• Title/Summary/Keyword: fungicidal

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Screening and Identification of Fungicidal Compounds Derived from Medicinal Plants against Cucumber Powdery Mildew (약용식물로부터 오이흰가루병에 대한 항균성물질 탐색 및 동정)

  • Paik, Su-Bong;Kyung, Suk-Hun;Doh, Eun-Soo;Oh, Yeon-Sun;Park, Byoung-Keun
    • Korean Journal of Environmental Agriculture
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    • v.13 no.3
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    • pp.301-310
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    • 1994
  • This experiment was conducted to test the fungicidal activity of extracts from 50 medicinal plants to powdery mildew (Sphaerotheca fulinginea) and identify the bioactive substances. Among the medicinal plants tested, the water extract of Rheum undulatum was the most effective in spore germination inhibition, which inhibited by 100% at 200-fold dilution. Also, 50-fold dilution of water extract, 100-fold dilution of alcohol extract, 500-fold dilution of crude extract from Rheum undulatum and even 1000-fold dilution of reference chemical inhibited powdery mildew of cucumber more than 60%. 500-fold dilution of crude extract inhibited powdery mildew of cucumber 100% by twice spray treatment. There was phytotoxcity at the 100-fold dilution, but was not recognized this injury at the 500-fold dilution of crude extract. From our research to identify bioactive substance using HPLC, GLC and Mass spectrum analysis, it indicated that Rheum undulatum extract contained tentatively 1,8-dihydroxy-3-methyl-9,10-anthracenedione and 1,8-dihydroxy-3-methoxy-6-methyl-9,10-anthracenedione.

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In Vivo Antifungal Effects of Coptis japonica Root-Derived Isoquinoline Alkaloids Against Phytopathogenic Fungi

  • LEE CHI-HOON;LEE HOI-JOUNG;JEON JU-HYUN;LEE HOI-SEON
    • Journal of Microbiology and Biotechnology
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    • v.15 no.6
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    • pp.1402-1407
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    • 2005
  • The fungicidal activities of Coptis japonica (Makino) extracts and their active principles were determined against Botrytis cineria, Erysiphe graminis, Phytophthora infestans, Puccinia recondita, Pyricularia grisea, and Rhizoctonia solani using a whole plant method in vivo, and compared with natural fungicides. The responses varied according to the plant pathogen tested. At 2,000 mg/l, the chloroform and butanol fractions obtained from methanolic extracts of C. japonica exhibited strong/moderate fungicidal activities against B. cinerea, E. graminis, P. recondita, and Py. grisea. Two active constituents from the chloroform fractions and one active constituent from the butanol fractions were characterized as isoquinoline alkaloids, berberine chloride, palmatine iodide, and coptisine chloride, respectively, using spectral analysis. Berberine chloride had an apparent $LC_{50}$ value of approximately 190, 80, and 50 mg/l against B. cinerea, E. graminis, and P. recondita, respectively; coptisine chloride had an $LC_{50}$ value of 210,20, 180, and 290 mg/l against B. cinerea, E. graminis, P. recondita, and Py. grisea, respectively; and palmatine iodide had an $LC_{50}$ value of 160 mg/l against Py. grisea. The isoquinoline alkaloids were also found to be more potent than the natural fungicides, curcumin and emodin. Therefore, these compounds isolated from C. japonica may be useful leads for the development of new types of natural fungicides for controlling B. cinerea, E. graminis, P. recondita, and Py. grisea in crops.

Retention, Tenacity and Effect of Insecticides in the Fungicidal Control of Apple Bitter Rot (사과 탄저병 방제약제의 지속성 및 전착제$\cdot$살충제 혼용의 효과)

  • Chung Hoo Sup
    • Korean journal of applied entomology
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    • v.9 no.2
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    • pp.75-80
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    • 1970
  • 1. Retention of fungicides and efect of the mixing of spreaders and insecticides with fungicides in control of apple bitter rot were evaluated by 'the assay of inhibition zones with apple exocarp disks:' 2. The effectiveness of chemicals was reduced gradually as the time after treatment increased. Of all the chemicals tested, Difolatan retained approximately 60 percent of the original activity even after IS days. Difolatan had the highest followed by Tuzet, Phaltan, Bordeaux mixture, and Delan, in that order. 3. The fungicidal acivity of Tuzet decreased with increasing application of simulated rain. The wash-offf of Tuzet was reduced by adding spreaders. Dry skim milk and soybean extract were better than commercial chemicals such as Lino No. 1,2 and Tween 20. 4. The mixing of insecticides such as EPN, Folithion, Parathion and Lebaycid with Phaltan resulted in no significant differences in fungicidal effect even after 12 days of storage at room temperature.

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A Synthesis of New Benzylimino-1,3-oxathioles and Their Fungicidal Activity (새로운 2-Benzoylimino-1,3-oxathiole 유도체의 합성 및 살균활성)

  • Nam, Kee-Dal;Shin, Sun-Ho;Mah, He-Duck;Lee, Seon-Woo;Cho, Kwang-Yun;Hahn, Hoh-Gyu
    • Applied Biological Chemistry
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    • v.45 no.3
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    • pp.157-161
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    • 2002
  • 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.

Fungicidal Activity of 46 Plant Extracts against Rice Leaf Blast, Rice Sheath Blight, Tomato Late Blight, Cucumber Gray Mold, Barley Powdery Mildew and Wheat Leaf Rust (46종 식물추출물의 식물병 방제효과)

  • Lee, Sang-Gil;Ahn, Young-Joon;Park, Ji-Doo;Kim, Jin-Cheol;Cho, Kwang-Yun;Lee, Hoi-Seon
    • The Korean Journal of Pesticide Science
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    • v.5 no.3
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    • pp.18-25
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    • 2001
  • Ethanol extracts from 46 plants were tested for their fungicidal activity against six plant diseases consisting of Maynaporthe grisea, Rhizoctonia solani, Botrytis cinerea, Phytophthora infestans, Puccinia recondita, and Erysiphe graminis in the greenhouse studies. Strong activity at 5 and 10 mg/pot was produced from the extracts of Helianthus annuus flowers and Zea mays leaves against P. grisea. In a test with B. cineara, extracts of H. annuus leaves, H. annuus flowers, Chrysanthmum coronarium var. spatiosum, Cucurbita moschata seeds, Lycopersicon esculentum, Z. mays, and Z. mays leaves had strong activities at 5 mg/pot. In a test with P. recondita, strong activity was obtained from the extracts of Capsicum frutescens, C. moschata seeds, H. annuus seeds, L. esculentum, and Malva veticillata at 5 mg/pot. Against E. graminis, extracts of Cucumis sativus, H. annuus seeds, Salanum tuberosum, Z. mays, and Z. mays leaves produced strong activities at 10 mg/pot. All the extracts were ineffective against P. infestans and R. solani. Among seven extracts tested, the extracts of H. annuus leaves and flowers were highly effective against all the strains of B. cinerea resistant to carbendazim, procymidone, and diethofencarb. Furthermore, potent fungicidal activity was produced from the extracts of C. coronarium var. spatiosum and C. moschata seeds against the SSR, SRR, and RSR strains of B. cinerea, and Z. mays and Z. mays leaves against SSR and RSR. Extract of L. esculentum showed very strong activity only against RRS of B. cinerea.

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Influence of substituted phenyl backbone on the fungicidal activity of phenyl or 2-pyridyl substituents in bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives (비스 방향족 $\alpha, \beta$ -불포화 케톤 유도체중 2-pyridyl 및 phenyl 치환체의 항균성에 관한 치환 phenyl backbone의 영향)

  • Sung, Nack-Do;Yu, Seong-Jae;Choi, Kyoung-Seob;Kim, Hyun-Jae
    • The Korean Journal of Pesticide Science
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    • v.2 no.3
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    • pp.45-51
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    • 1998
  • A series of bis-aromatic ${\alpha},{\beta}$-unsaturated ketone derivatives with mesaured fungicidal activities in vivo against rice blast(Pyricularia oryzae), tomato leaf blight (Phytophtora infestans) and barley powdery mildew(Erysiphe graminis) were studied by using quantitative structure activity relationship equations. The QSAR model for the activity of phenyl substituents, $1{\sim}11$, clearly reveals three important factors, namely, resonance(R<0), optimal molecular hydrophobicity(${\pi})_{opt.}=0.38$) and optimal distance($((L_{1})_{opt.}=5.69({\AA}))$ of substituent, respectively. But in case of 2-pyridyl substituents, $12{\sim}28$, the activity were governed by optimal molecular refractivity $((M_{R})_{opt.}=8.04{\sim}39cm^{3}/mol)$, steric effect(Es<0) and LUMO energy(e.v). The fungicidal activity relationship of phenyl and 2-pyridyl substituents against Erysiphe graminis have been proportioned.

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Fungicidal Effect of Slightly Acidic Hypochlorous Water against Phytopathogenic Fungi (미산성 차아염소산수의 식물병원균류에 대한 살균 효과)

  • Song, Jeong Young;Kim, Narae;Nam, Myeong Hyeon;Park, BeomJin;Whang, Eui-Il;Choi, Jong Myung;Kim, Hong Gi
    • The Korean Journal of Mycology
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    • v.41 no.4
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    • pp.274-279
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    • 2013
  • Slightly acidic hypochlorous water (SAHW) is well known for having a powerful and broad spectrum antimicrobial activity, and is harmless to the environment and humans. SAHW (pH 5~6.5, 20~30 ppm available chlorine concentration) was generated by electrolysis of dilute solution of HCl (4%) in a chamber of a non-membrane electrolytic cell. Our objective was to determine SAHW has a potential fungicidal activity on some phytopathogenic fungi. Spores of Botrytis cinerea, Colletotrichum acutatum and Phytophthora capsici were not culturable on agar media at approximately 10 seconds after treatment by SAHW. However, inactivation of Penicillium hirsutum was required over 3 min. Dilution of SAHW with sterilized distilled water (SDW) at the ratio of 1:1 (SAHW:SDW) against C. acutatum showed 100% inactivation but, the efficacy in 1:2 decreased until 63.2%. Control value of SAHW was 70.4% against C. acutatum on pepper fruits when applied upto 24 h postinoculation. SAHW has a powerful and wide spectrum antifungal activity and could be applied as a potential alternative to fungicidal agent for control of plant disease.

Substituent Effect on the Fungicidal Activity of New N-substituted Benzotriazol-1-yl Derivatives (새로운 N-치환 benzotriazol-1-yl유도체의 항균활성에 미치는 치환기 효과)

  • Yu, Seong-Jae;Sung, Min-Gyu;Kim, Dae-Whang;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.40 no.1
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    • pp.80-84
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    • 1997
  • Series of new chiral N-substituted benzotriazol-1-yl derivatives were synthesized and their fungicidal activities in vitro against gray mold(Botrytis cinerea), black spot(Alternaria kikuchiana) and phytophthora blight(Phytophthora capsici) were measured by the agar medium dilution method. The substituents effects between the fungicidal activities (obs. $pI_{50}$) and a various physicochemical parameters of phenoxy or thiophenoxy group(X) & alkyl or phenyl group(Y) were analyzed by the multiple regression technique. From the analyzed substituent effects, the structure-activity relationship(SAR) equations shows that the antifungal activities depend on the parameters for the optimal molecular hydrophobicity($({\Sigma}logP)_{opt}$), Van der Waals (${\Sigma}Vw$>0) volume(${\AA}^3$) and inductive constant with electron withdrawing group(${\sigma}_I$,Y>0). The activity in affected by the inductive effect (${\sigma}_I$,Y>${\sigma}_g$X) of Y-group rather than the X-group. The phenoxy substituents, 1, showed higher antifungal activity tn the thiophenoxy substituents, 2. For 1, polar substituent constant(${\sigma}^*$) was an important factor in determining the activity. And the tribromomethyl substituent, 1g showed the highest activity against the tee fungi.

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3D-QSAR Analysis on the Fungicidal Activity with N-Phenylbenzenesulfonamide Analogues against Phytophthora blight (Phytophthora capsici) and Prediction of Higher Active Compounds (고추역병균(Phytophthora capsici)에 대한 N-Phenylbenzenesulfonamide 유도체들의 살균활성에 관한 3D-QSAR 분석과 고활성 화합물의 예측)

  • Soung, Min-Gyu;Kang, Kyu-Young;Cho, Yun-Gi;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.50 no.3
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    • pp.192-197
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    • 2007
  • 3D-QSARs on the fungicidal activity of N-phenylbenzenesulfonamide and N-phenyl-2-thienylsulfonamide analogues (1-37) against Phytophthora blight (Phytophthora capsici) were studied quantitatively using CoMFA and CoMSIA methods. The statistical results of the optimized CoMFA (2) model ($r^2_{cv.}(q^2)$ = 0.692 & $r^2_{ncv.}$= 0.965) show better predictability and fitness than CoMSIA (2) model ($r^2_{cv.}(q^2)$ = 0.796 & $r^2_{ncv.}$= 0.958). The fungicidal activities according to the information of the optimized CoMFA (2) model were dependent upon the steric and electrostatic fields of the molecules. Therefore, from the contribution contour maps of CoMFA (2) model, it is expected that 63% contribution was caused by the steric bulk of meta-substituent ($R_1$) on the S-phenyl ring. Also, the other contribution level of 32.9% was represented by the positive charged $R_4-group$ ($R_1$) on the N-phenyl ring and para-substituent ($R_1$) on the S-phenyl ring. A series of higher active compounds, $R_1$= 3-decyl substituent ($pred.pI_50$= 5.88) etc. were predicted based on the findings.

Crystal Structure and Fungicidal Activity of N-[1-(benzotriazol-1-yl)alkyl]aniline Derivatives (N-[1-(benzotriazol-1-yl)alkyl]aniline 유도체의 결정구조와 항균활성)

  • Lim, Chi-Whan;Yi, Kyeong-Joon;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.38 no.4
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    • pp.359-363
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    • 1995
  • New ten N-[1-(benzotriazol-1-yl)alkyl]aniline(4) derivatives were synthesized and the crystal structure of 4h was shown by X-ray crystallography and the absolute configuration has been assigned as S form. The molecule crystallizes in the monoclinic system, space group $P2_{1}/n$. And the molecules in the crystal are linked with each other through the hydrogen bond $(N_{11}-H_{11}{\cdots}N3)$ with distance $2.300(11){\AA}$ The fungicidal activity($pI_{50}$) in-vitro against Botrytis cineria (BC), Phytophthora casici (PC) and Sclerotium cepinorum (SC) were determined by the agar dilution method. The structure activity ralationships (SAR) between structure of 4 and the activity were studied using a physicochemical parameters of substituents and multiple regression technique. Among these compounds, only the bromo group substituent(4f) showed higher activity, which depend on the hydrophobic(${\pi}$) of substituents. The relative orders of the activity are SC>BC> and PC, respectively. This implies that the activity is affected by the hydrophobic(${\pi}$) nature of the Z group rather than the X group. Linear free energy relationships(LFER) on the fungicidal activity with substituents has been also discussed.

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