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A kind of method for synthesizing trifloxystrobin

A technology of trifloxystrobin and compounds, which is applied in the field of organic synthesis reactions, can solve the problems of reducing industrial production profits, not suitable for industrialization, and expensive prices, and achieve the effects of improving market competitiveness, protecting safety, and reducing pollution

Active Publication Date: 2018-04-10
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] For the above reaction, method one involves the use of NBS in carbon tetrachloride to carry out the bromination reaction 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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  • A kind of method for synthesizing trifloxystrobin
  • A kind of method for synthesizing trifloxystrobin
  • A kind of method for synthesizing trifloxystrobin

Examples

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Effect test

Embodiment 1

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

[0037] A 50 mL Schlenk bottle was anhydrous and oxygen-free, and then added 1.48 g (10 mmol) o-hydroxymethylphenylacetic acid lactone, 1.236 g (12 mmol) TBN and 25 mL of anhydrous methanol, and stirred in an ice bath After 10 min, a solution of sodium methoxide (0.756 g, 14 mmol) in methanol (5 mL) was added dropwise, and stirred at room temperature for 24 h. 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 H NMR (600 MHz, DMSO- d 6 ): δ = 5.44 (s, 2H), 7.43-7.51 (m, 3H), 8.32 (d, J = 7.6 Hz, 1H), 13.2 (s, 1H) ppm.

Embodiment 2

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

[0039] Add 708 mg (4 mmol) ( E )-3-keto-4-(isonitroso)isochroman, 12 mL acetone and 828 mg (6 mmol) potassium carbonate, a large amount of light yellow solid appeared after a while, stirred at room temperature for 0.5 h, added dropwise 756 mg (6 mmol) dimethyl sulfate in acetone (3 mL), stirred at room temperature for 8 h, stopped the reaction, removed the acetone, added water and ethyl acetate, extracted three to four times with ethyl acetate, combined the organic phases, dried, and spun dried, and then purified by silica gel column chromatography to obtain 412 mg of product with a yield of 54%.

[0040] 1 H NMR (600 MHz, 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 = 7.8 Hz, 1H) ppm.

Embodiment 3

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

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

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

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Abstract

The invention discloses a method for synthesizing trifloxystrobin, which relates to the preparation of trifloxystrobin in organic chemistry. Using o-hydroxymethylphenylacetolactone as raw material, react with TBN, anhydrous methanol, and sodium methoxide to obtain (E)-3-keto-4-(isonitrosyl)isochroman; then use (E)-3- Ketone-4-(isonitroso) isochroman reacts with acetone and potassium carbonate. After a large amount of light yellow solid appears, the acetone solution of dimethyl sulfate is added dropwise to obtain (E)-3-keto-4-(methyl Oxyimino) isochroman; the obtained (E)-3-keto-4-(methoxyimino) isochroman is dissolved in methanol, and dichlorosulfoxide is added dropwise at low temperature to prepare (E)-2- Methyl chloromethyl-α-methoxyiminophenylacetate; use m-trifluoromethylacetophenone, hydroxylamine hydrochloride, absolute ethanol, and sodium hydroxide to obtain a light earthy yellow solid (E)-m-trifluoro Methyl acetophenone oxime; (E)-2-bromomethyl-α-methoxyiminophenylacetic acid methyl ester and (E)-m-trifluoromethylacetophenone oxime in potassium hydroxide in DMF The reaction gave trifloxystrobin as a white solid.

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 Patents(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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