Dinitro-ortho-cresol

Dinitro-ortho-cresol (DNOC) is an organic compound with the chemical formula C7H6N2O5. It is a yellow solid that is soluble in most organic solvents but not in water. DNOC is primarily used as a herbicide, insecticide, and fungicide. It belongs to the chemical class of nitrophenols, which are phenols substituted with nitro groups.

Properties

DNOC is characterized by its yellow color and crystalline form at room temperature. It has a melting point of 88-90°C. Being a nitrophenol, DNOC is acidic and can form salts with bases. Its solubility in water is limited, but it is readily soluble in organic solvents such as ethanol, acetone, and benzene.

Synthesis

DNOC is synthesized through the nitration of ortho-cresol with mixed nitric acid and sulfuric acid. The process involves careful control of temperature and acid concentrations to favor the formation of the dinitro product over other possible nitration products.

Uses

Historically, DNOC has been used in agriculture as a pesticide. It acts by uncoupling oxidative phosphorylation in mitochondria, leading to the inefficient use of energy in cellular respiration. This mechanism is effective against a wide range of pests, including insects, mites, and fungi. However, due to its high toxicity to humans and non-target species, its use has been significantly restricted or banned in many countries.

Agricultural Use

In agriculture, DNOC was applied to control a variety of pests and diseases on crops such as fruits, vegetables, and cereals. It was also used as a dormant spray on fruit trees to control overwintering pests and diseases.

Safety and Environmental Concerns

The use of DNOC poses significant health risks, including the potential for skin and eye irritation, respiratory distress, and more severe systemic effects such as convulsions and coma with high levels of exposure. Its environmental impact is also of concern, particularly its toxicity to aquatic life and potential to contaminate water sources.

Regulation

Due to these health and environmental risks, the use of DNOC is highly regulated. In the European Union, DNOC is banned for use as a pesticide under the Directive 2009/128/EC on the sustainable use of pesticides. Similar restrictions apply in other regions, reflecting the global move towards safer and more sustainable pest control methods.

See Also

• Pesticide
• Herbicide
• Insecticide
• Fungicide
• Nitrophenols