DCMU

DCMU
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	330-54-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:116509 ;
ChEMBL	ChEMBL278489 ;
ChemSpider	3008 ;
EC Number	206-354-4;
KEGG	C18428 ;
PubChem CID	3120;
RTECS number	YS8925000;
UNII	9I3SDS92WY;
UN number	3077, 2767
	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 ;
	SMILES Clc1ccc(NC(=O)N(C)C)cc1Cl;
Properties
Chemical formula	C9H10Cl2N2O
Molar mass	233.09 g·mol−1
Appearance	white crystalline solid
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)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H351, H373, H410
GHS precautionary statements	P201, P202, P260, P264, P270, P273, P281, P301+312, P308+313, P314, P330, P391, P405, P501
Flash point	noncombustible
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	TWA 10 mg/m3
IDLH (Immediate danger)	N.D.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	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.

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: monuron (4-chlorophenyl), chlortoluron (3-chloro-4-methylphenyl) and DCMU, the (3,4-dichlorophenyl) example.^[2]^[3] Subsequently, over thirty related urea analogs with the same mechanism of action reached the market worldwide.^[4]

Synthesis

As described in the du Pont patent, the starting material is a substituted aryl amine, an aniline, which is treated with phosgene to form its isocyanate derivative. This is subsequently reacted with dimethylamine to give the final product.^[2]

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 Q_B plastoquinone binding site of photosystem II, disallowing the electron flow from photosystem II to plastoquinone.^[5] 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 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.^[6]^[7]

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.^[8]^[9]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 NIOSH Pocket Guide to Chemical Hazards. "#0247". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0247.html.
↑ ^2.0 ^2.1 "3-(Halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same" US patent 2655445, 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". http://www.alanwood.net/pesticides/class_herbicides.html#urea_herbicides.
↑ 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. PMID 16665372.
↑ "Diuron". United States National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/source/hsdb/382.
↑ Template:Cite tech report

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[PGCH-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 NIOSH Pocket Guide to Chemical Hazards. "#0247". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0247.html.

[Todd-2] 2.0 ^2.1 "3-(Halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same" US patent 2655445, issued 1953-10-13, assigned to E. I. du Pont de Nemours & Co.

[Liu-3] 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.

[4] "Urea herbicides". http://www.alanwood.net/pesticides/class_herbicides.html#urea_herbicides.

[5] 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.

[6] 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

[7] 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. PMID 16665372.

[8] "Diuron". United States National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/source/hsdb/382.

[9] Template:Cite tech report

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