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Application of thio-thiadiazole containing nitrothiazole compound in prevention and treatment of agricultural plant diseases

A technology of nitrothiazole and thiadiazole, which can be used in applications, plant growth regulators, botanical equipment and methods, etc., and can solve problems such as residue toxicity, drug resistance, environmental pollution, etc.

Inactive Publication Date: 2021-01-22
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, people mainly use chemical pesticides to control plant pathogenic bacteria infection, but with the use of chemical pesticides, problems such as drug resistance, environmental pollution and residue toxicity continue to emerge, which poses new challenges to the prevention and control of plant fungal and bacterial diseases

Method used

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  • Application of thio-thiadiazole containing nitrothiazole compound in prevention and treatment of agricultural plant diseases
  • Application of thio-thiadiazole containing nitrothiazole compound in prevention and treatment of agricultural plant diseases
  • Application of thio-thiadiazole containing nitrothiazole compound in prevention and treatment of agricultural plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1: the synthesis of compound H-1

[0012]

[0013] The synthetic method of compound H-1 of the present invention is carried out according to the following reaction formula:

[0014]

[0015] Synthesis of Compound H-1: Dissolve 5-amino-1,3,4-thiadiazole-2-thiol (1mmol) in methanol (25mL), then add sodium methoxide (1.5mmol) and stir for 10min, then add 2-Bromo-5-nitrothiazole (1mmol), react for 6-7 hours. After the reaction, an appropriate amount of 1 mmol HCl solution was added to the solvent, stirred for 10 min, filtered with suction, and washed three times with a mixed solution of petroleum ether and petroleum ether: ethyl acetate (10:1). The filter residue was collected and dried to obtain the target compound H-1.

[0016] Yield: 66.3%; yellow solid; 1 HNMR (400MHz, DMSO-d 6 )δ:8.74(s,1H),7.94(s,2H). 13 CNMR (100MHz, DMSO-d 6 )δ: 173.51, 171.25, 148.68, 144.45, 140.54. MS-ESI m / z: C 5 h 3 N 5 o 2 S 3 :261.9[M+H] + .

Embodiment 2

[0017] Embodiment 2: the synthesis of compound H-2

[0018]

[0019] The synthetic method of compound H-2 of the present invention is carried out according to the following reaction formula:

[0020]

[0021] Synthesis of Compound H-2: Add Compound H-1 (1mmol) to DMF (15mL) and stir to dissolve under ice bath conditions, then add NaH (3mmol) to the solution and stir for 30min, then slowly add 1-bromo- 3-Methyl-2-butene (1 mmol), react at room temperature for 4 hours. After the reaction was completed, excess saturated ammonium chloride was added to quench the reaction, stirred for 5 min, extracted with dichloromethane, and the organic phases were combined and purified by column chromatography to obtain the target compound H-2.

[0022] Yield: 67.5%; yellow oily liquid; 1 H NMR (400MHz, CDCl 3 )δ: 8.35(s,1H), 5.42–5.28(m,1H), 3.92(d,J=7.8Hz,2H), 1.77(s,3H), 1.76(s,3H). 13 C NMR (100MHz, CDCl 3 )δ: 174.79, 143.51, 140.28, 116.58, 32.36, 25.89, 18.23. MS-ESI m / z: C 10 ...

Embodiment 3

[0023] Embodiment 3: the synthesis of compound H-3

[0024]

[0025] The experimental procedure is the same as in Example 2, except that 1-bromo-3-methyl-2-butene is replaced by 1-bromo-n-hexane. Yield: 64.3%; yellow oily liquid; 1 H NMR (400MHz, CDCl 3 )δ:8.34(s,1H),3.27(t,J=7.4Hz,2H),1.85–1.76(m,2H),1.50–1.31(m,4H),0.92(t,J=7.1Hz,3H ). 13 C NMR (100MHz, CDCl 3 )δ: 175.13, 143.55, 34.07, 30.97, 28.60, 22.25, 14.01. MS-ESI m / z: C 10 h 13 N 5 o 2 S 3 :332.0[M+H] + .

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Abstract

The invention relates to the field of medicinal chemistry, and discloses an application of 5-((5-nitrothiazole-2-yl)sulfo)-1,3,4-thiadiazole compounds H-1 to H-8 in resisting phytopathogens. Bioactivity tests find that the compound has potential inhibitory activity on eight agricultural diseases such as rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, cotton fusarium oxysporum, magnaporthe grisea, citrus canker and phytophthora parasitica, and part of the compounds have high inhibitory activity. The compound is simple to prepare, raw materials are cheap andeasy to obtain, and the compound is expected to be developed into a novel bacteriostatic agent.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and discloses a new application of 5-((5-nitrothiazol-2-yl)thio)-1,3,4-thiadiazole compounds, in particular to 5-(( 5-nitrothiazol-2-yl)thio)-1,3,4-thiadiazole compounds H-1~H-8 are effective in preventing and controlling Rhizoctonia solani, Sclerotinia sclerotiorum, wheat head blight, Application in Botrytis cinerea, Cotton Fusarium wilt, Magnaporthe grisea, Citrus canker and Potato blackleg. Background technique [0002] Plant pathogenic bacteria are one of the most harmful plant pathogenic microorganisms, which can cause serious plant diseases and crop yield reduction. At present, people mainly use chemical pesticides to control plant pathogenic bacteria infection, but with the use of chemical pesticides, problems such as drug resistance, environmental pollution and residue toxicity continue to emerge, which poses new challenges to the prevention and control of plant fungal and bacterial dis...

Claims

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Application Information

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IPC IPC(8): A01N43/824A01P3/00A01P1/00
CPCA01N43/82
Inventor 刘映前李海昕张智军贺颖慧杨程杰赵文斌吴天琳杜莎莎
Owner LANZHOU UNIVERSITY
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