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Pyrimidine-containing organophosphorus fungicide and application

A fungicide, organophosphorus technology, applied in the directions of fungicides, applications, biocides, etc., can solve problems such as the inability to obtain compounds

Inactive Publication Date: 2014-05-07
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Dow AgroSciences also applied for derivatives of 5-fluorocytosine (CAS NO.2022-85-7), such as CN 101977900, CN 102497781, CN 102574831, CN 102548979, CN 102548980, CN 102548981, CN 102762210, CN 102946730 and other series of patents, but Dow AgroSciences did not mention the compound involved in this patent in its patented invention, even if its structure is changed through the "bioisosteric theory" rule, the compound involved in this patent cannot be obtained Compound, the compound of the patent invention can effectively solve the resistance problem of current fungicides

Method used

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  • Pyrimidine-containing organophosphorus fungicide and application
  • Pyrimidine-containing organophosphorus fungicide and application
  • Pyrimidine-containing organophosphorus fungicide and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Preparation of O-(4-amino-5-fluoropyrimidin-2-yl)O,O-dimethylphosphorothioate

[0130]

[0131]In a 1000 ml four-necked flask with a stirring and thermometer, add 500 ml of anhydrous N,N-dimethylformamide, add 0.1 mole of 5-fluorocytosine, and slowly add 0.1 mole of metal After adding sodium, stir for 2 hours, add O, O-dimethylphosphoryl thiochloride, stir at room temperature for 48 hours, distill N, N-dimethylformamide at 1 mmHg until the solvent is distilled clean, and the distillation temperature is not When the temperature is greater than 80 degrees, the obtained product is dissolved in 500 ml of methanol, filtered to remove the salt, and the methanol is distilled off to obtain the crude product of O-(4-amino-5-fluoropyrimidin-2-yl)O,O-dimethyl phosphorothioate , the content was 78% by liquid chromatography analysis, and the yield was 80%. Using ethyl acetate-n-hexane (4:1) as the chromatographic solution, the pure product was obtained. The calculated data of e...

Embodiment 2

[0140] O-(4-acetamido-5-fluoropyrimidin-2-yl)OO-diethyl phosphorothioate

[0141]

[0142] In a 1000 ml four-neck flask with stirring and a thermometer, add 500 ml of anhydrous N,N-dimethylformamide, add 0.1 mole of 5-fluoroacetylcytosine, and slowly add 0.1 mole of Metal sodium, after adding, stir for 2 hours, add O, O-dimethylphosphoryl thiochloride, stir at room temperature for 48 hours, distill N,N-dimethylformamide at 1mmHg until the solvent is distilled clean, the distillation temperature Not more than 80 degrees, the obtained product was dissolved in 500 ml of methanol, filtered to remove the salt, and the methanol was distilled off to obtain O-(4-acetamido-5-fluoropyrimidin-2-yl)O,O-diethylthio The crude phosphoric acid ester was analyzed by liquid chromatography with a content of 42% and a yield of 39%. Purified by column chromatography using ethyl acetate-n-hexane (6:4) as the chromatographic liquid, the pure product was obtained, and the calculated data of eleme...

Embodiment 3

[0144] O-(5-fluoro-4-(methylamino)pyrimidin-2-yl)O,O-dimethylphosphorothioate

[0145]

[0146] In a 100 ml four-neck flask with stirring and a thermometer, add 50 ml of anhydrous methyl ethyl ketone, add 0.01 mole of 5-fluoro 4-methylamino-pyrimidin-2-one, and slowly add 0.011 mole of After adding sodium hydroxide, stir for 2 hours, add O, O-dimethylphosphoryl thiochloride, stir at room temperature for 96 hours, distill butanone at 10 mmHg until the solvent is distilled clean, the distillation temperature is not more than 40 degrees, and the residual After dissolving with 500 ml of toluene at night, remove the salt by filtration, and distill off the toluene to obtain the crude product of O-(5-fluoro-4-(methylamino)pyrimidin-2-yl)O,O-dimethyl phosphorothioate. The liquid chromatographic analysis showed that the content was 56%, and the yield was 49%. Purified by column chromatography using ethyl acetate-n-hexane (6:4) as the chromatographic fluid, the pure product was obta...

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PUM

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Abstract

The invention belongs to the technical field of fungicide compounds, and particularly relates to a pyrimidine-containing organophosphorus fungicide and application. The pyrimidine-containing organophosphorus fungicide can be used for controlling and preventing damage of fungi to plants in the farmland, the garden and the park, and is shown in a formula I described in the specification. According to a novel fungicide compound, by fully utilizing the characteristic of an existing compound, the structure is effectively modified, so that a brand-new compound structure is obtained, and thus a method is a known and feasible method of a novel pesticide product disclosed by the invention.

Description

Technical field: [0001] The invention belongs to the technical field of fungicide compounds, and specifically relates to a pyrimidine-containing organophosphorus fungicide and its application, which can be used in farmland, orchards and gardens to control and prevent fungal damage to plants. technical background: [0002] Organophosphorus fungicides are a type of fungicides used in the field of agrochemicals to control and prevent fungal damage to plants, among which commercial products include edifenphos, iprobenfos, pyritropin ( pyrazophos), tolclofos-methyl (tolclofos-methyl). These organophosphorus fungicides have been used in the field of agrochemicals to successfully control various fungal diseases such as powdery mildew, dry rot, rice blast, and soybean rust, and have achieved good results. Control effect. However, the problem is that due to the extensive use of these products for many years, the fungi in plants have developed resistance to these compounds, which red...

Claims

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Application Information

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IPC IPC(8): A01N57/16A01P3/00C07F9/6512C07F9/6558
Inventor 唐剑峰许辉刘杰潘光民吴雪李文宏
Owner SHANDONG UNITED PESTICIDE IND CO LTD
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