Details
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 |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20027135Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22720746 | https://www.ncbi.nlm.nih.gov/pubmed/15276715 | https://www.ncbi.nlm.nih.gov/pubmed/24512549 |
https://www.ncbi.nlm.nih.gov/pubmed/15884806
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20027135
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22720746 | https://www.ncbi.nlm.nih.gov/pubmed/15276715 | https://www.ncbi.nlm.nih.gov/pubmed/24512549 |
https://www.ncbi.nlm.nih.gov/pubmed/15884806
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2366481 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15884806 |
1.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Elongating responses to herbicides of heterotrophic and photoautotrophic hairy roots derived from pak-bung plant. | 2002 |
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Assessment of herbicidal toxicity based on non-destructive measurement of local chlorophyll content in photoautotrophic hairy roots. | 2003 |
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Light control of nuclear gene mRNA abundance and translation in tobacco. | 2003 Dec |
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Inorganic carbon limitation induces transcripts encoding components of the CO(2)-concentrating mechanism in Synechococcus sp. PCC7942 through a redox-independent pathway. | 2003 Dec |
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Photosynthesis and state transitions in mitochondrial mutants of Chlamydomonas reinhardtii affected in respiration. | 2003 Dec |
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Efficacy of cytotoxic agents used in the treatment of testicular germ cell tumours under normoxic and hypoxic conditions in vitro. | 2003 Dec 1 |
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Kinetic analyses of state transitions of the cyanobacterium Synechococcus sp. PCC 7002 and its mutant strains impaired in electron transport. | 2003 Dec 8 |
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[Neutrophil oxidative metabolism in children with chronic hepatitis C]. | 2004 |
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Diosgenin, a plant steroid, induces apoptosis in human rheumatoid arthritis synoviocytes with cyclooxygenase-2 overexpression. | 2004 |
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Induction of IL-10-producing CD4+CD25+ T cells in animal model of collagen-induced arthritis by oral administration of type II collagen. | 2004 |
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Screening for estrogen and androgen receptor activities in 200 pesticides by in vitro reporter gene assays using Chinese hamster ovary cells. | 2004 Apr |
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Changes in IgE- and antigen-dependent histamine-release in peripheral blood of Schistosoma mansoni-infected Ugandan fishermen after treatment with praziquantel. | 2004 Apr 21 |
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Chlorophyll fluorescence imaging of individual algal cells: effects of herbicide on Spirogyra distenta at different growth stages. | 2004 Aug 1 |
|
Reduction of the thylakoid electron transport chain by stromal reductants--evidence for activation of cyclic electron transport upon dark adaptation or under drought. | 2004 Dec |
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Differing involvement of sulfoquinovosyl diacylglycerol in photosystem II in two species of unicellular cyanobacteria. | 2004 Feb |
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The interactive effects of the antifouling herbicides Irgarol 1051 and Diuron on the seagrass Zostera marina (L.). | 2004 Feb 25 |
|
Evidence that involucrin, a marker for differentiation, is oxygen regulated in human squamous cell carcinomas. | 2004 Feb 9 |
|
Associations between plasma DDE levels and immunologic measures in African-American farmers in North Carolina. | 2004 Jul |
|
Molecular identification and expression of two non-P450 enzymes, monoamine oxidase A and flavin-containing monooxygenase 2, involved in phase I of xenobiotic biotransformation in the Pacific oyster, Crassostrea gigas. | 2004 Jul 13 |
|
Cyclic electron flow under saturating excitation of dark-adapted Arabidopsis leaves. | 2004 Jun 7 |
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Overcoming antigen masking of anti-amyloidbeta antibodies reveals breaking of B cell tolerance by virus-like particles in amyloidbeta immunized amyloid precursor protein transgenic mice. | 2004 Jun 8 |
|
Are NADP-dependent isocitrate dehydrogenases and ferredoxin-dependent glutamate synthase co-regulated by the same photoreceptors? | 2004 Mar |
|
Recovery of uptake and assimilation of nitrate in Scenedesmus sp. previously exposed to elevated levels of Cu2+ and Zn2+. | 2004 May |
|
Photosynthetic electron transport controls expression of the high light inducible gene in the cyanobacterium Synechococcus elongatus strain PCC 7942. | 2004 May |
|
[Oxidative potential of neutrophils in cyclosporine A treated children with idiopathic nephrotic syndrome]. | 2004 Oct |
|
Proinflammatory role of inducible nitric oxide synthase in acute hyperoxic lung injury. | 2004 Sep 15 |
|
Screening of an endothelial cDNA library identifies the C-terminal region of Nedd5 as a novel autoantigen in systemic lupus erythematosus with psychiatric manifestations. | 2005 |
|
The induction of vascular endothelial growth factor by ultrafine carbon black contributes to the increase of alveolar-capillary permeability. | 2005 Apr |
|
Light enables a very high efficiency of carbon storage in developing embryos of rapeseed. | 2005 Aug |
|
Effect of CO2 supply on formation of reactive oxygen species in Arabidopsis thaliana. | 2005 Dec |
|
The role of D1-Ala344 in charge stabilization and recombination in Photosystem II. | 2005 Dec |
|
Mediterranean diet or extended fasting's influence on changing the intestinal microflora, immunoglobulin A secretion and clinical outcome in patients with rheumatoid arthritis and fibromyalgia: an observational study. | 2005 Dec 22 |
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Carbon black nanoparticles induce type II epithelial cells to release chemotaxins for alveolar macrophages. | 2005 Dec 6 |
|
Wild animal mortality monitoring and human Ebola outbreaks, Gabon and Republic of Congo, 2001-2003. | 2005 Feb |
|
Characterization of photosynthetic electron transport in bundle sheath cells of maize. I. Ascorbate effectively stimulates cyclic electron flow around PSI. | 2005 Feb |
|
Non-photochemical quenching of chlorophyll a fluorescence by oxidised plastoquinone: new evidences based on modulation of the redox state of the endogenous plastoquinone pool in broken spinach chloroplasts. | 2005 Feb 17 |
|
Molecular identification and expression study of differentially regulated genes in the Pacific oyster Crassostrea gigas in response to pesticide exposure. | 2005 Jan |
|
FesM, a membrane iron-sulfur protein, is required for cyclic electron flow around photosystem I and photoheterotrophic growth of the cyanobacterium Synechococcus sp. PCC 7002. | 2005 Jul |
|
A new short-term toxicity assay using Aspergillus awamori with recombinant aequorin gene. | 2005 Jul 2 |
|
CCR2 and CXCR3 agonistic chemokines are differently expressed and regulated in human alveolar epithelial cells type II. | 2005 Jul 20 |
|
Reliability and validity of the DynEx dynamometer. | 2005 Jul-Sep |
|
Ebola virus antibody prevalence in dogs and human risk. | 2005 Mar |
|
Assessment of herbicide leaching risk in two tropical soils of Reunion Island (France). | 2005 Mar-Apr |
|
Movement of diuron and hexazinone in clay soil and infiltrated pond water. | 2005 Nov-Dec |
|
Biomarker measurements in a coastal fish-eating population environmentally exposed to organochlorines. | 2005 Oct |
|
Selection of gonadotrophin surge attenuating factor phage antibodies by bioassay. | 2005 Sep 26 |
|
Control of hyperuricemia in subjects with refractory gout, and induction of antibody against poly(ethylene glycol) (PEG), in a phase I trial of subcutaneous PEGylated urate oxidase. | 2006 |
|
Diuron in surface runoff and tile drainage from two grass-seed fields. | 2006 Jan-Feb |
|
Sorption kinetics and equilibria of organic pesticides in carbonatic soils from South Florida. | 2006 Jan-Feb |
|
Assessment of the risk posed by the antifouling booster biocides Irgarol 1051 and diuron to freshwater macrophytes. | 2006 May |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15276715
The oral LD50 in rats is 3.4 g/kg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26070144
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:22:09 UTC 2023
by
admin
on
Fri Dec 15 18:22:09 UTC 2023
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Record UNII |
9I3SDS92WY
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Record Status |
Validated (UNII)
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Record Version |
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-
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EPA PESTICIDE CODE |
35505
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DTXSID0020446
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3120
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diuron
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382
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D004237
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330-54-1
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116509
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DCMU
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8950
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m4695
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206-354-4
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9I3SDS92WY
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