Diethoxy thiophosphate organophosphorus pesticide hapten and preparation thereof

A technology of diethoxy phosphorothioate and diethoxy phosphorothioate, applied in the field of immunology, can solve problems such as not being well solved, and achieve the effect of good specificity and high titer

Active Publication Date: 2009-07-08
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the key issue of hapten design in this field has not been well resolved

Method used

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  • Diethoxy thiophosphate organophosphorus pesticide hapten and preparation thereof
  • Diethoxy thiophosphate organophosphorus pesticide hapten and preparation thereof
  • Diethoxy thiophosphate organophosphorus pesticide hapten and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Hapten B I (n=0) preparation method

[0030] At 0°C, 0.884g (6.4mmol) of p-hydroxybenzoic acid and 0.898g (16mmol) of KOH were dissolved in 50mL of methanol. While stirring, 1.81 g (9.6 mmol) of diethoxyphosphoryl thiochloride was added dropwise, the temperature was raised to 65°C, and the reaction was stirred for 18 hours. After the reaction was completed, the reaction was concentrated by rotary evaporation, and the obtained crude product was dissolved in ethyl acetate, extracted with 50 mL of 2M NaOH solution, the aqueous layer was acidified with 6M hydrochloric acid, and precipitated, washed with water to obtain 1.05 g of the product, with a yield of 56.4% . ESI-MS analysis (negative) m / z 289[M-H]-; 1H-NMR (400MHz, CDCl 3 and TMS): δ 1.36 (t, J=7.1Hz, 6H, CH 3 ); 4.24(qd,J 1 =7.1Hz,J 2 =7.1Hz,J 3 =7.1Hz,J 4 =10.0Hz, 4H, CH 2 ); 7.26 (d, J=8.1, 2H, ArH); 8.09 (d, J=8.5, 2H, ArH).

Embodiment 2

[0031] Example 2 Hapten B II (n=0) Preparation method

[0032]At 0°C, 0.884g (6.4mmol) of m-hydroxybenzoic acid and 0.898g (16mmol) of KOH were dissolved in 50mL of methanol. While stirring, 1.81 g (9.6 mmol) of diethoxyphosphoryl thiochloride was added dropwise, the temperature was raised to 65°C, and the reaction was stirred for 18 hours. After the reaction was completed, the reaction was concentrated by rotary evaporation, and the obtained crude product was dissolved in ethyl acetate, the solution was concentrated, and chloroform:methanol=8:1 was passed through a silica gel column to obtain 0.5 g of a yellow solid with a yield of 27.0%. ESI-MS analysis (negative) m / z 289[M-H]-; 1H-NMR (400MHz, CDCl 3 and TMS): δ1.37 (t, J=7.0Hz, 6H, CH 3 ); 4.25(qd, J 1 =7.1Hz,J 2 =7.1Hz,J 3 =7.1Hz,J 4 =9.6Hz, 4H, CH 2 ); 7.45 (d, J=4.7, 2H, ArH); 7.89 (s, 1H, ArH); 7.94 (d, J=4.6, 1H, ArH).

Embodiment 3

[0033] Example 3 Hapten B III (n=0) Preparation method

[0034] Take 4.8848g (0.04moL) of p-hydroxybenzaldehyde and dissolve it in pyridine, add a catalyst amount of DMAP, protect it with a drying tube, put it in a water bath at 85°C, and stir. Add 3.746 g (0.036 moL) of malonic acid dropwise to the above solution and react for 3 h. After the reaction was completed, the mixture was poured into a saturated sodium bicarbonate solution, stirred for 15 min, extracted with ethyl acetate, and the pH of the aqueous layer was adjusted to 3 with 4M hydrochloric acid, and 2.32 g of a white solid was precipitated, with a yield of 78.6%. ESI-MS analysis (negative) m / z 163[M-H]-; 1H-NMR (400MHz, d6-Acetone and TMS): δ 6.33 (d, J=16.0Hz, 1H, CH=CH); 6.89 (d, J=8.6Hz, 2H, ArH); 7.54(d, J=8.6Hz, 2H, ArH); 7.60(d, J=16.0Hz, 1H, CH=CH); 8.86(s, 1H, OH); 10.77 (s, 1H, COOH).

[0035] Weigh 0.7 (0.0125 moL) KOH and dissolve it in anhydrous methanol, weigh 0.821 g (0.005 moL) of the above soli...

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Abstract

The invention discloses a diethoxy phosphorothioate organic phosphorus pesticide haptens and a method for preparing the same. The haptens are products of nucleophilic substitution of diethylthiophosphoryl chloride and phenol derivates with a carboxyl or an amine acid. The invention provides a series of haptens aiming at a common structure of the organic pesticides of diethoxy phosphorothioate. The haptens are similar to the counterparts of organic pesticides having a common structure of the diethoxy phosphorothioate in terms of molecular structure, stereochemistry and electron distribution, wherein phenol derivative arms which have carboxyls and vary in length are introduced onto the oxygen atoms of the diethoxy phosphoramide to be bound with carrier proteins. The haptens and the metod lay a technical foundation for the preparation of antibodies of diethoxy phosphorothioate organic phosphorus pesticides and the development of quickly testing products.

Description

technical field [0001] The invention belongs to the technical field of immunology, and in particular relates to a diethoxy phosphorothioate-type organophosphorus pesticide hapten and a preparation method thereof. Background technique [0002] The problem of pesticide residues seriously endangers the health of the people. In recent years, incidents of mass poisoning and excessive pesticide residues in agricultural products caused by irrational use of pesticides have occurred frequently. The problem of pesticide residues has also seriously affected the international competitiveness of my country's agricultural products. Pesticide residue standards have become the main content of technical barriers to trade. In recent years, my country's vegetables, tea and other agricultural products and food have been rejected, detained, returned, Events of claims and contract terminations occur from time to time. In 2003, the amount of losses suffered by plantation agricultural products was...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/18G01N33/566
Inventor 沈玉栋孙远明雷红涛谢桂勉王弘徐振林杨金易
Owner SOUTH CHINA AGRI UNIV
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