Stereochemistry | ACHIRAL |
Molecular Formula | C9H10Cl2N2O |
Molecular Weight | 233.095 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1
InChI
InChIKey=XMTQQYYKAHVGBJ-UHFFFAOYSA-N
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)
Molecular Formula | C9H10Cl2N2O |
Molecular Weight | 233.095 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Diuron (3-(3,4-dichlorophenyl)-1,1-dimethylurea) is an algicide and herbicide of the phenylurea class that inhibits photosynthesis. Diuron blocks the plastoquinone binding site of photosystem II, disallowing the electron flow from where it is generated, in 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). Diuron 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 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. Diuron is generally persistent in soil, water and groundwater. It is also slightly toxic to mammals and birds as well as moderately toxic to aquatic invertebrates. However, its principal product of biodegradation, 3,4-dichloroaniline exhibits a higher toxicity and is also persistent in soil, water, and groundwater. Thus, diuron indirectly possesses a significant amount of toxicity and could be a potential poisoning pesticide contaminant of groundwater. Unfortunately, groundwater contamination will still persist despite the progressive suppression of diuron (Directive 200/60/CE). Therefore, determining the main factors influencing its degradation and its ecotoxicological effects on the environment and health could provide a basis for further development of bioremediation processes.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
1.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Sample Use Guides
The bioassays using the recombinant bioluminescent cyanobacterium Anabaena CPB4337 were based on the inhibition of constitutive luminescence caused by the presence of toxic substances and were performed in 1.5 mL AA/8 + N pH 7.8 growth medium (final volume) in transparent 24-well microtiter plates. Basically, Anabaena CPB4337 cultures were harvested, washed three times and re-suspended in fresh AA/8 + N growth medium to obtain an initial O.D.750nm = 0.1. The required amount of 2,4-D, Atrazine, Diuron, Paraquat, PFOA and PFOS was added from the concentrated stock solutions to get the desired final exposure concentrations. Based on preliminary assays, for the final experiments, cultures were exposed to a range between 0–60 mg/L of 2,4-D; 0–0.75 mg/L of Atrazine; 0–0.05 mg/L of Diuron; 0–0.05 mg/L of Paraquat and 0–200 mg/L of PFOA and PFOS. Transparent 24-well microtiter plates were incubated during 24 h at 28 C in the light under continuous illumination, ca. 65 mkmol photons m2 s_1 on a rotary shaker. Samples were taken at 15 min and 24 h exposure and bioluminescence measurements were performed. For that, 75 mkL of exposed and controls cells were transferred to a 96 opaque white microtiter plate and luminescence of each sample was recorded every 1 min in a Centro LB 960 luminometer up to 10 min. Three independent experiments with duplicate samples were conducted.