• The Korean Journal of Pesticide Science
• /
• v.9 no.2
• /
• pp.122-131
• /
• 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
• /
• v.3 no.1
• /
• pp.20-28
• /
• 1999

Chloronicotinyl derivatives were synthesized by substitution of amino in 3-pyridylmethylamine with phosphite groups and their insecticidal and fungicidal activities were determined. At 500 ppm, compound 4 with methyl and butyl group in phosphonate and compound 5, 6, 7, and 8 with two butyl, 2,2,2-trifluorotehtyl, 2-ethylhexyl, phenyl, respectively, in phosphonate showed 90% insecticidal activities against brown plant-hopper (Nilaparvate lugens). These compounds showed, however, poor insecticidal activities against diamond-back moth (Plutella xylostella) and two-spotted spider mite (Tetranychus urticae) (<65%), suggesting that insecticidal activity of chloronicotinyl derivatives containing phosphorus moieties are species-dependent. Newly synthesized chloronicotinyl derivatives with halogen and/or heterocycle (compound $10{\sim}21$) did not show insecticidal activities. We also determined fungicidal activity of the synthesized chloronicotinyl derivatives against rice sheath blight (Pyricularia grisea), cucumber gray mold (Bortytis cinerea), tomato late blight (Phytophthora infestans), wheat leaf rust (Puccinia recondita), and barley powdery mildew (Erysiphe graminis). Compound 10 with butyl and 4-nitrophenyl in phosphonate at 10 ppm showed 85% fungicidal activity against rice blast, suggesting that chloronicotinyl derivatives containing phosphorus moieties could be developed as a fungicidal agent of a novel chemical structure.

• The Korean Journal of Pesticide Science
• /
• v.16 no.3
• /
• pp.209-216
• /
• 2012

In the continued research on natural fungicides for control of plant diseases by using plant-derived products, we found that Spatholobus suberectus Dunn had a strong fungicidal activity against several plant pathogens. S. suberectus (1 kg) was extracted with 80% aqueous MeOH and then the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$ successively. The four layers were tested their disease contron efficacies against 6 plant diseases such as rice blast (RCB), rice sheath blight (RSB), tomato grey mold (TGM), tomato late blight (TLB), wheat leaf rust (WLR), and barley powdery mildew (BPM). The EtOAc fraction was highly active showing over 80% control against RCB, TGM, TLB, and BPM. By using silica gel chromatography, preparative TLC and HPLC, six compounds that were expected to have antifungal activity were separated. Their chemical structures were identified as ethanone, hydroxytyrosol, epicatechin, procyanidin B2, dimethoxy daizein and formononetin by ESI-MS, $^1H$-NMR, $^{13}C$-NMR, and 2D-NMR spectroscopic analyses. The chemicals except epicatechin were first reported in S. suberectus. Study on in vitro and in vivo antifungal activities of the isolated compounds is in progress.

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

• Proceedings of the Korean Society of Plant Pathology Conference
• /
• 2003.10a
• /
• pp.95.2-96
• /
• 2003

In order to develop a new microbial fungicide for the control of vegetable diseases using endophytic bacteria, a total of 260 bacterial strains were isolated from fresh tissues of 5 plant species. After they were cultured in broth media, their antifungal activities were screened by in vivo bioassays against Botrytis cinerea(tomato gray mold), Pythium ultimum(cucumber damping-off), Phytopkhora infestans(tomato late blight), Colletotrichum orbiculare(cucumber anthracnose), and Blumeria graminis f. sp. hordei(barley powdery mildew). As the results of screening, 38 bacterial strains showed potent antifungal activities against at least one of 5 plant pathogens. A bacterial strain EB072 displayed potent disease control activities against 3 plant diseases. Among the bacterial strains with a potent antifungal activity against cucunlber anthracnose, three bacterial strains, EB054, EB151 and EB215, also displayed a potent in vitro antifungal activity against C. acutatum, a fungal agent causing pepper anthracnose. A bacterial strain EB215 obtained from roots of cucumber was identified as Burkholderia cepacia based on its physiological and biochemical characteristics and 165 rRNA gene sequence. An antifungal substance was isolated from the liquid cultures of B. cepacia EB215 strain by ethyl acetate partitioning, repeated silica gel column chromatography, and invitro bioassay, Its structural determination is in progress by various instrumental analyses.

• Proceedings of the Korean Society of Plant Pathology Conference
• /
• 2003.10a
• /
• pp.121.2-122
• /
• 2003

Since the demonstration that the transgenic plants expressing tobacco mosaic virus(TMV) coat protein(CP) gene showed resistance to TMV infection, there have been numerous attempts to produce virus-resistant plant by introducing of a part of or modified viral genome. This study was conducted to investigate the characterization and variability of disease outbreak of transgenic potato(T-potato) with the CP gene of potato leaf roll virus(PLRV) in an isolated field from 2000 to 2002. In the field inspection, incidence of PLRV on T-potato showed only 3.5％, while non-transgenic potato(N-potato) revealed 13.4％. Infection rate of PLRV was considerably low on T-potato with 4.2％ compared to 15.4％ of N-potato in ELISA tests. Those of potato virus M, potato virus Y and potato virus X on both potatoes were not statistically different. Infection of potato virus A was not observed on both potatoes. Incidence of potato late blight caused by Phytopkhora infestans on T-potato and N-potato did not differ each other with 52.7％, and 50.8％, respectively, Mating type of the causal fungus isolated from both potatoes was all Al types. Results indicates that the CP gene of PLRV affects specifically to the virus in the transgenic potato.

• The Plant Pathology Journal
• /
• v.15 no.1
• /
• pp.14-20
• /
• 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 Mycology
• /
• v.29 no.1
• /
• pp.72-74
• /
• 2001

A destructive collar rot of water cress (Oenanthe javanicav) occurred in the commerical farm at Karye-myon, Uiryong-gun, Kyongsangnam-do in 2000. The causal fungus caused stem rot, crown rot, wilt or blight of water cress and the disease incidence in 3 fields ranged from 28.6 to 42.8%. White mycelia spread over tissues near the soil surface or stems, and sclerotia developed on the lesions at late season. The fungus grew well on PDA at $20^{\circ}C$ and the typical clamp connection was formed on its tough white mycelia $4.1{\sim}10.3{\mu}m$. The fungus also formed white mycelia mats and sclerotia at $20^{\circ}C$ on PDA. The sclerotia were globoid and sized $1.0{\sim}6.3{\times}1.0{\sim}5.2mm$ (av. $2.4{\sim}2.2mm$). The causal fungus of collar rot disease was identified as Sclerotium rolfsii on the basis of mycological characteristics and pathogenicity test, This is the first report on the collar rot of water cress caused by Sclerotium rolfsii in Korea.

• The Plant Pathology Journal
• /
• v.24 no.2
• /
• pp.125-130
• /
• 2008

Various kinds of leaf spots and blights were found in kiwifruit (Actinidia deliciosa) orchards on 2006 in Korea. Disease incidences were quite variable between open-field and rain-proof shelter. Rate of diseased leaves was recorded as about 70% at open-field orchards in late season but use of rain-proof vinyl shelters alleviated the disease incidences by 20%. Angular leaf spots appeared at early infection stage on June and several other symptoms were also recognized as the disease developed afterward. On September, brown leaf blights were the most frequent, followed by grayish brown ring spots, silvering gray leaf blights, zonate leaf blights, dark brown ring spots and angular leaf spots at open-field orchards. Four fungal species were frequently isolated from the disease symptoms. Phomopsis sp. was the most predominant fungus associated with the leaf spot and blight symptoms on kiwifruit, followed by Glomerella cingulata, Alternaria alternata and Pestalo-tiopsis sp. Phomopsis sp. was commonly isolated from angular leaf spots, silvering gray leaf blights, and zonate brown leaf blights. G. cingulata, A. alternata and Pestalotiopsis sp. were isolated from grayish brown ring spots (anthracnose), brown ring spots and zonate dark brown leaf blights. Typical symptoms appeared on the wounded and unwounded leaves, which were inoculated by each of Phomopsis sp., G. cingulata, and Pestalotiopsis sp., but A. alternata caused symptoms only on the wounded leaves.

• Journal of Microbiology and Biotechnology
• /
• v.16 no.3
• /
• pp.423-430
• /
• 2006

A total of 367 isolates of Phytophthora infestans was collected from the leaf samples of late blight disease from five provinces in Korea over the three growing seasons of 2002-2004. Of the 367 isolates, 337 isolates were of the A1 mating type, and 30 isolates were of A2 mating type, showing that the majority was A1 mating type. Profiles of Gpi and Pep defined four allozyme genotypes among the total of 367 isolates. All four allozyme genotypes could be distinguished on the basis of Gpi profiles alone, whereas all isolates were homozygous at the Pep locus (100/100). The mitochondrial DNA haplotype of all isolates were the IIa haplotype. Amplification of the genomic DNAs extracted from eight isolates of each mating type by polymerase chain reaction with the selected primer (OPC-5 primer) produced a total of 20 DNA bands, of which 11 bands were polymorphic. According to the RAPD analysis using the OPC-5 primer, 106 isolates including two standard isolates were separated into 8 groups at the similarity level of 92.5%. The RAPD groups were not correlated with the allozyme genotypes and the isolated locations. All of the eight RAPD groups were identified in Gangwon-do, suggesting that Gangwon-do is the center of origin of the P. infestans in Korea. A 600-bp DNA band generated with the OPC-5 primer was specific to A1 mating type isolates, but not detected with A2 mating type, showing that the specific PCR primer can distinguish different mating types in P. infestans.