- 同
- 3-(3,4-dichlorophenul)-1,1-dimethylurea
- 同
- 3-(3,4-dichlorophenul)-1,1-dimethylurea
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/08/23 21:43:06」(JST)
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DCMU
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Names |
Other names
3-(3,4-Dichlorophenyl)-1,1-dimethylurea, Karmex, Diuron, Direx
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Identifiers |
CAS Registry Number
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330-54-1 Y |
ChEBI |
CHEBI:116509 Y |
ChEMBL |
ChEMBL278489 Y |
ChemSpider |
3008 Y |
InChI
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InChI=1S/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14) Y
Key: XMTQQYYKAHVGBJ-UHFFFAOYSA-N Y
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InChI=1/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14)
Key: XMTQQYYKAHVGBJ-UHFFFAOYAZ
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Jmol-3D images |
Image |
KEGG |
C18428 Y |
SMILES
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Clc1ccc(NC(=O)N(C)C)cc1Cl
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Properties |
Chemical formula
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C9H10Cl2N2O |
Molar mass |
233.09 g·mol−1 |
Appearance |
white crystalline solid[1] |
Density |
1.48 g/cm3 |
Melting point |
158 °C (316 °F; 431 K) |
Boiling point |
180 °C (356 °F; 453 K) |
Solubility in water
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42 mg/L |
Vapor pressure |
0.000000002 mmHg (20°C)[1] |
Hazards |
EU classification |
Harmful (Xn); Dangerous for the environment (N) |
Flash point |
noncombustible [1] |
US health exposure limits (NIOSH): |
PEL (Permissible)
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none[1] |
REL (Recommended)
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TWA 10 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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Y verify (what is: Y/N?) |
Infobox references |
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DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is an herbicide that inhibits photosynthesis. It was introduced by Bayer in 1954 under the trade name of Diuron.
Mechanism of action
DCMU is a very specific and sensitive inhibitor of photosynthesis. It blocks the plastoquinone binding site of photosystem II, disallowing the electron flow from where it is generated, in photosystem II, to plastoquinone.[2] This interrupts the photosynthetic electron transport chain in photosynthesis and thus reduces the ability of the plant to turn light energy into chemical energy (ATP and reductant potential).
DCMU only blocks electron flow from photosystem II, it has no effect on photosystem I or other reactions in photosynthesis, such as light absorption or carbon fixation in the Calvin cycle.[citation needed]
However, because it absorbs electrons oxidized from water in PS II, the electron "hole" of PS I cannot be satisfied, effectively shutting down "linear" photosynthesis by blocking the reduction of NADP+ to NADPH. At the same time, it was found that DCMU not only does not inhibit the cyclic photosynthetic pathway, but, under certain circumstances, actually stimulates it.[3][4]
Because of these effects, DCMU is often used to study energy flow in photosynthesis.
References
- ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0247". National Institute for Occupational Safety and Health (NIOSH).
- ^ Metz, J; Pakrasi, H; Seibert, M; Arntzer, C (1986). "Evidence for a dual function of the herbicide-binding D1 protein in photosystem II". FEBS Letters 205 (2): 269. doi:10.1016/0014-5793(86)80911-5.
- ^ HUBER, S.C. EDWARDS, G.E. (1976), Studies on the Pathway of Cyclic Electron Flow in Mesophyll Chloroplasts of a C4 Plant, Biochimica et Biophysica Acta (BBA) – Bioenergetics, Volume 449, Issue 3, 6 December 1976, Pages 420-433, doi:10.1016/0005-2728(76)90153-5
- ^ "Regulation of Cyclic Photophosphorylation during Ferredoxin-Mediated Electron Transport : Effect of DCMU and the NADPH/NADP Ratio". Plant Physiol. 83 (4): 965–9. April 1987. doi:10.1104/pp.83.4.965. PMC 1056483. PMID 16665372.
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
- sulfentrazone
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English Journal
- Coupling between high-frequency ultrasound and solar photo-Fenton at pilot scale for the treatment of organic contaminants: an initial approach.
- Papoutsakis S1, Miralles-Cuevas S2, Gondrexon N3, Baup S3, Malato S2, Pulgarin C4.
- Ultrasonics sonochemistry.Ultrason Sonochem.2015 Jan;22:527-34. doi: 10.1016/j.ultsonch.2014.05.003. Epub 2014 May 14.
- This study aims to evaluate the performance of a novel pilot-scale coupled system consisting of a high frequency ultrasonic reactor (400kHz) and a compound parabolic collector (CPC). The benefits of the concurrent application of ultrasound and the photo-Fenton process were studied in regard to the d
- PMID 24857683
- Integrated electrochemical biosensor based on algal metabolism for water toxicity analysis.
- Tsopela A1, Lale A1, Vanhove E1, Reynes O2, Séguy I1, Temple-Boyer P1, Juneau P3, Izquierdo R3, Launay J1.
- Biosensors & bioelectronics.Biosens Bioelectron.2014 Nov 15;61:290-7. doi: 10.1016/j.bios.2014.05.004. Epub 2014 May 13.
- An autonomous electrochemical biosensor with three electrodes integrated on the same silicon chip dedicated to the detection of herbicides in water was fabricated by means of silicon-based microfabrication technology. Platinum (Pt), platinum black (Pt Bl), tungsten/tungsten oxide (W/WO3) and iridium
- PMID 24906088
- Dose and temporal effects on gene expression profiles of urothelial cells from rats exposed to diuron.
- Ihlaseh-Catalano SM1, Bailey KA2, Cardoso AP3, Ren H4, Fry RC5, Camargo JL6, Wolf DC7.
- Toxicology.Toxicology.2014 Nov 5;325:21-30. doi: 10.1016/j.tox.2014.08.005. Epub 2014 Aug 23.
- Diuron (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is a substituted urea herbicide that at high dietary levels (2500ppm) induces rat urinary bladder hyperplasia after 20 weeks of exposure and neoplasia after 2 years. The effects on the urothelium after short-term exposure have not been described. The
- PMID 25152437
Japanese Journal
- Photosynthesis-dependent and -independent responses of stomata to blue, red and green monochromatic light: differences between the normally oriented and inverted leaves of sunflower
- Wang Yin,Noguchi Ko,Terashima Ichiro
- Plant and Cell Physiology 52(3), 479-489, 2011-03
- NAID 40018733622
- Photosynthesis-Dependent Extracellular Ca2+ Influx Triggers an Asexual Reproductive Cycle in the Marine Red Macroalga Porphyra yezoensis
- Takahashi Megumu,Saga Naotsune,Mikami Koji
- American Journal of Plant Sciences 1(1), 1-11, 2010-09
- … Moreover, it was also observed that initiation of asexual life cycle required illumination, was repressed by DCMU, and was induced by a Ca2+ ionophore in the dark. …
- NAID 120002646846
Related Links
- 世界大百科事典 第2版 DCMUの用語解説 - 尿素系除草剤の一つ。3‐(3,4‐dichlorophenyl)‐1,1‐dimethylureaの略で,典型的な光合成阻害型除草剤である。殺草作用の発現はゆるやかで,普通土壌処理剤として用いられる。日本では,禾穀 ...
- Title 〔除草剤〕DCMUの毒性試験の概要 Created Date 3/1/2005 11:57:06 AM
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