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Method for synthesizing high-efficiency green agriculture bactericide

A technology of agricultural fungicide and synthesis method, which is applied in the field of synthesis of high-efficiency green agricultural fungicide

Inactive Publication Date: 2014-12-24
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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  • Method for synthesizing high-efficiency green agriculture bactericide
  • Method for synthesizing high-efficiency green agriculture bactericide
  • Method for synthesizing high-efficiency green agriculture bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The synthesis method of a high-efficiency green agricultural fungicide of this embodiment, as shown in Table 1, includes the following steps: 1) at 0°C, 100 g (0.67 mol, 99%) of 3-isochroman Pyrone (I) was added to a 2000 mL four-necked reaction flask, 400 mL of toluene was added thereto, 50 g (0.73 mol ) of sodium ethoxide and 54.8 g (0.74 mol ) of ethyl formate were added thereto under stirring, and the reaction was carried out for 3 hours After the analysis showed that the reaction was complete, 150 mL of ice-cold water was added thereto, and adjusted to neutrality with 100 mL of concentrated hydrochloric acid, the organic phase was separated, the aqueous phase was extracted with toluene (3*50 mL), the organic phases were combined, and dried with anhydrous magnesium sulfate And concentrated under reduced pressure to obtain 4-(α-hydroxy)methylene-2-H-benzopyran-3-(4 H)-one (II), which can be directly used in the next reaction.

[0042] 2) Add 4-(α-hydroxy)methylen...

Embodiment 2

[0046]The synthetic method of a kind of high-efficiency green agricultural fungicide of the present embodiment, as shown in Table 1, comprises the following steps: 1) at 30 ℃, 100 g (0.67 mol, 99%) 3-isochroman Add ketone (I) to a 2000 mL four-necked reaction flask, add 400 mL tetrahydrofuran to it, add 70 g (0.85 mol) of sodium n-propoxide to it under stirring, add 46.2 g (0.77 mol) of methyl formate to it ), reacted for 4 hours, after the reaction was finished, 150 mL of water was added thereto, and adjusted to neutrality with 100 mL of concentrated hydrochloric acid, the aqueous phase was extracted with ethyl acetate (3*100 mL), the organic phases were combined, and distilled under reduced pressure to obtain 4-(α-hydroxy)methylene-2-H-benzopyran-3-(4 H)-one (II) can be directly used in the next reaction.

[0047] 2) Add 4-(α-hydroxy)methylene-2-H-chromen-3-(4H)-one (II) obtained in step 1) into a 2000 mL four-necked reaction flask, and Add 400 mL dimethyl sulfoxide to it, ...

Embodiment 3

[0051] A kind of synthetic method of high-efficiency green agricultural fungicide of the present embodiment, the step is roughly as embodiment 1, and its difference is: the mol ratio of aryl formate and 3-isochromanone (I) is 1.5:1; the mol ratio of alkoxide anion source and 3-isochromanone (I) is 1.5:1; described step 2) in alkali and 3-isochromanone (I) ) is 1:1 in molar ratio; the molar ratio of methylating reagent and 3-isochromanone (I) is 1.5:1; halogenating reagent and 4-(methoxymethenyl)-3 - The molar ratio of isobenzopyrone (III) is 1.5:1; the molar ratio of base to 2-hydroxy-6-trifluoromethylpyridine (V) in the step 4) is 1.1:1; other differences are shown in Table 1. Crude product recrystallization obtains 73.9 g picoxystrobin, and mother liquor concentration continues to crystallize to obtain 10.3 g picoxystrobin, totally 84.2 g, content 98.6% (external standard method detects), yield 83.7% (with starting material 3-isophenyl and dihydropyrone (I) 40g as a benchm...

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Abstract

The invention discloses a method for synthesizing high-efficiency green agriculture bactericide. The method comprises the following steps: preparing 4-(alpha-hydroxyl) methylene-2-H-benzopyran-3-(4H)-ketone by taking 3-isodihydrocoumarin as an initial raw material, performing methylation to obtain 4-(methoxy-methylene)-3-isobenzopyrone, reacting 4-(methoxy-methylene)-3-isobenzopyrone with a halogenations reagent and methanol to obtain (E)-2-(2-halogen methyl phenyl)-3-methoxy-methyl acrylate, and reacting (E)-2-(2-halogen methyl phenyl)-3-methoxy-methyl acrylate with 2-hydroxyl-6-trifluoromethyl picoline or 6-trifluoromethyl-2-pyridine alcoholate, thereby obtaining picoxystrobin. The method is short in reaction step, gentle in condition, simple, convenient and feasible in aftertreatment, less in waste water, waste gas and waste residue, low in cost, high in yield, applicable to industrialization production and good in product appearance, and the external standard content is greater than 98%.

Description

technical field [0001] The invention relates to a synthesis method of a high-efficiency green 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....

Claims

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Application Information

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