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Chlorpropham, also known as Chlorprofen, is an organic compound with the chemical formula C10H12ClNO2 and CAS 101-21-3, which is a white crystalline powder with a bitter taste. It is solid at room temperature, not easily soluble in water, but soluble in organic solvents such as alcohols, ethers, benzene and chloroform. Relatively stable, but decomposition reactions may occur, eg when exposed to sunlight or oxidized by strong oxidizing agents. Also, it may react with strong bases and acids. It is a plant growth regulator and herbicide, which can effectively control wheat, corn, alfalfa, sunflower, purslane, beet, rice, kidney bean, carrot, spinach, lettuce, onion, pepper and other crops. Some broad-leaved grasses can also be used to inhibit the germination of potatoes during storage.
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Chemical Formula |
C10H12ClNO2 |
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Exact Mass |
213 |
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Molecular Weight |
214 |
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m/z |
213 (100.0%), 215 (32.0%), 214 (10.8%), 216 (3.5%) |
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Elemental Analysis |
C, 56.22; H, 5.66; Cl, 16.59; N, 6.56; O, 14.98 |
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Chloroaniline (chemical name: 3-Chloroaniline isopropyl ester, CAS number: 101-21-3) is an amino ester compound that serves as both a plant growth regulator and herbicide. Its core mechanism of action is to inhibit cell division, interfere with plant metabolic processes, and achieve specific application effects through steam fumigation.
Herbicide function
Chlorpheniramine, as a highly selective herbicide in the early pre - or post seedling stage, enters the plant body mainly through root absorption and supplemented by leaf absorption, and conducts bidirectionally in the body (up to the stem and leaves, down to the root system), disrupting the process of cell division. Its control targets include annual grass weeds (such as barnyard grass, wild oats, and early maturing grasses) and some broad-leaved weeds (such as shepherd's purse, amaranth, purslane, and field silk) in crops such as wheat, corn, alfalfa, sunflowers, potatoes, sugar beets, soybeans, rice, beans, carrots, spinach, lettuce, onions, and peppers.
Usage: Soil treatment should be carried out after crop sowing and before seedling emergence. Use 157-425 kilograms of 0.7% powder per hectare, either alone or in combination; By adjusting the dosage based on soil organic matter content and temperature, the spectrum of weed killing can be expanded. For example, in corn fields, chlorpheniramine can effectively control weeds such as dogweed and horsetail, reducing nutrient competition with crops.
Characteristics of action: Compared with traditional herbicides, Chlorpheniramine has the advantages of low toxicity, moderate shelf life (about 20-25 days), and high safety for subsequent crops.
Plant growth regulation function
Chlorpropham achieves multiple growth regulatory effects by inhibiting β - amylase activity, blocking RNA and protein synthesis, interfering with oxidative phosphorylation and photosynthesis
Inhibition of potato germination during storage: As the most typical commercial application, Chlorpheniramine sublimates into a gaseous state through steam fumigation, disrupting the dominance of potato apical buds and causing them to germinate synchronously with lateral buds but difficult to break through the epidermis, thereby extending the storage period to more than 6 months.
The specific operation is to use 1.4-2.1 kilograms of 0.7% powder (9.8-14.7 grams of active ingredient) or 400-600 grams of 2.5% powder (10-15 grams of active ingredient) per ton of potatoes 14 days after potato harvest (until mechanical damage naturally heals) until sprouting, mix with fine dry soil, evenly spread, and cover with plastic cloth for sealing.
Fruit tree thinning: Spraying chlorpheniramine during the flowering period of apple, pear and other fruit trees can induce partial flower shedding, optimize fruit distribution, and increase single fruit weight and commodity rate. For example, spraying 0.1% chlorpheniramine solution during the peak flowering period of apples can achieve a thinning rate of 30% -40%, and has no significant effect on the quality of the remaining fruit.
Tobacco control: In tobacco cultivation, chlorpheniramine can regulate the growth rhythm of plants, prevent premature flowering, promote leaf enlargement, and improve tobacco yield and quality.
Industrial field: Enhanced application of rubber and textile
Rubber industry antioxidant:
Chloroaniline can be used as an auxiliary antioxidant for rubber products, inhibiting free radical chain reactions and delaying rubber aging by chelating metal ions (such as Fe ³ ⁺, Cu ² ⁺). In tire manufacturing, adding 1% -2% chloroaniline can extend the service life of tires by 20% -30%, reduce cracking and performance degradation caused by oxidation. Its advantage lies in good compatibility with rubber and not interfering with the vulcanization process.
Textile industry reducing agent:
In the dye reduction process, chloroaniline can replace traditional reducing agents (such as sodium hydrosulfite) to reduce the quinone structure in the dye to a hidden color, improving dyeing uniformity and fastness. For example, in reactive dye dyeing, the use of chloroaniline can increase the dyeing depth by 15% -20% and reduce the difficulty of wastewater treatment. Its reaction conditions are mild (pH 8-10, temperature 60-70 ℃), suitable for large-scale continuous production.
Potato sprout suppression is the most commercially valuable application scenario of Chlorpheniramine, and its technical advantages and operating standards are as follows:
Sprout inhibition mechanism
Chlorpheniramine vapor permeates through the stomata of potato epidermis to the bud eye tissue, inhibiting the activity of cell division related enzymes (such as β - amylase) and blocking the energy supply required for bud eye germination. Compared with natural sprout suppressants such as peppermint oil and cinnamon powder, Chlorpheniramine has the advantages of long-lasting effect and easy operation; Compared with chemical sprout suppressants such as anthocyanins, its residual risk is lower and meets the food safety standards of developed markets such as the European Union.
Operating Specifications
Timing selection: After harvesting potatoes, they should be left to stand for at least 14 days until mechanical damage (such as cutting or scratching) naturally heals before applying the medicine. This is to avoid the medicine directly entering the inside of the potato block through the wound, causing discoloration or rotting of the skin.
Dosage control: Use 1.4-2.1 kilograms of 0.7% powder or 400-600 grams of 2.5% powder per ton of potatoes. Overuse may cause brown spots on the skin, affecting the appearance of the product.
Application method:
Powder application: Mix the pesticide with fine dry soil (particle size<2 mm) in a ratio of 1:10, evenly apply it to the surface of potatoes, and then cover and seal it with plastic cloth to create a fumigation environment.
Application of smoke agent: In large warehouses, 50% chloroaniline spirit smoke agent can be used, with a dosage of 40 grams per ton of potato. The gaseous agent is released through a smoke generator to achieve uniform distribution.
Environmental requirements: The storage temperature should be controlled at 4-10 ℃, and the humidity should be maintained at 85% -90%; Avoid contact with edible alcohol to prevent the production of toxic substances.
Effect Comparison
Potatoes that have not been treated with chlorpheniramine show significant apical bud dominance after 60-70 days of storage, with bud lengths exceeding 10 centimeters, completely losing their edible value; Potatoes treated with chlorpheniramine showed a bud length of less than 1 millimeter after 180 days of storage, and the cut surface showed no browning, maintaining a fresh state.
All Synthetic Methods of Chlorpropham:
1. Industrial synthesis method:
1.1 Esterification reaction of benzaldehyde and acrylic acid:
First put benzaldehyde and acrylate into the esterification reactor, and add sulfuric acid catalyst. The inside of the reactor was heated to 80°C, and the reaction solution was continuously stirred. The esterification reaction usually lasts for 5-6 hours until the pH value drops to 3-4 and ends. The reaction product is benzyl acrylate.
1.2 Reaction of Benzyl Acrylate and Ammonia:
Benzyl acrylate reacts with ammonia under acidic conditions to prepare benzyl acrylamide. The reaction condition is that the reaction temperature is 50-60° C., and the amount of ammonia solvent is excessive. The reaction can last for 4-5 hours, and the product is benzyl acrylamide.
1.3 Fluoroboric acid-catalyzed oxidation of benzyl acrylamide and Cl2O:
Inject benzyl acrylamide and Cl2O into the fluoroboric acid catalyst, and the reaction temperature is 0 °C. The reaction product is N-chlorobenzyl acrylamide.
1.4 Addition reaction of N-chlorobenzyl acrylamide and ammonia water:
N-chlorobenzyl acrylamide reacts with ammonia water under alkaline conditions to generate product. The reaction temperature is 25°C, the reaction time is 1 hour, and the yield is over 90%.
2. Laboratory synthesis method:
2.1 Fluoroboric acid-catalyzed oxidation of benzyl acrylamide and Cl2O:
Dissolve benzyl acrylamide and Cl2O in tetrahydrofuran solution, add fluoroboric acid catalyst, and react at 0°C for 2 hours. During the reaction, slowly add the Cl2O solution with a slow dropper to avoid side reactions of chlorinated compounds. The reaction product is N-chlorobenzyl acrylamide.
2.2 Addition reaction of N-chlorobenzyl acrylamide and ammonia water:
Dissolve N-chlorobenzylacrylamide in anhydrous methanol, add ammonia water and stir for 1 hour. The reaction temperature was maintained at 25°C.
The reaction product is it.
In 1945, Swiss chemist W. Stähelin first synthesized product. He realized that the compound might have potential as a herbicide and nematicide, and conducted a series of experiments to test its effectiveness. Stähelin found that it was effective in controlling weeds and nematodes in vegetables such as tomatoes and potatoes, so he recommended it to the Swiss Federal Research Institute of Agriculture (FAL).
In 1947, FAL promoted the compound as a herbicide throughout Europe. Due to its high efficacy and wide applicability, it soon became one of the most widely used herbicides in Europe. Its use covers a wide variety of crops such as vegetables, fruits and grains.
It was introduced to the United States in 1952 for use as a herbicide and nematode insecticide.
In the late 1950s and early 1960s, it became a major herbicide for vegetable and wheat crops in the United States, playing an especially important role in maintaining the color of beets, potatoes and sweet potatoes in the field.
In 1957, it was approved by the U.S. Environmental Protection Agency (EPA) for use in food processing and storage to prevent weeding of potatoes. It became an important tool for vegetable storage around the world at the time, as it was proven to significantly extend the storage life of vegetables.
However, some potential harms of product have also been discovered during use. It has been found to be somewhat toxic to humans and has negative effects on the environment, especially on fish and aquatic invertebrates. In addition, it may be toxic to shellfish, so its use in fruits and vegetables is strictly limited.
Despite its shortcomings and controversies, it remains the herbicide and nematode insecticide of choice for many farmers and crop growers. It is used to control weeds and nematodes in plantations, protect crop and fruit quality, increase yield and extend storage life. Although safety precautions are required during use, Chlorpropham remains an indispensable compound widely used in agricultural production worldwide.
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