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Cis-nitenpyram analogue containing glycylglycine, its preparation method and its application

A technology of bisglycine dipeptide and glycine dipeptide, which is applied in the field of its preparation and cis-nitenpyram analogs, can solve the problems of shortening the time required for the reaction and high insecticidal activity, and achieves safety for humans and animals, High insecticidal activity and the effect of shortening the reaction time

Inactive Publication Date: 2014-04-09
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cis-nitenpyram analogue containing diglycyl dipeptide ester can overcome the instability and poor hydrophobicity of traditional nitenpyram, has high insecticidal activity, and pests are not easy to develop drug resistance to it, and can Promote the growth of crops, in addition, the microwave heating method is used to greatly shorten the time required for the reaction

Method used

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  • Cis-nitenpyram analogue containing glycylglycine, its preparation method and its application
  • Cis-nitenpyram analogue containing glycylglycine, its preparation method and its application
  • Cis-nitenpyram analogue containing glycylglycine, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Preparation of cis-3-methyl-4-(N-6-chloro-3-pyridylmethyl)ethylamino-1-(N-methoxycarbonylmethyl)acetamido-5-nitro-1,2 , 3,6-tetrahydropyrimidine (Ia);

[0075] 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 ~ -15°C, add 3.60mL of freshly distilled thionyl chloride dropwise under magnetic stirring, and control the dropping rate so that The reaction temperature did not exceed -5°C. After 1 hour of reaction, the temperature was naturally raised to room temperature to obtain a thionyl chloride-methanol solution. Add 1.321g of diglycyl dipeptide to the thionyl chloride-methanol 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 from absolute ethanol-ether to obtain White needle-like crystals, that is, diglycine dipeptide methyl ester hydrochloride (IIa), the yield is 95.24%.

[0076] 2.707g ...

Embodiment 2

[0082] Preparation of cis-3-methyl-4-(N-6-chloro-3-pyridylmethyl)ethylamino-1-(N-ethoxycarbonylmethyl)acetamido-5-nitro-1,2 , 3,6-tetrahydropyrimidine (Ib);

[0083] Add 20mL of ethanol to a 100mL three-necked bottle (with 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 dropping rate so that The reaction temperature did not exceed -5°C. After 1 hour of reaction, the temperature was naturally raised to room temperature to obtain a thionyl chloride-methanol solution. Add 1.409g of diglycine dipeptide to the thionyl chloride-ethanol solution, heat to reflux for 1.2 hours, remove the solvent and excess thionyl chloride under reduced pressure to obtain a white solid, which is recrystallized from absolute ethanol-ether to obtain White needle-like crystals, that is, diglycyl dipeptide ethyl ester hydrochloride (IIb), the yield is 92.23%.

[0084] 2.708g nitenpy...

Embodiment 3

[0090] Preparation of cis-3-methyl-4-(N-6-chloro-3-pyridylmethyl)ethylamino-1-(N-n-propoxycarbonylmethyl)acetamido-5-nitro-1, 2,3,6-tetrahydropyrimidine (Ic);

[0091] Add 20mL of n-propanol to a 100mL three-necked bottle (with a dry lye absorption device), cool it in an ice-salt bath to -10°C~-15°C, add 3.70mL of freshly distilled thionyl chloride dropwise under magnetic stirring, and control the dropwise Acceleration keeps the reaction temperature below -8°C, and after 1.5 hours of reaction, the temperature is naturally raised to room temperature to obtain a thionyl chloride-methanol solution. Add 1.321g of diglycine dipeptide to the thionyl chloride-n-propanol solution, heat to reflux for 1.5 hours, remove the solvent and excess thionyl chloride under reduced pressure to obtain a white solid, which can be weighed with absolute ethanol-ether White needle crystals were obtained through crystallization, i.e. diglycine dipeptide n-propyl ester hydrochloride (IIc), with a yield...

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Abstract

The invention relates to a cis-nitenpyram analogue containing glycylglycine, a general formula of a structure of the analogue is: simultaneously the invention also provides a preparation method of cis-nitenpyram analogue containing glycylglycine, and provides an application of the analogue in the agricultural insecticidal field, the cis-nitenpyram analogue containing glycylglycine can be prepared into pesticide dosage types such emulsions, aqueous suspensions or emulsions in water. According to the invention, the cis-nitenpyram analogue containing glycylglycine shown in the general formula (I) has high activity and low toxicity, is safe to people and animals and promotes the growth of crops. In addition, the cis-nitenpyram analogue of the invention uses a microwave heating method which greatly shortens the required time of the reaction.

Description

technical field [0001] The invention belongs to the field of crop insecticide, in particular, relates to a nitenpyram analogue, its preparation method and application thereof, more specifically, relates to a cis-nitenpyram analogue containing diglycine dipeptide ester substances, their preparation methods and their applications. Background technique [0002] The discovery of neonicotinoid insecticides can be considered a milestone in agrochemical research over the past three decades. Neonicotinoid insecticides are the fourth generation of insecticides following organophosphorus, carbamate, and pyrethroid insecticides. As nicotinic acetylcholine receptors (nAChRs) agonists that act selectively on the nervous system (nAChRs) of insects, neonicotinoids not only show high affinity for (nAChRs), but also show non-ionizing Physicochemical properties such as high temperature resistance and moderate water solubility. Because of its unique insecticidal mechanism and high efficienc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/068C07K5/078A01N43/66A01N43/54A01P7/04
Inventor 孙传文陈艳霞薛思佳
Owner SHANGHAI NORMAL UNIVERSITY
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