• Title/Summary/Keyword: Dithiocarbamates

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Studies on the Synthesis of Bis-dithiocarbamates as Prodrugs of Isothiocyanates (Isothiocyanate 유도체의 Prodrug를 위한 합성 연구)

  • 심영섭;정오영;김완주;이문희
    • YAKHAK HOEJI
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    • v.26 no.2
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    • pp.91-96
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    • 1982
  • In an attempt to design prodrugs for the Derivatives of the Isothiocyanates R-N=C=S were synthesized eleven novel bis-dithiocarbamates. The best way of preparing the dithiocarbamates was the formation of the dithiocarbonates followed by the reaction of the dithiocarbonates with amines. Thus, the treatment of the diols with carbon disulfide in the presense of potassium hydroxide afforded the potassium salts of the ditniocarbonic acids. The potassium salts were then reacted with alkyl halides to give the dithiocarbonates, which upon treatment with amines produces the dithiocarbamates. In case of vicinal diol (n=o in the above formula), only one of the hydroxy groups was reacted to give the mono-dithiocarbonate. The dithiocarbonates failed to react with amides and aromatic amines. Dithiocarbonates of the different types were obtained when the active double bonds, such as $CH_{2}=CH-Z$ , (Z are electron withdrawing groups), were allowed to react with the free dithiocarbonic acids produced in situ by carefully neutralizing the Potassium salts of the corresponding acids. These compounds are considered to be of some value as prodrugs for the active double bonds.

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Underestimation of Dietary Exposure to Pesticide Residues in Relation to Residue Definition in South Korea (국내 잔류농약 residue definition과 관련된 식이노출의 과소평가)

  • Lee, Mi-Gyung
    • Journal of Food Hygiene and Safety
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    • v.35 no.5
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    • pp.452-458
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    • 2020
  • In this study we aimed to find out pesticide types with probability for underestimation of dietary exposure to pesticide residues in Korea by comparing the residue definitions between Korea and Codex standards. In addition, we sought to establish priorities regarding the necessity of review concerning pesticide types and their impacts based on the risk assessment and dietary exposure underestimation. As a result, we found that according to the residue definition information, 44 pesticides have probability for underestimation in terms of dietary exposure assessments. Among them, 24 pesticides have priority for review of dietary exposure underestimation and its impacts on risk assessment, based on the ADI values of pesticides, Korean MRL information and toxicological information of metabolite. The 24 pesticides were as follows: acibensolar-S-methyl, chlorfenapyr, chlorothalonil, cyantraniliprole, cyclaniliprole, cyflumetofen, dithiocarbamates, fenamidone, fenpyroximate, fluazifop-P-butyl, fluopicolide, flupyradifuron, fluxapyroxad, glyphosate, hexythiazox, isoprothiolane, isopyrazam, myclobutanil, penthiopyrad, propiconazole, spinetoram, spiromesifen, spirotetramat, trifloxystrobin. Furthermore, chlorfenapyr, chlorothalonil, dithiocarbamates and fenamidone may have considered a top priority for review due to greater toxicity of metabolite. This study could be of great use for improvement on risk assessment approaches in South Korea regarding pesticide residues in food commodities.

Determination of Dithiocarbamates in Agricultural Products Circulated in Korea (시판 농산물의 dithiocarbamates 분석)

  • Kim, Hee-Yun;Choi, Hee-Ju;Eom, Ji-Yoon;Seo, Eun-Chae;Choi, Sung-Hee;Cheong, So-Young;Choi, Sun-Hee;Lee, Hwa-Jeong;Choi, Jae-Chun
    • Korean Journal of Food Science and Technology
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    • v.42 no.1
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    • pp.1-7
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    • 2010
  • To revise the dithiocarbamates residue analysis method and survey the residues in agricultural products that were treated with these fungicides in Korea, we purchased 20 types of foodstuffs (rice, potato, cabbage, apple etc.) from markets in five major cities. 236 samples of the purchased foodstuffs were then analyzed for the presence of dithiocarbamates by HPLC/UV and HPLC/APCI-MS. The $R^2$, LOD and LOQ in the range of 0.5-107.3 mg/L were as follows: DCC: y=174.34x+18.315, $R^2=0.9999$, 0.01 mg/L, and 0.04 mg/L; EBDC: y=227.38x-14.715, $R^2=1.0000$, 0.01 mg/L and 0.02 mg/L; PBDC: y=38.46x-21.412, $R^2=0.9999$, 0.04 mg/L, and 0.1 mg/L; ETU: y=52.752x-4.4819, $R^2=0.9998$, 0.02 mg/L and 0.03 mg/L; PTU: y=128.28x+4.4624, $R^2=0.9998$, 0.02 mg/L, and 0.04 mg/L. The levels of DDC, EBDC, PBDC, ETU and PTU in 20 agricultural products fortified to 10.0-107.3 mg/L ranged from 61.7-117.5%, 65.3-110.1%, 61.5-109.6%, 69.3-116.3% and 70.2-97.2%, respectively. Overall, dithiocarbamates were detected in 100 samples and the detection ratio was 42.4%. Among these, only 3 samples (1.3%) of Lycii fructus had residue levels that were above the action limits, while the remaining samples (233 samples) contained levels of dithiocarbamates below the detection limit or below the Korea MRLs (Maximum Residue Limits).

Metal Complexes of Sulfur-containing Ligands Ⅰ. Syntheses and Properties of Nickel(Ⅱ) Complexes of Dithiocarbamates (황함유리간드의 금속착물 Ⅰ. 디티오카바메이트류의 니켈(Ⅱ)착물의 합성과 그 성질)

  • In-Sik Kim;Kim Chan-Woo;Chang-Su Kim
    • Journal of the Korean Chemical Society
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    • v.37 no.2
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    • pp.206-212
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    • 1993
  • Syntheses and properties of zwitterionic dithiocarbamates and their nickel(Ⅱ) complexes are described. The complexes have been characterized by mass infrared and electronic absorption spectroscopy, and conductivity measurement. Ni(Ⅱ)-dithiocarbamato complexes are soluble in polar solvents such as water, methanol, and acetone etc. The possible structures were proposed on the basis of elemental analyses and physical properties.

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Synthesis of New Triazolyl-N,N-Dialkyldithiocarbamates as Antifungal Agents

  • Ozkirimli Sumru;Apak T. Idil;Kiraz Muammer;Yegenoglu Yildiz
    • Archives of Pharmacal Research
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    • v.28 no.11
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    • pp.1213-1218
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    • 2005
  • N,N-Dialkylditihiocarbamate derivatives have been well known as broad-range fungicides. In this study, the triazole derivatives of ten new N,N-disubstituted dithiocarbamates (3a-j) were synthesized and their structures were identified by spectral and elemental analysis. Results of the antifungal activity studies showed that some of the compounds tested were active against M. canis, M. gypseum, and T rubrum at the concentration of 12.5 $\mu$g/mL when c1otrimazol was used as a standard.

A Study on Synthesis and Evaluation of Sb-DTC (Sb-DTC의 합성 및 물성 평가에 관한 연구)

  • Cho, Wonoh;Lee, Ki-Hun;Jeon, In-Sik;Baik, Jin-Wook;Chung, Keunwoo;Kim, Young Woon
    • Proceedings of the Korean Society of Tribologists and Lubrication Engineers Conference
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    • 2000.11a
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    • pp.90-99
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    • 2000
  • This report describes the results of analysis, synthesis and evaluation of antimony dithiocarbamates (SbDTC). Sb-DTC were synthesized by reacting antimony oxide with dithiocarbamates whish were prepared by reaction of dialkylamines and carbon disulfide. The chemical structures and properties of synthesized Sb-DTCs in lab. were discussed. The frictional properties of SbDTC were tested with Four-Ball Wear Scar Tester and Four-Ball Extreme Tester by ASTM method.

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Feasible Management of Southern Corn Leaf Blight via Induction of Systemic Resistance by Bacillus cereus C1L in Combination with Reduced Use of Dithiocarbamate Fungicides

  • Lai, Yi-Ru;Lin, Pei-Yu;Chen, Chao-Ying;Huang, Chien-Jui
    • The Plant Pathology Journal
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    • v.32 no.5
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    • pp.481-488
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    • 2016
  • Dithiocarbamate fungicides such as maneb and mancozeb are widely used nonsystemic protectant fungicides to control various plant fungal diseases. Dithiocarbamate fungicides should be frequently applied to achieve optimal efficacy of disease control and avoid either decline in effectiveness or wash-off from leaf surface. Dithiocarbamates are of low resistance risk but have the potential to cause human neurological diseases. The objective of this study was to develop a strategy to effectively control plant disease with reduced use of dithiocarbamtes. Southern corn leaf blight was the model pathosystem for the investigation. When corn plants were drench-treated with Bacillus cereus C1L, a rhizobacterium able to induce systemic resistance in corn plants against southern leaf blight, frequency of spraying dithiocarbamate fungicides could be decreased. The treatment of B. cereus C1L was able to protect maize from southern leaf blight while residues of dithiocarbamates on leaf surface were too low to provide sufficient protection. On the other hand, frequent sprays of mancozeb slightly but significantly reduced growth of corn plants under natural conditions. In contrast, application of B. cereus C1L can significantly promote growth of corn plants whether sprayed with mancozeb or not. Our results provide the information that plant disease can be well controlled by rhizobacteria-mediated induced systemic resistance in combination with reduced but appropriate application of dithiocarbamate fungicides just before a heavy infection period. An appropriate use of rhizobacteria can enhance plant growth and help plants overcome negative effects caused by dithiocarbamates.

Metal Complexes of Sulfur-Containing Ligands (II). Synthesis and Properties of Platinum(II) Complexes of Dithiocarbamates (황함유 리간드의 금속착물(II). 디티오카바메이트류의 백금(II) 착물의 합성과 성질)

  • Chan-Woo Kim;Chang-Su Kim
    • Journal of the Korean Chemical Society
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    • v.37 no.8
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    • pp.717-722
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    • 1993
  • Reactions of [PtCl$_4$]$^{2-}$ with excess of dithiocarbamates in water lead to facile replacement of the chloro ligand by dithiocarbamato ligand to give [Pt(A)], [Pt(B)$_2$]Cl$_2$, [Pt(C)$_2$], and [Pt(D)(CH$_2$=CH$_2$)Cl]Cl. The complexes of platinum have been characterized by elemental analyses, infrared and UV-visible spectra, and conductivity measurements. Platinum(II)-dithiocarbamate complexes were soluble in polar solvents such as water, alcohol, acetone, dimethylformamide, and dimethylsulfoxide etc. The possible structure was proposed on the basis of elemental analyses and physical properties.

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Development and Validation of Dithiocarbamates Fungicide Analytical Method using CS2 Trap Method in Livestock Product (축산물 중 CS2 포집방법을 이용한 Dithiocarbamate계 살균제 분석법 개발 및 검증)

  • Jo, Hyeong-Wook;Sun, Jung-Hun;Heo, Hyo-Min;Lee, Sang-Hyeob;Kim, Jang-Eok;Moon, Joon-Kwan
    • Korean Journal of Environmental Agriculture
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    • v.40 no.2
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    • pp.127-133
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    • 2021
  • BACKGROUND: Dithiocarbamte fungicides have been used in crop cultivation for diseases protection and treatment. And cultivated agricultrual products were used as feedstuff, and residual pesticides are likely to be absorbed and transferred to livestock. But the maximum residue limits (MRLs) were not established for dithiocarbate fungicides in livestock products, and thus an analysis method was developed and validated for dithiocarbamate fungicides to establish MRLs. METHODS AND RESULTS: Samples were prepared using CS2 trap method and detected with UV/VIS spectrophotometer. Calibration line (0.1 ~ 10 ㎍/mL) was linear with r2 > 0.99. For validation, the recovery tests were carried out at three fortification levels (MLOQ, 10 MLOQ and 50 MLOQ) from livestock samples (egg, milk, beef, pork, and chicken). The results for mancozeb, propineb, and thiram ranged between 76.8 to 109.6%, 79.4 to 108.8%, and 80.2 to 107.8%, respectively and % RSD (relative standard deviation) values were below 9.5%. Furthermore, inter-laboratory analysis was performed to validate the method. CONCLUSION: All values were corresponded with the criteria ranges requested by both the CODEX (CAC/GL 40-1993, 2003) and MFDS guidelines (2016). This might be used as an official analytical method for determination of dithiocarbamate fungicides at established MRLs and monitoring.

S-(N,N-Diallyldithiocarbamoyl)-N-acetylcysteine: Synthesis and Biochemical Properties Associated with Chemoprevention (S-(N,N-Diallyldithiocarbamoyl)-N-acetylcysteine의 합성 및 발암억제와 관련된 생화학적 특성)

  • 이병훈
    • Toxicological Research
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    • v.14 no.2
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    • pp.177-181
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    • 1998
  • Dithiocarbamate and mixed disulfide containing allyl functions were designed and synthesized as putative chemopreventive agents, i.e. N,N-diallyldithiocarbamate (DATC) and S-(N,N-diallyldithiocarbamoyl)-N-acetylcysteine (AC-DATC). DATC and AC-DATC were administered and the activities of cytosolic glutathione S-transferase (GST), glutathione reductase (GR) and microsomal N-nitrosodiethylamine (NDEA) deethylase were assayed in order to test the effects of these organosulfur com-pounds on the detoxification and metabolic activation system of NDEA. The amounts of hepatic glutathione (GSH and GSSG) was also determined. The administration of DATC to rats led to an increase in the activity of GR and to an inhibition of CYP2E1-mediated NDEA deethylation. AC-DATC induced the activity of GR and GST, increased the hepatic GSH content and inhibited the rate of NDEA deethylation. The level of GSSG was decreased as a consequence of the increased activity of GR. These effects may contribute to possible antimutagenic and anticarcinogenic action of the dithiocarbamates investigated.

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