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Cis-nitenpyram compound containing amino-acid ester as well as preparation method and application thereof

A technology of amino acid esters and nitenpyram, which is applied in the field of cis-nitenpyram compounds and their preparation, to achieve low toxicity, good insecticidal effect and the effect of promoting the growth of crops

Inactive Publication Date: 2012-01-04
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But up to now, countries in the world are seldom reported on the production and use of neonicotinoid insecticide pesticides containing amino acid esters, and domestic and foreign patent documents and publications are also to the neonicotinoid insecticides containing amino acid esters. less reported

Method used

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  • Cis-nitenpyram compound containing amino-acid ester as well as preparation method and application thereof
  • Cis-nitenpyram compound containing amino-acid ester as well as preparation method and application thereof
  • Cis-nitenpyram compound containing amino-acid ester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] cis-(+)-2-[4-N-ethyl-N-(6-chloro-3-pyridylmethyl)amino]-3-methyl-5-nitro-1,2,3,6- Tetrahydropyrimidin-1-yl]-4-carboxamido-butyric acid methyl ester (Ia);

[0055] no 1 =0n 2 = 2 R 1 =CH 3

[0056]Add 20mL of methanol into a 100mL three-necked bottle (with a dry lye absorption device), cool it in an ice-salt bath to -10°C to -15°C, add 3.60mL of freshly steamed thionyl chloride dropwise under magnetic stirring, and control the dropping rate so that The reaction temperature does not exceed -5°C, and after 1 hour of reaction, the temperature is naturally raised to room temperature to obtain a thionyl chloride-methanol solution. Add 1.46 g (0.01 mol) of glutamine to the thionyl chloride-methanol solution, heat to reflux for 1 hour, remove the solvent and excess thionyl chloride under reduced pressure, and proceed directly to the next step without purification.

[0057] The product after the first step reaction and 2.707g nitenpyram (0.01mol), 1.8mL triethylamine (0....

Embodiment 2

[0063] cis-(+)-2-[4-N-ethyl-N-(6-chloro-3-pyridylmethyl)amino]-3-methyl-5-nitro-1,2,3,6- Tetrahydropyrimidin-1-yl]-4-carboxamido-butyric acid ethyl ester (Ib);

[0064] no 1 =0 n 2 = 2 R 1 =CH 2 CH 3

[0065] Add 20mL of ethanol to a 100mL three-necked bottle (with dry lye absorption device), cool in an ice-salt bath to -10°C to -15°C, add 3.60mL of freshly steamed thionyl chloride dropwise under magnetic stirring, and control the dropping rate so that The reaction temperature does not exceed -5°C, and after 1 hour of reaction, the temperature is naturally raised to room temperature to obtain a thionyl chloride-ethanol solution. Add 1.46 g of glutamine (0.01 mol) to the thionyl chloride-ethanol solution, heat to reflux for 1 hour, remove the solvent and excess thionyl chloride under reduced pressure, and proceed directly to the next step without purification.

[0066] The product after the first step reaction and 2.707g nitenpyram, 1.8mL triethylamine (0.012mol), and ...

Embodiment 3

[0072] cis-(+)-2-[4-N-ethyl-N-(6-chloro-3-pyridylmethyl)amino]-3-methyl-5-nitro-1,2,3,6- Tetrahydropyrimidin-1-yl]-4-carboxamido-butyric acid n-propyl ester (Ic);

[0073] no 1 =0n 2 = 2 R 1 =CH 2 CH 2 CH 3

[0074] Add 20mL of n-propanol into a 100mL three-necked bottle (with a dry lye absorption device), cool it in an ice-salt bath to -10°C~-15°C, add 3.60mL of freshly distilled thionyl chloride dropwise under magnetic stirring, and control the dropwise The acceleration keeps the reaction temperature not exceeding -5°C, and after 1 hour of reaction, the temperature is naturally raised to room temperature to obtain a thionyl chloride-n-propanol solution. Add 1.46 g of glutamine (0.01 mol) to the thionyl chloride-n-propanol solution, heat to reflux for 1 hour, remove the solvent and excess thionyl chloride under reduced pressure, and proceed directly to the next step without purification.

[0075] The product after the first step reaction and 2.707g nitenpyram (0.01m...

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Abstract

The invention relates to the field of pesticides and discloses a cis-nitenpyram compound containing an amino-acid ester as well as a preparation method and application thereof. The compound has a structure represented by a formula II. The preparation method comprises the following steps: adding formaldehyde and triethylamine in amino-acid ester hydrochloride and high-efficiency low-toxicity anabasine pesticide nitenpyram which are used as raw materials; and carrying out microwave reaction so as to obtain the cis-nitenpyram compound containing the amino-acid ester. The cis-nitenpyram compound containing the amino-acid ester has the advantages of high-efficiency insecticidal activity, good insecticidal effect, low toxicity and simple use method, is safe for human and livestock, and can promote the growth of crops; and the preparation method is simple and short in reaction time.

Description

technical field [0001] The invention belongs to pesticides and insecticides, in particular to a cis-nitenpyram compound containing amino acid ester and its preparation method and application. Background technique [0002] Neonicotinoid insecticides are the fourth generation of insecticides following organophosphorus, carbamate, and pyrethroid insecticides. Neonicotinoids, as nicotinic acetylcholine receptors (nAChRs) agonists, act selectively on the nervous system (nAChRs) of insects. Due to their unique insecticidal mechanism and high efficiency and low toxicity, neonicotinoids have rapidly become the mainstay of modern agriculture. New varieties of high-efficiency and low-toxicity pesticides are needed. Since neonicotinoid compounds have C=N or C=C double bonds, neonicotinoid compounds have two configurations, cis and trans. Nitenpyram developed by Takeda Corporation of Japan is an excellent insecticide in the trans-configuration neonicotinoids, which has special effects...

Claims

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Application Information

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IPC IPC(8): C07D401/12A01N43/54A01P7/04
Inventor 薛思佳刘天雁孙传文
Owner SHANGHAI NORMAL UNIVERSITY
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