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Chiral imidazole fungicidal compositions and methods for their use

A composition and fungicidal technology, used in the prevention and/or inhibition of plant-related fungal growth, chiral fungicidal compositions, imidazole fungicides, fungal diseases, and the field of methimazole, which can solve the problem of methimazole No application suggestions etc.

Inactive Publication Date: 2002-01-23
CELGENE CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The currently used methazil is in its racemic form, and so far there are no reports of the use of methazil as a single enantiomer as a fungicide nor is there any suggestion for its application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The synthesis of embodiment 1 racemate

[0040] 2-Bromo-2', 4'-dichloroacetophenone: put 25g (0.1322mol) of 2', 4'-dichloroacetophenone into a three-necked circular tube equipped with a magnetic stirring bar, a reflux condenser and a dropping funnel in the bottom flask. Add anhydrous ether (30ml) and AlCl 3 (0.20g). The vial was stoppered and cooled to 0°C in an ice bath. Add Br dropwise (at a rate of about 0.5ml / min) 2 (21.13 g, 0.1322 mol). Join Br 2After the operation was complete, HBr and solvent were removed under reduced pressure. Residual HBr was removed by blowing a stream of nitrogen over the orange oily product. The obtained oily product was placed under high vacuum until all effervescence ceased. The product obtained was a viscous orange oil which solidified on storage in the refrigerator. Yield: 35.72g (100%); TLC: 95% n-hexane / 5% acetone, R f = 0.35.

[0041] 2-(1H-imidazole)-2',4'-dichloroacetophenone: 2-bromo-2',4'-dichloroacetophenone (35.72 g...

Embodiment 2

[0046] The synthesis of embodiment 2 (R)-(-)-carbendazim

[0047] (R)-2-Chloro-(2′,4′-dichlorophenyl)-1-ethanol: under nitrogen, -25°C (dry ice, CCl 4 ) to a solution containing 16 g (49.90 mmol) (-)-DIP-Cl in 30 ml of anhydrous THF was added 10 g (44.74 mmol) 2,2',4'-trichloroacetophenone. The bottle was stoppered and stirred at -25°C for about 7 hours, then at room temperature overnight. THF was removed under vacuum and (+)-α-pinene was removed under high vacuum at room temperature overnight. The resulting viscous colorless oil was dissolved in 200 ml of anhydrous ether and cooled to 0°C. Diethanolamine (10.50 g, 0.10 mol) was added to the filtrate and stirring was continued at room temperature for 3 hours. The white solid obtained was transferred by filtration and washed with anhydrous ether. Evaporation of the colorless solution to dryness yielded a viscous colorless oil. The above oil was analyzed by flash chromatography on silica gel, first removing (+)-α-pinene wit...

Embodiment 3

[0053] The synthesis of embodiment 3 (S)-(+)-carbendazim

[0054] (S)-2-Chloro-(2′,4′-dichlorophenyl)-1-ethanol: under nitrogen, -25°C (dry ice, CCl 4) to a solution containing 16 g (49.90 mmol) (+)-DIP-Cl in 30 ml of anhydrous THF was added in batches 10 g (44.74 mmol) 2,2',4'-trichloroacetophenone. The bottle was stoppered and stirred at -25°C for about 7 hours, then kept at room temperature under nitrogen for 2 days. 100 ml of 10% HCl was added and the solution was extracted with ether. The ether layer was washed with 100 mL of water, then concentrated in vacuo. The resulting colorless oil was placed under high vacuum for 7 hours with stirring to remove the (-)-α-pinene. The oil was dissolved in 250ml ether and cooled to 0°C. Diethanolamine (10.50 g, 0.10 mol) was added to the solution and stirring was continued at 0°C for 10 minutes. The ice bath was removed and the solution was stirred at room temperature for 2.5 hours. The solution was filtered and the solid was wa...

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Abstract

Chiral fungicides and compositions containing the same are provided. Also provided are methods for using the compositions of the present invention for inhibiting the growth of fungi, including phytotoxic fungi. The use of a single isomer in treating particular plant species and against particular fungi allows for selective inhibition of fungal growth with reduced fungicidal phytotoxic effects.

Description

[0001] invention technical field [0002] The present invention relates to a chiral fungicidal composition and methods of using the chiral fungicidal composition to inhibit and treat fungal diseases on plants, including plant seeds and plant products and crops. Background of the invention [0003] Fungicides are of great commercial value in protecting desired plants from fungal diseases. However, fungicides are toxic to the plants to which they have been applied, as well as to the beneficial organisms. Therefore, it is desirable to maximize the fungicidal effect of fungicides while minimizing their detrimental effects on plants. [0004] A wide variety of compounds differing in chemical structure, mechanism of action, and preferred mode of application are useful as fungicides. Typical compounds used as fungicides include chlorobenzene and its related compounds, quinones, dicarboximides, and systemic fungicides including sulfonamides, benzimidazoles, thiophanate-type systemic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/50
CPCA01N43/50A01C1/08
Inventor 理查德·A·纳尔逊诺曼·W·托马斯乔治·W·马恰姆林甦张明华克雷格·刘易斯
Owner CELGENE CORP
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