Name | 2-Chloroethyl phosphoric acid |
Synonyms | MH Ethrel 2-cepa Ethephon Ethephonww Chlorethephon ETHEPHON(BULK Ethephon S.P. ethephon (ansi,canada) (2-chloroethyl)phosphonate 2-Chloroethylphosphonicaicd 2-chloraethyl-phosphonsaeure Ethephon aqueous solution () 2-Chloroethyl phosphoric acid (2-chloroethyl)-phosphonicaci (2-chloroehtyl)phosphonicacid (2-chloroethyl)phosphonic acid 2-Chloroethylenephosphonic acid |
CAS | 16672-87-0 |
EINECS | 240-718-3 |
InChI | InChI=1/C2H6ClO3P/c3-1-2-7(4,5)6/h1-2H2,(H2,4,5,6)/p-2 |
InChIKey | UDPGUMQDCGORJQ-UHFFFAOYSA-N |
Molecular Formula | C2H6ClO3P |
Molar Mass | 144.49 |
Density | 1.2000 |
Melting Point | 70-72°C(lit.) |
Boling Point | 265°C(lit.) |
Flash Point | 155.4°C |
Water Solubility | Completely soluble in water |
Solubility | Soluble in water, methanol, acetone, ethylene glycol, propylene glycol, slightly soluble in toluene, insoluble in petroleum ether. |
Vapor Presure | 2.62E-05mmHg at 25°C |
Appearance | Solid |
Color | White to beige |
Merck | 14,3732 |
BRN | 1751208 |
pKa | 1.88±0.10(Predicted) |
Storage Condition | 2-8°C |
Sensitive | Hygroscopic |
MDL | MFCD00002142 |
Physical and Chemical Properties | Melting Point 65-75°C |
Use | As a plant growth regulator, it can release ethylene in the roots, pods, leaves, stems, flowers and fruits of plants to regulate the metabolism, growth and development of plants |
Hazard Symbols | C - Corrosive |
Risk Codes | R20/21 - Harmful by inhalation and in contact with skin. R34 - Causes burns R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S28A - |
UN IDs | UN 2928 6.1/PG 2 |
WGK Germany | 2 |
RTECS | SZ7100000 |
HS Code | 29319090 |
Hazard Class | 6.1 |
Packing Group | II |
Toxicity | LD50 orally in mice: 2850 mg/kg (Hennighausen) |
Raw Materials | Ethylene Oxide Sulfuric acid Phosphorus trichloride |
Reference Show more | 1. Zhang Miao Wang Tiaolan Li Yongcai et al. cAMP-mediated regulation of pear epidermis physicochemical signals on Alternaria infection [J]. Journal of Bacteriology 2019 38(004):521-532. 2. Wang Tiaolan, Zhang Miao, Li Yongcai, et al. MAPK signal level connection road participates in the recognition and response of Alternaria alternata to signal molecules in pear epidermis [J]. Journal of Gansu Agricultural University 2019(4). 3. Shi Si Hong Min, He Shanshan, et al. Effect of Different Flower and Fruit thinning agents on flower and fruit thinning of "Big Five Star" loquat [J]. Genomics and Applied Biology 2018 037(010):4501-4510. 4. Bao, x, Lin, g, dong, x, ma, x, han, x, zhang, h. Synergistic effects of copper and ethylene on resveratrol synthesis in peanuts. food sci nutr. 2021; 9: 1471-1479. https://doi.org/10.1002/fsn3.2117 5. WANG, Hao-jie, et al. "Identification and functional characterization of the MdHB-1 gene promoter sequence from Malus × domestica." Journal of integrative agriculture 16.8 (2017): 1730-1741.https://doi.org/10.1016/S2095-3119(16)61548-4 6. [IF = 3.463] Dejian Zhang et al. "Root hair development of Poncirus trifoliata grow in different growth cultures and treated with 3-indolebutyric acid and ethephon." Sci Hortic-Amsterdam. 2013 Aug;160:389 7. [IF = 2.863] Xuefeng Bao et al. "Synergistic effects of copper and ethylene on resveratrol synthesis in peanuts." Food Sci Nutr.2021 Mar;9(3):1471-1479 8. [IF = 5.279] Zengyu Gan et al.AcERF1B and AcERF073 Positively Regulate Indole-3-Acetic Acid Degradation by Activating AcGH3.1 Transcription during Postharvest Kiwifruit Ripening.J Agr Food Chem. 2021;69(46):13859-13870 9. [IF = 4.412] Zhanjiang Zhang et al. "Metabolic and Transcriptomic Analyses Reveal the Effects of Ethephon on Taraxacum kok-saghyz Rodin." MOLECULES 2022 Jan;27(11):3548 |
The Pure product was white needle-like crystals. Industrial products are light yellow viscous liquids or waxy solids. mp74 ~ 75. Soluble in water, alcohol, acetone, insoluble in benzene, insoluble in petroleum ether. It is easy to deliquescence in the air, and the aqueous solution is strongly acidic. Stable at pH<3 acidic conditions, ethylene evolution at pH>3 and alkaline conditions.
from ethylene oxide and phosphorus trichloride into trichloroethyl phosphite, heat isomerization, and acid hydrolysis. Alternatively, diethyl phosphite is heated, nitrogen is passed through, a small amount of initiator is added, and vinyl chloride is added for reaction to obtain ethephon. Ethylene, phosphorus trichloride and air (or oxygen) can also be reacted at low temperature or high pressure to obtain ethephon by hydrolysis.
organic phosphorus plant production regulator. With plant hormones to enhance the secretion of milk, accelerate the maturation, shedding, aging and promote the physiological effects of flowering. Under certain conditions, ethephon can not only release ethylene by itself, but also induce the production of ethylene in plants. Ethephon is used to promote the early maturity of cotton, centralized bolting, increase the income, improve the grade, can promote all kinds of fruits, such as banana, citrus, tomato, watermelon, etc, lacquer tree and other vomiting glue has a promoting effect.
mouse oral LD50 was 2850mg/kg. On the skin, eyes, mucous membrane irritation, no teratogenic, carcinogenic, mutagenic effect. On the carp LC50 290mg/L( 72h), low toxicity to humans and animals, low toxicity to bees.
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
plant growth regulator | ethephon is a common plant growth regulator, which is widely used in countries all over the world, mainly to promote seed germination, flowering and fruiting, ripening, falling, etc. In the agricultural industry standard NY/T 393-2013 "Guidelines for the Use of Green Food Pesticides", ethephon is also listed as a plant growth regulator that can be used, which shows that its safety is guaranteed. the general dosage form of ethephon is 40% ethephon aqua, and the effective ingredient is ethylene. ethylene is generally stable below the PH value of less than 3, and ethylene gas can be released only when the PH value is greater than 4. therefore, ethephon is generally strong acidic. secondary dilution is very important for ethephon, such as maintaining the activity requirements of ethylene. Ethephon has the physiological effects of plant hormones promoting emulsion secretion, accelerating maturity, shedding, aging and promoting flowering. Under certain conditions, ethephon can not only release ethylene by itself, but also induce plants to produce ethylene. Ethephon mainly enters the plant body through crop leaves, bark, fruits, and seeds, and then passes to the functional parts to release ethylene. It can promote fruit ripening and coloring, promote leaf and fruit shedding, dwarf plants, change the ratio of male and female flowers, induce male sterility of crops, etc. Ethephon can be used in a variety of crops, such as rice, corn, golden autumn pears, grapes, peaches, tomatoes, cucumbers, melons, cotton, etc. Reasonable use of ethylene can increase production and efficiency. For example, the application of ethephon in cotton can speed up the cracking of cotton bolls, reduce the flowers after frost, and effectively improve the quality of cotton, thereby increasing cotton yield. |
pesticide residues | the safe dose of ethephon is 0.05 mg per kilogram of body weight, that is to say, for adults weighing 60kg, the safe daily intake for life is 3 mg. The residue limit of ethephon in grapes is 1 mg per kilogram, which means that it is possible to have side effects by eating at least 3kg of grapes a day for life. Because plant growth regulators are self-limiting, more use is not worth the loss, so they are usually used in excess of the standard. For example, the farmers in the news lost all the grapes because they used too much. So you can rest assured that if plant growth regulators are used too much, it is the plants and farmers who will suffer first, not you. |
toxicity | acute oral LD50 in mice is 4229mg/kg, acute percutaneous LD50 in rabbits is 5730mg/kg, and acute inhalation of LC50 in rats is 90mg/m3 air (4h). It is irritating to skin, eyes and mucosa, and has no teratogenic, carcinogenic and mutagenic effects. LC50 for carp was 290mg/L (72h). Low toxicity to humans and animals, low toxicity to bees. |
use | organophosphorus plant growth regulator. It can promote the early maturity of various melons and fruits, such as bananas, citrus, tomatoes, watermelons, etc., can promote rubber, sumac, etc., can promote the early blooming of female flowers and more female flowers of cucumbers, and can be used for the ripening of cotton and tobacco. It also inhibits plant growth, makes plants shorter, and breaks seed dormancy. Cotton was sprayed with 40% ethephon 15~22.5g/100m2 half a month before early frost. Bananas are treated with 0.2~2g/L ethephon aqueous solution for ripening. Used as a plant growth regulator, it can release ethylene in the roots, pods, leaves, stems, flowers and fruits of plants to regulate plant metabolism, growth and development It is a plant growth regulator used for rubber, sumac, tobacco, cotton, sorghum, fruits, vegetables and other crops Ethephon is a plant growth regulator with plant hormones to enhance emulsion secretion, physiological effects of accelerating maturation, shedding, senescence and promoting flowering. Under certain conditions, ethephon can not only release ethylene by itself, but also induce plants to produce ethylene. It is applied to the production of natural rubber, benzoin and raw lacquer, and has a significant increase in production. Ethephon is used to promote early maturity of cotton, concentrate on blooming, increase income, and improve grade, which is conducive to the mechanization of cotton farming; it can also be used for the ripening of bananas and tomatoes, early rice ripening, yellowing of tobacco leaves, adjustment of pineapple opening, and tea removal Sex transformation of melon flowers such as flowers, cucumbers, wheat killing males, and coloring of apples and oranges. plant regulators. Ethylene can release ethylene in the roots, pods, flowers and fruits of plants to regulate plant metabolism, growth and development. This product can accelerate the pre-harvest and ripening of fruits and vegetables, and is used as a ripening agent after fruit harvest. |
Production method | It is obtained by esterification of ethylene oxide and phosphorus trichloride at low temperature, and then molecular rearrangement and acidolysis. Vinyl chloride route Diethyl phosphite is heated to 90 ℃, and nitrogen is passed for 30min. Add a little initiator, introduce vinyl chloride, and control the addition reaction temperature to obtain diethyl 2-chloroethylphosphinic acid. Then the addition product is added to concentrated hydrochloric acid for hydrolysis, refluxing at 120~130 ℃ for 24 hours to obtain ethephon, and part of the water is steamed out to obtain crude product, which can be formulated as a dosage form. The method is easy to obtain raw materials, simple equipment, low investment, three waste water, simple operation, easy recovery of unreacted raw materials, and 60% total yield based on phosphorus trichloride. The ethylene oxide route is directly added to phosphorus trichloride and ethylene oxide, and ethephon is synthesized through molecular rearrangement and acidolysis. The addition temperature is 20~25 ℃, the molecular ratio is 1:3 (ethylene oxide excess), the rearrangement reaction is 220~230 ℃, and the acidolysis temperature is 160~170 ℃. This method is the main domestic production method. The product is mixed with some impurities, but the production requirements are not high. The ethylene route consists of ethylene, phosphorus trichloride and air (or oxygen), which directly synthesize ClCH2CH2P(O)Cl2 at low temperature or high pressure, and hydrolyze to obtain ethephon. This method has simple production process and low cost, but the equipment requirements are high and the operation requirements are strict. The dichloroethane route is composed of dichloroethane and phosphorus trichloride to form a complex under the catalysis of anhydrous AlCl3, and water is added to decompose into ClCH2CH2P(O)Cl2, and water is further added to generate ethephon. The product purity of this method is high, but the operation is complicated and the yield is still low. |
category | pesticide |
toxicity classification | poisoning |
acute toxicity | oral-rat LD50: 3400 mg/kg; Oral-mouse LD50: 2850 mg/kg |
flammable hazard characteristics | flammable; decomposition of flammable ethylene gas in case of alkali |
storage and transportation characteristics | warehouse ventilation and low temperature drying; Separate storage with oxidant and alkali |
fire extinguishing agent | water, sand |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |