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Spiroheterocyclic tetrahydropyran compound as well as preparation method and application thereof

A technology for pyran compounds and spiro heterocycles, which is applied in the field of spiro heterocycle tetrahydropyran compounds and their preparation, and can solve problems such as drop

Active Publication Date: 2022-04-29
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the effect of spirotetramat on controlling diseases and insect pests decreased significantly at lower application concentrations, and in recent years, with the gradual increase in the use of spirotetramat, the resistance of diseases and insect pests has also gradually increased.

Method used

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  • Spiroheterocyclic tetrahydropyran compound as well as preparation method and application thereof
  • Spiroheterocyclic tetrahydropyran compound as well as preparation method and application thereof
  • Spiroheterocyclic tetrahydropyran compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] This embodiment provides a preparation method of the compound shown in formula (III):

[0082] Add 500g of dichloromethane and 68.7g of furfuryl alcohol (0.7mol) into a 1L four-neck flask, control the temperature at 0-5°C, add 173g (1.0mol) of m-chloroperoxybenzoic acid, keep stirring for 6 hours, remove insoluble matter by filtration, Control the temperature of the obtained clarified mother liquor at 0-5°C, add 80.8g (0.8mol) of triethylamine, stir for 10min, slowly drop in 60.4g (0.77mol) of acetyl chloride, keep it warm for 2h after the dripping, and then pour into the reaction solution Add 50 mL of saturated sodium bicarbonate solution, stir for 30 min, separate the layers, extract the aqueous layer with 30 mL of dichloromethane x 2 times, combine the organic phases, and dry over anhydrous magnesium sulfate to obtain 5-carbonyl-5,6-dihydro-2H- A solution of pyran-2-yl acetate in dichloromethane;

[0083] Add 84 g (1.4 mol) of isopropanol to the dried 5-carbonyl-5,6...

Embodiment 2-3

[0091] Compound IIIb and Compound IIIc were synthesized by referring to the above-mentioned method, and the specific process parameters can be obtained by routine adjustment in accordance with Example 1.

[0092]

Embodiment 4

[0094] The preparation of compound shown in formula (IV):

[0095] Weigh 120 g (1.52 mol) of ammonium bicarbonate, add 20 g (0.4 mol) of sodium cyanide into a mixed solution of 30 g of water and 100 g of tetrahydrofuran, stir and suspend, add 60.6 g (0.38 mol) of compound IIa prepared in Example 3 at room temperature, After mixing evenly, raise the temperature to 55°C and keep it warm for 6h, filter, wash the filter cake with 20g of tetrahydrofuran, combine the mother liquors, concentrate to dryness, and dry to obtain 85.7g of white solid (Compound IVa), with a yield of 98% and a purity of 96.2%.

[0096]

[0097] Compound IVb and Compound IVc were synthesized by referring to the above-mentioned method, and the specific process parameters could be obtained by routine adjustment according to the above-mentioned examples.

[0098]

[0099]

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PUM

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Abstract

The invention provides a spiroheterocyclic tetrahydropyran compound as well as a preparation method and application thereof. The structure of the spiroheterocyclic tetrahydropyran compound is shown as a formula (I). The compound disclosed by the invention has stable chemical properties, higher insecticidal activity and excellent insecticidal activity under the condition of lower medicament concentration, particularly has higher insecticidal activity on aphids and red spiders, is a novel and efficient biopesticide, can relieve the drug resistance of diseases and pests to spirotetramat or abamectin drugs, and has a broad application prospect. The compound has a very high pesticide research value, and has a wide application prospect in agriculture.

Description

technical field [0001] The invention relates to the field of agricultural chemicals and preparation technology, in particular to a spiroheterocyclic tetrahydropyran compound and its preparation method and application. Background technique [0002] The spiro compound has a rigid structure and a stable structure, and has important applications in many fields such as medicine, pesticides, and polymer adhesives. The planes of the two rings of the spiro compound are perpendicular to each other, and the heterocyclic spiro compound may also have special properties such as spiro conjugation, spiro hyperconjugation or anomer effect that general organic compounds do not have. Under certain conditions, due to the existence of the chiral axis, asymmetric molecules or asymmetric molecules can be formed, and the chiral spiro ring has strong rigidity and is not easy to racemize, which is incomparable to chiral carbon. Therefore, in recent years, spiro compounds have broad application pros...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107A01N43/90A01P7/04A01P7/02
CPCC07D491/107A01N43/90
Inventor 李立华王博侯红欣高永民田学芳孙良赵建芹李志峰贾成国
Owner HEBEI VEYONG BIO CHEM
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