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(Z) type tetrahydro-pyrimidine carboxylic ester derivative and preparation method thereof

A technology of tetrahydropyrimidine carboxylate and derivatives, which is applied in botany equipment and methods, chemicals for biological control, biocides, etc., can solve important role neglect, neonicotinoid insecticide research, Less production and use, etc., to achieve good effect, good insecticidal activity, and environmental safety

Inactive Publication Date: 2010-08-04
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, chemists and pesticide experts from all over the world have a full understanding of the high-efficiency and low-toxicity insecticidal effects of neonicotinoid insecticides containing amino acid esters, but their important role in promoting crop growth is often overlooked. ignore
As a result, there is very little research, production and use of neonicotinoid insecticides containing amino acid esters, and there are very few reports on neonicotinoid insecticides containing amino acid esters in domestic and foreign patent documents and public publications.

Method used

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  • (Z) type tetrahydro-pyrimidine carboxylic ester derivative and preparation method thereof
  • (Z) type tetrahydro-pyrimidine carboxylic ester derivative and preparation method thereof
  • (Z) type tetrahydro-pyrimidine carboxylic ester derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of (Z)-4-[(6-chloro-3-pyridylmethyl)ethylamino]-3-methyl-5-nitro-1-1,2,3,6-tetrahydropyrimidinyl-3 - methyl propionate (1a).

[0067] 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 4.453g of β-alanine to the thionyl chloride-methanol solution, heat and reflux for 1 hour, remove the solvent and excess thionyl chloride under reduced pressure to obtain a white solid, which is recrystallized with absolute ethanol-ether to obtain a white Needle crystals, namely β-alanine methyl ester hydrochloride (II a), the yield was 96.54%.

[0068] Dissolve 2.707g of nitenpyram, 1.675g o...

Embodiment 2

[0073] Preparation of (Z)-4-[(6-chloro-3-pyridylmethyl)ethylamino]-3-methyl-5-nitro-1-1,2,3,6-tetrahydropyrimidinyl-3 - ethyl propionate (1b).

[0074] Add 20mL of ethanol to a 100mL three-necked bottle (with a 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 rate of addition to make the reaction The 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 4.453g of β-alanine to the thionyl chloride-ethanol solution, heat to reflux for 1 hour, remove the solvent and excess thionyl chloride under reduced pressure to obtain a white solid, which is recrystallized with absolute ethanol-ether to obtain white Needle crystals, namely β-alaninate ethyl hydrochloride (II b), the yield was 95.76%.

[0075] Dissolve 2.707g of nitenpyram, 1.843g of β-alanin...

Embodiment 3

[0080] Preparation of (Z)-4-[(6-chloro-3-pyridylmethyl)ethylamino]-3-methyl-5-nitro-1-1,2,3,6-tetrahydropyrimidinyl-3 - isopropyl propionate (1c).

[0081] Add 20mL of isopropanol to a 100mL three-necked bottle (with dry lye absorption device), cool 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 dropping rate Keep the reaction temperature below -5°C. After 1 hour of reaction, the temperature is naturally raised to room temperature to obtain a thionyl chloride-isopropanol solution. Add 4.453g of β-alanine to the thionyl chloride-isopropanol solution, heat to reflux for 2 hours, remove the solvent and excess thionyl chloride under reduced pressure to obtain a white solid, which is recrystallized with absolute ethanol-ether White needle-like crystals, namely β-alanine isopropyl ester hydrochloride (II c), were obtained with a yield of 90.28%.

[0082] 2.707g of nitenpyram, 2.012g of β-alanin...

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PUM

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Abstract

The invention belongs to a pesticide and relates to a (Z) type tetrahydro-pyrimidine carboxylic ester derivative and a preparation method thereof. The structure of the target compound of the invention is expressed by a general formula (I). The preparation method comprises the following steps of: firstly preparing hydrochloride of amino-acid ester; and then putting the prepared hydrochloride of the amino-acid ester, nitenpyram, 37% formaldehyde and triethylamine in a three-mouth flask for microwave reaction for 25 minutes to prepare the target compound with the general formula (I) at the temperature of about 65 DEG G. The (Z) type tetrahydro-pyrimidine carboxylic ester derivative has the advantages of high insecticidal activity, good effect, low toxicity to people and livestock and safe use, can be made into various dosage forms with convenient use, and promotes the growth of crops.

Description

technical field [0001] The invention belongs to crop insecticides, in particular to a (Z)-type tetrahydropyrimidine carboxylate derivative with insecticidal activity and a preparation method thereof. Background technique [0002] Insecticides and pesticides used in agricultural production are important means of agricultural production for killing pests that harm crop growth and ensuring crop yield increase. Chemical insecticides and pesticides have played an important role in the development of agricultural production because of their good insecticidal effect and fast insecticidal speed. The long-term use of chemical pesticides has also brought some negative effects; for example, the residues of pesticides in plants, agricultural products, food, and soil have exceeded the specified indicators, causing harm to people's bodies and affecting the health of crops. growth has an impact. In order to reduce soil environmental pollution, promote crop growth, ensure people's food sa...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D405/14C07D401/14A01N43/54A01P7/04A01P21/00
Inventor 薛思佳许效
Owner SHANGHAI NORMAL UNIVERSITY
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