Nitenpyram

Nitenpyram 

CAS Registry Number :150824 -47-8 

English name: Nitenpyram 

Chemical Name: (E)-N-(6 - chloro -3-- pyridylmethyl)-N-ethyl-N '- methyl -2-- nitro-ethyl diamine 

(E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N-methyl-2-nitrovinylidenediamine 

Other names: imidacloprid amine 

Molecular formula: C11H15ClN4O2 

MW: 270.72 

Structure: 

Properties: pure product is light yellow crystals, melting point 83-84 ℃, density of 1.40 (26 ℃). Vapor pressure of 1.1 × 10-9Pa (25 ℃). Solubility (g / L, 20 ℃): Water (pH = 7) 840, 700 chloroform, acetone 290, xylene 4.5. 

Toxicity: Acute oral LD50: male 1680mg/Kg, female 1575 mg / Kg; mouse acute oral LD50: male 867mg/Kg, female 1281 mg / Kg; rat acute dermal LD50: male, female> 2000mg / Kg; rat inhalation LC50 (4 小时): 5.8g / L; quail LD50:> 2250mg/Kg, ducks 1124mg/Kg. quails and ducks LC50: 5620ppm. Carp LC50 (96 小时):> 1000mg / L. This product is a slight stimulation of rabbit eyes, on the rabbit skin irritation. No teratogenic, mutagenic, carcinogenic effects. 

Role of the characteristics and insecticidal spectrum: is tobacco Imide pesticides. Major role in the insect nervous, axis of the insect nerve block has the role of synaptic receptors. Excellent absorption and penetration within the role, with less, low toxicity, persistence length, safe and injury to crops, etc., are widely used in horticulture and agriculture control Homoptera and Hemiptera pests, persistence can be up to 14 days. Can be widely used in rice, wheat, cotton, cucumber, eggplant, radish, tomato, potato, melon, watermelon, peach, apple, pear, citrus, grapes, tea on the prevention and treatment of various planthoppers, aphids, thrips, whitefly whiteflies, leafhoppers, thrips, etc., have been resistant to traditional pesticides pests have better control effect, is by far the latest development of nicotine pesticide products. 

Usage: 

1. Controlling Vegetable tabaci, whitefly with 50% nitenpyram soluble granules 10000 ~ 15000-fold diluted evenly spray, when used in greenhouse attention to the surrounding wall and should be sprayed with liquid films. 

2. Planthopper with 50% control of water nitenpyram soluble granules 10000 ~ 15000-fold diluted evenly spray, spray spray when the focus in the lower part of the rice. 

3. Control aphids with 50% of vegetables nitenpyram 20000-25000 times diluted soluble granules evenly spray. 

4. The control of cotton aphids on the dosage of 3-4 g / kg foliar spray 45-60 acres exchange water, spray even when you do good, or the diluted spray evenly times 15000-20000. 

5. Thrips control of 50% vegetable nitenpyram soluble granules diluted 15,000 to 20,000 times the uniform spray. 

6. Against tea leafhopper, tea spiniferus with 50% nitenpyram soluble granules agent 10000 ~ 15000-fold diluted spray evenly. 

7. Aphid control fruit even when the spray-fold diluted 12500-15000. 

Formulation: 10% of solution agent, 50% of the soluble granule, 1.0% and 0.25% powder granules 

Production methods: 1,1,1,1 - trichloro -2-- Preparation of nitroethane: in concentrated hydrochloric acid and concentrated nitric acid mixture, dropping 1,1 - dichloroethylene, control temperature 14 ℃ ~ 17 ℃, stirring 1h, heated to <22 ℃, stir 1.5h. The lower ether extract, MgSO4 dried, concentrated, have 1,1,1 - trichloro -2-- nitroethane. 

2,1,1 - dimethyl sulfur -2-- preparation of nitro-ethylene mixture of carbon disulfide and nitromethane is heated to (30 ℃ ~ 35 ℃), stirring was added KOH powder in batches, stirring 3 ~ 4h, cooling, precipitation of yellow solid, water soluble and ethanol, overnight, a large number of solid precipitation. To the solid dissolved in water, dropping dimethyl sulfate, the reaction temperature is 15 ℃, reaction time 4h, filtered solid as crude product was brown. Recrystallization yellow crystals. 

3, N-ethyl -2-- chlorine -5-- pyridine Preparation of methyl amine: the 2 - chloro -5-- chloromethylpyridine triethylamine at room temperature dropped into the solution, stir 1.5h, concentrate, residue neutralization, ether extraction, drying, steaming out of ether, a yellow liquid. 

4 nitenpyram synthesis: the N-ethyl -2-- chlorine -5-- pyridine solution of methyl amine in ethanol was added 1,1 - dimethyl sulfur -2-- nitro mixture of ethylene and ethanol , the reflux 3h, cooled to room temperature, vacuum concentration, and a corresponding intermediate product, and then this intermediate product, methylamine aqueous solution and ethanol mixture is heated, stirring, reflux 1h, the mixture was cooled to room temperature, vacuum concentration , the crude product. Ethanol recrystallization, nitenpyram yellow crystal, melting point 83 

The key intermediate 2 - chloro -5-- chloromethylpyridine. 2 - chloro -5-- chloromethylpyridine is an important pesticide intermediates, not only for the synthesis of nitenpyram, or other important neonicotinoid pesticide imidacloprid, acetamiprid, thiacloprid other intermediates. 2 - chloro -5-- chloromethylpyridine research and production with imidacloprid, nitenpyram of the rise. The main method of industrial production at home and abroad are: ① the 3 - methyl-pyridine N-oxide as raw material through the reaction of 3 - chloro methyl pyridine, and then be directed chloride; ② Central lawful, benzyl amine and aldehyde reaction After ring chlorination to give 3 - chloromethyl pyridine, and then get through the chlorination; ③ Rayleigh domestic researchers developed in the United States direct cyclization cyclopentadiene, based on the development of cyclopentadiene as raw materials through customs cyclization direct preparation of 2 - chloro -5-- chloromethylpyridine, easy to get to the line of raw materials, production costs are lower, the current domestic Champ Dalian Chemical Industry Co., Ltd., Jiangsu Chemical Pesticide Group Corporation, Jiangsu Suke Sheng Co., Ltd. to use more The production of; ④ Jiangsu Pesticide Research Institute has developed to the production of morpholine as the raw material routes to morpholine as the raw material through the N-allyl morpholine, 1 - chloro -2-- (4 - morpholinyl) -3-- methyl Central butyl nitrile, 2 - chloro -4-- formyl nitrile E, 2 - chloro -5-- pyridine intermediates Synthesis of 2 - chloro -5-- chloromethylpyridine, the method has low cost of raw materials, mild reaction conditions etc., with industrial prospects.