• Weed & Turfgrass Science
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• v.2 no.3
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• pp.248-253
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• 2013

This study was conducted to select alternative herbicides to control herbicide-resistant and - troublesome weeds in rice fields, Korea. The resistant Echinochloa oryzicola to ACCase inhibitor was tested by herbicides registered to control Echinochloa oryzicola. And the resistant and troublesome weeds to sulfonylurea (SU) herbicides, ALS inhibitors, were tested by widely using herbicides to control the resistant weeds in Korea. The oxadiazon, pyrazolate, pretilachlor and benzobicyclone+thiobencarb effectively controlled resistant Echinochloa oryzicola to ACCase and ALS inhibitors at 0.5 leaf stage of the, Herbicides containing mefenacet or fentrazamide controlled effectively by the 2 leaf stage. In controlling other SU resistant weeds including Sagittaria trifolia and Ludwigia prostrate, benzobicyclon and mesotrione performed well all tested weeds, and carfentrazone and pytazolate were effective to broadleaf weeds. Sagittaria trifolia and Ludwigia prostrate, which were suspected to be resistance to SU herbicides, were well controlled by carfentrazone and pytazolate.

• BMB Reports
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• v.30 no.1
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• pp.13-17
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• 1997

The inhibitory effect of herbicides such as sulfonylurea derivatives, imidazolinones and pyrimidylsalicylate has been examined on the purified valine sensitive acetolactate synthase (ALS) from Serratia marcescens. The concentration of sulfometuron methyl which inhibits 50% of the ALS activity was 2.5 mM. The required concentrations of triasulfuron, primisulfuron methyl and imazaquin for the 50% inhibition of the ALS activity were 1 mM. The resistance of Serratia ALS to sulfometuron methyl, imazapyr and imazaquin is similar to that of E. coli ALS 1. However, pyrimidylsalicylate showed a potent inhibitory effect on the Serratia ALS almost 13 times more potent than on E. coli ALS II, which is known as herbicide-sensitive isozyme. The inhibitory mode was competitive against pyruvate. 150 value was determined to be $17{\mu}M$ in an assay mixture containing 20 mM pyruvate, and the $K_1$, value was calculated to be $0.4{\mu}m$ from the modified double reciprocal plot of 1/V versus $1/S^2$.

• The Korean Journal of Pesticide Science
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• v.17 no.4
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• pp.314-334
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• 2013

This study explored an efficient modified Quick, Easy, Cheap, Effective, Rugged and safe (QuEChERS) method combined with liquid chromatography-electrospray ionization with tandem mass spectrometric detection for the analysis of residues of 76 pesticides in brown rice, barley and corn including acidic sulfonylurea herbicides. Formic acid (1%) acid in acetonitrile and dispersive solid phase extractions used for extraction of pesticides and clean-up of the extract respectively. Two fortified spikes at 50 and 200 ng $g^{-1}$ levels were performed for recovery test. Mean recoveries of majority of pesticides at two spike levels ranged from 73.2 to 132.2, 80.9 to 136.8, 66.6 to 143.5 for brown rice, barley and corn respectively with standard error (CV) less than 10%. Good linearity of calibration curves were achieved with $R^2$ > 0.9907 within the observed concentration ranged. The modified method also provided satisfactory results for sulfonylurea herbicides. The method was applied to the determination of residues of target pesticides in real samples. A total of 26 pesticides in 36 out of 98 tasted samples were observed. The highest concentration was observed for tricyclazole at 1.17 mg $kg^{-1}$ in brown rice. This pesticide in two brown rice samples exceeded their MRLs regulated for rice in republic of Korea. Except tricyclazole none of the observed pesticides' concentration was higher than their MRLs. The results reveal that the method is effectively applicable to routine analysis of residues of target pesticides in brown rice, barley and corn.

• Korean Journal of Weed Science
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• v.32 no.1
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• pp.52-56
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• 2012

The occurrence of sulfonylurea-resistant weeds has recently increased in Korea. A survey was performed to investigate major paddy field weeds and frequently used herbicides in Gangwon province, Korea in order to establish a system to efficiently control herbicide-resistant weeds. The dominant paddy field weeds included Monochoria vaginalis (14%), Sagittaria trifolia (14%), Scirpus juncoides (13%), and Echinochloa spp. (13%), and the most widely used herbicides were oxadiazon 12% EC (27%), butachlor 5% GR (20%), oxadiargyl 1.7% EC (16%), and benzobicyclon+imazosulfuron+pyriminobac-methyl 6.1% SC (14%) in Gangwon province, Korea. Many paddy rice growers considered Scirpus juncoides, S. trifolia, Echinochloa spp. and M. vaginalis as herbicide-resistant weeds. An extensive research deserves to be conducted to monitor occurrence of herbicide-resistant paddy weeds in Gangwon province, Korea.

• Korean Journal of Weed Science
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• v.31 no.2
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• pp.192-198
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• 2011

This study was conducted to investigate the herbicidal activity against Scirpus planiculmis (SCPPL) which has been reported as resistant biotype on sulfonylurea (SU) herbicides at the west coast reclaimed area first and proliferated continuously at Hwasung and Pyeongtaek in Gyeonggi province, and some Chungnam province. In order to investigate resistance breakability against SCPPL, new rice herbicides containing tefuryltrione [p-hydrophenyl pyruvate dioxygenase (HPPD) inhibitor], pyrimisulfan and triafamone[actolactate synthethase (ALS) inhibitor] were tested. In both lab and field experiments, tefuryltrione GR, 4-HPPD inhibitor showed growth retardation with a bleaching on the young leaves of SCPPL at early time after treatment. However, it restored and regerminated with insufficient control effect. On the other hand, pyrimisulfan+mefenacet SC, triafamone+tefuryltrione GR, and ALS inhibitor showed excellent control effect on SU-resistant SCPPL with growth retardation and necrosis. In particular, pyrimisulfan+mefenacet SC showed excellent controlling effect on SU-resistant SCPPL in regional field experiments.

• 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.

• BMB Reports
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• v.29 no.5
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• pp.462-467
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• 1996

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 mazolopyrimidines, the pyrimidyl-oxy-benzoates, the pyrimidyl-thio-benzens, and the 4,6-dimethoxypyrimidines. An amino-terminal fragment of the sulfonylurea-resistant ALS gene (SurB) from Nicotiana tabaccum was cloned into the bacterial expression vector pGEX-2T. The resulting recombinant plasmid pGEX-ALS1 was used to transform Escherichia coli strain BL21, and the tobacco ALS was expressed in the bacteria as a protein fused with glutathione S-transferase (GST). Polyclonal antibodies against the fusion product (GST-ALS) were produced, and the sensitivity of GST-ALS with the rabbit anti-GST-ALS IgG was up to 50 ng. This antibody was used for Western blot analysis of the partially purified ALS from barley shoots. The results suggest that the polyclonal antibody produced in this study can be used to detect plant ALS.

• BMB Reports
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• v.28 no.6
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• pp.471-476
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• 1995

Acetolactate synthase (ALS) catalyzes the first common step in the biosynthesis of valine, leucine, and isoleucine. ALS is the target enzyme for several classes of structually diverse herbicides. We have synthesized 4,6-dimethoxypyrimidine derivatives as ALS inhibitors, and their inhibitory activities on barley ALS were determined. $IC_{50}$ values for the derivatives are 0.2~200 ${\mu}m$. K11570, the most potent ALS inhibitor with $IC_{50}$ of 0.2 ${\mu}m$, showed mixed-type inhibition with respect to substrate pyruvate, and the progress curves for ALS inhibition by K11570 indicated that the amount of inhibition increased with time. Inhibition-competition experiments were carried out and indicated that three different classes of inhibitors, K11570, a sulfonylurea Ally, and leucine, bind to ALS in a mutually exclusive manner. Chemical modification of tryptophanyl and tyrosyl residues of ALS decreased the sensitivity of ALS to K11570, while cysteine modification did not affect the sensitivity. These results suggest that tryptophanyl and tyrosynyl residues are probably located at or near the inhibitor binding site.

• Journal of Microbiology and Biotechnology
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• v.8 no.3
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• pp.295-299
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• 1998

Oligonucleotide primers were designed and successfully applied to amplify DNA fragments of P450 hydroxylase genes from actinomycetes which produce a large variety of medically important metabolites. Primers were designed based on several regions of strong similarities in amino acid sequence of P450 hydroxylases from a variety of actinomycetes, primarily in the regions of an oxygen binding site and a heme ligand pocket. These primers were used to amplify DNA fragments from seven different actinomycetes species producing a variety of different compounds. The deduced amino acid sequences of the isolated fragments revealed significant similarities to known P450 hydroxylase including the product of the suaC or subC genes from Streptomyces griseolus that is capable of metabolizing a number of sulfonylurea herbicides, and to the product of the $P450_{sca2}$ from S. carbophilus that produces a specific HMG-CoA reductase inhibitor. This method should help researchers in cloning the P450 hydroxylase genes involved in the biosynthesis of useful compounds.

• Journal of the Korean Chemical Society
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• v.43 no.4
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• pp.461-468
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• 1999

Acetolactate synthase (ALS) catalyzes the first common reaction in the biosynthesis of branched-chain amino acids, valine, leucine, and isoleucine. ALS is the common target of several classes of structurally diverse herbicides, the triazolopyrimidines, the imidazolinones, the sulfonylureas, and pyrimidyl-oxy-benzoates. We examined ihibitory activities of newly synthesized triazolopyrimidine sulfonamide derivatives using partially purified ALS from barley. $IC_{50}$ values for the active derivatives are 0.5nM∼8$\mu$M. Among them TP1 and TP2 are the most potent ALS inhibitors with $IC_{50}$ values of 0.5nM and 1.6nM, respectively. These inhibitors are more potent in the inhibition of barley ALS than commercial herbicides, Metosulam ($IC_{50}$;3.6 nM), Flumetsulam ($IC_{50}$;126 nM), and Cadre ($IC_{50};4 {\mu}M$). The progress curves for inhibition of ALS by TP2 showed that the amount of inhibition increases with time. The inhibition of ALS by TP2 was mixed-type inhibition with respect to pyruvate. Dual inhibition analyses of TP2 versus an imidazolinone, Cadre, and Leu showed parallel and intercepting kinetic pattern, respectively. The results suggest that TP2 binds to ALS competively with Cadre but not with Leu. Chemical modification of cysteinly residues in ALS decreased the sensitivity of ALS to Leu, while the modification did not affect the sensitivity of ALS to TP2 and Cadre.