• Title/Summary/Keyword: Fungicidal Activity

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Synthetis of 4H,6H-Furo[3,4-c]isoxazole Derivatives as New Potent Fungicides and Their Structure Activity Relationship

  • 김형진;황광진;이재현
    • Bulletin of the Korean Chemical Society
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    • v.18 no.5
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    • pp.534-540
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    • 1997
  • 4H,6H-Furo[3,4-c]isoxazoles (Ⅰ-Ⅳ), potential fungicides, have been designed and synthesized via intramolecular [2+3] cycloaddition of nitroalkyne 3 as a key step. The broad spectrum of fungicidal activities of furoisoxazoles (Ⅰ-Ⅳ) were observed on plant pathogens at 250 ppm. Furoisoxazoles Ⅱ, Ⅲ with chlorophenyl at 6-position and methyl or alkylated oxime group at 3-position gave effective control of plant diseases. The furoisoxazole Ⅳ with a chlorophenyl group at 4-position also resulted in high fungicidal activities.

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

  • Sung, Nack-Do;Yu, Seong-Jae;Kim, Tae-Young;Ok, Whan-Suk
    • The Korean Journal of Pesticide Science
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    • v.2 no.2
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    • pp.22-28
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    • 1998
  • Twenty six derivatives of bis-aromatic ${\alpha},{\beta}$-unsaturated ketones as substrate(S) were synthesized and their fungicidal activities in vivo against rice blast(Pyricularia oryzae), tomato leaf blight(Phytophtora infestans) and barley powdery mildew(Erysiphe graminis) were examined. The quantitative structure-activity relationship(QSAR) between the fungicidal activities($pI_{50}$) and a physicochemical parameters of substitued($R_{2}$) phenyl backbone group in 2-thienyl and 2-furyl substituents were analyzed with regression equations. The activities of substituted($R_{2}$) phenyl backbone in 2-thienyl substituents, $1{\sim}10$ would depend largely on the resonance(R>0), molecular refractivity($M_{R}<0$) and optimal length of substituent(($L_{1})opt.=5.50{\AA}$). Whereas, in case of 2-furyl substituents, $10{\sim}26$ optimal molar attraction constant ($F_{opt}=0.49{\sim}l.11$), optimal steric($Es_{opt}=1.78$) constant and indicator variables(Io & Ip) for position of substituents. The fungicidal activity relationship of 2-thienyl substituents against Pyricularia oryzae and Phytophtora infestans have been a reciprocal proportioned.

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3D-QSARs Analysis on the Fungicidal Activity with N-phenylbenzenesulfonamide Analogues against Fusarium wilt (Fusarium oxysporum) (N-phenylbenzenesulfonamide 유도체들에 의한 시들음병균(Fusarium oxysporum)의 살균활성에 관한 3D-QSARs 분석)

  • Soung, Min-Gyu;Hwang, Tae-Yeon;Kang, Kyu-Young;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.51 no.1
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    • pp.38-43
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    • 2008
  • 3D-QSARs on the fungicidal activity with N-phenylbenzenesulfonamide and N-phenyl-2-thienylsul-fonamide analogues (1-34) against Fusarium wilt (Fusarium oxysporum) were discussed quantitatively using CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indices analysis) methods, respectively. Generally, the CoMFA models have better predictability and fitness than the CoMSIA models. The fungicidal activities, according to the information of the optimized CoMF A 2 model $(r^2\;_{cv.}=0.523\;&\;r^2\;_{ncv.}=0.956)$, were dependent on the electrostatic field of the N-phenylbenzenesulfonamide analogues. Therefore, from the results of graphical analyses on the contour maps with the optimized CoMFA 2 model, it is expected that the characters of $R_4-substituents$ on the N-phenyl ring as steric and positive charge favor will contribute to the fungicidal activity against Fusarium wilt.

Synthesis and fungicidal activity of new ${\beta}$-methoxyacrylate derivatives having thio-enol side chain (티오엔을 곁가지를 가진 메톡시아크릴레이트 화합물의 합성 및 살균활성 연구)

  • Lee, Hyeon-Kyu;Kim, Ji-A;Choi, Eun-Bok;Park, Chwang-Siek;Choi, Gyung-Ja
    • The Korean Journal of Pesticide Science
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    • v.9 no.2
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    • pp.132-139
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    • 2005
  • New ${\beta}$-methoxyacrylate derivatives 1-4 having thio-enol side chain were prepared and subjected to in vivo screening for fungicidal activity against phytopathogenic fungi and many of them showed good fungicidal activities against especially rice blast and wheat leaf rust at 100 ppm.

Pesticidal Constituents Derived from Piperaceae Fruits

  • Lee, Hoi-Seon
    • Journal of Applied Biological Chemistry
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    • v.48 no.2
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    • pp.65-74
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    • 2005
  • Fungicidal, insecticidal, and mosquito larvicidal activities of piperidine alkaloids, pipernonaline and piperoctadecalidine, and isobutylamide alkaloids, pellitorine, guineensine, pipercide, and retrofractaminde A, derived from Piperaceae fruits were studied. Pipernonaline and piperoctadecalidine showed potent fungicidal activities against Puccinia recondita with 91 and 80% control values at 500 ppm. Against Phytophthora infestans, pipernonaline showed strong fungicidal activity with 91 and 80% control values at 1,000 and 500 ppm. $LD_{50}$ values of pipernonaline and piperoctadecalidine against Plutella xylostella were 125 and 95.5 ppm, respectively, and that of piperoctadecalidine against Tetranychus urticae was 246 ppm. Against larvae of Aedes aegypti and Culex pipiens pallens, $LD_{50}$ values of pipernonaline were 0.35 and 0.21 ppm, respectively. Highest larvicidal activities of pipercide and retrofractamide A were found against A. aegypti, A. togoi, and C. pipiens pallens. $LD_{50}$ values of pipercide and retrofractamide A were 0.10 and 0.039 ppm against A. aegypti, 0.26 and 0.01 ppm against A. togoi, and 0.004 and 0.028 ppm against C. pipiens pallens, respectively. Based upon these results and earlier findings, bioactive components derived from Piperaceae fruits may be valuable for development of useful lead product of possibly safer fungicidal, insecticidal, and mosquito larvicidal agents.

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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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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Enhancement of Foliar Uptake and Leaf Deposit of Thifluzamide Formulation and Fungicidal Activity Against Rice Sheath Blight (Thifluzamide 제제의 경엽 침투성과 부착량 증진이 벼 잎집무늬마름병 방제 효과에 미치는 영향)

  • Yu, Ju-Hyun;Choi, Gyung-Ja
    • The Korean Journal of Pesticide Science
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    • v.15 no.1
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    • pp.1-7
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    • 2011
  • In order to enhance the fungicidal activity of the thifluzamide formulation against rice sheath blight, the surfactants which was able to facilitate the foliar uptake or increase the leaf deposit of thifluzamide on rice plants were selected, and the formulations containing the surfactants were tested to compare the fungicidal efficacy against the rice sheath blight with a control WP formulation. The WP suspension containing dodecaethylene glycol monohexadecyl ether as an activator increased the foliar uptake of thifluzamide on rice plants, but its fungicidal efficacy against rice sheath blight was decreased. The addition of the combined surfactants with either heptaethylene glycol monoisododecy ether or heptaethylene glycol monotridecyl ether and sodium dioctylsulfosuccinate to WP suspension increased the leaf deposition of thif1uzamide at around 5 times of that without a spreader-sticker that median control concentrations of thifluzamide against rice sheath blight were decreased to 4.4 mg $L^{-1}$ and 3.4 mg $L^{-1}$, respectively.

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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