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Method for preparing strobilurin fungicide

A technology of methoxyacrylic acid and bactericide, which is applied in oxime preparation, organic chemistry, etc., can solve the problems of poor repeatability, difficult preparation, and high difficulty, and achieve a process environment-friendly, easy-to-obtain raw materials, and easy operation Effect

Active Publication Date: 2013-04-10
上海禾本药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] (3) 4,6-dichloropyrimidine is sequentially condensed with o-cyanophenol and methyl o-hydroxyphenylacetate to obtain 2-(2-(6-(2-cyanophenoxy)pyrimidine-4-oxyl)benzene base)-methyl acetate, and then prepare azoxystrobin by alkylation with a strong base such as organolithium. The risk is high in chemical production, and the reaction requires a low temperature of -78°C
[0018] CN200710163386, WO2009052719 methods (2) and (4) are the main methods used in actual production at present, method (2) calculates the total yield with benzofuranone at about 60%; A certain increase (69%), but titanium tetrachloride is used as a catalyst in the production process
The chemical properties of titanium tetrachloride are unstable, white smoke will be emitted immediately when it encounters moisture, and it is inconvenient to use. In addition, many insoluble substances titanium dioxide will be obtained in the post-reaction treatment to form a paste-like colloid, and product separation is troublesome.
[0028] Specifically, in the large-scale production of picoxystrobin, the bromination reaction step is a free radical reaction, the reaction selectivity is not good, and there are many brominated products. In addition, the controllability of the free radical reaction in production is poor, and the repeatability is not good.
[0029] In addition, the actual synthesis reaction process of enestroburin enestroburin and syringstrobin coumoxystrobin is more difficult and difficult to prepare

Method used

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  • Method for preparing strobilurin fungicide
  • Method for preparing strobilurin fungicide
  • Method for preparing strobilurin fungicide

Examples

Experimental program
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Effect test

Embodiment 1

[0088]

[0089]36.1 grams (0.1mol) (I) was dissolved in 100 milliliters of toluene, 15 grams (0.126mol) DMF-DMA was added, and a distillation device with a small rectification column was installed, and the temperature was slowly raised to 90 ° C, and low boiling fractions slowly Come out; control the distillation rate to be moderate, continue to heat up to 120 ° C, TLC tracking until the conversion of the raw material is complete. Evaporate under reduced pressure to remove the residual low boiler as the intermediate of azoxystrobin, cool and set aside.

Embodiment 2

[0091]

[0092] The product in embodiment (1) was dissolved in 50 milliliters of 10% hydrochloric acid, stirred at room temperature for 3 hours; extracted three times with 150 milliliters of toluene, combined the toluene phase, added 1 gram of benzyltriethylammonium chloride, 30 grams of 20 % sodium hydroxide solution and 20 grams of dimethyl sulfate, stirred at room temperature for 3 hours, and heated to 50 ° C for 2 hours; the toluene phase was separated, washed once with 20 ml of 5% hydrochloric acid, the toluene was concentrated under reduced pressure, and the residue was used in 20 ml Methanol recrystallization obtained 35 grams of azoxystrobin product, with a content of 98.5% (detected by external standard method), and a yield of 85.1%. 1 HNMR (CDCl 3 ), δ3.64 (s, 3H), 3.75 (s, 3H), 6.42 (s, 1H), 7.22 (d, 1H), 7.26-7.43 (m, 5H), 7.49 (s, 1H), 7.66 ( t, 1H), 7.71 (d, 1H), 8.4 (s, 1H)

Embodiment 3

[0094]

[0095] The product in embodiment (1) was dissolved in 80 milliliters of 20% hydrogen chloride / methanol solution, stirred at room temperature for 12 hours; Atmospheric distillation reclaimed most of the excess hydrogen chloride / methanol solution, then steamed under reduced pressure to remove low boilers, residue Add 1 gram of potassium bisulfate, heat to 140-150°C for 6 hours under reduced pressure with a water pump; cool to room temperature, add 150 ml of toluene, filter, wash once with 25 ml of 5% sodium bicarbonate, concentrate the toluene under reduced pressure, and the residue 32.9 g of the product was obtained by recrystallization with 20 ml of methanol, with a content of 98.8% (HPLC detected by external standard method), and a yield of 80.6%.

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Abstract

The invention relates to a method for preparing strobilurin fungicide. The method comprises the following steps: (1) mixing the compound in formula (II) with the compound in formula (III) for reaction for 5 to 10 h at the temperature of 90 to 120 DEG C to obtain the compound in formula (IV), wherein the compound in formula (III) is acetal of formamides compound, R1, R2 and R3 are substituted alkyl or aryl; and (2) hydrolyzing the compound in formula (IV) under an acidic condition, and then stirring the hydrolyzed product at the room temperature for 2 to 4 h under the condition of alkali, methylating reagent and phase transfer catalyst to obtain the product, wherein X is 6-(2'-cyanophenoxyl) pyrimidine-4-oxy or 6-trifluoromethylpyridine-2-oxymethyl; 6-(2'-cyanophenoxyl) pyrimidine-4-oxy or 6-trifluoromethylpyridine-2-oxymethyl;[2-[[[[4-(4-chlorophenyl)-but-3-en-2-yl]imido]oxy]methyl]phenyl]; and 2-(2-((3-butyl-4-methyl-coumarin-7-yloxy)metyl)phenyl). The total yield of the method reaches above 85%.

Description

Technical field [0001] The present invention relates to a preparation method of methoxyacrylate fungicides. Background technique [0002] The discovery of strobilurins fungicides was inspired by β-methoxyacrylic acid derivatives, natural compounds with fungicidal activity. After nearly 20 years of research and application, it has become an important class of fungicides. It is a class of low-toxicity, high-activity, broad-spectrum, systemic fungicides with protective, therapeutic, and eradication effects. They have good activity against Ascomycetes, Basidiomycetes, Deuteromycetes and Oomycetes, and can prevent and control diseases such as powdery mildew, rust, downy mildew and rice blast in a variety of crops. And it can effectively prevent and control pathogenic bacteria that are resistant to other fungicides, such as strains that are resistant to 14-demethylase inhibitors, benzamides, dicarboxamides and benzimidazole fungicides. Its mechanism of action is a mitochondrial ...

Claims

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Application Information

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IPC IPC(8): C07D239/52C07D213/64C07D311/16C07C251/60C07C249/12
Inventor 叶光武张小兵汪青松赵泽斌李舣孟叶挺
Owner 上海禾本药业股份有限公司
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