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Carbamate sterilization compound containing vinyl oxime ether

A technology of carbamates and vinyl oximes, which is applied in the direction of fungicides, biocides, and chemicals for biological control, etc., and can solve the problems that there are no literature reports on carbamate fungicidal active compounds

Active Publication Date: 2006-10-11
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the carbamate bactericidal activity compound that the present invention relates to contains vinyl oxime ether group does not have bibliographical information

Method used

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  • Carbamate sterilization compound containing vinyl oxime ether
  • Carbamate sterilization compound containing vinyl oxime ether
  • Carbamate sterilization compound containing vinyl oxime ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of the compound N-methoxy-N-2-[1-(2-phenylvinyl) ethyleneiminooxymethyl] phenyl carbamate (compound 1)

[0022] In 20ml of toluene, add 0.64g (4mmol) of 1-(2-phenylvinyl)-acetaldoxime and 0.25g (5mmol) of 60% NaH, add 1.37g( 5.0 mmol) of N-(2-bromomethylphenyl)-N-methoxy-carbamic acid methyl ester in toluene. After dripping, react at this temperature for 10-15 minutes, and wash the reactant with water until it is neutral and anhydrous Na 2 SO 4 Dry, desolvate under reduced pressure to obtain a crude product. The crude product was washed by column chromatography with a mixture of ethyl acetate and petroleum ether (1:3) to obtain 0.54 g of the target compound with a yield of 38.3%.

[0023] Target compound 1 H NMR(300MHZ, CDCl 3 ): 2.14 (s, 3H, CH3), 3.77, 3.79 (2s, 6H, 2OCH3), 5.25 (s, 2H, CH2O), 6.78 ~ 6.91 (q, 2H, CH = CH), 7.25 ~ 7.55 (m, 9H, Ar-H)

Embodiment 2

[0025] Preparation of N-methoxy-N-2-[1-(2-(3-chlorophenyl)-vinyl) ethyleneiminooxymethyl] phenyl carbamate (compound 3)

[0026] In 20ml of dimethylformamide, add 0.92g (5mmol) of 1-(2-(3-chlorophenyl)vinyl)-acetaldoxime, 0.42g (3mmol) potassium carbonate, 1.37g (5mmol) N -(2-Bromomethylphenyl)-N-methoxy-carbamic acid methyl ester. Stir at 25-30°C for 1 hour. After the reaction is complete, the reaction solution is poured into 100ml of water and extracted twice with ethyl acetate. The ethyl acetate layer is washed with water until it is neutral, and then with anhydrous Na 2 SO 4 After drying and removing the solvent, a crude product is obtained. The crude product was washed by column chromatography with a mixture of ethyl acetate and petroleum ether (1:3) to obtain 1.16 g of the target compound with a yield of 60%.

[0027] Target compound 1 H NMR(300MHZ, CDCl 3 ): 2.12(s, 3H, CH3), 3.76, 3.79(2s, 6H, 2×OCH3), 5.25(s, 2H, CH2O), 6.79(s, 2H, CH=CH), 7.24~7.53(m, 8H, Ar-H)

Embodiment 3

[0029] Preparation of N-methoxy-N-2-[1-(2-(4-chlorophenyl)-vinyl) ethyleneiminooxymethyl] phenyl carbamate (compound 4)

[0030] In 20ml dimethylformamide, add 0.92g (5mmol) of 1-(2-(4-chlorophenyl)vinyl)-acetaldoxime, 0.42g (3mmol) potassium carbonate, 1.37g (5mmol) N-(2-Bromomethylphenyl)-N-methoxy-carbamic acid methyl ester. Stir at 25~30℃ for half an hour. After the reaction is complete, the reaction solution is poured into 100ml of water and extracted twice with ethyl acetate. The ethyl acetate layer is washed with water until it is neutral, and then with anhydrous Na 2 SO 4 After drying and removing the solvent, a crude product is obtained. The crude product was washed by column chromatography with a mixture of ethyl acetate and petroleum ether (1:3) to obtain 1.22 g of the target compound with a yield of 62%.

[0031] Target compound 1 H NMR(300MHZ, CDCl 3 ): 2.09(s, 3H, CH3), 3.75, 3.76(2s, 6H, 2×OCH3), 5.21(s, 2H, CH2O), 6.82, 6.88(d, 2H, CH=CH), 7.27~7.55( m, 8H, Ar-H)

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Abstract

The invention discloses a methyl carbamate group compounds containing ethenyl oxime ether represented by general formula (I) and the preparing process, wherein R1, R2, R3 is alkyl, R4, R5 is hydrogen or alkyl, R6 is substituted aryl or substituted heteroaryl. The compounds can be used for the prevention and cure of various crop diseases caused by a plurality of fungus, such as Phycomycetes, Oomycetes, Ascomycetes, Basidiomycetes and imperfect fungi.

Description

Technical field [0001] The invention relates to carbamate compounds containing vinyl oxime ether groups with bactericidal activity and their preparation methods. Background technique [0002] At present, many carbamate compounds containing substituents have been used for insecticide, sterilization and weeding of crops at home and abroad. German patent DE4423612 discloses N-substituted phenyl carbamate compounds, which have fungicidal properties. . However, there is no literature report on the carbamate fungicidal active compounds containing vinyl oxime ether groups in the present invention. Summary of the invention [0003] The object of the present invention is to provide a vinyl oxime ether group-containing carbamate compound with bactericidal activity represented by the general formula (I) and a preparation method thereof. The general formula (I) is as follows: [0004] [0005] In the general formula (I): R 1 , R 2 , R 3 Is an alkyl group; R 4 , R 5 Respectively hydrogen o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N47/20A01P1/00A01P3/00
CPCC07C291/04A01N47/24
Inventor 刘卫东杜升华张承来兰世林毛春晖黄路王晓光
Owner HUNAN CHEM RES INST
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