A synthetic process of a green efficient agricultural fungicide

A technology of agricultural fungicides and synthetic processes, applied in organic chemistry and other directions

Active Publication Date: 2015-01-07
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-mentioned preparation method is to improve the enol synthesis part in the patent CN1168718, using N,N-dimethyl formaldehyde with a 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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  • A synthetic process of a green efficient agricultural fungicide
  • A synthetic process of a green efficient agricultural fungicide
  • A synthetic process of a green efficient agricultural fungicide

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0038] The synthesis process of a green and high-efficiency agricultural fungicide of this embodiment, as shown in Table 1, includes the following steps: 1) at 0°C, 30g (0.20 mol, 99%) of 3-isochroman Ketone (I) was added to a 1000 mL four-necked reaction flask, 200 mL of tetrahydrofuran was added thereto, 20.4 g (0.3 mol ) of sodium ethylate was added thereto under stirring, 17.8 g (0.24 mol ) of ethyl formate was added thereto, and the reaction 3 h, after the reaction was detected by the liquid phase, 150 mL of water was added thereto, adjusted to neutral with concentrated hydrochloric acid, extracted with 200 mL of chlorobenzene, separated from water, and 31.8 g of sodium carbonate (0.3 mol ), dimethyl sulfate 30.3g (0.24mol ), controlled temperature 0°C, reacted for 3 h, after the reaction was detected by liquid phase, 150 mL of water was added thereto, and the aqueous phase was extracted with chlorobenzene (3*30 mL) , combined the organic phases, and evaporated the solven...

Embodiment 2

[0042] The synthesis process of a green and high-efficiency agricultural fungicide in this embodiment, as shown in Table 1, includes the following steps: 1) at 40°C, 100 g (0.67 mol, 99%) of 3-isochroman Add ketone (I) to a 2000 mL four-necked reaction flask, add 400 mL of ethylene glycol dimethyl ether to it, add 82.5 g (0.74 mol) of potassium tert-butoxide to it under stirring, add phenyl formate to it 97.6 g (0.8 mol ), reacted for 4 hours, after the liquid phase detected the reaction was complete, added 150 mL of water to it, adjusted to neutral with concentrated hydrochloric acid, added 400 mL of methyl tert-butyl ether for extraction, separated water, and poured into the organic phase 117.3 g (0.85 mol ) of potassium carbonate and 93.0 g (0.74 mol ) of dimethyl sulfate were added to the solution, the temperature was controlled at 40°C, and the reaction was carried out for 4 h. Extracted with butyl ether (3*100 mL), combined the organic phases, and evaporated the solven...

Embodiment 3

[0046] The synthesis technique of a kind of green high-efficiency agricultural fungicide of the present embodiment, the step is roughly as embodiment 1, and its difference is: the mol ratio of alkyl formate and 3-isochromanone (I) is 1.5:1; the molar ratio of alkoxide anion source and 3-isochromanone (I) is 1.5:1; described step 1) in alkali and 3-isochromanone (I) ) in a mol ratio of 0.5:1; the mol ratio of a methylating reagent to 3-isochromanone (I) is 1.5:1; in the step 2), the halogenating reagent and 4-(methoxy The mol ratio of methenyl)-3-isobenzopyrone (II) is 1.5:1; the mol ratio of base and 2-hydroxyl-6-trifluoromethylpyridine (IV) in the step 3) is 1.5:1; other differences are shown in Table 1. Crude product recrystallization obtains 68.3 g picoxystrobin, mother liquor concentration continues crystallization and obtains 15.3 g picoxystrobin, totally 83.6 g, content 98.1% (external standard method detects), yield 82.7% (with starting material 3-isophenyl and dihydr...

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Abstract

A synthetic process of a green efficient agricultural fungicide is disclosed. The synthetic process includes: preparing 4-(methoxymethene)-3-isobenzofuranone by adopting 3-isochromanone as an initial raw material; preparing methyl (E)-2-(2-halomethylphenyl)-3-methoxy acrylate from the 4-(methoxymethene)-3-isobenzofuranone in methanol, a third inert solvent and a halogenating agent; and reacting the methyl (E)-2-(2-halomethylphenyl)-3-methoxy acrylate and 2-hydroxy-6-(trifluoromethyl)pyridine or 6-trifluoromethyl-2-pyridinol salt to obtain picoxystrobin. The synthetic process has characteristics of short reaction steps, mild reaction conditions, simple, convenient and feasible post-treatment, little three-waste, low cost, high yield, and suitability for industrial production. A product is good in appearance, and has external standard purity higher than 98%.

Description

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

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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