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A kind of 2,5-disubstituted-1,3,4-thiadiazole compound containing furan ring and its preparation method and application

A technology of thiadiazoles and disubstitution, which is applied in the field of synthesis of heterocyclic compounds, and achieves the effects of simple preparation method, good biological activity and high yield

Inactive Publication Date: 2015-10-28
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compounds with thiadiazole and furan rings have not been reported

Method used

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  • A kind of 2,5-disubstituted-1,3,4-thiadiazole compound containing furan ring and its preparation method and application
  • A kind of 2,5-disubstituted-1,3,4-thiadiazole compound containing furan ring and its preparation method and application
  • A kind of 2,5-disubstituted-1,3,4-thiadiazole compound containing furan ring and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of furan ring-containing 2,5-disubstituted-1,3,4-thiadiazole compounds shown in formula I (R 1 for hydrogen, R 2 for 4-fluoro):

[0036]

[0037] In a dry 25mL three-necked flask, add 2mmol N-benzoyl-N'-5-(4'-fluorophenyl)-2-furyl hydrazide and 3mmol Lawesson Reagent, 10mL anhydrous toluene , under nitrogen protection, stirred at 110°C for 6h. After the reaction was completed, most of the toluene was evaporated, and the residual solid was dissolved in ethyl acetate, and then separated by silica gel column chromatography. The eluent was petroleum ether + ethyl acetate (volume ratio 4:1), and a yellow solid was obtained, m.p.: 178 -179°C, yield 68%.

[0038] Infrared and proton nuclear magnetic resonance spectrum data of the compound represented by formula Ⅰ

[0039] IR (cm -1) 1683.25, 1616.32, 1583.46, 1497.63, 1454.12, 1437.65, 1284.92, 1239.63, 1192.42, 1081.23, 1014.21; 1 H NMRδ H (ppm): 7.32(d,J=3.60Hz,1H,FuH),7.42-7.49(m,3H,FuH+2ArH...

Embodiment 2

[0040] Agricultural fungicidal activity of 2,5-disubstituted-1,3,4-thiadiazole compounds containing furan ring shown in Example 2 Formula I

[0041] Pathogenic strains for testing: as shown in Table 1 (a total of 40 species).

[0042] Table 1 The pathogenic bacteria and the diseases caused by the test

[0043] serial number

Pathogen name

cause disease

11

Helminthosporium root rot

Wheat Root Rot

13

Fusarium moniliforme

Rice bakanae disease

14

Fusarium graminearum I

Wheat scab I

16

Fusarium graminearum II

Wheat Scab II

18

Pythium oryzae I

Rice blast I

19

Pythium oryzae II

Rice Blast II

21

Helminthosporium spp.

corn leaf spot

23

Phytophthora infestans

potato

25

Fusarium solani

potato dry rot

41

Apple rot fungus I

Apple Tree Rot I

42

Apple black spot fungus

Apple Black Spot

43

Apple rot fung...

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Abstract

The invention discloses a furan ring-containing 2,5-disubstituted-1,3,4-thiadiazole compound as well as a preparation method and application thereof. The furan ring-containing 2,5-disubstituted-1,3,4-thiadiazole compound has a structure shown in the formula I, wherein R1 or R2 is a substitute on a corresponding benzene ring, R1 is hydrogen and R2 is 4-fluoro. According to the preparation method of the furan ring-containing 2,5-disubstituted-1,3,4-thiadiazole compound, the compound shown in the formula II reacts with a vulcanizing cyclization reagent at 40-160 DEG C in an inert atmosphere in the presence of a thinner. The furan ring-containing 2,5-disubstituted-1,3,4-thiadiazole compound has excellent bioactivity and is applicable to sterilizing agents.

Description

technical field [0001] The invention belongs to the field of synthesis of heterocyclic compounds, in particular to a furan ring-containing 2,5-disubstituted-1,3,4-thiadiazole compound and its preparation method and application. Background technique [0002] In recent years, heterocyclic compounds have played an important role in the creation of new ultra-high-efficiency pesticides. When looking for compounds with novel structures and biological activities, designing and synthesizing various heterocyclic compounds is one of the very important ways, and has become quite active. field of. Among the heterocyclic compounds, thiazole compounds have attracted more and more attention from researchers (Liu Changling, Thiazole Series Compounds. Fine and Specialty Chemicals, 2007, 15(9), 36-37), of which 1,3,4- Thiadiazoles have been widely used in pesticides and medicine because of their high efficiency, low toxicity, excellent biological activity and diverse structural changes, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04A01N43/824A01P3/00
CPCA01N43/82C07D417/04
Inventor 崔紫宁程莹莹刘诗胤陈昱帆周佳暖陈少华
Owner SOUTH CHINA AGRI UNIV