cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate
Decamethrin
CAS: 52918-63-5
Molecular Formula: C22H19Br2NO3
cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate - Names and Identifiers
cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate - Physico-chemical Properties
| Molecular Formula | C22H19Br2NO3 |
| Molar Mass | 505.2 |
| Density | 1.5214 (rough estimate) |
| Melting Point | 98°C |
| Boling Point | 300°C |
| Specific Rotation(α) | +56～+64°(20℃/D)(c=4,C6H6) |
| Flash Point | -18°C |
| Water Solubility | <0.0002 mg l-1 (25 °C) |
| Solubility | Soluble in DMSO (up to 50 mg/ml) |
| Vapor Presure | 1.24×10-2Pa (25 °C) |
| Appearance | Crystalline |
| Color | Colorless |
| Maximum wavelength(λmax) | ['278nm(Hexane)(lit.)'] |
| Merck | 14,2883 |
| BRN | 6746312 |
| Storage Condition | −20°C |
| Stability | Stable. Incompatible with acids, alkalies, strong oxidizing agents. |
| Refractive Index | 1.6220 (estimate) |
| Physical and Chemical Properties | Melting point 98°C boiling point 300°C |
| Use | It is a pyrethroid insecticide, which can effectively control pests on cotton, tobacco, fruit trees, vegetables and other crops |
cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate - Risk and Safety
| Risk Codes | R23/25 - Toxic by inhalation and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R38 - Irritating to the skin R11 - Highly Flammable |
| Safety Description | S24 - Avoid contact with skin. S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S38 - In case of insufficient ventilation, wear suitable respiratory equipment. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S16 - Keep away from sources of ignition. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | GZ1233000 |
| HS Code | 29269090 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 in female rats (mg/kg): 31 orally; 4 i.v. (Kavlock) |
cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate - Upstream Downstream Industry
| Raw Materials | Butyryl chloride Sodium cyanide Octoxinol Bromine |
cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 53) 1991 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| pyrethroid insecticides | deltamethrin, also known as kessen, dimethrin and dimethrin, is one of the most efficient pyrethroid insecticides in the contemporary era, with an order of magnitude higher efficacy than permethrin. The dosage is only 7.5~15g/hm2, but it is ineffective for vermicularia, and its virulence to housefly is about 1000 times higher than that of natural pyrethrin. This product is stable in nature and has long effect. Deltamethrin is a pyrethroid insecticide. Its insecticidal activity is high. It mainly has contact and stomach toxicity. It has certain repellent and anti-feeding effects on pests, but it has no absorption and fumigation effects. The insecticidal spectrum is wide, the knockout speed is fast, especially for Lepidoptera larvae and aphids. Its site of action is the insect nervous system, which is a nerve agent. |
| development history | deltamethrin is a variety first developed by Aventis (now Bayer) in 1977. it was not approved in the United States until the mid-2090s, and its sales continued to grow in both agricultural and non-agricultural fields. From 2009 to 2013, the global sales of deltamethrin increased year by year, from US $0.285 billion to US $0.37 billion. In 2014, the sales of deltamethrin began to decline year by year, partly due to the potential risks of deltamethrin to people and the environment. Similar to cypermethrin, India is currently the main producer of deltamethrin. However, it should be noted that on October 27, 2017, the list of carcinogens published by the International Agency for Research on Cancer of the World Health Organization was preliminarily compiled for reference. Deltamethrin was listed in the list of three types of carcinogens (the existing evidence failed to grade the carcinogenicity of human beings). |
| mechanism of action | the main target of deltamethrin is the basal voltage-gated sodium channel (VGSCs) of nerve cell excitation conduction. the mechanism of action is to prolong the opening time of VGSCs in insects and continuously depolarize the cell membrane, thus causing poisoning symptoms after dyskinesia, that is, immediately spasm and quickly enters paralysis state, and finally paralysis and death. In addition, deltamethrin can also act on other insect targets, such as chloride ion channels, ATPase, aminobutyric acid receptor, glutamate receptor, acetylcholine receptor, and voltage-gated calcium ion channels. |
| toxicity | acute oral LD50155mg/kg(128 mg/kg) in male rats and 60 mg/kg(138 mg/kg) in female rats; Acute oral LD5065mg/kg in male mice and 69 mg/kg in female mice; Acute percutaneous LD50>2940 mg/kg in rats; Acute inhalation LC50600mg/m3 in rats; No irritation to skin, mild irritation to eyes. The subacute non-effective dose in rats is 2.5~10 mg/kg per day. The concentration of chronic non-action in rats was 50mg/kg, 100mg/kg in mice and 40mg/kg in dogs. Animal experiments showed no carcinogenic, teratogenic and mutagenic effects. No abnormal phenomenon was found in the three-generation reproduction test. Blue gill fish LC500.001mg/L (96h), rainbow trout 0.006~0.008mg/L (96h). The acute oral LD50 of wild ducks is 4640mg/kg. The oral LD50 of bees is 0.079 μg/bee. High toxicity to silkworms. |
| environmental impact | deltamethrin is generally sprayed into the soil environment through farmland drugs, and then enters the water body through surface runoff. the residual time in the water is very short, and the elimination half-life is generally less than 6 days. It is easy to degrade in the environment and is easily adsorbed by solid substances. Sediment adsorption is the most important factor to accelerate the degradation of deltamethrin. The higher the pH value, the shorter the half-life of deltamethrin degradation, and the role of microorganisms can also accelerate the elimination of deltamethrin in water. |
| use | a pyrethroid insecticide with high insecticidal activity, wide insecticidal spectrum, rapid efficacy and safety to crops. It mainly has the effects of contact killing and stomach poison, and has a certain repellent and anti-feeding effects, without absorption and fumigation effects. It has poor effect on mites and scales, is highly toxic to silkworm, bee and fish, and has cross-resistance to other pyrethroid resistant pests. For example, to control cotton red bollworm, cotton bollworm and leaf hopper, spray at a concentration of 25mg/L; spray at a concentration of 15mg/L for cotton aphids and thrips; use 2.5% EC 2000~3000 times for prevention and control of rapae, diamondback moth and Spodoptera litura; spray with 2.5% EC 2500~3000 times for prevention and control of tea geometrid and tea caterpillar. In addition, it can control rice stem borer, rice thrips, rice leaf roller, soybean heartworm, citrus leaf miner, pear heartworm, peach heartworm, sugar cane borer and sanitary pests. Avoid hot weather when using. Deltamethrin is a high-efficiency pyrethroid insecticide, which is mainly used to control cotton aphid, cotton bollworm and other crop pests, and can effectively control cotton, tobacco, fruit trees, vegetables and other crops Pests. |
| Production method | There are 3 asymmetric carbon atoms and 8 isomers in the deltamethrin molecule, and only one of them has the highest activity. In order to reduce ineffective (or inefficient), reduce costs, and reduce pollution during synthesis, the French Russell-Eukford company adopts the following process route:(1R, cis) 2, 2-dimethyl-3-(2,2, 2-dibromovinylcyclopropane carboxylic acid), that is, dibromopyranic acid, chlorinated with thionyl chloride to produce dibromochroyl chloride. The addition of m-phenoxybenzaldehyde and hydrocyanic acid to obtain α-cyano-phenoxybenzyl alcohol. In the presence of pyridine, dibromoyl chloride reacts with ()α-cyano phenoxybenzyl alcohol to obtain deltamethrin. DibromThere is an esterification reaction between dibromemic acid and α-cyano-3-phenoxybenzyl alcohol to produce deltamethrin; or dibromemic acid is acylated with thionyl chloride to generate dibromochracyl chloride, and then reacts with α-cyano-3-phenoxybenzyl alcohol. Raw material consumption quota: 640kg/t of dibromocyanate and 460kg/t of α-cyanide -3-phenoxybenzyl alcohol. |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 9.36 mg/kg; Oral-mouse LD50: 20 mg/kg |
| flammability hazard characteristics | flammability; combustion produces toxic nitrogen oxides and bromide gases |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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View History
Raw Materials for cyano(3-phenoxyphenyl)methyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate