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Unsaturated oximino ether compound with fungicidal, insecticidal activity

A compound, unsaturated technology, applied in the field of pesticides and agricultural fungicides, can solve the problem of no further research and achieve high fungicidal effect

Active Publication Date: 2005-02-16
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no further research has been done on the four geometric isomers formed by the carbon-carbon double bonds and carbon-nitrogen double bonds identified as 1 and 2 above due to the connection of different substituents.

Method used

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  • Unsaturated oximino ether compound with fungicidal, insecticidal activity
  • Unsaturated oximino ether compound with fungicidal, insecticidal activity
  • Unsaturated oximino ether compound with fungicidal, insecticidal activity

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0043] Synthesis of compounds in Example 1 Table 1:

[0044] 14 grams of p-chlorobenzaldehyde was dissolved in 30 milliliters of acetone, 5 grams of 10% sodium hydroxide solution was added dropwise thereto, the temperature was maintained not higher than 25° C., and stirring was continued for 1 hour after the addition was completed. The mixture was poured into water, extracted with ethyl acetate, washed with water three times, then dried and concentrated to give 15.5 g of light yellow oily 4-chlorostyryl methyl ketone, with a yield of 86%.

[0045] 54 g of 4-chlorostyryl methyl ketone, 52 g of hydroxylamine hydrochloride and 30 g of sodium hydroxide were refluxed in 1000 ml of methanol for 2 hours, then the reaction solution was concentrated, diluted with water and extracted with ethyl acetate. The combined extracts were dried and concentrated to obtain 32 g of 4-chlorostyryl methyl ketone oxime as an oil.

[0046] A solution of 9.5 g of 4-chlorostyrylmethylketoxime in DMF (10...

example 2

[0047] The separation of compound in example 2 table 1

[0048] The above oil was subjected to column chromatography with a mixture of ethyl acetate and petroleum ether (1:10) as the eluent, and the mixture of the above oil with ethyl acetate and petroleum ether (1:10) was collected separately. Column chromatography was carried out for the eluent, and each component was collected separately. The Rf values ​​were 0.3 (compound 1), 0.28 (compound 2), 0.23 (compound 3), and 0.21 (compound 4), and four compounds were obtained.

[0049] Biotest example

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Abstract

The invention is an unsaturated oxime-aether compound with sterilization and insecticidal activity, whose general equation is as figure (I). The R1and R2 is selected from the H, halogen, CN or NO2 respectively; the double bond of carbon-carbon is E-isomer and the methoxy acrylic ester on the benzene ring is E-isomer.

Description

technical field [0001] The invention belongs to the field of agricultural fungicides and insecticides. Background technique [0002] Because fungicides, insecticides or combinations thereof are used for a period of time, pathogenic bacteria and pests will develop resistance to them, therefore, there is a constant need to invent new and improved fungicides, insecticide compounds and compositions. [0003] Chinese invention patent CN 1191670A reports the fungicidal and insecticidal activities of certain unsaturated oxime ether compounds, and discloses compounds with the following general structure: [0004] [0005] In the above general formula, R 1 , R 2 They are respectively selected from H, methyl, methoxy, trifluoromethyl or halogen; at the same time, the methoxy acrylate on the benzene ring is disclosed as the E-isomer. However, no further research has been done on the four geometric isomers formed by the carbon-carbon double bonds and carbon-nitrogen double bonds m...

Claims

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Application Information

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IPC IPC(8): A01N37/52C07C251/60
Inventor 吕良忠孙克司乃国张弘王凤宇赵静曹巍李斌
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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