| Revision as of 20:44, 22 January 2019 editJzG (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, New page reviewers, Pending changes reviewers, Rollbackers155,091 edits →top: Remove personal websiteTag: AWB← Previous edit | Latest revision as of 22:05, 19 September 2024 edit undoIngratis (talk | contribs)Autopatrolled, Extended confirmed users, New page reviewers29,766 editsm edit space | ||
| (31 intermediate revisions by 19 users not shown) | |||
| Line 1: | Line 1: | ||
| {{hatnote group| | |||
| {{Distinguish|text = the mercurial diuretic ]}} | |||
| {{for|the DC comics Movie Universe|DC Extended Universe}} | |||
| }} | |||
| {{chembox | {{chembox | ||
| | Watchedfields = changed | |||
| | verifiedrevid = 443556666 | |||
| | ImageFile = Diuron.svg | | ImageFile = Diuron.svg | ||
| | ImageAlt = Skeletal formula of DCMU | | ImageAlt = Skeletal formula of DCMU | ||
| | ImageFile1 = DCMU-3D-balls.png | | ImageFile1 = DCMU-3D-balls.png | ||
| | ImageAlt1 = Ball-and-stick model of the DCMU molecule | | ImageAlt1 = Ball-and-stick model of the DCMU molecule | ||
| | PIN = ''N''′-(3,4-Dichlorophenyl)-''N'',''N''-dimethylurea | |||
| | OtherNames = 3-(3,4-Dichlorophenyl)-1,1-dimethylurea, Karmex, Diuron, Direx | | OtherNames = 3-(3,4-Dichlorophenyl)-1,1-dimethylurea, Karmex, Diuron, Direx | ||
| | Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
| | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ||
| | ChemSpiderID = 3008 | | ChemSpiderID = 3008 | ||
| | 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) | |||
| | ChEBI_Ref = {{ebicite|correct|EBI}} | | ChEBI_Ref = {{ebicite|correct|EBI}} | ||
| | ChEBI = 116509 | | ChEBI = 116509 | ||
| | SMILES = Clc1ccc(NC(=O)N(C)C)cc1Cl | | SMILES = Clc1ccc(NC(=O)N(C)C)cc1Cl | ||
| | InChIKey = XMTQQYYKAHVGBJ-UHFFFAOYAZ | |||
| | ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| | ChEMBL = 278489 | | ChEMBL = 278489 | ||
| Line 45: | Line 46: | ||
| | REL = TWA 10 mg/m<sup>3</sup><ref name=PGCH/> | | REL = TWA 10 mg/m<sup>3</sup><ref name=PGCH/> | ||
| | FlashPt = noncombustible | | FlashPt = noncombustible | ||
| | |
| FlashPt_ref =<ref name=PGCH/> | ||
| | GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} | | GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}} | ||
| | GHSSignalWord = Warning | | GHSSignalWord = Warning | ||
| | HPhrases = {{H-phrases|302|351|373 |
| HPhrases = {{H-phrases|302|351|373|410}} | ||
| | PPhrases = {{P-phrases|201|202|260|264|270|273|281|301+312|308+313|314|330|391|405|501}} | | PPhrases = {{P-phrases|201|202|260|264|270|273|281|301+312|308+313|314|330|391|405|501}} | ||
| }} | }} | ||
| }} | }} | ||
| '''DCMU''' ('''3-(3,4-dichlorophenyl)-1,1-dimethylurea''') is an ] and ] of the aryl] class that inhibits ]. It was introduced by ] in 1954 under the trade name of '''Diuron'''. | '''DCMU''' ('''3-(3,4-dichlorophenyl)-1,1-dimethylurea''') is an ] and ] of the aryl ] class that inhibits ]. It was introduced by ] in 1954 under the trade name of '''Diuron'''. | ||
| ==History== | |||
| In 1952, chemists at ] patented a series of ] ] derivatives as ]. Several compounds covered by this patent were commercialized as herbicides: ] (3-chloro-4-methylphenyl) and DCMU, the (3,4-dichlorophenyl) example.<ref name=Todd>{{cite patent |country=US |number=2655445 |status=patent |gdate=1953-10-13 |fdate=1952-02-14 |pridate=1949-12-06 |invent1 =Todd C.W. |title=3-(Halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same |assign1=E. I. du Pont de Nemours & Co.}}</ref><ref name=Liu>{{cite book |doi=10.1016/B978-0-12-374367-1.00080-X |chapter=Phenylurea Herbicides |title=Hayes' Handbook of Pesticide Toxicology |year=2010 |last1=Liu |first1=Jing |pages=1725–1731 |isbn=9780123743671 }}</ref> Subsequently, over thirty related urea ] with the same mechanism of action reached the market worldwide.<ref>{{cite web |url=http://www.alanwood.net/pesticides/class_herbicides.html#urea_herbicides |title=Urea herbicides |website=alanwood.net|access-date=2021-03-26}}</ref> | |||
| ==Synthesis== | |||
| As described in the du Pont patent, the starting material is 3,4-dichloro], which is treated with ] to form a ] derivative. This is subsequently reacted with ] to give the final product.<ref name=Todd /> | |||
| :Aryl-NH<sub>2</sub> + COCl<sub>2</sub> → Aryl-NCO | |||
| :Aryl-NCO + NH(CH<sub>3</sub>)<sub>2</sub> → Aryl-NHCON(CH<sub>3</sub>)<sub>2</sub> | |||
| ==Mechanism of action== | ==Mechanism of action== | ||
| DCMU is a very specific and sensitive inhibitor of photosynthesis. It blocks the ] binding site of ], disallowing the electron flow from |
DCMU is a very specific and sensitive inhibitor of photosynthesis. It blocks the Q<sub>B</sub> ] binding site of ], disallowing the electron flow from photosystem II to plastoquinone.<ref>{{Cite journal | doi = 10.1016/0014-5793(86)80911-5 | title = Evidence for a dual function of the herbicide-binding D1 protein in photosystem II | year = 1986 | last1 = Metz | first1 = J | last2 = Pakrasi | first2 = H | last3 = Seibert | first3 = M | last4 = Arntzer | first4 = C | journal = FEBS Letters | volume = 205 | issue = 2 | pages = 269| s2cid = 84205263 | doi-access = free }}</ref> This interrupts the photosynthetic ] in photosynthesis and thus reduces the ability of the plant to turn light energy into chemical energy (] and ]). | ||
| 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 ].{{Citation needed|reason=reliable source needed for the whole sentence|date=April 2014}} | 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 ].{{Citation needed|reason=reliable source needed for the whole sentence|date=April 2014}} | ||
| However, because it |
However, because it blocks electrons produced from water oxidation in ] from entering the plastoquinone pool, "linear" photosynthesis is effectively shut down, as there are no available electrons to exit the photosynthetic electron flow cycle for reduction of ] to NADPH. | ||
| In fact, it was found that DCMU not only does not inhibit the ], but, under certain circumstances, actually stimulates it.<ref>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}}</ref><ref>{{cite journal | pmc = 1056483 | pmid=16665372 | volume=83 | issue=4 | title=Regulation of Cyclic Photophosphorylation during Ferredoxin-Mediated Electron Transport : Effect of DCMU and the NADPH/NADP Ratio |date=April 1987 | journal=Plant Physiol. | pages=965–9 | doi=10.1104/pp.83.4.965| last1=Hosler | first1=J. P. | last2=Yocum | first2=C. F. }}</ref> | |||
| Because of these effects, DCMU is often used to study energy flow in ]. | Because of these effects, DCMU is often used to study energy flow in ]. | ||
| ==Toxicity== | |||
| DCMU (Diuron) has been characterized as a known/likely human carcinogen based on animal testing.<ref>{{cite web |title=Diuron |url=https://pubchem.ncbi.nlm.nih.gov/source/hsdb/382 |website=National Center for Biotechnology Information |publisher=United States National Library of Medicine |number=382 |access-date=9 November 2021}}</ref><ref>{{cite tech report |type=Memorandum |first1=Taylor |last1=Linda |first2=Rinde |last2=Esther |title=Carcinogenicity Peer Review of Diuron |number=20460 |institution=United States Environmental Protection Agency |date=1997-05-08 |url=https://www3.epa.gov/pesticides/chem_search/cleared_reviews/csr_PC-035505_8-May-97_042.pdf |format=PDF |place=Washington, D.C.}}</ref> | |||
| ==References== | ==References== | ||
| Line 72: | Line 82: | ||
| ] | ] | ||
| ] | ] | ||
| ] | |||
| ] | ] | ||
| ] | ] | ||
| ] | |||
Latest revision as of 22:05, 19 September 2024
Not to be confused with the mercurial diuretic Diurone. For the DC comics Movie Universe, see DC Extended Universe. | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name N′-(3,4-Dichlorophenyl)-N,N-dimethylurea | |
| Other names 3-(3,4-Dichlorophenyl)-1,1-dimethylurea, Karmex, Diuron, Direx | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.778 
|
| EC Number |
|
| KEGG | |
| PubChem CID | |
| RTECS number |
|
| UNII | |
| UN number | 3077, 2767 |
| CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
| Properties | |
| Chemical formula | C9H10Cl2N2O |
| Molar mass | 233.09 g·mol |
| Appearance | white crystalline solid |
| Density | 1.48 g/cm |
| Melting point | 158 °C (316 °F; 431 K) |
| Boiling point | 180 °C (356 °F; 453 K) |
| Solubility in water | 42 mg/L |
| Vapor pressure | 0.000000002 mmHg (20°C) |
| Hazards | |
| GHS labelling: | |
| Pictograms |   
|
| Signal word | Warning |
| Hazard statements | H302, H351, H373, H410 |
| Precautionary statements | P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P314, P330, P391, P405, P501 |
| Flash point | noncombustible |
| NIOSH (US health exposure limits): | |
| PEL (Permissible) | none |
| REL (Recommended) | TWA 10 mg/m |
| IDLH (Immediate danger) | N.D. |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references | |
DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is an algicide and herbicide of the aryl urea class that inhibits photosynthesis. It was introduced by Bayer in 1954 under the trade name of Diuron.
History
In 1952, chemists at E. I. du Pont de Nemours and Company patented a series of aryl urea derivatives as herbicides. Several compounds covered by this patent were commercialized as herbicides: chlortoluron (3-chloro-4-methylphenyl) and DCMU, the (3,4-dichlorophenyl) example. Subsequently, over thirty related urea analogs with the same mechanism of action reached the market worldwide.
Synthesis
As described in the du Pont patent, the starting material is 3,4-dichloroaniline, which is treated with phosgene to form a isocyanate derivative. This is subsequently reacted with dimethylamine to give the final product.
- Aryl-NH2 + COCl2 → Aryl-NCO
- Aryl-NCO + NH(CH3)2 → Aryl-NHCON(CH3)2
Mechanism of action
DCMU is a very specific and sensitive inhibitor of photosynthesis. It blocks the QB plastoquinone binding site of photosystem II, disallowing the electron flow from photosystem II to plastoquinone. 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.
However, because it blocks electrons produced from water oxidation in PS II from entering the plastoquinone pool, "linear" photosynthesis is effectively shut down, as there are no available electrons to exit the photosynthetic electron flow cycle for reduction of NADP to NADPH. In fact, it was found that DCMU not only does not inhibit the cyclic photosynthetic pathway, but, under certain circumstances, actually stimulates it.
Because of these effects, DCMU is often used to study energy flow in photosynthesis.
Toxicity
DCMU (Diuron) has been characterized as a known/likely human carcinogen based on animal testing.
References
- ^ NIOSH Pocket Guide to Chemical Hazards. "#0247". National Institute for Occupational Safety and Health (NIOSH).
- ^ US patent 2655445, Todd C.W., "3-(Halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same", issued 1953-10-13, assigned to E. I. du Pont de Nemours & Co.
- Liu, Jing (2010). "Phenylurea Herbicides". Hayes' Handbook of Pesticide Toxicology. pp. 1725–1731. doi:10.1016/B978-0-12-374367-1.00080-X. ISBN 9780123743671.
- "Urea herbicides". alanwood.net. Retrieved 2021-03-26.
- 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. S2CID 84205263.
- 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
- Hosler, J. P.; Yocum, C. F. (April 1987). "Regulation of Cyclic Photophosphorylation during Ferredoxin-Mediated Electron Transport : Effect of DCMU and the NADPH/NADP Ratio". Plant Physiol. 83 (4): 965–9. doi:10.1104/pp.83.4.965. PMC 1056483. PMID 16665372.
- "Diuron". National Center for Biotechnology Information. United States National Library of Medicine. Retrieved 9 November 2021.
- Linda, Taylor; Esther, Rinde (1997-05-08). Carcinogenicity Peer Review of Diuron (PDF) (Memorandum). Washington, D.C.: United States Environmental Protection Agency. 20460.