The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
권호 표지
DOI QR코드

DOI QR Code

A facile synthesis of (E)-2-hexenyl (E)-2-hexenoate and (E)-2-hexenyl (Z)-3-hexenoate, pheromone components of Riptortus pedestris

톱다리개미허리노린재 페로몬, (E)-2-hexenyl (E)-2-hexenoate과 (E)-2-hexenyl (Z)-3-hexenoate의 합성

  • Kim, Junheon (Division of Applied Life Science (BK21), Gyeongsang National University) ;
  • Park, Chung Gyoo (Institute of Agriculture and Life Sciences, Gyeongsang National University)
  • 김준헌 (경상대학교 응용생명과학부(BK21)) ;
  • 박정규 (경상대학교 농업생명과학연구원)
  • Received : 2012.11.09
  • Accepted : 2013.04.05
  • Published : 2013.08.30
Download PDF
⟨ Previous Next ⟩

Abstract

We investigated optimal condition for synthesis of (E)-2-hexenyl (E)-2-hexenoate (1) and (E)-2-hexenyl (Z)-3-hexenoate (2), the pheromone components of Riptortus pedestris, by Steglich esterification. The reaction with 1.1-1.5 equivalent of dicyclohexylcarbodiimide (DCC), 1.5-2.0 equivalent of (E)-2-hexenol, and 0.1 equivalent 4-dimethylaminopyrinde (DMAP) to (E)-2-hexenoic acid in toluene or (Z)-3-hexenoic acid in dichloromethane led 1 and 2 in 76-78% and 87-91% yield, respectively.

톱다리개미허리노린재의 페로몬 성분인 (E)-2-hexenyl (E)-2-hexenoate (1) 과 (E)-2-hexenyl (Z)-3-hexenoate (2)의 합성에 있어 Steglich 에스테르화 반응의 최적 조건을 검토하였다. (E)-2-헥센산 또는 (Z)-3-헥센산에 대하여 1-1.5 당량의 디사이클로카보다이이미드 (DCC), 1.5-2.0 당량의 (E)-2-헥센놀과 0.1 당량의 4-디메틸아미노피리딘(DMAP)과 반응하였을 때, 각각 76-78% 와 87-91%의 수율로 1과 2를 얻었다.

Keywords

References

  1. Aldrich, J. R., G. K. Waite, C. Moore, J. A. Payne, W. R. Lusby and J. P. Kochansky (1993) Male-specific volatiles from nearctic and Australasian true bugs (Heteroptera: Coreidae and Alydidae). J. Chem. Ecol. 19:2767-2781. https://doi.org/10.1007/BF00980582
  2. Chung, B.-K., S.-W. Kang and J.-H. Kwon (1995) Damages, occurrences and control of Hemipterous insects in nonastringent persimmon orchards. RDA J. Agric. Sci. 37:376-382.
  3. Endo, N., T. Wada, Y. Nishiba and R. Sasaki (2006) Interspecific pheromone cross-attraction among soybean bugs (Heteroptera): Does Piezodorus hybneri (Pentatomidae) utilize the pheromone of Riptortus clavatus (Alydidae) as a kairomone? J. Chem. Ecol. 32:1605-1612. https://doi.org/10.1007/s10886-006-9093-0
  4. Huh, H. -S., K. H. Park, W. D. Seo and C. -G. Park (2005) Interaction of aggregation pheromone components of the bean bug, Riptortus clavatus (Thunberg) (Heteroptera: Alydidae). Appl. Entomol. Zool. 40:643-648. https://doi.org/10.1303/aez.2005.643
  5. Huh, H. S., K. H. Park, H. Y. Choo and C. G. Park (2006) Attraction of Piezodorus hybneri to the aggregation pheromone components of Riptortus clavatus. J. Chem. Ecol. 32:681-691. https://doi.org/10.1007/s10886-005-9024-5
  6. Leal, W. S., H. Higuchi, N. Mizutani, H. Nakamori, T. Kadosawa and M. Ono (1995) Multifunctional communication in Riptortus clavatus (Heteroptera: Alydidae): Conspecific nymphs and egg parasitoid Ooencyrtus nezarae use the same adult attractant pheromone as chemical cue. J. Chem. Ecol. 21:973-985. https://doi.org/10.1007/BF02033802
  7. Mizutani, N., T. Wada, H. Higuchi, M. Ono and W. S. Leal (1997) A component of a synthetic aggregation pheromone of Riptortus clavatus (Thunberg) (Heteroptera: Alydidae), that attracts an egg parasitoid, Ooencyrtus nezarae Ishii (Hymenoptera: Encyrtidae). Appl. Entomol. Zool. 32:504-507. https://doi.org/10.1303/aez.32.504
  8. Muto, Y. (2011) Method for producing (E)-2-hexenyl (E)-2- hexenoate. Japan Kokai Tokkyo Koho JP 20111-53099.
  9. Neises, B. and W. Steglich (1978) Simple method for the esterification of carboxylic acid. Angew. Chem., Int. Ed. Engl. 17:522-524. https://doi.org/10.1002/anie.197805221
  10. Son, J. K., H. Y. Choo, J. Y. Choi, C. H. Paik and C. G. Park (2009) Enhancement of Riptortus clavatus (Thunberg) (Hemiptera: Alydidae) egg parasitism by a component of the bug's aggregation pheromone. J. Asia Pac. Entomol. 12:159-163. https://doi.org/10.1016/j.aspen.2009.02.009
  11. Wada, T., N. Endo and M. Takahashi (2006) Reducing seed damage by soybean bugs by growing small-seeded soybeans and delaying sow time. Crop Prot. 25:726-731. https://doi.org/10.1016/j.cropro.2005.10.003
  12. Yasuda, T., N. Mizutani, N. Endo, T. Fukuda, T. Matsuyama, K. Ito, S. Moriya and R. Sasaki (2007) A new component of attractive aggregation pheromone in the bean bug, Riptortus clavatus (Thunberg) (Heteroptera: Alydidae). Appl. Entomol. Zool. 42:1-7. https://doi.org/10.1303/aez.2007.1

Cited by

  1. Thunberg (Hemiptera: Coreidae) vol.47, pp.2, 2017, https://doi.org/10.1111/1748-5967.12204
  2. (Hymenoptera: Encyrtidae) pp.09312048, 2018, https://doi.org/10.1111/jen.12468
  3. Olfactory attraction to aggregation pheromone is mediated by disti-flagellum of antennal segments in Riptortus pedestris vol.24, pp.1, 2013, https://doi.org/10.1016/j.aspen.2021.01.005