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N-(2-substituted phenyl)-N-methoxy carbamate compounds and their preparation and use

A kind of technology of methoxycarbamic acid and ester compound, which is applied in N--N-methoxycarbamic acid methyl ester compound and its preparation and application fields

Active Publication Date: 2008-10-01
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But N-(2-substituted phenyl)-N-methoxycarbamate methyl ester compound as shown in the present invention has no report

Method used

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  • N-(2-substituted phenyl)-N-methoxy carbamate compounds and their preparation and use
  • N-(2-substituted phenyl)-N-methoxy carbamate compounds and their preparation and use
  • N-(2-substituted phenyl)-N-methoxy carbamate compounds and their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: Preparation of methyl N-methoxy-N-[2-[[(3,5,6-trichloropyridin-2-yl)oxy]methyl]phenyl]carbamate (compound 13)

[0062] Reaction formula:

[0063]

[0064] With 0.4 gram (2mmol) 3,5,6-trichloropyridinol (commercially available) and 0.6 gram (2.2mmol) methyl N-2-bromomethylphenyl-N-methoxycarbamate (with reference to WO02 / 46142) was dissolved in 5 ml of dimethylformamide, 0.45 g of potassium carbonate was added, and the reaction was stirred at room temperature for 6 hours.

[0065] The reaction solution was absorbed in ethyl acetate, washed with water, washed with saturated brine and dried over anhydrous sodium sulfate, and then precipitated under reduced pressure. 0.55 g of a light yellow solid was obtained as compound 13 by separation on a silica gel column. Content: 95%, melting point: 94.0-94.7°C.

Embodiment 2

[0066] Example 2: Preparation of methyl N-methoxy-N-[2-[[(2,6-difluoro-3,5-dichloropyridin-4-yl)amino]methyl]phenyl]carbamate (compound 17)

[0067] Reaction formula:

[0068]

[0069] 0.43 g (2.5 mmol) of 4-amino-2,6-difluoro-3,5-dichloropyridine and 0.77 g (2.8 mmol) of N-2-bromomethylphenyl-N-methoxycarbamate The ester was dissolved in 5 ml of dimethylformamide, 1.0 g of potassium carbonate was added, and the reaction was stirred at 30-35°C for 4 hours.

[0070] The reaction solution was absorbed in ethyl acetate, washed with water, washed with saturated brine and dried over anhydrous sodium sulfate, and then precipitated under reduced pressure. 0.6 g of a light yellow solid was obtained as compound 17 by separation on a silica gel column. Content: 95%, melting point: 82-83°C.

[0071] According to the above method, other compounds in the general formula I can be obtained by appropriately changing the starting compound.

[0072] NMR data of some compounds ( 1 HNMR,...

Embodiment 3

[0077] Embodiment 3 60% wettable powder

[0078] Compound 13 60%

[0079] Sodium dodecylbenzenesulfonate 1%

[0080] Sodium lignosulfonate 6%

[0081] Diffuser NNO 5%

[0082] Diatomaceous earth make up to 100%

[0083] All components (all solid) are mixed together and pulverized in a pulverizer until the fineness reaches the standard (≤44 μm) to obtain a wettable powder with an active ingredient of 60%.

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Abstract

The invention belongs to agricultural use antiseptic field. It discloses N-(2- substituted benzene group) N-methoxy methyl carbamate compound, its preparation and application. The compound has good fungicidal property, can be used to prevent and cure wheat powdery mildew, apple powdery mildew, wheat rust, green smut, corn southern leaf blight, and so on.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides, and relates to N-(2-substituted phenyl)-N-methoxycarbamate methyl ester compounds and their preparation and application. Background technique [0002] WO-93 / 15046 discloses carbamate compounds for crop protection, the general formula is as follows: [0003] [0004] WO-96 / 01256 discloses amides of 2-[(dihydro)pyrazol-3'-yloxymethylene]anilines for the control of animal pests and harmful fungi with the general formula: [0005] [0006] However, the methyl N-(2-substituted phenyl)-N-methoxycarbamate compound as shown in the present invention has not been reported. Contents of the invention [0007] The object of the present invention is to provide a kind of N-(2-substituted phenyl)-N-methoxycarbamate methyl ester compound which can control crop harmful fungi at a small dose. [0008] Technical scheme of the present invention is as follows: [0009] The present invention provides a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/60A01N43/40A01P3/00
CPCC07D213/80A01N47/24C07D213/74C07D213/64
Inventor 杨春河耿丽文周德锋张弘崔东亮李志念王良清臧寿国张则勇
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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