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Tetrazole phosphate compound with nematocidal activity and synthesizing method

A technology of tetrazolium phosphate and azole phosphate, applied in the field of organic compound synthesis, can solve the problems of less cross-resistance, short residual effect period, easy to be degraded and the like, achieve good nematicidal activity, low cost, and easy realization of reaction conditions Effect

Active Publication Date: 2016-11-09
ANHUI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Organophosphorus insecticides have the advantages of a wide variety, a wide range of applications, a wide insecticidal spectrum, high efficiency and quick killing, less cross-resistance, easy detoxification, and easy degradation. They also have different insecticidal effects such as contact killing, stomach poisoning, and fumigation; 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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  • Tetrazole phosphate compound with nematocidal activity and synthesizing method
  • Tetrazole phosphate compound with nematocidal activity and synthesizing method
  • Tetrazole phosphate compound with nematocidal activity and synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Preparation of intermediate 1-hydroxymethyl-5-benzyltetrazole Ⅱ-1

[0038] To a dry reaction flask with a thermometer, add 2 mL of N,N-dimethylformamide and 0.30 g (3 mmol) of 1-hydroxymethyl tetrazole, 0.40 g (3.17 mmol) of benzyl chloride and 0.62 g (4.50 mmol) of Potassium carbonate water (by molar ratio, hydroxymethyl tetrazole:halogenated compound:alkali=1:1.06:1.5), slowly heated to 100°C under stirring to react overnight. The reaction was cooled to room temperature and poured into 8 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 a crude product, which was purified on a silica gel column with ethyl acetate: petroleum ether = 1:5 (v / v) to obtain the intermediate 1-hydroxymethyl-5-benzyltetrazole II-1, which was white Solid, yield 43%, structural formula is as follows:

[0039]

...

Embodiment 2

[0048] (1) Preparation of intermediate 2-hydroxymethyl-5-benzyltetrazole II-2

[0049]To a dry reaction flask with a thermometer, add 2 mL of N,N-dimethylformamide and 0.30 g (3 mmol) of 2-hydroxymethyl tetrazole, 0.40 g (3.17 mmol) of benzyl chloride and 0.68 g (4.95 mmol) of Potassium carbonate water (in molar ratio, hydroxymethyl tetrazole:halogenated compound:alkali=1:1.06:1.65), slowly heated to 100°C under stirring to react overnight. The reaction was cooled to room temperature and poured into 8 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 a crude product, which was purified on a silica gel column with ethyl acetate: petroleum ether = 1:5 (v / v) to obtain the intermediate 2-hydroxymethyl-5-benzyltetrazole II-2, which was white Solid, yield 44.5%, structural formula is as follows:

[0050] ...

Embodiment 3

[0059] (1) Preparation of intermediate 2-hydroxymethyl-5-p-chlorobenzyltetrazole Ⅱ-3

[0060] In a dry reaction flask with a thermometer, add 2mL N, N-dimethylformamide and 0.30g (3mmol) 2-hydroxymethyltetrazole, 0.51g (3.17mmol) p-chlorobenzyl chloride and 0.51g (5.0mmol) ) triethylamine (in molar ratio, hydroxymethyltetrazole:halogenated compound:alkali=1:1.06:1.67), slowly heated to 100°C under stirring and reacted overnight. The reaction was cooled to room temperature and poured into 8 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 a crude product, which was purified on a silica gel column with ethyl acetate: petroleum ether = 1:5 (v / v) to obtain the intermediate 2-hydroxymethyl-5-p-chlorobenzyltetrazole II-3, It is a white solid with a yield of 40%. The structural formula is as follows:

[006...

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PUM

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Abstract

The invention relates to a tetrazole phosphate compound with nematocidal activity. The chemical formula of the tetrazole phosphate compound is shown as the general formula I in the description, wherein in the formula I, R1 is alkyl or phenyl or benzyl or halogenated phenyl or halogenated benzyl with 1-6 carbon atoms, R2 is a hydrogen atom or an acetic ester group or phenyl or benzyl or halogenated phenyl or halogenated benzyl, and the position of hydroxymethyl is the first digit or the second digit. Biological assay experiment results show that by means of the tetrazole phosphate compound at the concentration of 50 mg / L, the corrected death rate of hirschmanniella oryzae, wheat cyst nematode and grape parasitic nematodes within 24 h is 65-94%, and high nematocidal activity is achieved.

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 a wide variety, a wide range of applications, a wide insecticidal spectrum, high efficiency and quick killing, less cross-resistance, easy detoxification, and easy degradation. They also have different insecticidal effects such as contact killing, stomach poisoning, and fumigation; 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. The current development tre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6524A01N57/16A01P5/00
CPCA01N57/16C07F9/6524
Inventor 王毅花日茂吴祥为刘佳那日松唐俊范世锁王振滕婧
Owner ANHUI AGRICULTURAL UNIVERSITY
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