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방사성 동위원소 $^{32}P$를 이용한 멸구류에 대한 품종저항성 검정방법에 관한 연구 (II)
이정운,김용헌,박중수,Lee Jeong Oon,Kim Yong Heon,Park Joong Soo,Lippold P.C. 한국응용곤충학회 1981 한국식물보호학회지 Vol.20 No.3
멸구류에 대한 수도품종 저항성 검정방법을 개발하고저 방사성 동위원소 $^{32}P$를 이용하여 본 시험을 수행하였다. 전편에서 얻어진 결과를 활용하여 멸구별, 멸구충태별, 접종시간별 벼멸구 흡즙량 차이와 품종별 벼멸구 흡즙량을 조사한 바 다음과 같은 결과를 얻었다. 가. 벼멸구, 흰등멸구, 애멸구 순으로 $^{32}P$ 흡즙량이 많았으며 암컷이 숫컷보다 공시멸구류 모두 흡즙량이 많았다. 나. 벼멸구의 각태별 흡즙량은 성충, 5령충, 성충), 4령 순으로 많았으며 충접종시간은 접종 24시간$\~$48시간에서는 일정한 흡즙령을 나타냈다. 다. 벼멸구의 벼품종별 흡즙량은 저항성 품종인 밀양 47호에서는 839 CPM인 반면 감수성 품종인 TN 1에서는 88,603 CPM을 나타 내었다. 따라서 본시험에서의 검정방법과 유묘집단검정방법과는 일치하였다. New screening method of varietal resistance by isotope $^{32}P$ was examined in these experiments. Insects were fed for 24 hrs. in the vials, with rice seedlings absorbed the solution if $0.6\~7{\mu}\;Ci\;^{32}P$ for 24 to 48 hrs. Feeding amounts of 3 species of plant-hoppers at the different stages and duration of infestation were investigated for effective process of screening method of the varietal resistance using isotope $^{32}P$. Feeding amount of $^{32}P$ of brown plant-hopper was observed for the different varieties. The results may be summarized as follows: 1. Brown planthopper fed greatest and the feeding amount were increased in order of white-backed planthopper and small brown planthopper. Female hoppers fed more than male. 2. Feeding amount was increased in order of adult, 5th instar, adult, 4th instar, 3rd instar 2nd instar and 1st instar. The duration of $24\~48\;hours$ is considered sufficient for insect infestation. 3. New screening method by $^{32}P$ was compared with seedling bulk screening method in view of feeding amount and plant reaction. Feeding amount of $^{32}P$ by brown planthopper in Milyang 47, resistant variety to this insect, was very low, while in TN 1, susceptible variety, it was very high about one hundred tines of Milyang 47.
강석구,이철희,김정한,이정운,Suk-Ku Kang,Chul-Hee Lee,Jung Han Kim,Jeong-Oon Lee 대한화학회 1988 대한화학회지 Vol.32 No.1
배추좀나방의 성 유인물질인 (Z)-11-헥사데센-1-올, (Z)-11-헥사데센-1-알, (Z)-11-헥사데센-1-일 아세테이트를 합성하여 생물활성 시험을 수행하였다. 1-헥신의 리튬음이온을 10-브로모데칸-1-올 THP 에테르와 반응시켜 11-헥사데신-1-올 THP 에테르를 얻었다. 이를 수소환원시킨 후 (Z)-11-헥사데센-1-올 THP 에테르를 생성시킨 다음 보호기를 제거시켜 (Z)-11-헥사데센-1-올을 합성하였다. 아세틸화시켜 (Z)-11-헥사데센-1-일 아세테이트를 산화시켜 (Z)-11-헥사데센-1-알을 각각 합성하였다. 합성된 성 페로몬에 대한 배추좀나방 숫컷의 성 유인력을 시험해 본 결과 활성이 있음을 밝혀졌다. Synthesis and biological activity test are described for the (Z)-11-hexadecen-1-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al, the sex pheromone of the diamond back moth, Plutella xylostella L.. Lithium acetylide was alkylated with 10-bromodecan-1-ol THP ether to give 11-hexadecyn-l-ol THP ether. 11-Hexadecyn-l-ol THP ether was stereoselectively reduced over Pd/BaSO4to yield (Z)-11-hexadecen-l-ol THP ether, which was in turn deprotected to provide (Z)-11-hexadecen-l-ol. (Z)-11-Hexadecen-l-ol was acetylated and oxidized to afford (Z)-11-hexadecen-1-yl acetate and (Z)-11-hexadecen-l-al, respectively. Biological activity test of the synthetic compounds, (Z)-11-hexadecen-l-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al in the ratio of 0.1 : 5 : 5 was tested in the field using polyethylene capsules as containers. The numbers of moth trapped with pheromone vials were counted.
강석구,구민숙,노광현,이정운,Suk-Ku Kang,Min-Suk Ku,Kwanghyun No,Jeong-Oon Lee 대한화학회 1987 대한화학회지 Vol.31 No.6
사과무늬잎말이나방의 성 유인물질인 (Z)-11-테트라데센-1-일 아세테이트(1)와 (E)-11-테트라데센-1-일 아세테이트(2)를 합성하여 생물활성시험을 수행하였다. 10-브로모데칸-1-올과 DHP에서 얻어지는 10-브로모데칸-1-올 THP에테르를 아세틸렌소디움음이온과 알킬화시켜 11-도데신-1-올 THP에테르를 합성하였다. 이것을 부틸리튬으로 처리하여 얻어지는 리튬음이온을 브로모에탄과 반응시켜 11-테트라데센-1-올 THP에테르를 얻었다. 이것을 $Pd/BaSO_4$하에서 수소환원시켜 (Z)-11-테트라데센-1-올 THP에테르를 얻었고, $Na/NH_3$와 금속환원시켜 (E)-11-테트라데센-1-올 THP에테르를 얻었다. (Z)-와 (E)-형의 화합물을 보호기를 제거한 후 아세트산무수물로 아세틸화하여 (Z)-11-테트라데센-1-일 아세테이트와 (E)-11-테트라데센-1-일 아세테이트를 각각 얻었다. 합성된 성 페로몬에 대한 사과무늬잎말이나방 숫컷의 성 유인력을 시험해 본 결과 활성이 있음이 밝혀졌다. Synthesis and Biological activity test are described for the (E)-11-tetradecen-1-yl acetate and (Z)-11-tetradecen-1-yl acetate, the sex pheromone of the Asiatic leafroller moth (Archippus breviplicanus Walsingham). 10-Bromodecan-1-ol THP ether was prepared from 10-bromodecan-1-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-1-al THP ether to give 11-dodecyn-1-ol THP ether. 11-Dodecyn-1-ol THP ether was then treated with n-Buli in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-1-ol THP ether. 11-Tetradecyn-1-ol THP ether was then reduced over $Pd/BaSO_4$ and with Na in liquid $NH_3$ to give (Z)-11-tetradecen-1-ol THP ether and (E)-11-tetradecen-1-ol THP ether, respectively. (Z)-and (E)-11-Tetradecen-1-ol THP ether thus obtained were deprotected by refluxing in the presence of PPTS and ethanol. (Z)-and (E)-11-tetradecen-1-ol were acetylated with acetic anhydride to afford the final products, (Z)-11-tetradecen-1-yl acetate (1) and (E)-11-tetradecen-1-yl acetate (2), respectively. The synthetic pheromone thus obtained was attractive to the males of the Asiatic leafroller moth in the field.
강석구,안상순,김정한,이정운,Suk-Ku Kang,Sang Soon Ahn,Jung Han Kim,Jeong-Oon Lee 대한화학회 1988 대한화학회지 Vol.32 No.1
애모무늬잎말이나방의 성 유인물질 (Z)-9-인테트라데센-1-일 아세테이트(1)와 (Z)-11-테트라데센-1-일 아세테이트(2)를 합성하여 생물활성시험을 수행하였다. 1,8-옥탄디올에서 쉽게 얻을 수 있는 8-브로모옥탄-1-올 THP 에테르를 1-헥신의 리튬음이온과 알킬화시켜 9-테트라데신-1-올 THP 에테르를 얻었다. 이를 Pb/BaSO4 촉매하에서 수소환원시킨 후 PPTS로 보호기를 제거하여 (Z)-9-테트라데센-1-올을 얻었으며 이를 아세틸화시켜 (Z)-9-테트라데센-1-일 아세테이트(1)를 합성하였다. 한편 1,10-데칸디올에서 쉽게 얻을 수 있는 10-브로모데칸-1-올 THP 에테르를 아세틸렌나트륨음이온과 알킬화시켜 11-도데신-1-올 THP 에테르를 얻는다. 이를 다시 부틸리튬으로 처리하여 얻어지는 리튬음이온을 브로모에탄과 반응시켜 11-테트라데신-1-올 THP 에테르를 형성시켰다. 이를 Pd/BaS$O_4$ 하에서 수소환원, 보호기제거 후 (Z)-11-테트라데신-1-올을 거쳐, 아세틸화시켜 (Z)-11-테트라데센-1-일 아세테이트 (2)를 합성하였다. 합성된 성 페로몬에 대한 애모무늬잎말이나방 숫컷의 성 유인력을 시험해본 결과 활성이 있음이 밝혀졌다. Synthesis and biological activity test are described for the (Z)-9-tetradecen-1-yl acetate(1) and (Z)-11-tetradecen-1-yl acetate(1) and (Z)-11-tetradecen-1-yl acetate(2), the sex pheromone of the summer fruit tortrix moth, Adoxophyes orana. 8-Bromoctan-l-ol THP ether was prepared from 8-bromoctan-l-ol. The lithium anion of 1-hexyne was alkylated with 8-bromoctan-l-ol THP ether gave 9-tetradecyn-l-ol THP ether. Catalytic hydrogenation over Pd/BaSO4 followed by deprotection afforded (Z)-9-tetradecen-l-ol. Acetylation gave (Z)-9-tetradecen-1-yl acetate(1). l0-Bromodecan-l-ol THP ether was obtained from l0-bromodecan-l-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-l-ol THP ether to give 11-dodecyn-l-ol THP ether. 11-Dodecyn-l-ol THP ether was then treated with n-BuLi in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-l-ol THP ether. Catalytic hydrogenation, deprotection, and acetylative gave (Z)-11-tetradecen-1-yl acetate(2). The synthetic pheromone thus obtained was attractive to the males of the summer fruit tortrix in the field.
진딧물의 경보페로몬인 (E)-β-Farnesene의 합성과 생물활성시험
강석구,정경운,이정운,고현관 성균관대학교 기초과학연구소 1986 論文集 Vol.37 No.1
(E)-β-Farnesene, the alarm pheromone of aphids was synthesized from nerolidol by reacting in a sealed tube at 150℃ for 24h with DMSO. Base(KOtBu/DMSO) catalized elimination of HCl from farnesyl chloride at 50℃ for 4h afforded (E)-β-farnesene as the major product. Farnesyl chloride was prepared from nerolidol or farnesol with SOCl_2 or HCl. Biological activity test of (E)-β-farnesene thus synthesized was conducted.