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Preparation method of agricultural bactericide

A technology of agricultural fungicides and inert solvents, applied in the field of preparation of agricultural fungicides

Inactive Publication Date: 2014-11-19
ZHEJIANG TIDE CROP TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The above preparation method is to improve the enol synthesis part in the patent CN1168718, using N,N-dimethyl formaldehyde with higher boiling point Amide dimethyl acetal is used as solvent to form enamine and then hydrolyzed to obtain enol. Although the raw materials are easy to get, there are many reaction steps, complex operations, large catalyst consumption and difficult recovery, and are not suitable for large-scale production. Moreover, the present invention allows The expensive 2-hydroxy-6-trifluoromethylpyridine intermediate first participates in the reaction, which leads to large consumption of raw materials, high cost and low market competitiveness

Method used

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  • Preparation method of agricultural bactericide

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Experimental program
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Embodiment 1

[0041] The preparation method of a kind of agricultural fungicide of the present embodiment, as shown in table 1, comprises the following steps: 1) 3-isochromanone (I) 40 g (0.27 mol), add 150 1 mL of dimethylformamide dimethyl acetal (DMFDMA), heated to 40°C to reflux for 4 h, the analysis showed that the reaction had stopped, the solvent was distilled off under reduced pressure, and 200 mL of toluene and 21.4 g (0.09 mo1) of chlorine hexahydrate were added Nickel, stirred at room temperature for 3h, filtered, and the solid was washed with 30mL of toluene. The filtrate was concentrated to obtain 4-(α-hydroxy)methylene-2-H-chromen-3-(4 H)-one (II), which could be directly used in the next reaction.

[0042] 2) Dissolve 4-(α-hydroxy)methylene-2-H-benzopyran-3-(4 H)-one (II) obtained in step 1) in 150 mL dimethyl sulfoxide, and stir Add 41.4 g (0.3 mol) of potassium carbonate and 50.4 g (0.4 mol) of dimethyl sulfate to it, and control the temperature at 40 ° C. After reacting f...

Embodiment 2

[0046] The preparation method of a kind of agricultural fungicide of the present embodiment, the step is roughly as embodiment 1, and its difference is: described step 2) in the molar ratio of alkali and 3-isochromanone (I) is 1:1; the molar ratio of methylating reagent to 3-isochromanone (I) is 1.5:1; halogenating reagent and 4-(methoxymethenyl)-3-isobenzo The molar ratio of pyrone (III) is 1.5:1; the molar ratio of base and 2-hydroxy-6-trifluoromethylpyridine (V) in the step 4) is 1.1:1; other differences are shown in the table shown in 1. Crude product obtains 74.2g picoxystrobin through crystallization, mother liquor concentrates and continues crystallization to obtain 9g picoxystrobin, adds up to 83.2g, content 98.4% (external standard method detects), yield 82% (with starting material 3-isobenzo Dihydropyrone (I) 40g is a benchmark). This embodiment has a short reaction route, simple and safe operation, mild conditions, simple and easy post-treatment, less waste, hig...

Embodiment 3

[0048] The preparation method of a kind of agricultural fungicide of the present embodiment, the step is roughly as embodiment 1, and its difference is: described step 2) in the molar ratio of alkali and 3-isochromanone (I) is 1:1; the molar ratio of methylating reagent to 3-isochromanone (I) is 1.5:1; halogenating reagent and 4-(methoxymethenyl)-3-isobenzo The molar ratio of pyrone (III) is 1.5:1; the molar ratio of base and 2-hydroxyl-6-trifluoromethylpyridine (V) in the step 4) is 1.2:1; other differences are shown in the table shown in 1. Crude product obtains 76g picoxystrobin through crystallization, mother liquor concentrates and continues to crystallize and obtains 9.6g picoxystrobin, adds up to 85.6g, content 98.2% (external standard method detects), yield 84.8% (with starting material 3-isobenzo Dihydropyrone (I) 40g is a benchmark). This embodiment has a short reaction route, simple and safe operation, mild conditions, simple and easy post-treatment, less waste, h...

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Abstract

The invention discloses a preparation method of an agricultural bactericide. The method includes following steps: carrying out a reaction between 3-isochromanone, which is used for a starting raw material, and an acetol of a formamide compound, performing hydrolysis to obtain 4-([alpha]-hydroxyl)-methylene-2-H-benzopyrane-3-(4H)-one, performing methylation to obtain 4-(methoxylmethylene)-3-isobenzopyrone, preparing (E)-2-(2-halomethyl)-3-methoxylmethyl acrylate from the 4-(methoxylmethylene)-3-isobenzopyrone in methanol, a third inert solvent and a halogenation reagent, and performing a reaction between the (E)-2-(2-halomethyl)-3-methoxylmethyl acrylate and 2-hydroxyl-6-trifluoromethylpyridine or 6-trifluoromethyl-2-pyridine alkoxide to obtain picoxystrobin. The method is short in reaction processes, is mild in conditions, is simple and convenient in post treatment, is less in waste gas, waste water and waste solid, is high in yield and is suitable for industrial production. Appearance of the agricultural bactericide is good and an external standard content of the agricultural bactericide is more than 98%.

Description

technical field [0001] The invention relates to a preparation method of an agricultural fungicide, which belongs to the field of organic synthesis. Background technique [0002] Picoxystrobin is a mitochondrial respiration inhibitor, and its mechanism of action is through the cytochrome b and C 1 Inter-electron transfer inhibits mitochondrial respiration. Effective against strains resistant to 14-demethylase inhibitors, benzamides, dicarboxamides and benzimidazoles. Once taken up by the leaves, picoxystrobin moves in the xylem, following the water flow in the transport system; it also flows in the gas phase on the leaf surface and flows in the xylem after being absorbed into the leaves from the gas phase. Use picoxystrobin (250g a.i. / hm 2 ) sprayed crops were compared with crops exposed to 10 mm of rainfall 2 hours after the same spray treatment for 1 hour, and the results showed that the control effects of the two on barley leaf blight were consistent. It is precisely ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64C07C69/734
CPCC07D213/64
Inventor 杨征宇郝树林
Owner ZHEJIANG TIDE CROP TECH
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