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Organophosphorus compound containing tetrazole heterocycle and its synthesis method and application

A synthesis method and technology for azole compounds, applied in the field of organic compound synthesis, can solve the problems of easy degradation, short residual period, less cross-resistance, etc., and achieve the effect of improving the efficiency of activity screening

Active Publication Date: 2017-06-30
濮阳天健生物科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Organophosphorus insecticides have the advantages of wide variety, wide range of application, wide insecticidal spectrum, high efficiency and quick killing, less cross resistance, easy detoxification, and easy degradation. The disadvantage is that most varieties have high toxicity, short residual period, easy to be degraded in the outside world or in animals, and easy to decompose under alkaline conditions

Method used

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  • Organophosphorus compound containing tetrazole heterocycle and its synthesis method and application
  • Organophosphorus compound containing tetrazole heterocycle and its synthesis method and application
  • Organophosphorus compound containing tetrazole heterocycle and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Intermediate 1-Benzyl-1H-tetrazole III-1

[0030]

[0031] Add 1mL of N,N-dimethylformamide, tetrazole (2mmol), benzyl chloride (2.1mmol) and anhydrous potassium carbonate (3mmol) to a dry reaction flask with a thermometer, and slowly heat to 100°C under stirring React overnight. The reaction was cooled to room temperature and poured into 4 ml of water. Transfer to a separatory funnel, extract with ethyl acetate, collect the organic phase, wash with water, wash with brine, dry, and filter. The filtrate was concentrated to dryness under reduced pressure to obtain the crude product of the mixture of III-1 and IV-1, which was precipitated by recrystallization or purified by silica gel column with ethyl acetate:petroleum ether=1:5 (V / V) to obtain white solid III-1, which was recovered rate 43%. 1 H NMR (400 MHz, Chloroform-d) δ 8.56 (d, J = 5.5 Hz, 1H), 7.51 - 7.25 (m, 6H), 5.61 (s, 2H).

Embodiment 2

[0032] Example 2: 1-(2-chlorobenzyl)-1H-tetrazolyl-diethyl phosphate

[0033]

[0034] Under nitrogen protection, 1-benzyltetrazole (1 mmol) was added to the dry reactor, and 10 mL of dry THF was added. Cool down to below -10°C, and slowly add butyllithium (2.2mmol, 1M, 1.1eq) dropwise. After the dropwise addition, react at this temperature for 1 hour, and then add diethyl chlorophosphate (1mmol, 1eq) dropwise. After the dropwise addition, this temperature was maintained for 1 hour. Rising to room temperature, stirring for 1 hour, the raw materials were completely reacted. Washed twice with water and dried over anhydrous magnesium sulfate. Filtrate, spin and concentrate the solvent to obtain a crude product, which is purified by a silica gel column with ethyl acetate:petroleum ether=1:8 (V / V), and the yield is 91%. 1H NMR (400MHz, Chloroform-d) δ7.50–7.33(m, 5H).4.49(d, J=8.7Hz, 2H), 4.28–4.03(m, 4H), 1.34(td, J=7.1, 1.2 Hz, 6H). 13 CNMR (101MHz, CDCl 3 )δ134.48, 134...

Embodiment 3

[0035] Example 3: 1-(2-chlorobenzyl)-1H-tetrazolyl-diethyl phosphate

[0036]

[0037] Add 1mL of N,N-dimethylformamide, tetrazole (2mmol), 2-chlorobenzyl (2.1mmol) and anhydrous potassium carbonate (3mmol) into a dry reaction flask with a thermometer, and heat slowly under stirring React overnight at 100°C. The reaction was cooled to room temperature and poured into 4 ml of water. Transfer to a separatory funnel, extract with ethyl acetate, collect the organic phase, wash with water, wash with brine, dry, and filter. The filtrate was concentrated to dryness under reduced pressure to obtain the crude product of the mixture of III-2 and IV-2 with a yield of 95%.

[0038] Under nitrogen protection, the crude product of the mixture of III-2 and IV-2 was added to a dry reactor, and 10 ml of dry tetrahydrofuran was added. Cool down to below -10°C, and slowly add butyllithium (2.2mmol, 1M, 1.1eq) dropwise. After the dropwise addition was completed, the reaction was carried ou...

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PUM

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Abstract

The invention relates to organophosphorus compounds containing tetrazole heterocycle and a synthetic method and application of the organophosphorus compounds. The organophosphorus compounds containing tetrazole heterocycle provided by the invention are described in the general formula I and the general formula II. The preparation method comprises the following steps: reacting tetrazole with halide to generate multifarious substituted tetrazole III and IV; reacting substituted tetrazole III or IV with chloride phosphate compounds under the action of alkali, so as to obtain the organophosphorus compounds I and II containing tetrazole heterocycle. The invention provides an easy, feasible and novel method for synthesis of multifarious tetrazolium phosphate active compounds; the compounds required to be protected are not reported; the synthetic method provided by the invention is easy and feasible, and is applicable to preparation of multifarious small molecule compound library; the compounds are subjected to nematode disease activity related screening.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and relates to a tetrazole phosphate derivative, a preparation method thereof, and an application of nematicide activity. Background technique [0002] Organophosphorus insecticides are a class of commonly used agricultural insecticides, and their insecticidal mechanism is to inhibit the activity of cholinesterase and poison the pests. Organophosphorus insecticides have the advantages of wide variety, wide range of application, wide insecticidal spectrum, high efficiency and quick killing, less cross resistance, easy detoxification, and easy degradation. The disadvantages are that most varieties have high toxicity, short residual period, easy to be degraded in the outside world or in animals, and easy to decompose under alkaline conditions. The current development trend of organophosphorus insecticides is as follows: 1. Develop low-toxic and high-efficiency pesticide varieties...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6524C07F9/6558A01N57/24A01P5/00A01P3/00A01P7/04A01P13/00
CPCA01N57/24C07F9/6524C07F9/65583C07F9/65586
Inventor 刘佳那日松李洪连张猛蒋士军彭伟东郭线茹周琳李文明何睿卢世超孙铖侯伯男王长青刘炳杉
Owner 濮阳天健生物科技有限公司
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