• The Korean Journal of Pesticide Science
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• v.2 no.3
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• pp.64-69
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• 1998

New thirty derivatives of 5,6-dihydro-2-trifluoromethyl-1,4-oxathiin carboxanilide as substrate(S) were synthesized and their fungicidal activities in vivo against rice sheath blight(Rhizoctonia solani) and wheat leaf rust(Puccinia recondita) were examined. The structure activity relationships(SAR) between the activities($pI_{50}$) and a physicochemical parameters of substituents(X) at the phenylcarbamoyl group were analyzed using the adaptive regression analysis method. The 3-methoxy, 11, 3-isopropyloxy, 13 and 3-isopropyl substituent, 25 as X on the phenylcarbamoyl group exhibited the most highest fungicidal activity against the two fungi. The fungicidal potency of the (S) against Puccinia recondita was higher than Rhizoctonia solani. In case of Rhizoctonia solani, the molecular hydrophobicity(${\pi}>0$) and resonance effect(R<0) by meta-alkyl substitutents with electron donating were important factors in determining fungicidal activity. And the HOMO energy(HOMO>0), ABSQ, sum of absolute values of the atomic charges on each atom and specific polarizability(Sp.Pol<0) of (S) were significantly influential towards fungicidal activity against Puccinia recondita.. The interaction between (S) and receptor agonist from the based on SAR studies proceeds through charge-control reaction, and conditions to show higher activity has been also discussed.

• The Korean Journal of Pesticide Science
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• v.2 no.3
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• pp.21-27
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• 1998

Methanol extracts from 25 leguminous seeds were tested for their fungicidal activities toward six phytopathogenic fungi, using whole plant test in a greenhouse. The efficacy varied with both the plant pathogen and legume species used. At 5 mg/pot, potent fungicidal activities were produced from extracts of Cassia obtusifolia, Glycine max var. solitae, G. max var. yagkong, G. max var. hooktae, Phaseolus multiflorus, P. radiatus var. aurea, and Vigna sinensis against Botrytis cinerea, Puccinia recondita, and Erysiphe graminis. These seed extracts were highly effective against three B. cinerea strains resistant to carbendazim, procymidone, and diethofencarb. All leguminous seed extracts revealed weak or no fungicidal effect against Rhizoctonia solani, Pyricularia grisea, and Phytophthora infestans. As a naturally occurring fungicide, leguminous seed-derived materials described could be useful as new fungicidal products against various plant diseases induced by phytopathogenic fungi.

• The Korean Journal of Pesticide Science
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• v.3 no.1
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• pp.29-36
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• 1999

A series of N-phenyl-O-phenylthionocarbamate derivatives were synthesized and determinated fungicidal activities in vitro against gray mold (Botrytis cinerea) and capsicum phytophthora blight (Phytophthora capsici) which showed resistance and sensitivity to benomyl and metalaxyl as systemic fungicides, respectively. The structure-activity relationship (SAR) was investigated by Free-Wilson analysis method and Hansch method. From the basis on the findings, the N-phenyl(X) groups had more contributions than O-phenyl(Y) groups did and ortho-substituents on the N-phenyl group showed high fungicidal activities. Especially, 4-cyano substituent, 2 as X-group showed 50% inhibition($pI_{50}=5.50$) of hyphae growth at 0.8ppm against resistance P. capsici (RPC) And hydroxyl substituents, 12 and 23 displayed the highest fungicidal activity against resistant B. cinerea (RBC), sensitive B. cinerea (SBC), and sensitive P. capsici (SPC). Antifungal activities of SPC were dependent upon molar refractivity (MR) constant and those of others relied on hydrophobic parameters (${\sigma}$ and logP). For increasing fungicidal activity against RPC and SBC, the optimum values of the sigma (${\sigma}$) and field(F) constants as electron withdrawing groups were 0.32 and 0.18, respectively.

• The Korean Journal of Pesticide Science
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• v.11 no.1
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• pp.8-17
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• 2007

Three-dimensional quantitative structure-activity relationships (3D-QSARs) on the fungicidal activity against damping-off (Pythium ultimum) with N-phenylbenzenesulfonamide and N-phenyl-2-thienylsulfonamide analogues (1-34) were studied quantitatively using CoMFA (comparative molecular field analysis) and CoMSIA (comparative molecular similarity indeces analysis) methodologies. On the whole, the statistical qualities of CoMSIA models with field fit alignment (FF1-FF5) were slightly higher than that of atom based fit alignment (AF1-AF5) but, the deviations of statistical quality between two alignments in case of CoMFA models were slightly lower. The statistical results of CoMFA and CoMSIA model showed that the optimized CoMSIA model (FF1: $r_{cv.}^2\;(q^2)=0.674$ & $r_{ncv.}^2=0.964$) for damping-off is better predictability and fitness for fungicidal activities than CoMFA model (AF5: $r_{cv.}^2\;(q^2)=0.616$ & $r_{ncv.}^2=0.930$). The fungicidal activities according to the information of the CoMSIA (FF1) model were dependence upon the electrostatic and hydrophobic field of the N-phenylbenzene sulfonamide analogues. Therefore, from the results of graphical analyses on the contour maps with CoMSIA (FF3) model, it is expected that the characters of R4-substituent on the N-phenyl ring as hydrophobic and hydrogen bond acceptor will be contributed to the fungicidal activity against damping-off.

• The Korean Journal of Pesticide Science
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• v.11 no.2
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• pp.59-66
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• 2007

Three dimensional quantitative structure-activity relationships (3D-QSARs) on the fungicidal activity of N-phenyl-O-phenylthionocarbamate analogues against resistant and sensitive gray mold (Botrytis cinerea) (RBC & SBC) were studied quantitatively using CoMFA and CoMSIA methods. The correlation coefficient and predict- ability of optimized CoMFA model with the atom based fit alignment were better ($r^2$ & $q^2=CoMFA{\gg}CoMSIA$) than that of CoMSIA model. And statistical values of the models on the fungicidal activity against SBC were showed higher ($r^2=SBC{\gg}RBC$) than that of RBC. In CoMFA models, steric field on the activity was more influenced than electrostatic field. And in case of CoMSIA models, the influence of CoMSIA field on the activity against RBC and SBC was differ from each other but the influence of H-bond donor field was same to the two fungi. It is revealed that the selectivity factor with CoMFA model on the fungicidal activity between the two fungi was caused on the difference of steric field. Therefore, it is predicted that the large steric field with meta- and para-substituents on the N-phenyl ring will be improved to the fungicidal activity with SBC.

• The Korean Journal of Pesticide Science
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• v.12 no.2
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• pp.111-117
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• 2008

The comparative molecular field analysis (CoMFA) for the fungicidal activity with N-phenylbenzenesulfonamide analogues (1-45) against gray mold (Botriyts cinerea) were studied quantitatively. The statistical values of CoMFA models had much better predictability and fitness than those of comparative molecular similarity indices analysis (CoMSIA) models. The statistical values of the optimized CoMFA I model were predictablity, $r^2_{cv.}(or\;q^2)=0.457$ and correlation coefficient, $r^2_{ncv.}=0.959$, and their fungicidal activity was dependent on the steric field (52%) and electrostatic field (35.6%) of the substrate molecules. And also, it was found that the optimized CoMFA I model with the sensitivity to perturbation ($d_q^{2'}/dr^2_{yy'}=0.898$) and prediction ($q^2=0.346$ & SDEP=0.614) produced by a progressive scrambling analysis was not dependent on chance correlation. From the results of graphical analyses on the contour maps with the optimized CoMFA I model, it is expected that the $R_3$ and $R_4$-substituents on the N-phenyl ring as steric favor group and para-substituents ($R_1$) on the S-phenyl ring as steric disfavor group will contribute to the fungicidal activity. Therefore, the optimized CoMFA I model should be applicable to the prediction of the fungicidal activities against gray mold.

• The Korean Journal of Pesticide Science
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• v.4 no.3
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• pp.7-14
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• 2000

Methanol extracts from 21 grains were tested for fungicidal activities against six phytopathogenic fungi and for insecticidal activities toward five insect pests in a greenhouse. The efficacy varied with both the plant pathogen/insect pest and grain species used. Potent fungicidal activity at 5 mg/pot, were produced from extracts of Elymus sibiricus and Hordeum vulgare var. nudum against Pyricularia grisea and Erysiphe graminis and these of Sesamum indicum (W) and Triticum aestivum against Puccinia recondita and Erysiphe graminis. At 2,500 ppm, potent insecticidal activities were exhibited from the extracts of Fagopyrum esculentum against Myzus persicae and Ischaemum crassipes, and these of Oryzo sativa var. glutinosa, Panicum miliaceum, Setaria italica, Sorghum bicolor, and T. aestivum against Tetranychus urticae. All grain extracts revealed weak or no fungicidal and insecticidal effect against Phytophthora infestans, Plutella xylostella and Spodoptera litura. As a naturally occurring fungicide and insecticide, grain-derived materials described could be useful as new fungicidal and insecticidal products against phytopathogenic fungi and insect pests.

• Archives of Pharmacal Research
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• v.21 no.3
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• pp.326-329
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• 1998

Four derivatives of 6-oxo-3,4,4a,5-tetrahydro-3-hydroxy-2,2-dimethylnaphtho-1,2-pyran (1), known as bacterial, bacteriostatic, fungicidal, fungistatic agents, were synthesized to investigate the effect of substituents on the aromatic ring.

• 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.

• Research in Plant Disease
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• v.20 no.4
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• pp.295-298
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• 2014

Oak wilt caused by Raffaelea quercus-mongolicae was first noticed in South Korea in 2004 and, ever since, its distribution and damage have been increasing. To screen a fungicide effective for oak wilt control by tree injection, laboratory and field experiments were conducted. Ten fungicides and one antibiotic were examined in vivo for their effectiveness in restricting the growth of R. quercus-mongolicae and R. quercivora (Japanese oak wilt pathogen) isolates. To the Korean isolates of R. quercus-mongolicae, chlorothalonil showed the highest fungicidal effects, followed by benomyl and propiconazole. To the Japanese one, propiconazole was highest in the fungicidal effectiveness, followed by benomyl and bitertanol. Propiconazole was selected for field-testing of its control efficacy because it showed good fungicidal effects in vitro and systemic activity. The control efficacy in the field was 87.5% in the first year of injection and 66.7% in the second year, indicating the fungicidal effects last at least over one year.