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Sulfonamide-substituted abamectin B2a/B2b derivative and preparation method and application thereof

A technology of avermectin and sulfonamide group, which can be used in the preparation of sugar derivatives, botanical equipment and methods, sugar derivatives, etc., and can solve problems such as poor chemical stability, pest resistance, and poor control effects.

Active Publication Date: 2018-10-23
HEBEI VEYONG BIO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the existing abamectin B 2a / B 2b Derivatives generally have problems such as poor stability of chemical properties, short duration of effect or resistance of pests, resulting in poor control effect

Method used

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  • Sulfonamide-substituted abamectin B2a/B2b derivative and preparation method and application thereof
  • Sulfonamide-substituted abamectin B2a/B2b derivative and preparation method and application thereof
  • Sulfonamide-substituted abamectin B2a/B2b derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 4"-Deoxy-4"-N,N-p-toluenesulfonylmethylaminoabamectin B 2a / B 2b The preparation method:

[0070] 10g 5-allyloxycarbonyl-4"-N-methylaminoabamectin B 2a / B 2b (Content >90%) dissolved in 40ml of sec-butyl acetate, after heating up to 60°C, add 1.8g of p-toluenesulfonyl chloride dropwise, 2.0g of tetramethylethylenediamine and keep warm for 0.5h; cool down to -10°C, add 2g Methanol, 1.3g sodium borohydride, 0.005g Pd(PPH 3 ) 2 Cl 2 React for 0.5h; then add 7.6% phosphoric acid solution to adjust the pH to 2, and then use 10% sodium hydroxide solution to adjust the pH to 7. After standing and layering, the organic phase is dried with anhydrous sodium sulfate, and concentrated after removing the inert solvent under reduced pressure The residue was purified by column chromatography to obtain a light yellow solid (content>90%).

[0071] Compound 4"-deoxy-4"-N,N-p-toluenesulfonamidomethylaminoabamectin B 2a / B 2b The structural identification data for:

[0072] l HN...

Embodiment 2

[0076] 4"-Deoxy-4"-N,N-cyclopropanesulfonamidomethylaminoabamectin B 2a / B 2bThe preparation method:

[0077] 10g compound 5-allyloxycarbonyl-4"-N-methylaminoabamectin B 2a / B 2b (Content >90%) was dissolved in 30g of dichloromethane (solvent), 1.9g of cyclopropanesulfonyl chloride and 2.0g of triethylamine were added dropwise at -10°C, and the reaction was kept for 2 hours. After the reaction of the raw materials was completed, the temperature was lowered to -20°C, and 1.5 g of methanol, 1.0 g of sodium borohydride and 0.003 g of palladium acetate were added to react for 2 h. Add 7.6% phosphoric acid solution to adjust the pH to 2.5, and then use 10% sodium hydroxide solution to adjust the pH to 7.5. After standing and stratifying, the organic phase is dried with anhydrous sodium sulfate, and the inert solvent is removed under reduced pressure. After purification by column chromatography, a light yellow solid (content >90%) was obtained.

[0078] Compound 4"-deoxy-4"-N,N...

Embodiment 3

[0083] 4"-Deoxy-4"-N,N-(4-pyridine)sulfonamidoaminoabamectin B 2a / B 2b The preparation method:

[0084] 10g compound 5-allyloxycarbonyl-4"-N-methylaminoabamectin B 2a / B 2b (Content>90%) was dissolved in 40ml of dimethylformamide, and after heating up to 50°C, 2.9g of pyridine-4-sulfonyl chloride and 2.0g of pyridine were added dropwise, and the reaction was kept for 1h. Cool down to 0°C, add 4g of methanol, 1.5g of sodium borohydride, and 0.008g of palladium chloride to react for 1 hour. Add 10% phosphoric acid solution to adjust the pH to 1.5, and then use 15% sodium hydroxide solution to adjust the pH to 6.5. After standing and stratifying, the organic phase is dried with anhydrous sodium sulfate, and the inert solvent is removed under reduced pressure. After purification by column chromatography, a light yellow solid (content >90%) was obtained.

[0085] LC-MS[M+H] + : 1045.5301. 4"-Deoxy-4"-N,N-(4-pyridine)sulfonamidomethylaminoabamectin B 2a [M+H] of + Calculate...

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PUM

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Abstract

The invention discloses a sulfonamide-substituted abamectin B2a / B2b derivative and a preparation method and application thereof. A chemical structural formula of a compound is shown as a formula I. The sulfonamide-substituted abamectin B2a / B2b derivative has stable chemical properties, durable effects and high pesticidal activity, has a special effect on mites, aphids and lepidoptera pests and isespecially capable of effectively preventing and controlling pesticide resistant aphids.

Description

technical field [0001] The present invention relates to compound, especially a kind of abamectin B 2a / B 2b Derivatives belong to crop pesticides. Background technique [0002] Abamectin fermentation broth contains multiple components at the same time, including Abamectin A 1a , Abamectin A 1b , Abamectin A 2a , Abamectin A 2b , Abamectin B 1a , Abamectin B 1b , Abamectin B 2a , Abamectin B 2b etc., of which abamectin B 1 As the main ingredient, Abamectin B 2 The content is second, and the content of other components is less. [0003] Currently commercially available avermectin pesticides are avermectin B 1 as the main insecticidal active ingredient. Abamectin B 1 The large and widespread use of abamectin B 1 Research on derivatives has also made great progress. Extraction of Abamectin B from Abamectin Fermentation Broth 1 After that, the abamectin B remaining in the mother liquor 2a / B 2b Will be shelved or discarded in large quantities, resulting in a hu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00A01N43/90A01P7/04A01P7/02
CPCA01N43/90C07H1/00C07H17/08
Inventor 王博田学芳范朝辉闫燕燕张博李合军左会旭魏亚欣刘新兆贾成国
Owner HEBEI VEYONG BIO CHEM