DCMU

DCMU
Names
	Other names 3-(3,4-Dichlorophenyl)-1,1-dimethylurea, Karmex, Diuron, Direx
Identifiers
CAS Number	330-54-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:116509 ;
ChEMBL	ChEMBL278489 ;
ChemSpider	3008 ;
ECHA InfoCard	100.005.778
EC Number	206-354-4;
KEGG	C18428 ;
PubChem CID	3120;
RTECS number	YS8925000;
UNII	9I3SDS92WY;
UN number	3077, 2767
CompTox Dashboard (EPA)	DTXSID0020446 ;
	InChI 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) Key: XMTQQYYKAHVGBJ-UHFFFAOYSA-N ; 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;
	SMILES Clc1ccc(NC(=O)N(C)C)cc1Cl;
Properties
Chemical formula	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	42 mg/L
Vapor pressure	0.000000002 mmHg (20°C)[1]
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H351, H373, H400, H410
GHS precautionary statements	P201, P202, P260, P264, P270, P273, P281, P301+312, P308+313, P314, P330, P391, P405, P501
Flash point	noncombustible [1]
	NIOSH (US health exposure limits):
PEL (Permissible)	none[1]
REL (Recommended)	TWA 10 mg/m3[1]
IDLH (Immediate danger)	N.D.[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is an algicide and herbicide of the arylurea class 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 Q_B plastoquinone binding site of photosystem II, disallowing the electron flow from 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.

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.[3][4]

Because of these effects, DCMU is often used to study energy flow in photosynthesis.

References

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
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.

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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0247". National Institute for Occupational Safety and Health (NIOSH).

[2] 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.

[3] 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

[4] 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.