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Derivatives containing 2, 5-substituted heterocyclic radical sulphone and synthesis method and application thereof

A technology of heterocyclic groups and derivatives, applied in the field of sulfone derivatives and their synthesis, can solve the problems of low cost, unsatisfactory activity of soil-borne diseases and migratory diseases, and high cost

Active Publication Date: 2011-06-01
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the cost of compound b is relatively high, and the activity of inhibiting soil-borne diseases and migratory diseases is not very ideal. Therefore, we use compound b as a guide to optimize the structure of b, in order to find out that it is more active against soil-borne diseases and migratory diseases. Good and lower cost compound

Method used

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  • Derivatives containing 2, 5-substituted heterocyclic radical sulphone and synthesis method and application thereof
  • Derivatives containing 2, 5-substituted heterocyclic radical sulphone and synthesis method and application thereof
  • Derivatives containing 2, 5-substituted heterocyclic radical sulphone and synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0113] Example 1: Preparation of 2,5-substituent-1,3,4-oxadiazole compounds

[0114] Series I compounds of the present invention contain 2,5-substituent-1,3,4-oxadiazole derivatives preparation process steps and conditions with 2-(methylsulfonyl)-5-phenyl-oxadiazole as For example, others can refer to synthesis.

[0115]

[0116] (1) preparation of methyl benzoate intermediate

[0117] Throw benzoic acid (37.8 g, 0.31 mol) and anhydrous methanol (198.0 g, 6.2 mol) into a 500 mL three-neck flask, slowly add concentrated sulfuric acid (61 g, 0.62 mol) dropwise at room temperature and then raise the temperature to reflux, and the reaction ends for 8 hours. After demethanolization under reduced pressure, it was washed with saturated sodium bicarbonate solution until neutral. Liquid separation obtained 39.1 g of methyl benzoate, the refractive index: n20 / D 1.516 (lit.), and the yield was 92.8%. 1 H NMR (500MHz, CDCl 3 )δ: 8.04-7.31 (m, 5H, benzyl-H), 3.81 (s, 3H, CH 3 );

...

Embodiment 2

[0138] Example 2: Preparation of 2-(methylsulfonyl)-5-p-chlorophenyl-1,3,4-thiadiazole

[0139] The preparation process steps and conditions of series II compounds of the present invention containing 2,5-substituent-1,3,4-thiadiazole derivatives are based on 2-(methylsulfonyl)-5-p-chlorophenyl-thiadiazole Azole is taken as an example, others can be synthesized with reference. The preparation of methyl p-chlorobenzoate and p-chlorobenzohydrazide intermediate is completed with reference to Example 2.

[0140] (1) Preparation of 2-mercapto-5-p-chlorophenyl-1,3,4-thiadiazole

[0141]Weigh p-chlorobenzohydrazide (8g, 0.047mol) into a 500mL three-neck round bottom flask, add 200mL of absolute ethanol, and then potassium hydroxide (2.6g, 0.047mol), stir to dissolve. Control the temperature to room temperature, add carbon disulfide (5.3 g, 0.07 mol) dropwise, and stir rapidly for 5 h. Filtrate with suction and wash with absolute ethanol to obtain potassium chlorobenzoyl hydrazide d...

Embodiment 3

[0154] Embodiment three: the bacteriostatic activity test of compound

[0155] The antibacterial activity of the compounds was determined by the in vitro growth rate method. Heat potato dextrose agar medium (PDA medium: 200g potato, 20g agar, 20g glucose, 1000mL distilled water) to a molten state (40-60°C), pour 10mL of the drug solution (10 times the final concentration of the drug solution) into 90mL PDA In the culture medium, shake well, evenly pour into the petri dish with a diameter of 9cm, place it horizontally, and let it cool and solidify. Use a puncher to punch a 4mm-diameter fungus dish at the edge of the fresh pathogenic bacteria colony that has been cultured for 4 days, put the fungus dish upside down in the center of the PDA plate containing the drug, and then place it in a constant temperature and humidity incubator at 27°C for upside-down culture, and wait for the blank control When the colony grows to nearly two-thirds of the plate, observe it, measure the dia...

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Abstract

The invention relates to derivatives containing 2, 5- substituted heterocyclic radical sulphone and a synthesis method and application thereof, and provides compounds which can prevent soil-borne diseases and diseases caused by migration, namely the derivatives containing 2, 5-substituted heterocyclic radical sulphone. The derivatives can be expressed by the following general expression shown in the specification, wherein the Z, X and R are defined in the specification. Parts of the compounds have good inhibition activity for the soil-borne diseases, the diseases caused by migration and otherfungus diseases. When the drug concentration reaches 50ppm, the inhibition ratio of a compound I-5 for fusarium graminearum, fusarium oxysporum f.sp.capsicum and cytospora mandshurica is 100%, 99.9% and 100% respectively, thus showing a preferable activity in preventing plant diseases.

Description

technical field [0001] The invention relates to chemical industry and pesticide, and the specific technology is a kind of sulfone derivatives and its synthesis method and application. Background technique [0002] Chitin, also known as chitin, is a homogeneous polysaccharide polymerized by N-acetyl-D-glucosamine, which is widely found in insects, crustacean hard shells, fungal cell walls and some green algae but not in plants and vertebrates substances in. Chitin is the main component of the cell wall of most fungi (Ascomycetes, Basidiomycetes and Deuteromycetes), and it constitutes 3% to 60% of the mass of the cell wall. It is in the innermost layer of the cell wall of filamentous fungi, near the plasma membrane, and is radial . Chitin is closely related to the growth of fungal hyphae, and is the main component of the tip extension of fungal hyphae. Chitin is regulated by chitin synthase and chitinase, and chitin synthase is responsible for the growth of chitin. The synt...

Claims

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Application Information

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IPC IPC(8): C07D271/113C07D413/04C07D285/125A01N43/824A01P3/00
Inventor 杨松徐维明宋宝安陈卓胡德禹何江贺鸣薛伟潘昭喜
Owner GUIZHOU UNIV
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