• The Plant Pathology Journal
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• v.24 no.3
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• pp.317-321
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• 2008

In a search for plant extracts with in vivo antifungal activity for plant diseases, we found that the methanol extract of Myristica malabarica fruit rinds effectively suppressed the development of several plant diseases. The methanol extract exhibited potent 1-day protective activity against rice blast, tomato late blight, wheat leaf rust and red pepper anthracnose. It also showed 7-day and 4-day protective activities against the plant diseases. Three antifungal resorcinols were isolated from the methanol extract of M. malabarica fruit rinds and identified as malabaricones A(MA), B(MB), and C(MC). Inhibitory activity of the three resorcinols against mycelial growth of plant pathogenic fungi varied according to compound and target species. All three compounds effectively reduced the development of rice blast, wheat leaf rust and red pepper anthracnose. In addition, MC was highly active for reducing the development of tomato late blight. This is the first report on the antifungal activities of malabaricones against filamentous fungi.

• Microbiology and Biotechnology Letters
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• v.33 no.1
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• pp.16-23
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• 2005

In order to develop a new microbial fungicide using endophytic bacteria for the control of anthracnoses occurring on various crops, a total of 260 bacterial strains were isolated from fresh tissues of 5 plant species. After they were cultured in broth medium, their antifungal activities were tested for in vivo antifungal activity against cucumber anthracnose caused by Colletotrichum orbiculare. As the results, liquid cultures of 28 strains showed potent antifungal activities more than $90\%$ against cucumber anthracnose. At 3-fold dilutions of liquid cultures, 18 strains inhibited the development of cucumber anthracnose of more than $70\%$. They were further tested for in vivo antifungal activity against red pepper anthracnose caused by C. coccodes and in vitro antifungal activity against C. acutatum, a fungal agent causing red pepper anthracnose. Among 18 strains, a bacterial strain EB215 isolated from cucumber roots displayed the most potent antifungal activity against Colletotrichum species. It was identified as Burkholderia cepacia based on its physiological and biochemical characteristics, Biolog test and 16S rDNA gene sequence. It also controlled effectively the development of rice blast (Magnaporthe grisea), rice sheath blight (Corticium sasaki), tomato gray mold (Botrytis cinerea), and tomato late blight (Phytophthora infestans). Studies on the characterization of antifungal substances produced by B. cepacia EB215 are in progress.

• Applied Biological Chemistry
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• v.47 no.3
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• pp.339-343
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• 2004

Anionic surfactants such as sodium dioctyl sulfosuccinate (SDSS) and sodium dodecylbenzene sulfonate (NaDBS) and a nonionic surfactant, polyoxyethylene oleyl ether (OE-7) were tested for their protective, curative, and persistent activities on tomato late blight (TLB, Phytophthora infestans), red pepper blight (RPB, P. capsici), and cucumber downy mildew (CDM, Pseudoperonospora cubensis). They exhibited a strong protective activity on TLB, RPB, and CDM. Among them, $NaDBS\;(500\;{\mu}g/ml)$ showed the most in vivo antifungal activities(1-day protective activity) with control values of 99%, 100%, and 85% against TLB, RPB, and CDM, respectively. However, the three surfactants represented a weak disease controlling efficacy on TLB, RPD, and CDM in a 1-day curative application. SDSS and NaDBS exhibited a good persistent activities on TLB and RPB. Especially, NaDBS, at $500\;{\mu}g/ml$, showed control values of more than 88% on TLB and RPB in a 7-day protective application. The results indicate SDSS and NaDBS have a potential for the control of TLB, RPB, and CDM in the fields.

• The Korean Journal of Pesticide Science
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• v.9 no.2
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• pp.122-131
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• 2005

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 ${\alpha},{\beta}$-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.

• The Korean Journal of Pesticide Science
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• v.7 no.1
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• pp.51-57
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• 2003

For the purpose of a development of new agrochemical fungicides, new compound 4 in which 1,3-thiazoline scaffold as well as urea moiety in the structure was designed through molecular modification of lead compound, 2-imino-1,3-thiazone based on isosterism. The reaction of N-alkylthiourea 5 and bromoacetonitrile in ethanol gave 2,4-diimino-1,3-thiazolidine hydrobromide 6 regioselectively, which was treated with isocyanates gave the corresponding 8 which is tautomer of 4. Antifungal screening (in vivo) of the synthesized compound 8 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. Antifungal activities against rice blast of the compound 8 were weaker than those of 2-phenylimino-1,3-thiazoline 1. Some compounds showed weak antifungal activities against wheat leaf rust.

• The Korean Journal of Pesticide Science
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• v.5 no.2
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• pp.26-32
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• 2001

[ ${\alpha},{\beta}$ ]-Unsaturated carboxamides 12 with trifluromethylated dihydro-1,4-dithiins were synthesized for the purpose of development of new agrochemical fungicide. Chlorination of trifluoromethylated ${\beta}$-ketoester 4 followed by tile reaction with 1,2-ethanedithiol gave intermediate 1,4-dithiane 9. Without purification of 9 substitution of hydroxy by chlorine followed by dehydrochlorination in the presence of triethylamine afforded trifluoromethylated dihydro-1,4-dithiin ethyl ester 7. Activation of the hydroxy of the carboxylic acid 10 obtained from the hydrolysis of 7 and then reacted with various amines gave the corresponding trifluoromethylated dihydro-1,4-dithiin carboxamides. Antifungal screening (in vivo) against typical plant diseases, Rice Blast, Rice Sheath Blight, Cucumber Gray Mold, Tomato Late Blight, Wheat Leaf Rust, and Barley Powdery Mildew of the synthesized compounds was carried out. As a result, most of the compounds shlowed weak antifungal activities and some compounds in which isopropyl group was substituted in meta of the phenyl showed antifungal activity (99%) at 250 ppm against the disease Wheat Leaf Rust.

• Research in Plant Disease
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• v.17 no.2
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• pp.155-160
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• 2011

To develop the efficient screening methods for antifungal compound active to Chinese cabbage clubroot caused by Plasmodiophora brassicae, the control efficacy of three fungicides fluazinam, ethaboxam, and cyazofamid on the disease was tested under several conditions such as soil types, cultivars of Chinese cabbage, growth stages of the host, and inoculum concentrations. The in vivo antifungal activities of the fungicides on clubroot of two Chinese cabbage cultivars were hardly different. At 7- and 14-day-old seedlings, the fungicides were more effective to control of clubroot than at 21-day-old seedlings. In a commercial horticulture media soil (CNS), disease severity of untreated controls was higher and control activity of the fungicides was less than in a mixture of CNS and upland soil (1:1, v/v). Disease development of the seedlings inoculated with P. brassicae at $1.8{\times}10^7$ spores/pot to $1.1{\times}10^9$ spores/pot was almost same, but control efficacy of the fungicides was negatively correlated with inoculum dosages. To effectively select in vivo antifungal compound on Chinese cabbage clubroot, 14-day-old seedlings need to be inoculated with P. brassicae by drenching the spore suspension to give $1{\times}10^8$ spores/pot 1 day after chemical treatment. To develop clubroot, the inoculated plants are incubated in a growth chamber at $20^{\circ}C$ for 2 days, and then cultivated in a greenhouse ($20{\pm}5^{\circ}$) for four weeks.

• The Plant Pathology Journal
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• v.15 no.1
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• pp.14-20
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• 1999

Twenty isolates of Helminthosporium species were obtained from various grass plants and tested for controlling efficacy on the development of plant diseases. An isolate of Helminthosporium sp. TP-4 was chosen and six antibiotic substances were purified from cultures of the fungus by repeated silica gel column chromatography and preparative thin-layer chromatography. They were identified as ophiobolin a, 6-epiophiobolin A, 3-anhydroophiobolin A, 3-anhydro-6-epiophiobolin A, iphiobolin B, and iphiobolin I mainly by mass spectrometry and nuclear magnetic resonance spectrometry. Ophiobolins inhibited the growth of a grampositive bacterium Streptomyces griseus, but were not active against gram-negative bacteria. They also showed an antifungal activity. In in vivo tests, iphiobolin B exhibited potent controlling activities against rice blast, tomato late blight, and wheat leaf rust with control values more than 90% and 70% at concentration of $500\mu\textrm{m}$/ml and 100 ${\mu}{\textrm}{m}$/ml. Ophiobolin A and 6-epiophiobolin A controlled the development of wheat leaf rust more than 80% at concentrations of 100 /ml and $500\mu\textrm{m}$/ml respectively. 3-Anhydro-6-epiophiobolin A was not active against any plant disease. On the other hand, the A-series ophiobolins other than 3-anhydroophiobolin A showed stronger phytotoxic activity in a leaf-wounding assay using 8 plant species than those of 3-anhydroophiobolin A, ophiobolin B, and ophiobolin I. The results indicate that there is little correlation between antifungal activity and phytotoxicity of ophiobolins.

• The Korean Journal of Pesticide Science
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• v.16 no.4
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• pp.267-272
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• 2012

Vitex trifolia L. is a full grown fruit of Vitex rotundifolia L. (Verbenaceae). It has been used for treating headache, dizziness, toothache and removal of fever as a traditional medicine in Korea. V. trifolia (500 g) were extracted three times with 80% aqueous MeOH at room temperature. The MeOH extract (38 g) was successively partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$. Both n-hexane and EtOAc fractions showed more than 80% antifungal activity in vivo against several plant pathogens at 2000 ppm. Successive repeated silica gel, Sephadex LH-20, preparative TLC, and preparative HPLC of these fractions led to isolation of three compounds. Using mainly mass spectroscopy and nuclear magnatic resonance (NMR) spectroscopy, their chemical structures were determined as agnuside(1), chrysosplenol B(2), and artemetin(3). Compound 2 was isolated for the first time from V. trifolia. Study on in vitro and in vivo antifungal activities of the isolated compounds is in progress.

• Research in Plant Disease
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• v.17 no.2
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• pp.129-135
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• 2011

Chitosan is a linear polysaccharide composed of randomly distributed ${\ss}$-(1-4)-linked D-glucosamine and Nacetyl-D-glucosamine. There have been many reports on the induced systemic resistance and in vivo antifungal activities of higher molecular weight chitosans with molecular weights over 3,000 amu (atomatic mass unit), but there are few papers on in vivo antifungal activities of low molecular weight chitosans (oligochitosans) with molecular weights less than 3,000 amu. In our study, an oligochitosan sample (320.3,000 amu) showed a potent 1-day protective activity with control values more than 94% at concentrations of 500 and 1,000 ${\mu}g$/ml especially against tomato late blight caused by Phytophthora infestans under growth chamber conditions. It also displayed a moderate 1-day protective activity with control values of 67.89% at concentrations of 500 and 1,000 ${\mu}g$/ml against wheat leaf rust and red pepper anthracnose. On the other hand, it showed a 16-hr curative activity against red pepper anthracnose, but not against tomato late blight and wheat leaf rust. In field experiments, oligochitosan effectively suppressed the development of late blight on potato and tomato plants with control values of 72% and 48%, respectively. The results strongly indicate that oligochitosan can be used as an eco-friendly organic material for the control of late blight on tomato and potato plants.