• Journal of the Korean Chemical Society
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• v.48 no.4
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• pp.385-393
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• 2004

2-Ethoxycarbonyl-3-methylquinoxaline 1,4-dioxide (8) was synthesized from benzofuroxan and ethyl acetoacetate. The reaction of compound 8 with hydrazine hydrate or selenium dioxide gave 2-hydrazinocarbonyl-3-methylquinoxaline 1,4-dioxide (9) or 2-ethoxycarbonyl-3-formylquinoxaline 1,4-dioxide (10), respectively. The reaction of compound 9 with alkanoyl chlorides, benzoyl chlorides, heteroacyl chlorides, and benzenesulfonyl chlorides afforded 3-methyl-2-(substituted hydrazinocarbonyl)quinoxaline 1,4-dioxides (11-14), respectively. The reaction of compound 9 with sodium azide gave 2-azidocarbonyl-3-methylquinoxaline 1,4-dioxide (15), and then its refluxing in dioxane/alcohols resulted in the Curtius rearrangement to give N-(3-methyl-1,4-dioxoquinoxalin-2-yl)-alkyl carbamates (16). The reaction of compound 15 with substituted anilines afforded 2-(3-substituted phenylureido)-3-methylquinoxaline 1,4-dioxides (17). The reaction of compound 10 with benzoic hydrazide or substituted anilines provided quinoxaline 1,4-di-oxides (18, 19), respectively. The herbicidal and fungicidal activities of the synthesized compounds were investigated.

• Korean Journal of Weed Science
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• v.31 no.2
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• pp.212-219
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• 2011

The water dispersible granule flupoxam showed over 95% of weeding effect on the annual weeds of Poaceae such as Poa annua L., Digitaria ciliaris (Rets.) Koel and broad-leaf weeds. Efficacy of treatment had been lasted over 120 days in the $2kg\;ha^{-1}$ when it was treated from March to April while lasted over 180 days when it was treated from September to October. Because the flupoxam has a high soil absorptivity, a perfected herbicide layer is formed. This results in perfect weeding effect regardless of the presence or absence of thatch. Because the flupoxam has a different mechanism of action from the conventional herbicides such as dinitroanilines, pyridines, and carbamates, it is very effective with the alternative spray. Phytotoxicity symptoms was not observed and/or produced antocyan in new leaves in the landscape trees around the lawngrass by flupoxam treatment.

• The Korean Journal of Pesticide Science
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• v.6 no.4
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• pp.264-270
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• 2002

Studies on the resistance monitoring of green peach ahpid, Myzus persicae, its development pattern by artificial selection with imidacloprid and cross-resistance were carried out to develope resistance management strategy. Resistance ratios of M. persicae collected at Hwachon and Dunnae among 5 locations in alpine cultivation area appeared to be high as 37.2 and 16.5, respectively. Resistance of aphid to imidacloprid developed slowly up to 20 time selection, and after that it grew quickly. Imidacloprid-resistant aphid strain showed low cross-resistance ratios(<10) to most of organophosphates, carbamates, and mixed insecticides except pirimicarb(487.8), but high ratios to acetamiprid(143.0) which is one of the neonicotinoids like imidacloprid, and pyrethroids such as deltamethrin(14.9), flucythrinate(12.9) and halothrin(15.9).

• Asian Pacific Journal of Cancer Prevention
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• v.17 no.9
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• pp.4267-4273
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• 2016

Previous studies suggested that dithio-carbamates are potent apoptosis and anti-apoptosis inducing agents in various cancer cells. Here, the anti-proliferative and apoptosis inducing effects of a new derivative (2-NDC) from the dithio-carbamate family was examined in human leukemia K562 cells. We use thiazolyl blue tetrazolium bromide (MTT) to measure viability and cell growth inhibition. The 2-NDC showed effects on viability in a dose and time-dependent manner, inhibiting proliferation at concentrations of $10-30{\mu}M$ after 24-48 hours of treatment and increasing values after 72 hours at $40-120{\mu}M$. The cytotoxic effect of the compound was calculated with an $IC_{50}$ of $30{\mu}M$ after 24-hour. Apoptosis induction was confirmed by acridine orange-ethidium bromide (AO/EtBr) staining, DNA fragmentation assay, flow cytometric assessment and also caspase-3 activation assay. Furthermore, enzymes level such as superoxide dismutase (SOD) and catalase (CAT) involved in oxidative stress were evaluated. The results of this study demonstrated insignificant increase of intracellular ROS levels for 24 hours and reduction after 48-72 hours. In addition to reduction of intracellular thiol, caspase-3 like activity was also decreased in a time-dependent manner in cells treated with 2-NDC. Thus 2-NDC can be considered as a good candidate for further pharmaceutical evaluations.

• The Korean Journal of Pesticide Science
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• v.15 no.3
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• pp.329-334
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• 2011

Insecticidal activity of 31 registered insecticides was tested against Metcalfa pruinosa adults. All experiments were conducted at the recommended concentration (ppm) of each insecticide. Among them, 16 insecticides from organophosphates (dichlorvos, fenitrothion, fenthion, methidathion, phenthoate), carbamates (methomyl), pyrethroids (${\alpha}$-cypemethrin, deltamethrin, fenpropathrin, ${\gamma}$-cyhalothrin), neonicotinoids (acetamiprid, clothianidin, dinotefuran, imidacloprid, thiamethoxam), and other (endosulfan) showed 100% mortality by spraying on the body of M. pruinosa adults. Dichlorvos, fenitrothion, fenthion, methidathion, phenthoate and endosulfan showed 100% mortality by plant-dipping method. The residual effect was showed 100% mortality in four insecticides (fenitrothion, fenthion, methidathion, phenthoate) at one day after treatment, and three insecticides (fenitrothion, methidathion, phenthoate) were showed the mortality of 90% at three days after treatment.

• Applied Biological Chemistry
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• v.32 no.2
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• pp.170-177
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• 1989

In order to seek the molecular basis of higher insecticidal activity of the carbamates with two methyl groups, m-xylyl-N-methylcarbamate(MXNMC) than the corresponding unsubstituted phenyl N-methylcarbamate(PNMC), these two derivatives have been studied by molecular orbital(MO) theoretically using extended $H\ddot{u}ckel$ theory(EHT), and analysis of regression and linear free energy relationship(LFER). The most stable stereo structure(Z, Z) shows that the phenyl group occupies vertical(${\theta}=90^{\circ}$) position on the plane of the N-methylcarbamyl group. Regression analysis shows that especially good correlation exists between the $pI_{50}$ values and the calculated MO quantities when the hydrogen atomic charge of metaposition and of m-methyl groups, and LUMO energy are taken as variables. The LFER analysis on the carbamylation indicates that field(F) effect(60%) is slightly larger than resonance(R) effect(40%) in PNMC(E>R), whereas, in case of MXNMC, R effect(98.6%) is much larger than F effect(1.4%)($R{\gg}F$). From the basis on the findings, the enhancement of insecticidal activity of MXNMC may be the result of hyperconjugation by m-methyl groups.

• Proceedings of the Korean Society of Applied Pharmacology
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• 1998.11a
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• pp.108-113
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• 1998

Egasyn is accessory protein of ${\beta}$-glucuronidase(${\beta}$-G) in the liver microsomes. Liver microsomal ${\beta}$-G is stabilized within the luminal site of the microsomal vesicles by complexation with egasyn which is one of carboxylesterase isozymes. We investigated the effects of organophosphorus compounds(OPs) such as insecticides on the dissociation of egasyn-${\beta}$-glucuronidase(EG) complex. The EG complex was easily dissociated by administration of OPs, i.e., Fenitrothion, EPN, Phenthionate, and bis-p-nitrophenyl phosphate(BNPP), and resulting ${\beta}$-G dissociated was released into blood, leading to the rapid and transient increase of plasma ${\beta}$-G level with a concomitant decrease of liver microsomal ${\beta}$-G level. In a case of phenthionate treatment, less increase in plasma ${\beta}$-G level was observed, as compared with those of other OPs. This may be explained by a fact that phenthionate was easily hydrolyzed by carboxylesterase. Similarly, carbamate insecticides such as Carbaryl caused rapid increase of plasma ${\beta}$-G level. In contrast, no significant increase of plasma ${\beta}$-G level was observed when pyrethroid insecticides were administered to rats. This is due to a fact that pyrethroids such as Phenthrin and Allethrin were easily hydrolyzed by A-esterase as well as carboxylesterase. On the other hand, addition of OPs to the incubation mixture containing liver microsomes caused the release of ${\beta}$-G from microsomes to the medium. From these in vivo and in vitro data, it is concluded that increase of the plasma ${\beta}$-G level after OPs administration is much more sensitive biomarker than cholinesterase inhibition to acute intoxication of OPs and carbamates.

• Bulletin of the Korean Chemical Society
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• v.28 no.6
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• pp.929-935
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• 2007

The objective of this study was to develop a rapid, simple, and qualitative acetylcholinesterase (AChE)- detection kit, based on a modification of the Ellman and ELISA methods, for the detection of organophosphorus (OP) and carbamate (CB) pesticide. The developed kits were used to screen a large number of agricultural samples (spiked and real) for OP and CB pesticide residues. AChE was extracted from the heads of honeybees (Apis mellifera L.) using Triton X-100, and was purified through 3 steps: diethylaminoethylcellulose chromatography (DEAE), affinity chromatography and membrane filtering, and Mono-Q column chromatography. Epoxy-activated Sepharose 6B affinity chromatography was used for large-scale purification. The presence of OP and CB pesticide residues in agricultural samples was assayed on the basis of AchE inhibition value. The presence (6 bands) or absence of some colored bands on the test line indicated a negative or positive result, respectively. The limits of detection for measured organophosphorus (OP) and carbamates (CB) pesticide residues in standard pesticide solutions and fortified samples were ranged from 0.50 to 2.50 ppm and 0.50 to 4.75 ppm, respectively.

• The Korean Journal of Pesticide Science
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• v.9 no.4
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• pp.365-373
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• 2005

This study was carried out for looking into the status of susceptibility of pest insects to insecticides. Each insect Brown planthopper(BPH), Green leaf hopper(GLH), Smaller brown plant hopper(SBPH), Rice water weevil(RWW), were captured at various areas where the host crops were being cultivated and the susceptibility level of each pest insect was investigated. The susceptibility of each pest insect varied by insect species and areas where they were caught. BPHs kept higher level of susceptibility comparing to susceptible reference strain except to most of tested insecticides except imidacloprid (Resistance ratio was 68). The susceptibilities of GLH and SBPH to most of insecticides for their control did not developed markedly since 1976 except fipronil and imidacloprid which is widely used for WRR control. The insecticides used for control of WRR were very effective even at the concentration of one fourth of recommending concentration, but in 2000 suwon strain of WRR showed markedly reduction of susceptibility to carbofuran.

• The Korean Journal of Pesticide Science
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• v.11 no.3
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• pp.194-200
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• 2007

Insecticidal activity of 33 registered insecticides was tested against last nymphal instars and adults of ussur brown katydid (Paratlanticus ussuriensis). All experiments were tested at the recommended concentration of each insecticides by producer. Acephate, chlorpyrifos, diazinon, EPN and fenitrothion which were organophates, and a mixture combined with chlorpyrifos+${\alpha}$-cypemethrin showed 100% mortality of P. ussuriensis. But fipronil showed only 100% mortality in leaf-dipping method. Carbamates insecticidal groups, benfuracarb and furathiocarb were showed over 80% and phenthoate was $60{\sim}80%$ in mortality of P. ussuriensis. Among the mixture, etofenprox+diazinon and esfenvalerate+fenitrothion were showed 60-80% against last nymphal instars of P. ussuriensis. Otherwise, acephate, chlorpyrifos, diazinon, EPN and fenitrothion were showed 100% mortality of P. ussuriensis within only 24 hours after treatment, but there was no effective after then in residual tests with leaves.