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Synthetic process of O-ethyl-S-n-proply-(3-ethyl-2-cyano imine-1-imidazole) phosphate

A technology of cyanoimidodimethyl carbonate and cyanoimine, which is applied in the field of pesticide technical preparation, can solve problems such as large air pollution, achieve the effects of shortening reaction steps and time, and increasing yield

Inactive Publication Date: 2013-07-24
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The use of flammable carbon disulfide and toxic dimethyl sulfate, and release of methyl mercaptan during cyclization, resulting in greater air pollution

Method used

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  • Synthetic process of O-ethyl-S-n-proply-(3-ethyl-2-cyano imine-1-imidazole) phosphate
  • Synthetic process of O-ethyl-S-n-proply-(3-ethyl-2-cyano imine-1-imidazole) phosphate
  • Synthetic process of O-ethyl-S-n-proply-(3-ethyl-2-cyano imine-1-imidazole) phosphate

Examples

Experimental program
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Embodiment 1

[0024] 1.1 Synthesis of S-n-propylphosphoryl dichloride

[0025]

[0026] Add 57.7g (0.38mol) of dipropyl disulfide, 150ml of toluene, and 103g (0.75mol) of phosphorus trichloride into a 500ml four-necked reaction flask, cool to -2--5°C, and then add 75g of sulfuryl chloride dropwise (0.56mol), the dropping temperature does not exceed 0°C, after the dropwise addition is completed, rise to room temperature and continue the reaction for 10h; at 50°C, distill toluene under reduced pressure to obtain a light yellow oil, distill under reduced pressure, and collect 92-96 ℃ / 5mmHg fraction 121.5g, yield 84%;

[0027] 1. Synthesis of 2O,O-diethyl-S-n-propylphosphoryl chloride

[0028]

[0029] Dissolve 38.6g (0.2mol) of S-n-propylphosphoryl dichloride obtained in step 1) in 75ml of toluene solvent, cool to 0-5°C, and add 9.2g (0.2mol) of ethanol dropwise under stirring, 18.2 The mixture of g (0.18mol) triethylamine and 75ml toluene, after the dropwise addition is completed, ris...

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Abstract

The invention relates to a synthetic process of O-ethyl-S-n-proply-(3-ethyl-2-cyano imine-1-imidazole) phosphate. The process comprises the following steps of: 1) synthesis of O-ethyl-S-n-proply-S-propyl phosphoryl chloride; 2) synthesis of 1-ethyl-2-(N-cyano imine) imidazole; and 3) synthesis of O-ethyl-S-n-proply-(3-ethyl-2-cyano imine-1-imidazole) phosphate. The process provided by the invention has the beneficial effects that the reaction step and time are shortened, the yield is improved from 50% to over 70%, and the total yield is improved; according to the process, potassium carbonate replaces flammable and combustible sodium hydride, so that the reaction condition is more mild and the production process is safer; based on dipropyl dithio and phosphorus trichloride as initial raw materials, S-n-proply phosphoryl dichloride is synthesized and reacted with ethanol to obtain O-ethyl-S-n-propyl-phosphoryl chloride; the line is short and the raw material is easy to get with less wastewater, and the method is suitable for industrialization.

Description

technical field [0001] The invention belongs to the technical field of pesticide technical preparation, in particular to a neonicotinoid nematicide O-ethyl-S-n-propyl-(3-ethyl-2-cyanoimine-1-imidazole ) Synthesis process of phosphate ester. Background technique [0002] Nematicide Imicyafos, chemical name: O-ethyl-S-n-propyl-(3-ethyl-2-cyanoimine-1-imidazole) phosphate, phosphorothioate reported by Agro Kanesho, Japan class of nematicides. Imicyafos, like the neonicotinoid insecticide thiacloprid, is a cyanamide heterocyclic organic compound and an organophosphate. It is a combination of an asymmetric organophosphorus and a cyanoimidazolidine of a neonicotinoid insecticide. It is mainly used to control pests and nematodes in radish, carrot, strawberry, eggplant, tomato, cucumber, melon, watermelon, sweet potato and potato. [0003] The existing literature discloses that the intermediates are O-ethyl-S-n-propylphosphoryl chloride (I) and 1-ethyl-2-(N-cyanoimine) imidazole...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6506
Inventor 刘安昌杜长峰邹晓东陈露
Owner WUHAN INSTITUTE OF TECHNOLOGY
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