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Thioether kind bacteriocide

A technology of compound and general formula, applied in the field of agricultural fungicides

Active Publication Date: 2006-11-15
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many fungicides are available, there is still a need for more effective fungicides

Method used

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  • Thioether kind bacteriocide
  • Thioether kind bacteriocide
  • Thioether kind bacteriocide

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0070] The preparation of example 1 intermediate (V)

[0071]

[0072] Add 45 grams of phenol, 2.4 grams of formaldehyde, and 4.96 grams of ethanethiol to the reaction flask equipped with a stirrer and a condenser, and heat up to reflux. After reacting for 8 hours, the mixture was dephenolized by distillation and vacuum distillation to obtain 8.99 g of 2-ethylthiomethylphenol product with a content of 98% and a yield of 66.5%.

[0073] 1 HNMR: 1.22(3H, t), 2.42(2H, m), 3.81(2H, s), 6.84(1H, m), 7.89(1H, t), 7.08(1H, m), 7.19(1H, m) .

example 2

[0074] Example 2 Preparation of Compound 2

[0075]

[0076] Add 30 milliliters of N, N-dimethylformamide, 10.8 millimoles of anhydrous potassium carbonate, 1.76 grams (10.5 millimoles) of compound (V) and 2.85 grams (10 millimoles) in the reaction flask equipped with stirrer and condenser millimole) compound (VI), then heated to 60 ° C and stirred for 6 hours. The reaction solution was cooled and poured into 200 ml of water, extracted three times with ethyl acetate (3×150 ml), the extract was dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. Column chromatography (developing solvent: ethyl acetate:petroleum ether=1:5) gave pure compound 2, weighing 3.01 g (yield 81%).

[0077] 1 HNMR: 1.22(3H,t), 2.49(2H,m), 3.70(3H,s), 3.81(2H,s), 3.83(3H,s), 5.02(2H,s), 6.78(1H,d) , 6.89 (1H, t), 7.17 (2H, m), 7.28 (3H, m), 7.61 (1H, m), 7.63 (1H, s).

example 3

[0078] Preparation of Example 3 Compound 6

[0079]

[0080] Add 30 milliliters of N,N-dimethylformamide and 0.53 grams (22.0 mmol) of sodium hydride washed with petroleum ether into a reaction flask equipped with a stirrer and a condenser, and add 3.36 grams of it under stirring at room temperature. (20.0 mmol) 20 milliliters of N, N-dimethylformamide solution of compound (V), there is gas evolution, and the dropwise addition is completed in 20 minutes, and then stirred for another 30 minutes without gas emission. Add 5.72 g (20 mmol) compound (VI) / 35 ml N,N-dimethylformamide solution, react at room temperature for 3 h, stop stirring. The reaction solution was poured into 400 ml of water, extracted three times with ethyl acetate (3×250 ml), the extract was dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product. Column chromatography (eluent: ethyl acetate:petroleum ether=1:5) yielded 5.97 g of pure compound 6 (yield 80%).

[0081] 1 HNMR...

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PUM

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Abstract

The invention belongs to the field of agricultural fungicides. It relates to fungicidal compounds having the chemical structure of general formula (I) and its three-dimensional structure, methods of using these compounds to control plant diseases, and the use of fungicides containing these compounds. In the formula: A is N or CH; B is O or NH; Y is O, S, SO or SO2; R1, R2, R3 are H, optionally substituted alkyl, cycloalkyl, alkenyl or alkynyl; R4 , R5, R6, R7 are H, halogen, optionally substituted alkyl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl or cyano. ∴

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. It relates to thioether compounds and their preparation methods, methods of using these compounds to control plant diseases and the use of fungicides containing these compounds. Background technique [0002] Avoiding or reducing damage to crops while preventing and controlling plant diseases is an effective way to improve agricultural production. Although many fungicides are available, there is still a need for more effective fungicides. Fungicides having a methoxyacrylate structure are disclosed in patents WO9715189, WO9956551, WO0101779, and EP278595, but they are significantly different from the compounds of the present invention. Contents of the invention [0003] In order to obtain effective compounds that can control various fungal diseases at a very small dose, the inventors of the present invention synthesized compounds of general formula (I), and found that such compounds have ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/57A01N37/06
Inventor 刘长令张明星李志念吕良忠郭胜侯春青
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD