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Diuron, also known as N-(3,4-Dichlorophenyl)-N',N'-dimethylurea, is a potent herbicide belonging to the class of substituted ureas. Its CAS number is 330-54-1, and its EINECS number is 206-354-4. It has a molecular formula of C9H10Cl2N2O and a molecular weight of 233.09 g/mol (or 236.09 g/mol as per some sources). This chemical compound is commonly utilized in agricultural and horticultural settings to manage various weeds and pests, thanks to its systemic and contact action mechanisms. It typically exists as a white or light yellow crystalline solid with a melting point ranging from approximately 125-127°C. It exhibits relatively low solubility in water but is soluble in organic solvents such as ethanol and dichloromethane.
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Chemical Formula |
C9H10Cl2N2O |
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Exact Mass |
232.02 |
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Molecular Weight |
233.09 |
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m/z |
232.02 (100.0%), 234.01 (63.9%), 236.01 (10.2%), 233.02 (9.7%), 235.02 (6.2%) |
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Elemental Analysis |
C, 46.38; H, 4.32; Cl, 30.42; N, 12.02; O, 6.86 |
Crop Applications
Diuron is applied in various crops, including but not limited to:
Rice, Cotton, Soybeans, Tomatoes, Tobacco, Strawberries, Sugarcane, Grapes, Orchards, Rubber Plantations, Tea Gardens, and Mulberry Fields. It effectively controls annual grasses such as barnyardgrass, crabgrass, and foxtail, as well as some broadleaf weeds like amaranth and water hyacinth.
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Mode of Action
- Systemic and Contact Action: A substituted urea herbicide that exhibits both systemic and contact activity. It is absorbed by plant roots and leaves, with primary absorption through the roots. Once absorbed, it is translocated throughout the plant, inhibiting photosynthesis.
- Inhibition of Photosynthesis: It inhibits the Hill reaction in photosynthesis, leading to the loss of chlorophyll and subsequent yellowing of leaves. This ultimately results in the death of the weed due to starvation.
Instructions
- Pre-Emergence Application: Often applied pre-emergence, before weed seeds germinate, to prevent weed infestation. It can be applied to the soil surface or incorporated into the soil.
- Post-Emergence Application: In some cases, it can also be used post-emergence, targeting young weed seedlings. However, its efficacy as a post-emergence herbicide may be limited compared to pre-emergence applications.
Dosage & Timing
- Dosage: The recommended dosage varies depending on the crop, weed species, and soil conditions. It is essential to follow the manufacturer's instructions and local agricultural guidelines for precise dosage.
- Timing: The optimal timing application is crucial for effective weed control. It is typically applied before weed seeds germinate, ensuring maximum contact with the soil and reducing the risk of crop injury.
Efficacy & Duration
- Efficacy: Provides effective weed control when used as directed, reducing competition for nutrients, water, and light from weeds.
- Duration: The duration of weed control can vary depending on environmental conditions and weed species. In general, it provides long-lasting control, reducing the need for frequent reapplications.
Environmental Considerations
- Low Water Solubility: Has a low solubility in water (42 ppm at 25°C), which reduces the risk of groundwater contamination. However, it is important to use it responsibly to minimize environmental impact.
- Stability: It is stable under normal conditions but can decompose under high heat, releasing toxic fumes. Therefore, proper storage and handling are crucial.
Safety Precautions
- Personal Protection: When handling it, it is essential to wear protective clothing, including gloves, a respirator, and eye protection. Avoid inhaling dust or coming into direct contact with the chemical.
- Emergency Measures: In case of skin or eye contact, immediately wash the affected area with soap and water or rinse the eyes with copious amounts of water. If ingested, seek medical attention immediately and do not induce vomiting without medical advice.
Regulatory Status
It is subject to various regulations globally, with maximum residue limits (MRLs) set for food and water to ensure consumer safety. Users must comply with local laws and regulations regarding its use and disposal.
The synthesis of Diuron, a phenylurea herbicide, involves a series of chemical reactions starting from specific precursors. Here is a detailed overview of the synthesis method, drawing from authoritative sources:
Raw Materials
1
2
3
Synthesis Steps
- This intermediate is typically prepared by chlorinating p-chloronitrobenzene with chlorine gas in the presence of a catalyst such as anhydrous iron(III) chloride (FeCl3).
- The reaction is carried out at a temperature range of 100–110°C for 8–9 hours.
- The nitro group in 3,4-Dichloronitrobenzene is reduced to an amine group, yielding 3,4-Dichloroaniline.
- This reduction can be achieved using various methods, including reduction with iron powder and hydrochloric acid in an aqueous electrolyte solution.
- The reaction is typically carried out at a temperature range of 95–100°C for 3 hours.
- 3,4-Dichloroaniline is reacted with phosgene in the presence of a solvent like toluene to form 3,4-Dichlorophenyl Isocyanate.
- The reaction is carried out at a controlled temperature, typically starting at 0°C and gradually increasing to 65–75°C over 1–2 hours.
- 3,4-Dichlorophenyl Isocyanate is then reacted with dimethylamine in a solvent like toluene to form Diuron.
- The reaction is typically carried out at a temperature range of 45–70°C for 2 hours, with the pH adjusted to 8–9 using dimethylamine.
- The resulting product is filtered, washed, and dried to obtain pure Diuron.
alternative Synthesis Methods
There are also alternative synthesis methods, including the use of triphosgene (a safer alternative to phosgene) in the preparation of 3,4-Dichlorophenyl Isocyanate. These methods offer the advantages of improved safety and environmental profiles.
Safety Considerations
◆ Personal Protective Equipment (PPE): When handling the raw materials and intermediates involved in the synthesis, it is essential to wear appropriate PPE, including chemical-resistant gloves, protective clothing, and a respirator.
◆ Environmental Impact: Special attention should be given to minimizing environmental impacts, as some of the raw materials and intermediates used in the synthesis are hazardous.
◆ Waste Management: Proper waste management practices should be followed to ensure the safe disposal of any hazardous waste generated during the synthesis process.
In summary, the synthesis involves a multi-step process starting from 3,4-Dichloroaniline and proceeding through the preparation of intermediates and the final reaction with dimethylamine. The process requires careful control of reaction conditions and adherence to safety and environmental regulations.
Toxicity Profile and Ecological Impacts
● Acute Toxicity
Diuron exhibits moderate acute toxicity to mammals, with an oral LD50 (lethal dose 50%) of approximately 3400 mg/kg in rats. However, high concentrations of Diuron can cause irritation to the eyes and mucous membranes. In aquatic organisms, Diuron's toxicity varies depending on the species and life stage. For example, studies have shown that Diuron can induce oxidative stress and inhibit photosynthesis in algae, leading to reduced growth and reproduction. Similarly, Diuron has been found to cause developmental abnormalities and mortality in fish and invertebrates at concentrations exceeding their tolerance thresholds.
● Chronic Toxicity and Carcinogenicity
Chronic exposure to Diuron at low concentrations can have sublethal effects on non-target organisms, including disruptions to endocrine function, immune system impairment, and reproductive toxicity. In laboratory studies, Diuron has been shown to promote the development of bladder cancer in rodents when administered at high doses over extended periods. Although the relevance of these findings to human health remains uncertain, they underscore the need for caution in the use and management of Diuron.
● Ecological Impacts
The widespread use of Diuron has raised concerns regarding its ecological impacts, particularly on non-target plant species and beneficial organisms such as pollinators and soil microorganisms. Diuron's inhibition of photosynthesis can lead to the decline of sensitive plant species, altering plant community composition and biodiversity. Additionally, Diuron's toxicity to soil microorganisms can disrupt nutrient cycling and soil fertility, with potential cascading effects on ecosystem functioning.
Future Research Directions
Future research on Diuron should focus on several key areas, including its long-term environmental fate and transport, interactions with other pesticides and contaminants, and potential effects on human health. Additionally, the development of novel degradation technologies, such as bioremediation and advanced oxidation processes, could provide effective means for removing Diuron residues from contaminated soils and water bodies. Finally, the integration of Diuron into broader discussions on sustainable agriculture and pesticide management will be crucial for addressing the complex challenges posed by its use in modern farming systems.
Diuron has been a valuable herbicide in agricultural and non - agricultural weed control for many decades. Its chemical properties, modes of action, and broad - spectrum activity have made it a popular choice for growers. However, its environmental persistence and potential adverse effects on non - target organisms have raised concerns about its long - term use. International and national regulatory measures have been implemented to manage the use of diuron and mitigate its risks. To ensure sustainable weed management in the future, it is essential to continue researching alternative herbicides and promoting integrated weed management practices that reduce the reliance on single - herbicide strategies and protect the environment and human health.
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