• Title, Summary, Keyword: (E)-2-hexenyl (E)-2-hexenoate

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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;Park, Chung Gyoo
    • The Korean Journal of Pesticide Science
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    • v.17 no.2
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    • pp.140-143
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    • 2013
  • 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.

Variation in Aggregation Pheromone Secretion of Bean Bug, Riptortus clavatus (톱다리개미허리노린재 집합페로몬의 분비변이에 관한 연구)

  • Huh, Hye-Soon;Jang, Sin-Ae;Park, Chung-Gyoo
    • Korean journal of applied entomology
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    • v.48 no.1
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    • pp.73-79
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    • 2009
  • Male adults of bean bug, Riptortus clavatus Thunberg (Heteroptera: Alydidae), release aggregation pheromone (AP) which consists of (E)-2-hexenyl (Z)-3-hexenoate (E2HZ3H), (E)-2-hexenyl (E)-2-hexenoate (E2HE2H), and tetradecyl isobutyrate (TI). Variation in the pheromonal secretion were checked by the factors of age, mating status, seasons, body weight and time in a day. There were no significant differences in the amounts of AP secretion by mating, body weight, and time in a day. Higher amount of AP was detected from older males than younger ones. The amount of AP detected was higher in the males collected from April to September than in those collected during October. No AP was detected in the males of November and December. These phenomena in the AP secretion were discussed in relation to food exploitation and reproductive diapause of the bean bug.

Composition of the Aggregation Pheromone Components of Korean Bean Bug and Attractiveness of Different Blends (한국산 톱다리개미허리노린재 집합페로몬 성분의 조성과 배합비율별 유인력)

  • Huh, Hye-Soon;Yun, Ji-Eun;Takashi, Wada;Mizutani, Nobuo;Park, Chung-Gyoo
    • Korean journal of applied entomology
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    • v.47 no.2
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    • pp.141-147
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    • 2008
  • Male adults of bean bug, Riptortus clavatus Thunberg (Heteroptera: Alydidae), release aggregation pheromone (AP) attracting both sexes of adult and nymphs, which its egg parasite, Ooencyrtus nezarae (Hymenoptera: Encyrtidae) exploits the pheromone to find host. The AP consists of three components; (E)-2-hexenyl (Z)-3-hexenoate (E2HZ3H), (E)-2-hexenyl (E)-2-hexenoate (E2HE2H), and tetradecyl isobutyrate (TI). We analyzed composition of the pheromone components of bean bugs from different geo graphical locations of Korea and Japan. The attractiveness of different blends of AP components to R. clavatus was also tested in the fields in Jinju, Korea and in Kumamoto, Japan. Composition ratios (E2HZ3H: E2HE2H:TI) of the AP of Jinju and Iksan populations were 1:1.4:0.2 and 1:0.8:0.2, and those of Tsukuba and Kumamoto populations were 1:2.8:0.2 and 1:1.5:0.1, respectively. In field tests, traps baited with ratio of 1:1:1 (E2HZ3H:E2HE2H:TI=16.7:16.7:16.7mg/rubber septum) and 1:1:0.5(E2HZ3H:E2HE2H:TI= 20:20:10mg/rubber septum) attracted significantly greater number of adult bugs than that of 1:5:1 (E2HZ3H:E2HE2H:TI=7.1:35.7:7.1mg/rubber septum).

Seasonal Occurrence and Attraction of Egg Parasitoid of Bugs, Ooencyrtus nezarae, to Aggregation Pheromone of Bean Bug, Riptortus clavatus (톱다리개미허리노린재의 집합페로몬에 의한 노린재류의 난기생봉 Ooencyrtus nezarae의 유인과 발생소장)

  • Huh Wan;Park Chung-Gyoo
    • Korean journal of applied entomology
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    • v.44 no.2
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    • pp.131-137
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    • 2005
  • Seasonal occurrence of the egg parasitoid of bugs, Ooencyrtus nezarae (Hymenoptera: Encyrtidae), was monitored at soybean fields and university campus using traps baited with aggregation pheromone of bean bug, Riptortus clavatus, in Jinju, Gyeongnam province, Korea. The female O. nezarae captured at university campus in 2003 and 2004 was 317.5 and 103.4 times as many as males, respectively, and it was 12.6 times at soybean field in 2004. The female began to occur from late August, showing its peak around September 20 at soybean field in 2004. At university campus in 2003 and 2004, the female began to occur from mid or late August, and showed its peak early or mid September. At the two monitoring sites the catches of female sharply declined after October The E2HZ3H only showed attractiveness to O. nezarae, among three components of the aggregation pheromone of bean bug, (E)-2-hexenyl (Z)-3-hexenoate (E2HZ3H), (E)-2-hexenyl (E)-2-hexenoate (E2HE2H), and myristyl isobutyrate (MI). A mixture in a ratio of 20:20:10 or 16.7:16.7:16.7 of E2HZ3H:E2HE2H:MI attracted significantly more females than the mixture of 7:36:7 ratio did. This higher attractiveness of the former two blends may be attributed to the higher amounts of E2HZ3H in the blends.

Attraction and Seasonal Occurrence of Piezodorus hybneri monitored with Aggregation Pheromone Traps of Riptortus clavatus (톱다리개미허리노린재의 집합페로몬 트랩에 의한 가로줄노린재의 유인과 발생양상)

  • Huh, Wan;Huh, Hye-Soon;Park, Chung-Gyoo
    • Korean journal of applied entomology
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    • v.44 no.4
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    • pp.265-270
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    • 2005
  • Seasonal occurrence of the stink bug Piezodorus hybneri (Gmelin) (Heteroptera: Penta-tomidae) was monitored at a soybean field and the campus of Gyeongsang National University, Gyeongnam. Korea, in which host plants are less available for the bug with aggregation pheromone traps of Riptortus clavatus Thunberg (Heteroptera: Alydidae) in 2004. At soybean field, P. hybneri began to be attracted to traps from June 28, earlier than flowering stage of soybean plants. Number of P. hybneri attracted increased sharply after October 11. At the campus the bugs were not attracted to traps from March 21 to October 5, but began to be attracted since October 11. Difference in the occurrences in the two sites may suggest that the stink bug immigrates actively into soybean field to find host plant. P. hybneri that had been attracted to traps since October 11 was assumed to be diapausing adults emigrating to hibernation sites. There was no difference between sexes in trap catches. The fact that P. hybneri was attracted from June to late November may suggest that the aggregation pheromone of R. clavatus was attractive to both non-diapausing and diapausing adults of P. hybneri. The aggregation pheromone traps, when baited with 16.7+16.7+16.7 mg or 7+36+7 mg of (E)-2-hexenyl (Z)-3-hexenoate, (E)-2-hexenyl (E)-2-hexenoate, and myristyl isobutyrate, attracted significantly higher number of both sexes of P. hybneri adults than the live male traps baited with ten R. clavatus males and hexane control.

Effect of Day Length and Temperature on the Diapause Termination of Riptortus pedestris (Hemiptera: Alydidae) Male Adults (일장과 온도 처리가 톱다리개미허리노린재 수컷 성충의 휴면종료에 미치는 영향)

  • Huh, Wan;Park, Chung-Gyoo
    • Korean journal of applied entomology
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    • v.49 no.3
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    • pp.205-210
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    • 2010
  • The bean bug, Riptortus pedestris (=clavatus) Fabricius (Hemiptera: Alydidae) is a serious pest of soybean in many countries. It enters a reproductive diapause in the winter by short day length (<13.5 h.) in Korea and Japan. The combined effects of temperatures ($25^{\circ}C$ and $8^{\circ}C$) and day lengths (10L:14D and 14L:10D) upon the termination of the male's diapause were studied. The combinations are (1) HTLD = $25^{\circ}C$, 14L:10D treatment for 1, 2, 3 weeks and 30 days; (2) HTSD = $25^{\circ}C$, 10L:14D treatment for 1, 2, and 3 weeks; (3) LTLD$\rightarrow$HTLD = $8^{\circ}C$, 14L:10D treatment for 1, 2, and 3 weeks followed by HTLD treatment; (4) LTSD$\rightarrow$HTLD = $8^{\circ}C$, 10L:14D treatment for 1, 2, and 3 weeks followed by HTLD. The amount of aggregation pheromone components secreted was adopted as the criteria for diapause termination in males. Males did not secrete aggregation pheromone under HTSD conditions. However, the males treated with HTLD for more than 21 days secreted significantly higher amounts of aggregation components, (E)-2-hexenyl (Z)-3-hexenoate and (E)-2-hexenyl (E)-2-hexenoate, compared to the control or HTSD treatments. The three components of the aggregation pheromone were secreted by the 14%, 29%, and 100% males treated with HTLD for 7 days, respectively. However more than 83% of the HTLD-treated males secreted all three components by the $30^{th}$ day under the treatment. In comparison, the pheromone amounts secreted by the males treated with LTLD$\rightarrow$HTLD or LTSD$\rightarrow$HTLD were equal or less than those secreted by males with continuous HTLD treatment.