CAS number：52918-63-5
molecular formula：C22H19Br2NO3
molecular weight：505.2
EINECS number：258-256-6

English synonyms

(1r-(1-alpha(s*),3-alpha))-oxyphenyl)methyleste;(S).alpha.-Cyano-phenoxybenzyl(1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate;(s)-alpha-cyano-3-phenoxybenzyl-(1r)-cis-3-(2,2-dibromovinyl)-2,2-dimethyl-cyc;(s)-alpha-cyano-3-phenoxybenzyl(1r,3r)-3-(2,2-dibromovinyl)-2,2-dimethyl-cyc;(S)-α-cyano-3-phenoxybenzyl(1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate;[1R-[1alpha(S*),3alpha]]-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dibromomethenyl)-2,2-dimethylcyclopropanedicarboxylate;[1r-[1alpha(s*),3alpha]]-cyano(3-phenoxyphenyl)methyl3-[2,2-dibromoethenyl)-2,;2,2-dimethylcyclopropanecarboxylate)

Related categories

Pyrethroid insecticide; pesticide; insecticide (mite) agent; organochlorine insecticide; insecticide; feed additive; pesticide residue, veterinary drug and fertilizer; agricultural raw material;
Aromatics Compounds;INSECTICIDE;Aromatics;Chiral Reagents;Mutagenesis Research Chemicals;Alpha sort;D;Pesticide intermediates;Aromatics, Chiral Reagents, Mutagenesis Research Chemicals;
Agricultural raw materials and preparations - insecticides; APIs; insecticides; pesticides - insecticides; chemical reagents; pesticide chemicals; other raw materials;
DA - DHMethod Specific;DAAlphabetic;Insecticides;Oeko-Tex Standard 100;Pesticides&Metabolites;PesticidesPesticides;Pyrethroids;Alphabetic

Introduction

Deltamethrin, also known as kasuling, dishaling, and fluchongjing, is one of the most effective pyrethroid insecticides in contemporary times, and its efficacy is an order of magnitude higher than that of permethrin. The dosage is only 7.5-15g/hm2, but it has no effect on worms, and its toxicity to houseflies is about 1000 times higher than that of natural pyrethrins. This product is stable in nature and long lasting.

Chemical properties

The original drug is a white powder, odorless, recrystallized with isopropanol into orthorhombic needle crystals. Original drug (98%) m.p.98～101℃, pure product m.p.101～102℃. [α]D+61 o, vapor pressure 1.999×10-6Pa (25°C). Soluble in various organic solvents such as acetone, cyclohexanone, benzene, dimethylformamide, dimethyl sulfoxide, and dioxane; the solubility in water is 10mg/L. There is no obvious decomposition at 100°C for 24 hours, and there is obvious decomposition at higher than 190°C. It is stable to light, stable in acidic solution, and unstable in alkaline solution.

Use

●  A pyrethroid insecticide with high insecticidal activity, wide insecticidal spectrum, rapid efficacy and safety to crops. It mainly has contact and stomach poisoning effects, and has certain repelling and antifeedant effects, and has no systemic and fumigation effects. It has poor effect on mites and scales, is highly toxic to silkworms, bees, and fish, and has cross-resistance to other pyrethroid-resistant pests. For example, to control cotton pink bollworm, cotton bollworm and leaf springworm, spray at a concentration of 25mg/L; spray at a concentration of 15mg/L for cotton aphids and thrips; control cabbage caterpillar, diamondback moth, and Spodoptera litura with 2.5% EC 2000~ 3000 times liquid spray; control tea inchworm and tea caterpillar with 2500-3000 times liquid spray of 2.5% emulsifiable oil. In addition, it can control rice borer, rice thrips, rice leaf roller, soybean borer, citrus leafminer, pear borer, peach borer, sugarcane borer and sanitary pests. Avoid high temperature weather when using.

●  Deltamethrin is a high-efficiency pyrethroid insecticide, which is mainly used to control various crop pests such as cotton aphid and cotton bollworm, and can effectively control pests on cotton, tobacco, fruit trees, vegetables and other crops.

Production method

●  There are 3 asymmetric carbon atoms in the deltamethrin molecule, and there are 8 isomers, and only one of them has the highest activity. In order to reduce the ineffective body (or low-efficiency body), reduce cost, and reduce pollution during synthesis, the French Russell-Ukford Company adopts the following process route: (1R, cis) 2,2-dimethyl-3-(2 , 2-dibromovinylcyclopropane carboxylic acid), that is, dibromochrysanthemic acid, chlorinated with thionyl chloride to generate dibromochrysanthemum acid chloride. The addition of m-phenoxybenzaldehyde and hydrocyanic acid gives α-cyano-m-phenoxybenzyl alcohol. In the presence of pyridine, dibromochrysantheyl chloride reacts with (+) α-cyano-phenoxybenzyl alcohol to obtain deltamethrin.

●  Dibromochrysanthemic acid is esterified with α-cyano-3-phenoxybenzyl alcohol to obtain deltamethrin; or dibromochrysanthemic acid is acyl chlorinated with thionyl chloride to generate dibromochrysanthemic acid chloride, Then react with α-cyano-3-phenoxybenzyl alcohol. Raw material consumption quota: dibromochrysanthemic acid 640kg/t, α-cyano-3-phenoxybenzyl alcohol 460kg/t.

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