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Trifloxystrobin synthesizing method

A technology for trifloxystrobin and compounds, which is applied in the field of organic synthesis reactions, can solve the problems of reducing the profit of industrialized production, being unsuitable for industrialization, and being dangerous, and achieves the effects of enhancing market competitiveness, protecting safety, and reducing pollution

Active Publication Date: 2016-02-03
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] For the above reactions, method one involves bromination in carbon tetrachloride using NBS instead of the relatively cheap chlorination; the last step of method two uses the expensive catalyst Pd(PPh 3 ) 4 , the cost is high, which reduces the profit of industrial production; the first step of method three requires the use of n-butyllithium, which is expensive and dangerous, and is not suitable for industrialization

Method used

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  • Trifloxystrobin synthesizing method

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Embodiment one, ( E )-3-keto-4-(isonitroso)isochroman

[0037] A 50mL Schlenk bottle was subjected to anhydrous and oxygen-free treatment, and then added 1.48g (10mmol) o-hydroxymethylphenylacetic acid lactone, 1.236g (12mmol) TBN and 25mL anhydrous methanol, stirred in an ice bath for 10min, and then added dropwise Sodium methoxide (0.756g, 14mmol) in methanol (5mL) was stirred at room temperature for 24h. After the reaction, spin off the methanol, add 20 mL each of water and ethyl acetate, then use dilute hydrochloric acid to neutralize the system to a pH of about 7, extract three to four times with ethyl acetate, combine the organic phases, dry, spin dry, and then Purified by silica gel column chromatography to obtain 1.15 g of product with a yield of 65%. (TBN tert-butyl nitroso ester) 1 HNMR (600MHz, DMSO- d 6 ): δ =5.44(s,2H),7.43-7.51(m,3H),8.32(d, J =7.6Hz,1H),13.2(s,1H)ppm.

Embodiment 2

[0038] Embodiment two, ( E Preparation of )-3-keto-4-(methoxyimino)isochroman

[0039] To a clean 50mL round bottom flask, add 708mg (4mmol) ( E )-3-keto-4-(isonitroso)isochroman, 12mL acetone and 828mg (6mmol) potassium carbonate, a large amount of light yellow solid appeared after a while, stirred at room temperature for 0.5h, added dropwise 756mg (6mmol) sulfuric acid The acetone (3mL) solution of dimethyl ester was stirred at room temperature for 8h to stop the reaction, the acetone was rotated off, water and ethyl acetate were added, and ethyl acetate was extracted three to four times. The organic phases were combined, dried, spin-dried, and passed through a silica gel column Analysis and purification, to obtain 412mg product, productive rate 54%.

[0040] 1 HNMR (600MHz, DMSO- d 6 ): δ =4.13(s,3H),5.47(s,2H),7.45-7.47(m,2H),7.52-7.55(m,1H),8.18(d, J =7.8Hz, 1H)ppm.

Embodiment 3

[0041] Embodiment three, ( E ) Preparation of -2-chloromethyl-α-methoxyiminophenylacetic acid methyl ester

[0042] Add 320mg (1.68mmol) ( E )-3-keto-4-(methoxyimino)isochroman, 4mL of methanol, 2.998g (25.2mmol) of thionyl chloride was added dropwise in ice bath, then stirred at room temperature for 28h, quenched with water, ethyl acetate Extracted three to four times, combined the organic phases, dried, spin-dried, and then purified by silica gel column chromatography to obtain 296 mg of the product with a yield of 73%.

[0043] 1 HNMR (600MHz, CDCl 3 ): δ =3.87(s,3H),4.05(s,3H),4.43(s,2H),7.17(d, J =7.4Hz,1H),7.38-7.44(m,2H),7.51(d, J =7.5Hz, 1H)ppm.

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Abstract

The invention discloses a trifloxystrobin synthesizing method, and relates to the preparation of trifloxystrobin in organic chemicals. The trifloxystrobin synthesizing method comprises the following steps of using hydroxy methyl phenylacetic acid lactone as raw material to react with TBN (tributyrin), absolute methanol and sodium methoxide to obtain (E)-3-keto-4-(isonitroso)isochroman; using the (E)-3-keto-4-(isonitroso)isochroman to react with acetone and potassium carbonate, and dropwise adding the acetone solution of dimethyl sulfate after a large amount of bright yellow solids occurs, so as to obtain (E)-3-keto-4-(methoxyimino)isochroman; dissolving the obtained (E)-3-ketone-4-(methoxyimino)isochroman by methanol, and dropwise adding thionyl chloride under the low-temperature condition to prepare (E)-2-chlororated methyl-alpha-methoxyimino methyl phenylacetate; after the catalysis of 3-(trifluoromethyl)acetophenone and hydroxylamine hydrochloride, using absolute ethyl alcohol and as solvent to obtain light earthy yellow solid (E)-3-(trifluoromethyl)acetophenone oxime; enabling the (E)-2-bromomethyl-alpha-methoxyimino methyl phenylacetate and the (E)- 3-(trifluoromethyl)acetophenone oxime to react in a DMF (dimethyl formamide) solution of the potassium hydroxide, so as to obtain the white solid of trifloxystrobin.

Description

Technical field [0001] The invention relates to organic synthesis reactions, and in particular to a method for synthesizing trifloxystrobin. technical background [0002] Trifloxystrobin broad-spectrum fungicides are a new class of fluorinated fungicides successfully developed from the natural product Strobilurins as lead compounds for fungicides. They have many advantages. Trifloxystrobin has a bactericidal effect because it contains the E-type β-methoxymethyl acrylate structure. Research has found that its mechanism of action is accomplished by blocking the respiratory channels in the fungus. It has good activity against almost all fungal diseases (Ascomycetes, Basidiomycetes, Oomycetes and Deuteromycetes) such as powdery mildew, rust, blight, net spot, downy mildew, rice blast, etc. . It has the characteristics of high efficiency, broad spectrum, protection, treatment, eradication, penetration, systemic absorption, activity, resistance to rain erosion, and long lasting ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/60C07C249/12
Inventor 吕良忠金朝俊丁华平袁宇
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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