• Title/Summary/Keyword: sulfonylurea

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A new and efficient synthesis of sulfonylurea (술포닐 우레아유도체의 용이하고 새로운 합성방법)

  • Youn, In-Kwon;Seo, S.U.
    • The Journal of Natural Sciences
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    • v.12 no.1
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    • pp.81-84
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    • 2002
  • We developed new process for the large scale preparation of pyrazole sulfonyl urea and pyrazole sulfonyl urea carboalkoxyl benzene sulfonyl urea 1) in high yields and convenience. As compound with know procedure this procedure have found to be far large scale preparation. During the preparation we obtains two new sulfonyl urea 5a and 5b in 70% and 74% ( purified by crystallization).

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Effective Weed Control in Direct Seeded Rice on Puddled Paddy Surface of Southern Region (남부지역 무논직파 재배 논에서 잡초 방제)

  • Park, Tae-Seon;Park, Hong-Kyu;Kang, Sin-Koo;Ku, Bon-Il;Choi, Min-Kyu;Lee, Keong-Bo;Ko, Jae-Kwon
    • Korean Journal of Weed Science
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    • v.32 no.1
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    • pp.57-69
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    • 2012
  • This study was conducted to find the effective management of main weeds including herbicide-resistant Echinochloa oryzicola, Scirpus juncoides and Monochoria vaginalis in direct seeded rice on puddled paddy surface. The dominant dominances in direct seeded rice on puddled paddy surface were increased for three years between 2009-2011. In weed distribution in 2011, the occurrence density of S. juncoides decreased greatly, but it of E. oryzicola increased especially as compared with it of 2009. Benzobicyclon, mesotrione and pyrimisulfan were effective to sulfonylurea(SU)-resistant S. juncoides and M. vaginalis at 5 and 12 days after seeding, however, the efficacy of bromobutide to sulfonylurea-resistant M. vaginalis was decreased slightly at 12 days after seeding. And carfentrazon and pyrazolate were ineffective to S. juncoides. In direct seeded rice on puddled paddy surface which ACCase and ALS inhibitor-resistant E. oryzicola was not occurred, benzobicyclon+penoxsulam+pyrazosulfuron-ethyl ET, bromobutide+imazosulfuron+metamifop GR, and flucetosulfuron+mesotrione+pretilachlor GR showed the control effect over 94% to main weeds included sulfonylurea-resistant S. juncoides and M. vaginalis. The E. oryzicola dominating in direct seeded rice on puddled paddy surface were not any affected to the survival by treatment with recommended doses of cyhalofop-butyl and penoxsulam tested. The ACCase and ALS inhibitor-resistant E. oryzicola was effectively controlled by mefenacet and fentrazamide up to the 2nd leaf stage. In direct seeded rice on puddled paddy surface domiating coincidentally by herbicide-resistant E. oryzicola, S. juncoides and M. vaginalis, "one-shot herbicide" included with mefenacet, fentrazamide, penoxsulam and metamifop could't be used because of low control effect or rice injury. The sequential treatment of benzobicyclon+thiobencarb SE and bensulfuron+mefenacet+thiobencarb GR controlled effectively the herbicide-resistant E. oryzicola, S. juncoides and M. vaginalis in direct seeded rice on puddled paddy surface. The days required by the 3rd leaf stage of herbicide-resistant E. oryzicola, S. juncoides and M. vaginalis in direct seeded rice on puddled paddy surface seeded in May 20 shortened by 4 days as compared with it of June 10.

A Survey on Farm Management and Occurrence Area of Herbicide Resistant Paddy Weeds in Chungbuk Province (충북지역 제초제 저항성 논잡초의 농가 관리실태 및 발생면적 조사)

  • Kim, Eun-Jeong;Park, Jae-Seong;Lee, Chae-Young;Lim, Sang-Cheol;Song, Beom-Heon
    • Weed & Turfgrass Science
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    • v.2 no.1
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    • pp.1-7
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    • 2013
  • Studies were carried out to provide basic information for establishing the weed control in Chungbuk, Korea. The present surveys targeting 260 farmers in Chungbuk province were conducted for the cultivation system, weeds occurrence and usage of herbicides. To estimate the occurring area of herbicide resistant weeds, soil samples from 400 paddy fields were collected twice on August, 2011 and April, 2012. In the results of survey, the 99.6% of farmers used the rice planting machine and the 78% of the farmers disseminated herbicides twice to control weeds before and after planting rice. The most commonly used herbicide were as follows; soil-applied herbicide : butachlor 46.6%, mid-term herbicide : mefenacet + pyrazosulfuron-ethyl 10.7%, foliar herbicides : bentazone 62%. The dominant paddy field weeds included Echinochloa crusgalli (16.2%), Scirpus juncoides (12.2%), Monochoria vaginalis (11.9%) and Sagittaria trifolia (9.5%). Occurrence area of sulfonylurea herbicide resistant weeds was 13,659 ha in 26.8% of the paddy area. Monochoria vaginalis showed the highest with 4,605 ha (36.4%) followed Scirpus juncoides (30.7%), and Lindernia dubia (10.6%) at 2011. Monochoria vaginalis and Scirpus juncoides occurred were evenly distributed and the most problematic weed in Chungbuk, Korea.

Herbicidal Efficacy Affected by Different Formulation of Benzobicyclon-Mixtures Herbicides in Paddy Rice Field (Benzobicyclon 혼합제의 제형에 따른 제초활성 특성)

  • Song, Jae-Eun;Park, Mae-Sol;Jeong, Jong-Hee;Park, Eun-Hee;Jeong, Chang-Kuk
    • Korean Journal of Weed Science
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    • v.31 no.4
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    • pp.384-393
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    • 2011
  • Sulfonylurea herbicide-resistant weeds are spreading widely and distributed about 106,951 hectare in paddy rice fields in Korea. Morever all biotype of Scirpus juncoides which were collected at 69 spots all over paddy rice fields in 2008 were identified biotype of sulfonylurea herbicide-resistant. Benzobicyclon is a p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, which is absorbed through root and basal stem of weeds so cause bleaching of newly developing leaves. Benzobicyclon was very effective to control Scirpus juncoides, Monochoria vaginalis, sedges and broadleaves weeds, so it have been developed various formulation like a suspension concentrate (SC), a water dispersible granule (WG), a granule (GR) and a DT (tablet for Direct application). During recently 6 years, benzobicyclon-mixtures herbicides have been registered over than 54 products in paddy fields. Herbicidal efficacy by formulations of benzobicyclon and its mixture herbicides were highest in DT, followed by SC and GR. Herbicidal efficacy of the kaolin and $CaCO_3$ carrier of GR was better and stable than that of talc and bentonite carrier. Growth and yield of rice were not affected much by formulations, application rates and rice cultivation methods.

Herbicidal action mechanism of chlorsulfuron (Acetolactate synthase 저해 제초제인 chlorsulfuron의 작용기작)

  • Kim, Song-Mun;Kim, Yong-Ho;Hur, Jang-Hyun;Han, Dae-Sung
    • The Korean Journal of Pesticide Science
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    • v.2 no.3
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    • pp.1-20
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    • 1998
  • Chlorsulfuron, one of sulfonylurea herbicides acts through inhibition of acetolactate syuthase (EC 4.1.3.18; ALS, also known as acetohydroxyacid synthase) in the branched-chain amino acid biosynthesis process. After chlorsulfuron-ALS interaction, many physiological and metabolic disruptions occur in plants. However, it is not clear how this chlorsulfuron-ALS interaction affects those physiological and metabolic processes and how this interaction leads subsequently to plant death. Several researchers suggested that the death of chlorsulfuron-treated plants might be due to a shortage of the branched-chain amino acids, an accumulation of toxic metabolites, and/or a depletion of photoassimilates. It remains as a mystery presently, however, if such changes result in the plant death. In this review, we discussed how the chlorsulfuran-ALS interaction leads to physiological and metabolic disruptions in plants.

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Characterization of Two Forms of Acetolactate Synthase from Barley

  • Yoon, Jong-Mo;Yoon, Moon-Young;Kim, Young-Tae;Choi, Jung-Do
    • BMB Reports
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    • v.36 no.5
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    • pp.456-461
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    • 2003
  • Acetolactate synthase (ALS) catalyzes the first common step in the biosynthesis of valine, leucine, and isoleucine. ALS is the target site for several classes of herbicides, including sulfonylureas, imidazolinones, and triazolopyrimidines. Two forms of ALS (designated ALS I and ALS II) were separated from barley shoots by heparin affinity column chromatography. The molecular masses of native ALS I and ALS II were determined to be 248 kDa and 238 kDa by nondenaturing gel electrophoresis and activity staining. Similar molecular masses of two forms of ALS were confirmed by a Western blot analysis. SDS-PAGE and Western blot analysis showed that the molecular masses of the ALS I and ALS II subunits were identical - 65 kDa. The two ALS forms exhibited different properties with respect to the values of $K_m$, pI and optimum pH, and sensitivity to inhibition by herbicides sulfonylurea and imidazolinone as well as to the feedback regulation by the end-product amino acids Val, Leu, and Ile. These results, therefore, suggest that the two ALS forms are not different polymeric forms of the same enzyme, but isozymes.

Differential Responses of Two Freshwater Cyanobacteria, Anabaena variabillis and Nostoc commune, to Sulfonylurea Herbicide Bensulfuron-methyl

  • KIM JEONG-DONG;LEE CHOUL-GYUN
    • Journal of Microbiology and Biotechnology
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    • v.16 no.1
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    • pp.52-56
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    • 2006
  • The effect of bensulfuron-methyl on the nontargeted cyanobacteria was greater on A. variabillis than N. commune. Both A. variabillis and N. commune were initially able to utilize low concentrations of the herbicide, bensulfuron-methyl, whereas higher concentrations of bensulfuron-methyl or the hydrolyzed products of the herbicide were found to be toxic. Growth and photosynthesis inhibitions of over $50\%$ were observed, when 8 to 10 ppm of the herbicide was applied. Nitrogenase activities of the cyanobacteria were decreased by $94-98\%$ in A. variabillis and by $85-86\%$ in N. commune after 24 h of incubation with 10 ppm and 20 ppm of bensulfuron-methyl. Nitrogenase activities were also inhibited by the addition of ammonium salts as low as 0.05 mM. Furthermore, the toxic effect of the herbicide was the highest at pH 4-6, showing approximately $42-60\%$ toxicity, whereas much lower toxicity $(9-28\%)$ was observed at higher pH of 7-10, due to base-catalyzed hydrolysis of bensulfuron-methyl.

Expression of Acetohydroxyacid Synthase from Bacillus anthracis and Its Potent Inhibitors

  • Choi, Kyoung-Jae;Pham, Chien Ngoc;Jung, Hoe-Il;Han, Sung-Hwan;Choi, Jung-Do;Kim, Jin-Heung;Yoon, Moon-Young
    • Bulletin of the Korean Chemical Society
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    • v.28 no.7
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    • pp.1109-1113
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    • 2007
  • Acetohydroxyacid synthase (AHAS, EC 2. 2. 1. 6) is the enzyme that catalyses the first step in the common pathway of the biosynthesis of the branched chain amino acids, valine, leucine and isoleucine. For the first time, the AHAS gene from Bacillus anthracis was cloned into the expression vector pET28a(+), and was expressed in the E. coli strain BL21(DE3). The purified enzyme was checked on 12% SDS-PAGE to be a single band with molecular weight of 65 kDa. The optimum pH and temperature for B. anthracis AHAS was at pH 7.5 and 37 oC, respectively. Kinetic parameters of B. anthracis were as follows: Km for pyruvate, K0.5 for ThDP and Mg2+ was 4.8, 0.28 and 1.16 mM respectively. AHAS from B. anthracis showed strong resistance to three classes of herbicides, Londax (a sulfonylurea), Cadre (an imidazolinone), and TP (a triazolopyrimidine). These results indicated that these herbicides could be used in the search for new anti-bacterial drugs.

TROGLITAZONE, A NOVEL ANTIDIABETIC DRUG -NEW AVENUE FOR TREATING INSULIN RESISTANCE-

  • Horikoshi, Hiroyoshi
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1998.05a
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    • pp.1-4
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    • 1998
  • Impaired insulin action in Type 2 diabetes is thought to lead to hyperglycemia, with both environmental and complex genetic factors playing key roles. Although the primary lesion in Type 2 diabetes is unknown, a number of studies suggest that metabolic defects in the liver, skeletal muscle and fat, and pancreatic ${\beta}$-cells contribute to the disease. These metabolic abnormalities are characterized by the overproduction of hepatic glucose, impaired insulin secretion, and peripheral insulin resistance. In current pharmacological treatment of Type 2 diabetes, sulfonylurea (SU) drugs have mainly been used as oral hypoglycemic drugs to stimulate endogenous insulin secretion from ${\beta}$ cells. SU drugs, however, sometimes aggravate the disease by causing fatigue of the pancreatic ${\beta}$ cells, which leads to reduced drug efficacy after long-term treatment. This class of drugs also leads to enhanced obesity arising from the stimulation of endogenous insulin secretion in obese Type 2 diabetic patients, plus an increased incidence of SU-induced hypoglycemia. Since 1980, a major challenge has been made by us to develop a potential pharmacological therapy for the treatment of insulin resistance in peripheral tissues and/or suppression of abnormal hepatic glucose production in Type 2 diabetic patients. Such a drug would be expected to have fewer side effects and retain long-term efficacy.

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15-Hydroxyprostaglandin Dehydrogenase Is Associated with the Troglitazone-Induced Promotion of Adipocyte Differentiation in Human Bone Marrow Mesenchymal Stem Cells

  • Noh, Min-Soo;Lee, Soo-Hwan
    • Biomolecules & Therapeutics
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    • v.18 no.1
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    • pp.16-23
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    • 2010
  • Adipocyte differentiation in human bone marrow mesenchymal stem cells (hBM-MSCs) is not as efficient as that in murine pre-adipocytes when induced by adipogenic agents including insulin, dexamethasone, and 3-isobutyl-1-methylxanthine (IDX condition). Therefore, the promotion of adipocyte differentiation in hBM-MSCs has been used as a cell culture model to evaluate insulin sensitivity for anti-diabetic drugs. In hBM-MSCs, $PPAR{\gamma}$ agonists or sulfonylurea anti-diabetic drugs have been added to IDX conditions to promote adipocyte differentiation. Here we show that troglitazone, a peroxisome proliferator-activated receptor-gamma ($PPAR{\gamma}$) agonist, significantly reduced the levels of anti-adipogenic $PGE_2$ in IDX-conditioned hBM-MSC culture supernatants when compared to $PGE_2$ levels in the absence of $PPAR{\gamma}$ agonist. However, there was no difference in the mRNA levels of cyclooxygenases (COXs) and the activities of COXs and prostaglandin synthases during adipocyte differentiation in hBM-MSCs with or without troglitazone. In hBM-MSCs, troglitazone significantly increased the mRNA level of 15-hydroxyprostaglandin dehydrogenase (HPGD) which can act to decrease $PGE_2$ levels in culture. These results suggest that the role of $PPAR{\gamma}$ activation in promoting adipocyte differentiation in hBM-MSCs is to reduce anti-adipogenic $PGE_2$ levels through the up-regulation of HPGD expression.