chien5Jui-Chang Tseng6Da Wei Lou7Department of Analytical Chemistry, Jilin Institute of Chemical Technology, 45 Chengde Street, Jilin 132022, ChinaDepartment of Applied Chemistry, Chaoyang University of Technology, 168, Jifeng E. Rd., Wufeng District, Taichung 41349, TaiwanDepartment of Analytical Chemistry, Jilin Institute of Chemical Technology, 45 Chengde Street, Jilin 132022, ChinaDepartment of Applied Chemistry, Chaoyang University of Technology, 168, Jifeng E. Rd., Wufeng District, Taichung 41349, TaiwanDepartment of Applied Chemistry, Chaoyang University of Technology, 168, Jifeng E. Rd., Wufeng District, Taichung 41349, TaiwanDepartment of Applied Chemistry, Chaoyang University of Technology, 168, Jifeng E. Rd., Wufeng District, Taichung 41349, TaiwanDepartment of Applied Chemistry, Chaoyang University of Technology, 168, Jifeng E. Rd., Wufeng District, Taichung 41349, TaiwanDepartment of Analytical Chemistry, Jilin Institute of Chemical Technology, 45 Chengde Street, Jilin 132022, ChinaRice 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.http://dx.doi.org/10.1155/2020/5632534 |
| spellingShingle | Bin Liu Kun-Jie Syu Yuan-Xin Zhang Sachin Gupta Yu-Jhe Shen Wei-Jynn Chien Jui-Chang Tseng Da Wei Lou Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae) Journal of Chemistry |
| title | Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae) |
| title_full | Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae) |
| title_fullStr | Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae) |
| title_full_unstemmed | Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae) |
| title_short | Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae) |
| title_sort | practical synthesis and field application of the synthetic sex pheromone of rice stem borer chilo suppressalis lepidoptera pyralidae |
| url | http://dx.doi.org/10.1155/2020/5632534 |
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