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새로운 2-이미노티아졸린 유도체의 합성과 항균활성 (II)
남기달,최경자,조광연,한호규,Nam, Kee-Dal,Choi, Gyung-Ja,Cho, Kwang-Yun,Hahn, Hoh-Gyu 한국응용생명화학회 1998 Applied Biological Chemistry (Appl Biol Chem) Vol.41 No.6
신 농약을 개발할 목적으로 선도화합물인 티아졸린의 곁가지를 변화시킨 새로운 2-이미노티아졸린 유도체를 합성하여 항균활성을 검색하였다. 디키틴과 아닐린으로부터 제조된 아세토아세트아닐리드 유도체를 브롬화하여 상응하는 감마-브로모아세토아세트아닐리드 유도체를 얻고 이를 티오우레아 유도체와 반응시켜 2-이미노티아졸린 유도체를 합성하였다. 2-이미노티아졸린의 항균활성을 검색하고자 6 종류의 대표적인 식물 병원균에 대한 시험(in vivo)을 하였다. 2-페노치환체들은 벼도열병균에 대하여 250 ppm에서 탁월한 항균성을 나타냈다. 1차 활성시험에서 방제가 90이상으로 평가된 것만 선발하여 2차 활성시험(농도저하 시험)을 수행하였다. 2-아릴기에 전자주게보다 전자 끌게, 전자끌게 중에서도 할로겐치환체가 도입된 경우에 고 활성을 나타냈으며 불소원자가 치환된 경우에 활성이 비교적 양호하였다. A synthesis and the screening of new 2-iminothiazolines (IV) of which structures are modified based on a lead compound, thiazoline for development of new agrochemical fungicide were described. Bromination of acetoacetanilides (I) which were prepared by the reaction of diketene with anilines gave the corresponding ${\gamma}-bromoacetoactanilide\;(II)$. Treatment of II with N-phenyl-N'-methyl thiourea (III) afforded IV, structure of which was confirmed by various spectroscopic methods. Antifungal activity of the new IV was tested against six kinds of typical plant diseases (in vivo). The IV with aromatic substituents showed remarkable activity against the Pyricuraria oryzae at 250 ppm in primary screening. The candidates with control value over 90% in primary screening were selected and further tested for second screening at lower concentrations. The IV which has an electron-withdrawing substituent such as halogen, especially fluorine in aryl group showed a higher activity as compared to those with electron-donating group and meta substituent was for optimal position.
새로운 2-Benzoylimino-1,3-oxathiole 유도체의 합성 및 살균활성
남기달,신선호,마혜덕,이선우,조광연,한호규,Nam, Kee-Dal,Shin, Sun-Ho,Mah, He-Duck,Lee, Seon-Woo,Cho, Kwang-Yun,Hahn, Hoh-Gyu 한국응용생명화학회 2002 한국농화학회지 Vol.45 No.3
새로운 살균제를 개발할 목적으로 새로운 2-benzoylimino-1,3-oxathiole 유도체 3을 합성하고, 그들의 살균활성을 시험하였다. ${\gamma}-Chloro-{\beta}-keto$ anilide 유도체 5를 potassium thiocyanate와 반응시킨 다음 산성 촉매로 처리하여 고리화된 2-imino-lf-oxathiole 3을 얻었다. 새로운 화합물 3을 benzoyl chloride 유도체와 반응시켜 상응하는 2-benzoylimino-1,3-oxathiole유도체 7들을 얻었다. 합성된 화합물 7들의 대표적인 식물병원균인 벼 도열병, 벼 잎 집무늬마름병, 오이 잿빛곰팡이병, 토마토 역병, 밀 붉은녹병 및 보리 흰가루병 등 』6종에 대한 항균력(in vivo)을 시험하였다. 합성된 모든 화합물은 100mg/l에서 특별한 살균력을 나타내지 않았다. New 2-benzoylimino-1,3-oxathile derivatives 3 were synthesized and tested their fungicidal activities for the development of new agrochemical fungicide. Reaction of ${\gamma}-chloro-{\beta}-keto$ anilide derivative 5 with potassium thiocyanate followed by the treatment of acid catalyst gave cyclyzed 2-imino-1,3-oxathiole 3. New compound 3 reacted with benzoyl· chlorides to afford the corresponding 2-benzoylimino-1,3-oxathiole derivatives 7. Antifungal screening (in vivo) of the synthesized compounds against typical plant diseases, which include rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, was carried out. No significant fungicidal activities were shown of the synthesized compounds at 100 mg/l.
닭 성장 및 육질개선을 위한 수용성키토산의 사료첨가 급이효과
남기달 ( Kee Dal Nam ),한호규 ( Hoh Gyu Hahn ),조승주 ( Seung Joo Cho ),박길현 ( Gil Hyun Park ),김종태 ( Chong Tai Kim ) 한국키틴키토산학회 2008 한국키틴키토산학회지 Vol.13 No.1
The objectives of this study were (1) to investigate the effects of chitosan-based feed additive(CFA) on the growth performance, feed intake, feed conversion, carcass characteristics, and (2) to explore the composition of biochemical components and on the textural and microstructural properties growing-finishing broiler chickens. The body weight gain of chicken fed with CFA was increased about 18% when compared to than that of commercial feed group. The mortalities of chicken fed with CFA were reduced about 55% when compared to than that of commercial feed group. There were no differences between control and broiler chicken fed with CFA in chemical components. Among fatty acids, comparably higher contents of 16 : 0, 16 : 1, 18 : 1 ω9 and 18 : 1 ω7 were observed in broiler chicken fed with CFA. The texture of breast meat in broiler chicken fed CFA exhibited a higher value for storage modulus compared than that of control. The microstructure of breast muscle showed a great difference between control and broiler chicken fed with CFA. This result might be greatly related to the hardness of texture. As a result, this study may suggest that the CFA effectively increased the body weight and reduced the mortality of chicken, and the CFA may be useful in poultry industry as cost-effective and eco-friendly feed additives.
새로운 2-이미노티아졸린 유도체의 합성과 항균 활성 (1)
한호규,남기달,김병섭,조광연 ( Hoh Gyu Hahn,Kee Dal Nam,Byung Sup Kim,Kwang Yun Cho ) 한국응용생명화학회 1997 Applied Biological Chemistry (Appl Biol Chem) Vol.40 No.2
This research aims at developing a new pesticide by means of synthesizing new 2-iminothiazoline derivatives and testing their bilolgical activity. In an effort to prepare 2-iminothiazolines, primary amines were treated to have reaction with isothiocyanate, followed by a treatment of a-halo ketone derivatives. Their antifungal activity was tested against six different plant diseases. A compound that has a phenylimino group at C-2, methyl at C-3, phenylcarbamoylmethyl at C-4, and hydrogen at C-5 on the thiazoline skeleton was found to be most active.
새로운 hydroxyethyl 2-iminothiazoline 유도체의 모델링 및 합성
한호규(Hoh-Gyu Hahn),남기달(Kee Dal Nam),전진호(Jinho Jeon),마혜덕(Heduck Mah) 한국농약과학회 2003 농약과학회지 Vol.7 No.2
Modeling and synthesis of novel hydroxyethyl 2-iminothiazolines were carried out through molecular modification of lead compound, 2-phenyliminothiazolines 1, for the purpose of development of new fungicidal agrochemicals. Oxygen atom of the hydroxyethyl group in 2-iminothiazolines 3 would locate in the proximity of the imino carbon at C-2 of 2-iminothiazoline moiety through neighboring group participation, and so that it would affect the biological activity of the molecule. Reaction of v-chloroacetoacetanilides 5 with hydroxyethylureas 6 gave 29 kinds of new corresponding hydroxyethyl 2-iminothiazolines 3 in high yields.
토마토 역병균과 벼 도열병균에 선택적인 살균활성의 3-아미노-2-벤질이미노-1,3-티아졸린 유도체 발굴
한호규(Hoh-Gyu Hahn),남기달(Kee Dal Nam),신동윤(Dong Yoon Shin),최경자(Gyung Ja Choi),조광연(Kwang Yun Cho) 한국농약과학회 2006 농약과학회지 Vol.10 No.3
A new 3-amino-1,3-thiazoline chemical library was synthesized through parallel synthetic technology and in vivo antifungal activity of the compounds were investigated against the typical 6 plant diseases (100 ppm). The characteristic feature of these derivatives was that both a benzyl moiety in C-2 imino and an amino group in C-3 of 2-imino-1,3-thiazoline scaffold were substituted in the molecule respectively. Some compounds showed antifungal activity with selectivity against tomato late blight and rice blast. The fungitoxicity would be attributed to 3,4-dichlorophenyl moiety of the benzyl group.
Pyrrolo[2,1-b]thiazole 카르복스아닐라이드 유도체의 합성 및 그들의 벼도열병균과 밀 붉은녹병균에 대한 선택적인 항균활성
한호규(Hoh-Gyu Hahn),남기달(Kee Dal Nam),양범승(Bum-Seung Yang),최경자(Kyung-ja choi),조광연(Kwang Yun Cho) 한국농약과학회 2005 농약과학회지 Vol.9 No.2
For development of new agrochemical fungicide, syntheses of pyrrolo[2,1-b]thiazole carboxanilide derivatives 9 and antifungal screening against 6 kinds of plant pathogens were carried out. Functionalization of carboxylic acid on C-2 into carboxanilide in the pyrrolo[2,1-b]thiazole resulted in new 20 candidates, in which are α,β-unsaturated carboxanilide and methyl groups that are in cis relationship. Treatment of acetoxy-1,4-thiazin with magnesium in refluxing methanol gave pyrrolo[2,1-b]thiazole ethyl ester 4 in higher yield than that of the previous report. Hydrolysis of this compound afforded the corresponding acid 5, which reacted with aniline derivatives in the presence of coupling reagent, DIC to give pyrrolo[2,1-b]thiazole carboxanilides 9. As the result of in vivo antifungal assay of 9 against rice blast, rice sheath blight, cucumber gray mold, tomato late blight, wheat leaf rust, and barley powdery mildew, some compounds showed selectively antifungal activities against the rice blast and wheat leaf rust.
2-이미노-1,3-티아졸린 유도체의 최적화 및 벼 도열병에 대한 방제활성 (Ⅰ)
한호규(Hoh-Gyu Hahn),남기달(Kee Dal Nam),배수열(Suyeal Bae),박익규(Ik Kyu Park) 한국농약과학회 2004 농약과학회지 Vol.8 No.3
In a course of the process for a lead optimization of 2-imino-l,3-thiazolines 1 which show a selective in vivo antifungal activity against rice blast, new compounds 2 in which C-5 was substituted by methyl group of the lead compound were synthesized and tested for the biological activity. Bromination of β-keto ester 7 followed by the reaction with thiourea and hydrolysis gave 2-imino-5-methyl-l,3-thiazoline carboxylic acid 3. Coupling reactions of 3 with aniline derivatives afforded 17 kinds of the corresponding 2-imino-5-methyl-l,3-thiazoline carboxanilides 2. Their in vivo antifungal activity against rice blast was weaker than that of 1, indicating that the in vivo antifungal activity of 2-imino-l,3-thiazolines was affected by the substituent at C-5. These results would be an important data for the molecular design in the lead optimization process of this series.