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L-alpha-amino acid ester contained Z-configuration anabasine pesticide and preparation method thereof

A neonicotinoid, amino acid ester technology, applied in the directions of insecticides, biocides, biocides, etc., can solve problems such as the production and use of pesticides that have never been seen in neonicotinoid insecticides, and achieve obvious novelty and efficiency. Creativity, remarkable utility, high yield and high purity effects

Active Publication Date: 2009-10-21
SHANGHAI NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, all countries in the world have not seen the production and use of neonicotinoid pesticides containing L-α-amino acid esters
There are no reports of neonicotinoid insecticides containing L-alpha-amino acid esters in domestic and foreign patent documents and publications

Method used

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  • L-alpha-amino acid ester contained Z-configuration anabasine pesticide and preparation method thereof
  • L-alpha-amino acid ester contained Z-configuration anabasine pesticide and preparation method thereof
  • L-alpha-amino acid ester contained Z-configuration anabasine pesticide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of (2H,6H)-4-[[(6-chloro-3-pyridylmethyl)ethylamino]-2,6-dihydro-3-methyl-5-nitro]-1-pyrimidineacetic acid ethyl Esters (Ia):

[0051] Put 20mL of absolute ethanol and 3.76g of glycine in a 100mL round-bottomed three-necked flask, cool it with an ice-salt bath, add 6mL of freshly distilled thionyl chloride dropwise, keep the temperature below -5°C, and add in about 30 minutes. Finish. After naturally rising to room temperature, it was heated to reflux until all the solids were dissolved, continued to reflux for 15 minutes, and then cooled slightly to obtain a white foamy solid. Remove excess thionyl chloride under reduced pressure, wash with diethyl ether and filter with suction after cooling, and recrystallize with absolute ethanol-diethyl ether to obtain white needle-like crystals (IIa).

[0052] Dissolve 5.30g of nitenpyram, 3.33g of ethyl glycine hydrochloride, 3.3mL of triethylamine and 3.8mL of 37% formaldehyde solution in 30mL of ethanol, and place ...

Embodiment 2

[0057] Preparation of (2H,6H)-4-[[(6-chloro-3-pyridylmethyl)ethylamino]-2,6-dihydro-3-methyl-5-nitro]-1-pyrimidine-( 1'-isopropyl)-ethyl acetate (Ib):

[0058] Put 20mL of absolute ethanol and 5.85g of L-α-leucine in a 100mL round-bottomed three-neck flask, cool with an ice-salt bath, add 6mL of freshly distilled thionyl chloride dropwise, and control the temperature at -5°C Below, it takes about 30 minutes to add. After naturally rising to room temperature, it was heated to reflux until all the solids were dissolved, continued to reflux for 15 minutes, and then cooled slightly to obtain a white foamy solid. Remove excess thionyl chloride under reduced pressure, wash with diethyl ether and filter with suction after cooling, and recrystallize with absolute ethanol-diethyl ether to obtain white needle-like crystals (IIb).

[0059] Dissolve 5.30g of nitenpyram, 4.67g of L-α-leucine ethyl ester hydrochloride, 3.3mL of triethylamine and 3.8mL of 37% formaldehyde solution in 30mL ...

Embodiment 3

[0065] Preparation of (2H,6H)-4-[[(6-chloro-3-pyridylmethyl)ethylamino]-2,6-dihydro-3-methyl-5-nitro]-1-pyrimidine-( 1'-benzyl)-ethyl acetate (Ic);

[0066] Put 20mL of absolute ethanol and 8.25g of L-α-phenylalanine in a 100mL round-bottomed three-neck flask, cool with an ice-salt bath and add 6mL of freshly distilled thionyl chloride dropwise, and control the temperature at -5 Below ℃, add in about 30 minutes. After naturally rising to room temperature, it was heated to reflux until all the solids were dissolved, continued to reflux for 15 minutes, and then cooled slightly to obtain a white foamy solid. Remove excess thionyl chloride under reduced pressure, wash with diethyl ether and filter with suction after cooling, and recrystallize with absolute ethanol-diethyl ether to obtain white needle-like crystals (IIc).

[0067] Dissolve 5.30g of nitenpyram, 5.47g of L-α-phenylalanine ethyl ester hydrochloride, 3.3mL of triethylamine and 3.8mL of 37% formaldehyde solution in 30...

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Abstract

The invention discloses an L-alpha-amino acid ester contained Z-configuration anabasine pesticide and a preparation method thereof. The structure is shown by a general formula (I). The prior anabasine pesticide only has a function of disinsection and has no function of promoting the growth of crops. The preparation method comprises the following steps: preparing a hydrochlorate of an L-alpha-amino acid methyl ester or ethyl ester; adding the prepared hydrochlorate of the L-alpha-amino acid methyl ester or the ethyl ester, nitenpyram, 37 percent formaldehyde and triethylamine into a round-bottom three-necked flask; and placing the round-bottom three-necked flask containing the solution in a microwave reactor, controlling the reaction temperature not more than 75 DEG C, and carrying out microwave reaction for 30 minutes to prepare the L-alpha-amino acid ester contained Z-configuration anabasine pesticide shown by the general formula (I). The L-alpha-amino acid ester contained Z-configuration anabasine pesticide has the advantages of high efficient insecticidal activity, good insecticidal effect, low toxicity, safety of human beings and livestock, crop growth promotion, simple using method, simple preparation method, and short reaction time.

Description

technical field [0001] The invention belongs to pesticides and insecticides, in particular to a Z-configuration neonicotinoid insecticide containing L-alpha-amino acid ester and its preparation. Background technique [0002] 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 efficiency and low toxicity performance, it has quickly become a new type of high efficiency and low toxicity pesticide required by modern agriculture. Since the neonicotinoid compound has a C=N or C=C double bond, the neonicotinoid compound has two configurations of Z form...

Claims

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Application Information

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IPC IPC(8): A01N43/54A01P7/00A01P7/04C07D401/12
Inventor 薛思佳杨定荣金甲陈志明方治坤
Owner SHANGHAI NORMAL UNIVERSITY
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