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Diquat dibromide
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Names |
IUPAC name
6,7-Dihydrodipyrido[1,2-a:2',1'-c]pyrazinediium dibromide
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Other names
1,1'-Ethylene-2,2'-bipyridyldiylium dibromide
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Identifiers |
CAS Number
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85-00-7 Y |
ChEMBL |
ChEMBL1599022 N |
ChemSpider |
6536 Y |
Jmol 3D model |
Interactive image |
KEGG |
C18577 Y |
PubChem |
6794 |
UNII |
A9A615U4MP Y |
InChI
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InChI=1S/C12H12N2.2BrH/c1-3-7-13-9-10-14-8-4-2-6-12(14)11(13)5-1;;/h1-8H,9-10H2;2*1H/q+2;;/p-2 Y
Key: ODPOAESBSUKMHD-UHFFFAOYSA-L Y
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InChI=1/C12H12N2.2BrH/c1-3-7-13-9-10-14-8-4-2-6-12(14)11(13)5-1;;/h1-8H,9-10H2;2*1H/q+2;;/p-2
Key: ODPOAESBSUKMHD-NUQVWONBAO
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SMILES
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[Br-].[Br-].c2cccc3c1[n+](cccc1)CC[n+]23
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Properties |
Chemical formula
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C12H12Br2N2 |
Molar mass |
344.05 g·mol−1 |
Appearance |
Yellow crystals[1] |
Density |
1.22 - 1.27 g/cm3 |
Melting point |
335 °C (635 °F; 608 K) |
Boiling point |
Decomposes[1] |
Solubility in water
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70% (20°C)[1] |
Vapor pressure |
<0.00001 mmHg (20°C)[1] |
Hazards |
US health exposure limits (NIOSH): |
PEL (Permissible)
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none[1] |
REL (Recommended)
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TWA 0.5 mg/m3[1] |
IDLH (Immediate danger)
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N.D.[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N verify (what is YN ?) |
Infobox references |
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Diquat is a contact herbicide that produces desiccation and defoliation most often available as the dibromide, diquat dibromide.[2] Brand names for this formulation include Aquacide, Dextrone, Preeglone, Deiquat, Spectracide, Detrone, Reglone, Reglon, Reglox, Tribune, Ortho-Diquat, Weedtrine-D,[3] Weedol 2 and, in combination with glyphosate, Resolva.[4]
Diquat is a non-selective herbicide that acts quickly to damage only those parts of the plant to which it is applied.[5] It has been used in pre-harvest crop desiccation.[6] It bonds strongly to mineral and organic particles in soil and water where it remains without significant degradation for years. However, bound to clays diquat is biologically inactive at concentrations typically observed in agricultural soils.[5]
Diquat dibromide is moderately toxic. It may be fatal to humans if swallowed, inhaled, or absorbed through the skin in large quantities.[5]
Production
Pyridine is oxidatively coupled to 2,2'-bipyridine over a heated Raney nickel catalyst. The ethylene bridge is formed by the reaction with 1,2-dibromoethane:[7]
See also
References
- ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0243". National Institute for Occupational Safety and Health (NIOSH).
- ^ Merck Index, 11th Edition, 3359.
- ^ PubChem listing for diquat dibromide
- ^ Weedkillers for Home Gardeners. RHS Advisory Service, Royal Horticultural Society, February 2013. Accessed May 2013.
- ^ a b c EXTOXNET, Pesticide Information Project
- ^ "The agronomic benefits of glyphosate in Europe" (PDF). Monsanto Europe SA. February 2010. Retrieved June 2, 2013.
- ^ "Paraquat and Diquat". IPCS INCHEM.
Pest control: herbicides
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Anilides/anilines |
- acetochlor
- alachlor
- asulam
- benfluralin
- butachlor
- diethatyl
- diflufenican
- dimethenamid
- flamprop
- metazachlor
- metolachlor
- pendimethalin
- pretilachlor
- propachlor
- propanil
- trifluralin
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Aromatic acids |
- aminopyralid
- chloramben
- clopyralid
- dicamba
- picloram
- pyrithiobac
- quinclorac
- quinmerac
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Arsenicals |
- cacodylic acid
- copper arsenate
- DSMA
- MSMA
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Organophosphorus |
- bensulide
- bialaphos
- ethephon
- fosamine
- glufosinate
- glyphosate
- piperophos
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Phenoxy |
- 2,4-D
- 2,4-DB
- dichlorprop
- fenoprop
- MCPA
- MCPB
- 2,4,5-T
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Pyridines |
- dithiopyr
- fluroxypyr
- imazapyr
- thiazopyr
- triclopyr
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Quaternary |
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Triazines |
- ametryn
- atrazine
- cyanazine
- hexazinone
- prometon
- prometryn
- propazine
- simazine
- simetryn
- terbuthylazine
- terbutryn
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Ureas |
- chlortoluron
- DCMU
- metsulfuron-methyl
- monolinuron
- tebuthiuron
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Others |
- 3-AT
- aminocyclopyrachlor
- bromoxynil
- clomazone
- DCBN
- dinoseb
- juglone
- mesotrione
- methazole
- metam sodium
- metamitron
- metribuzin
- sulfentrazone
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UpToDate Contents
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English Journal
- Determination of paraquat and diquat: LC-MS method optimization and validation.
- Pizzutti IR1, Vela GM2, de Kok A3, Scholten JM3, Dias JV2, Cardoso CD2, Concenço G4, Vivian R5.
- Food chemistry.Food Chem.2016 Oct 15;209:248-55. doi: 10.1016/j.foodchem.2016.04.069. Epub 2016 Apr 19.
- This study describes the optimization and single-laboratory validation of a single residue method for determination of two bipyridylium herbicides, paraquat and diquat, in cowpeas by UPLC-MS/MS in a total run time of 9.3min. The method is based on extraction with an acidified methanol-water mixture.
- PMID 27173559
- Polyurethane foam loaded with sodium dodecylsulfate for the extraction of 'quat' pesticides from aqueous medium: Optimization of loading conditions.
- Vinhal JO1, Lima CF2, Cassella RJ3.
- Ecotoxicology and environmental safety.Ecotoxicol Environ Saf.2016 Sep;131:72-8. doi: 10.1016/j.ecoenv.2016.05.012. Epub 2016 May 20.
- The cationic herbicides paraquat, diquat and difenzoquat are largely used in different cultures worldwide. With this, there is an intrinsic risk of environmental contamination when these herbicides achieve natural waters. The goal of this work was to propose a novel and low-cost sorbent for the remo
- PMID 27213562
- Determination of polar pesticides in olive oil and olives by hydrophilic interaction liquid chromatography coupled to tandem mass spectrometry and high resolution mass spectrometry.
- Nortes-Méndez R1, Robles-Molina J1, López-Blanco R1, Vass A2, Molina-Díaz A3, Garcia-Reyes JF4.
- Talanta.Talanta.2016 Sep 1;158:222-8. doi: 10.1016/j.talanta.2016.05.058. Epub 2016 May 24.
- This article reports the development of two HPLC-MS methods for the determination of polar pesticides in olive oil and olive samples by hydrophilic interaction liquid chromatography (HILIC) separation followed by mass spectrometry detection with tandem mass spectrometry using a triple quadrupole ins
- PMID 27343599
Japanese Journal
- 大容量試料導入-高速液体クロマトグラフィー法を用いる水道中ジクワットの迅速分析
- 吉川 循江,堀切 佳代,前沢 仁
- Chromatography : Journal of separation and detection sciences 33(3), 191-196, 2012
- NAID 40019548461
- Effects of Oxidative Stress Caused by tert-Butylhydroquinone on Cytotoxicity in MDCK Cells
- SHIBUYA Naoko,KOBAYASHI Shigeki,YOSHIKAWA Yasunaga,WATANABE Kiyotaka,ORINO Koichi
- Journal of Veterinary Medical Science 74(5), 583-589, 2012
- … Cell toxicity tests were carried out using the crystal violet (CV) assay with the following prooxidants: t-BHQ, diethyl maleate (DEM), hydrogen peroxide (H2O2), diquat (DQ) and β-naphthoflavone (β-NF). …
- NAID 130001879875
- Wheat Bran Protects Fischer-344 Rats from Diquat-Induced Oxidative Stress by Activating Antioxidant System : Selenium as an Antioxidant
- HIGUCHI Masashi,OSHIDA Junichi,ORINO Koichi,WATANABE Kiyotaka
- Bioscience, biotechnology, and biochemistry 75(3), 496-499, 2011-03-23
- … Wheat bran had a protective effect against diquat toxicity in rats fed a purified diet (PD). … We studied the effects of wheat bran on the antioxidant system in the liver of rats treated with saline and diquat. …
- NAID 10028201670
Related Links
- Diquat dibromide has a moderate acute toxicity. The oral LD50 is 120 mg/kg for rats, 233 mg/kg in mice, and 188 mg/kg in rabbits. Repeated dermal doses of diquat dibromide caused redness, thickening, and scabbing to the skin of ...
- TRADE OR OTHER NAMES Aquacide, Dextrone, Reglone, Reglox, Weedtrine-D, Aquakill, Vegetrole, Deiquat, Reglon, Tag. REGULATORY STATUS Diquat dibromide is classified as a general use herbicide by the U.S ...
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