• KOREAN JOURNAL OF CROP SCIENCE
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• v.47 no.4
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• pp.328-334
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• 2002

A Lindernia dubia (L.) Pennell var. dubia accession from Jeonnam province, Korea was tested for resistance to sulfonylurea (SU) herbicides, imazosulfuron and pyrazosulfuron-ethyl in whole-plant response bioassay. The accession was confirmed resistant to both herbicides. The $GR_{50}$ (herbicide concentration that reduced shoot dry weight by 50%) values of resistant accession were 264 and 19 times higher to imazosulfuron and pyrazosulfuronethyl, respectively, than that of the standard susceptible accession. The surviving resistant L. dubia after pyrazosulfuron-ethyl + molinate application can be controlled by sequential applications of soil-applied herbicides, butachlor, dithiopyr, pyrazolate, and thiobencarb and foliar herbicides, bentazon. Sulfonylurea-based mixtures such as mixtures of azimsulfuron + anilofos, bensulfuron-methyl + oxadiazon, pyrazosulfuron-ethyl + fentrazamide, and pyrazosulfuron-ethyl + anilofos + carfentrazon can also be used to control the surviving resistant L. dubia. However, use of these mixtures should be restricted to a special need basis. Thus, we suggest that sequential applications of non-SU-based mixtures such as butachlor + pyrazolate and MCPB + molinate + simetryne be used to control the surviving resistant L. dubia after SU herbicide applications. Rice yield was reduced 24 % by resistant L. dubia that survived after the pyrazosulfuron-ethyl + molinate application compared with pyrazolate + butachlor in transplanted rice culture. In vitro ALS activity of the resistant biotype was 40 and 30 times more resistant to imazosulfuron and pyrazosulfuron-ethyl, respectively, than the susceptible biotype. Result of in vitro ALS assay that the resistance mechanism of L. dubia to SU herbicides may be due, in part, to an alteration in the target enzyme, ALS.

• Korean Journal of Weed Science
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• v.17 no.2
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• pp.135-138
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• 1997

Sulfonylureas are highly active herbicides which can be applied at very low rate(10-50g/ha) to control broadleaf weeds. The nature of this category of compound is, however, very unstable toward hydrolysis. Therefore, the preparation of these compounds as liquid formulation was not possible. Most of the current formulations of sulfonylurea are in dry forms such as water dispersible granule or wettable powder. Even in these dry forms, the active ingredients also encounter significant chemical decomposition. This study involves the preparation of the sulfonylurea salts by reacting the parent compound with base such as sodium hydroxide. The salt becomes stable toward hydrolysis and it turns soluble when diluted with water. This discovery makes the preparation for liquid formulation or soluble granule of sulfonylurea possible. The stoichiometry of base added to the neutral sulfonylurea is controlled quite precisely. The base has to be added enough to quench the acidic impurities in the technical material and to convert the active ingredient into salt. However, the base should not be overused to cause further saponification of the sulfonylurea salts. The chemical nature of these compounds is presented and the chemical reaction is described. New soluble liquid formulation and solid granule formulation of sulfonylurea are suggested.

• Korean Journal of Environmental Agriculture
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• v.8 no.2
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• pp.136-141
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• 1989

An alternative method for the synthesis of sulfonylurea derivatives, some of which considered to be a new recommendable herbicides, with oxalylchloride was investigated. Sulfonamides read with oxalylchloride to sulfonyloxamoylchlorides, which convert easily under pyrolysis to sulfonylisocyanates. The isocyanates react further with amines to yield corresponding sulfonylurea derivative quantitatively.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.48 no.4
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• pp.286-291
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• 2003

Monochoria vaginalis is one of the most troublesome resistant weeds in Korean rice culture. Thus, the objectives of this study were to evaluate the response of M. vaginalis resistant to sulfonylurea(SU) herbicides and to determine alternative herbicides for the control of resistant M. vaginalis in direct seeded and transplanted rice culture in Korea. In greenhouse studies, the resistant biotype was 31-, 38-, 3172-, and 7-fold more resistant to ben-sulfuron-methyl, cyclosulfamuron, imazosulfuron, and pyrazosulfuron-ethyl, respectively, than the susceptible biotype, indicating cross-resistance to the SU herbicides used in this study. Non-SU herbicides, butachlor, carfentrazone-ethyl, mefenacet, pretilachlor, pyrazolate, and thiobencarb, several SU herbicide-based mixtures, ethoxysulfuron plus fentrazamide, pyrazosulfuron-ethyl plus pyrazolate plus simetryn, and non-SU herbicide-based mixtures, pyrazolate plus butachlor, pyrazolate plus pretilachlor, simetryn plus molinate, carfentrazone-ethyl plus butachlor, and carfentrazone-ethyl plus thiobencarb can be used to control both the resistant and susceptible biotypes of M. vaginalis when applied before the second leaf stage. In the field experiment, the resistant biotype of M. vaginalis that survived from the paddy fields treated with a SU herbicide-based mixture could effectively be controlled by using mixtures of bentazone plus MCPA, bentazone plus mecoprop-P, and bentazone plus 2,4-D when applied at 2 or 4 main leaves. Our results suggest that the SU-resistant M. vaginalis had not developed multiple resistances to herbicides with different modes of action. In particular, bentazone plus MCPA and bentazone plus mecoprop-P were effective control measures after failure to control resistant M. vaginalis in Korean rice culture.

• BMB Reports
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• v.28 no.3
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• pp.265-270
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• 1995

Acetolactate synthase (ALS, EC 4.1.3.18) is the first common enzyme in the biosynthesis of leucine, isoleucine, and valine. It is the target enzyme for several classes of herbicides, including the sulfonylureas, the imidazolinones, the triazolopyrimidines, the pyrimidyl-oxy-benzoates and the pyrimidyl-thio-benzens. The sulfonylurea-resistant ALS gene (SurB) from Nicotiana tabaccum [Lee et al. (1988) The EMBO J. 7, 1241-1248] was cloned into the bacterial expression plasmid pT7-7. The resulting recombinant plasmid pT7-ALS was used to transform an ALS-deficient Escherichia coli strain MF2000. MF2000 cells transformed with pT7-ALS grew in the absence of valine and isoleucine. ALS activities of 0.042 and 0.0002 ${\mu}mol/min/mg$ protein were observed in the crude extracts prepared from MF2000 cells transformed with plasmids pT7-ALS and pT7-7, respectively. In addition, the former crude extract containing mutant ALS was insensitive to inhibition by K11570, a new chemical class of herbicides. $IC_{50}$ values for K11570 were $0.13{\pm}0.01$ mM. For comparison, a plasmid pTATX containing the wild-type Arabidopsis thaliana ALS coding sequences was also expressed in MF2000. ALS activities of 0.037 ${\mu}mol/min/mg$ protein were observed, and the wild type ALS was sensitive to two different classes of herbicides, K11570 and ALLY, a sulfonylurea. $IC_{50}$ values for K11570 and ALLY were $0.63{\pm}0.07$ and $80{\pm}5.6$ nM, respectively. Thus, the results suggest that the sulfonylurea-resistant tobacco ALS was functionally expressed in the bacteria, and that K11570 herbicides bind to the regulatoty site of ALS enzymes.

• BMB Reports
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• v.31 no.3
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• pp.287-295
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• 1998

Acetolactate synthase (ALS) is the first common enzyme in the biosynthesis of L-Ieucine, L-isoleucine, and L-valine. The sulfonylurea-resistant ALS gene from Nicotiana tabacum was cloned into the bacterial expression vector pGEX-2T. The resulting recombinant plasmid pGEX-ALS3 was used to transform Escherichia coli strain XL1-Blue, and the mutant tobacco ALS (mALS) was expressed in the bacteria as a protein fused with glutathione S-transferase (GST). The fusion product GST-mALS was purified in a single step on a glutathione-Sepharose column. ALS activities of 0.9-2.5 ${\mu}mol/min/mg$ protein were observed in the GST-mALS, and the Km values for pyruvate, FAD, and TPP were 10.8-24.1, $(1.9-8.9){\times}10^{-3}$, and 0.14-0.38 mM, respectively. The purified GST-mALS was resistant to both the sulfonylurea and the triazolopyrimidine herbicides, and lost its sensitivity to end products, L-valine and L-leucine. For comparision, the tobacco wild-type recombinant ALS fused with GST, GST-wALS, was also characterized with respect to its pyruvate and cofactor bindings. These results suggest that the purified mutant recombinant tobacco ALS was functionally active, that the mutations resulting in herbicide resistance has affected pyruvate and cofactor bindings," and that the two classes of herbicides interact at a common site on the plant ALS.

• The Korean Journal of Pesticide Science
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• v.11 no.4
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• pp.269-275
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• 2007

Four sulfonylurea(SU)-resistant Monochoria vaginalis(M. vaginalis) accessions were tested for levels of resistance to four SU herbicides which have been widely using in paddy fields of Korea, based on whole plant response and sensitivity of the target enzyme, acetolactate synthase(ALS). The resistant Naju, Nonsan and Gimje accessions were not affected to the survival by treatment with recommended dose of all SU herbicides tested. The $GR_{50}$ values for the Naju, Nonsan and Gimje accessions were 8- to 33-fold, 8- to 30-fold and 7- to 32-fold higher to recommended doses of all SU herbicides tested than the susceptible Cheongdo accession, respectively. However, the $GR_{50}$ values for Kimhae accession displayed an intermediate response and was only 4-to 13-fold more resistant than the susceptible accession. The ALS $I_{50}$ values for the Naju, Nonsan and Gimje accessions were 25- to 66-fold, 9- to 26-fold and 10- to 24-fold higher to recommended doses of all SU herbicides tested than the susceptible Cheongdo accession, respectively. However, the $I_{50}$ value for Kimhae accession was 4- to 9-fold more resistant than the susceptible accession, as determined by $I_{50}$ values of ALS.

• Weed & Turfgrass Science
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• v.6 no.1
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• pp.28-31
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• 2017

The mutation rate of proline in the position 197 (Pro197) in acetohydroxy acid synthase (AHAS) is highest among sulfonylurea (SU) herbicide-resistance mutants. Therefore, it is significant to investigate the resistance mechanism for the mutation and to develop the herbicides specific to the mutants. SU herbicide resistance mechanism of the mutants, 197Ser, 197Thr and 197Ala, in AHAS were targeted for designing new SU-herbicide. We did molecular dynamics (MD) simulation for understanding SU herbicide-resistance mechanisms of AHAS mutants and designed new herbicides with docking and MD evaluations. We have found that mutation to 197Ala and 197Ser enlarged the entrance of the active site, while 197Thr contracted. Map of the root mean square derivation (RMSD) and radius gyrations (Rg) revealed the domain indicating the conformations for herbicide resistant. Based on the enlarging-contracting mechanism of active site entrance, we designed new herbicides with substitution at the heterocyclic moiety of a SU herbicide for the complementary binding to the changed active site entrances of mutants, and designed new herbicides. We confirmed that our screened new herbicides bonded to both AHAS wild type and mutants with higher affinity, showing more stable binding conformation than the existing herbicides.

• The Korean Journal of Pesticide Science
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• v.9 no.3
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• pp.205-213
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• 2005

This study was conducted to evaluate the response of the selected aquatic plants to sulfonylurea(SU)-herbicides, which have been used widely in rice-cultivating areas in Korea, and the possibility of using them as bio-indicator species for biodiversity conservation. The aquatic plants identified in Kangwon province where butachlor have been used extensively for many years were much more varied than those in Chonnam where SU-herbicides have been used extensively for many years. The growth responses of Monochoria korsakowii, Marsilea quadrifolia and Salvinia natans to sulfonylurea herbicides such as bensulfuron-methyl(BSM) and pyrazosulfuron-ethyl(PSE), were much more sensitive than those to butachlor and molinate. The $GR_{50}$ values of BSM and PSE for M. korsakowii, M. quadrifolia and S. natans were relatively very low when compared with those of butachlor and molinate. The number of internode and dry weight of M. quadrifolia which was exposed to herbicides runoff from rice fields were seriously affected. The acetolactate synthase(ALS) activities of M. quadrifolia sensitively inhibited by BSM and PSE were, and $I_{50}$(Inhibition 50%) were 5.6 and 2.1 nM, respectively.

• The Korean Journal of Pesticide Science
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• v.12 no.1
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• pp.1-8
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• 2008

The widespread and diverse sulfonylurea (SU) resistance problem has found in Korea, where one-shot-treatment herbicides such as pylazosulfuron/molinate and bensulfuron/molinate have been used continuously since 1989. The SU-resistant weeds of 7 annual weeds and 3 perennial weeds as of 2008 have confirmed in paddy fields in Korea. An effective management to SU-resistant weeds requires an integrated approach toward the weed control system, in particular, as to the drastic changes of herbicides development. Recent trend of new paddy herbicides in Japan has been developing to maximize the management of SU-resistant weeds. In the future, it is expected that the development of paddy herbicides in Korea is likely to be shifted toward the new "one-shot-treatment" included with herbicides of over 3-ways to maximize the control of resistant weeds. Bromobutide and carfentrazone are effective against sedges and broad-leaved weeds, respectively, and benzobicyclone and pyrimisulfam are effective against sedges and broad-leaved weeds.