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Pyridyl-N-cyano sulfo oxime compound and preparation method thereof

A technology of cyanosulfooxime and pyridylsulfinyl imide, applied in organic chemistry, pesticides and other directions, can solve problems such as poor resistance, and achieve the effects of low cost, mild reaction conditions and high yield

Active Publication Date: 2015-06-17
BEIJING GREENCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The N-cyanosulfoxime compound with pyridyl group is a new type of structure. It is considered that insects have poor resistance to it and may have better insecticidal activity. However, there is currently no information on this type of compound and its specific preparation method. see the report

Method used

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  • Pyridyl-N-cyano sulfo oxime compound and preparation method thereof
  • Pyridyl-N-cyano sulfo oxime compound and preparation method thereof
  • Pyridyl-N-cyano sulfo oxime compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Preparation of S-methyl-S-(4-pyridyl)-N-cyanosulfoxime

[0065] (1) Preparation of S-methyl-S-(4-pyridyl)sulfimine

[0066]

[0067] Dissolve 10 g of 4-methylthiopyridine in 200 mL of chloroform, add dropwise 150 mL of a chloroform solution of 68.8 g of 2,4,6-trimethylbenzenesulfonyl hydroxylamine (MSH), and react at room temperature for 14 hours. After the reaction is complete, spin out most of the solvent from the reaction solution, adjust the pH of the residue to 8-12 with 10% aqueous sodium hydroxide solution, let stand and separate the layers, extract the water layer twice with ethyl acetate, and use anhydrous sulfuric acid for the organic phase. Dried over magnesium, concentrated, and purified by column chromatography to obtain 9.9 g of S-methyl-S-(4-pyridyl)sulfimine, the yield was 88.2%, and S-methyl-S-( 4-pyridyl) sulfimine product purity is 99.8%.

[0068] (2) Preparation of S-methyl-S-(4-pyridyl)sulfinimide

[0069]

[0070] Dissolve 9.9 g of the abo...

Embodiment 2

[0076] Preparation of S-methyl-S-(2-chloro-3-methoxypyridin-4-yl)-N-cyanosulfoxime

[0077] (1) Preparation of S-methyl-S-(2-chloro-3-methoxypyridin-4-yl)sulfimide

[0078]

[0079] Dissolve 5 g of 2-chloro-3-methoxy-4-methylthiopyridine in 100 mL of acetonitrile, add dropwise 50 mL of acetonitrile solution of 19.9 g of 2,4,6-trimethylbenzenesulfonyl hydroxylamine (MSH), at room temperature Under reaction 13h. After the reaction is complete, spin out most of the solvent from the reaction solution, adjust the pH of the residue to 8-12 with 10% potassium hydroxide aqueous solution, let stand to separate layers, extract the water layer twice with dichloromethane, and use anhydrous sulfuric acid for the organic phase. Dried over magnesium, concentrated, and purified by column chromatography to obtain 4.6 g of S-methyl-S-(2-chloro-3-methoxypyridin-4-yl)sulfimine with a yield of 85.6%, which was detected by liquid chromatography The purity of the obtained S-methyl-S-(2-chloro-3...

Embodiment 3

[0087] Preparation of S-ethyl-S-(2-trifluoromethyl-3-methoxypyridin-4-yl)-N-cyanosulfoxime

[0088] (1) Preparation of S-ethyl-S-(2-trifluoromethyl-3-methoxypyridin-4-yl)sulfimide

[0089]

[0090] Dissolve 15 g of 2-trifluoromethyl-3-methoxy-4-ethylthiopyridine in 300 mL of dichloromethane, add 43.4 g of 2,4,6-trimethylbenzenesulfonyl hydroxylamine (MSH) dropwise Dichloromethane solution 100mL, react at room temperature for 12h. After the reaction is complete, spin out most of the solvent from the reaction solution, adjust the pH of the residue to 8-12 with 20% aqueous sodium carbonate solution, let stand to separate layers, extract the aqueous layer twice with ethyl acetate, and use anhydrous sodium sulfate for the organic phase. Dry, concentrate, and purify by column chromatography to obtain 13.8 g of S-ethyl-S-(2-trifluoromethyl-3-methoxypyridin-4-yl)sulfimine with a yield of 86.5%. The purity of the S-ethyl-S-(2-trifluoromethyl-3-methoxypyridin-4-yl)sulfimide product...

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Abstract

The invention discloses a novel pyridyl-N- cyano sulfo oxime compound, which has good insecticidal activity and has a good control effect for controlling insects and other invertebrates, particularly aphids, plant hoppers and the like. The invention further discloses a preparation method of the pyridyl-N- cyano sulfo oxime compound. The preparation method comprises the following steps of: catalyzing oxidation reaction of pyridyl sulfilimine and an oxidant by using univalent copper salt as a catalyst to obtain pyridyl sulfoximine; carrying out cyanation on the pyridyl sulfoximine by using cyaniding agent to obtain the pyridyl-N- cyano sulfo oxime compound in the presence of alkaline, wherein the pyridyl sulfoximine can be prepared by using 4-alkyl sulphanyl pyridine as the material and carrying out imidization on 2,4,6-trimethyl benzene sulfonyl hydroxylamine. The preparation method of the pyridyl-N- cyano sulfo oxime compound is available in materials, low in catalyst price, gentle and safe in reaction condition, short in reaction time, less in byproduct, high in yield, low in cost and suitable for industrial production.

Description

technical field [0001] The invention relates to a new pyridyl-N-cyanosulfoxime compound and a preparation method thereof, belonging to the technical field of organic synthesis. Background technique [0002] It has been found that during the application of insecticides, insects will gradually develop more and more resistance to the insecticides used for a period of time, resulting in a reduction in the insecticidal efficacy of currently used insecticides. Therefore, there is an urgent need to develop insecticides with new structures and greatly improve insecticidal activity. [0003] The N-cyanosulfoxime compound with pyridyl group is a new type of structure. It is considered that insects have poor resistance to it and may have better insecticidal activity. However, there is currently no such compound and its specific preparation method. See report. Contents of the invention [0004] The purpose of this invention is to provide a kind of new pyridyl-N-cyanosulfoxime compou...

Claims

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Application Information

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IPC IPC(8): C07D213/71A01P7/04
Inventor 宫宁瑞
Owner BEIJING GREENCHEM TECH