Pyridyloxy phenoxyalkanoic acids compound and application

A technology of pyridyloxyphenoxycarboxylic acid and compound, which is applied in the field of pyridyloxyphenoxycarboxylic acid compounds and applications, and can solve the problems of no bactericidal activity and other problems

Active Publication Date: 2010-06-23
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] So far, there have been no reports of th

Method used

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  • Pyridyloxy phenoxyalkanoic acids compound and application
  • Pyridyloxy phenoxyalkanoic acids compound and application
  • Pyridyloxy phenoxyalkanoic acids compound and application

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0139] Example 1 (compound 1)

[0140] 1.1 Preparation of 2,3-dichloro-N-methoxypyridine-5-carboxamide

[0141]

[0142] 2.0 g of substituted pyridine acid chloride and 0.49 g of methoxylamine were stirred in 50 ml of toluene at 35-40°C for 8 hours, heated under reduced pressure to remove the toluene, added water and ethyl acetate, separated the organic layer, and washed with water and brine , dried and concentrated. The residue was purified by silica gel column chromatography to obtain 2.05 g of the target product with a yield of 94%.

[0143] 1.2 Preparation of intermediates

[0144]

[0145] 2,3-dichloro-N-methoxypyridine-5-carboxamide, 0.83 g of 2-(4-hydroxyphenoxy) propionic acid, 0.95 g of potassium carbonate, added to a 100 ml single-necked bottle, and 40 ml N,N-Dimethylformamide. Heat and stir at 80-90°C for four hours. After the reaction is complete, pour it into 100 ml of water, adjust the pH to about 2 with dilute hydrochloric acid, and extract with ethyl...

example 2

[0149] Example 2 (compound 52)

[0150]

[0151] 5.0 grams of 2,3-dichloro-5-cyanopyridine, 5.2 grams of 2-(4-hydroxyphenoxy)propionic acid, and 6 grams of potassium carbonate were added to a 250-milliliter single-necked bottle, and 80 milliliters of N,N -dimethylformamide. Heat and stir at 80-90°C for four hours. After the reaction is complete, adjust the pH to about 2 with dilute hydrochloric acid, and extract with ethyl acetate. Washed with saturated brine and concentrated to obtain 8.48 g of product. Yield 92%. 90% purity.

example 3

[0152] Example 3 (compound 46)

[0153]

[0154] 0.4 g of substituted phenoxypropionyl chloride and 0.1 g of ethylene glycol monomethyl ether were stirred in 50 ml of toluene at 35-40°C for 8 hours, heated under reduced pressure to remove toluene, added water and ethyl acetate, separated the organic layer, and Washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to obtain 0.2 g of the desired compound, melting at 130-132°C.

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Abstract

The invention belongs to agricultural fungicides, particularly discloses a pyridyloxy phenoxyalkanoic acids compound and application thereof. The structure of the compound is shown as the general formula (I), and the definition of each group in the formula is shown in specifications. The compound has excellent bactericidal activity and can be used for preventing and controlling germs on crop plants.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides. Specifically, it relates to a pyridyloxyphenoxycarboxylic acid compound and its application. Background technique [0002] Aryloxyphenoxypropionate esters are a class of compounds known to have herbicidal activity. [0003] As disclosed in the patent US4505743 the herbicide clodinafop-propargyl (clodinafop-propargyl), its chemical structure is as follows: [0004] [0005] Patent GB1599121 discloses the herbicide fluazifop-butyl (fluazifop-butyl), its chemical structure is as follows: [0006] [0007] Patent US4840664 discloses the herbicide fine haloxyfop-p-methyl (haloxyfop-P-methyl), its chemical structure is as follows: [0008] [0009] So far, there have been no reports of such compounds having bactericidal activity. Contents of the invention [0010] The object of the present invention is to provide a kind of pyridyloxyphenoxy carboxylic acid compound with novel struc...

Claims

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Application Information

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IPC IPC(8): C07D213/84A01N43/40A01P3/00
Inventor 刘长令周银平李志念刘远雄张弘
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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