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Applications of benzimidazole derivatives in prevention and treatment of agricultural plant diseases

A technology of benzimidazole and its derivatives, applied in the field of medicinal chemistry, can solve problems such as the astonishing growth rate of fungal drug resistance and the single use of drugs

Inactive Publication Date: 2020-02-28
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, chemical reagents are mostly used to control plant fungal diseases in agricultural production, but due to the long-term single use of drugs, the growth rate of fungal drug resistance is alarming

Method used

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  • Applications of benzimidazole derivatives in prevention and treatment of agricultural plant diseases
  • Applications of benzimidazole derivatives in prevention and treatment of agricultural plant diseases
  • Applications of benzimidazole derivatives in prevention and treatment of agricultural plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Embodiment 1: the synthesis of compound Y-0

[0012]

[0013] The synthetic method of compound Y-0 of the present invention is carried out according to the following reaction formula:

[0014]

[0015] Synthesis of the target compound Y-0: at 0°C, add 60% potassium hydroxide aqueous solution (3mL) and benzaldehyde (1mmol) to a solution of 2-acetylbenzimidazole (1mmol) in ethanol (10mL), and Stir until the reaction is complete, and monitor the progress of the reaction by TLC. After the reaction was complete, crushed ice and dilute hydrochloric acid solution were added, the pH was adjusted until a precipitate formed, the crude extract was obtained by filtration and drying, and purified by column chromatography to obtain the target compound Y-0. (Refer to the literature for the synthesis method: European Journal of Medicinal Chemistry 143 (2018) 66-84) Yield: 62.6%; yellow powder; m.p.: 204-205°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 7.89(d, J=6.8Hz, 1H), 7.68(d, J=8.4Hz...

Embodiment 2

[0016] Example 2: Synthesis of Compound Y-1 The synthesis method is the same as in Example 1, except that benzaldehyde is replaced by 4-fluorobenzaldehyde.

[0017]

[0018] Yield: 72.1%; light yellow powder; m.p.: 200-201°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 8.38(d, J=9.6Hz, 1H), 8.01(d, J=8.1Hz, 2H), 7.52(t, J=7.9Hz, 2H), 7.34–7.27(m, 2H), 7.24( s, 2H), 7.10(d, J=7.9Hz, 1H), 6.94(d, J=8.5Hz, 1H), 6.20(d, J=4.1Hz, 1H). 13 C NMR (100MHz, DMSO-d 6 )δ: 181.20, 162.43, 145.66, 141.40, 137.29, 135.76, 132.28, 131.52, 131.36, 123.32, 123.06, 121.04, 121.82, 120.96, 117.34, 115.62, 112.38 / z: ms-ci 16 h 11 FN 2 O: 267.7 [M+H] +

Embodiment 3

[0019] Embodiment 3: the synthesis of compound Y-2

[0020] The synthetic method is the same as that of Example 1, except that benzaldehyde is replaced with 4-methylbenzaldehyde.

[0021]

[0022] Yield: 68.8%; orange powder; m.p.: 200.0-201°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 13.53(s, 1H), 8.09(d, J=16.1Hz, 1H), 7.97(d, J=16.0Hz, 1H), 7.78(d, J=7.5Hz, 4H), 7.39(s, 2H), 7.32(d, J=7.4Hz, 2H), 2.37(s, 3H); 13 C NMR (100MHz, DMSO-d 6 )δ: 181.39, 149.52, 144.78, 143.51, 141.79, 132.07, 130.24, 130.24, 129.43, 129.43, 126.13, 123.62, 121.61, 121.01, 113.34, 21.59. MS-ESI m / z: C 17 h 14 N 2 O: 263.1 [M+H] +

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Abstract

The invention relates to the field of medicinal chemistry, and discloses applications of any compound from benzimidazole derivatives Y-0 to Y-12 in prevention and treatment of agricultural plant diseases. It is found through bioactivity test that compounds have certain inhibition activity on six plant fungi including Phyllosticta zeae, botrytis cinerea, sclerotinia sclerotiorum, magnaporthe grisea, rhizoctonia solani and fusarium oxysporum, the inhibition rate of part of the compounds on the six pathogenic fungi under 100 ppm reaches 70% or above, and particularly, the growth of Phyllosticta zeae is almost completely inhibited. The compounds are simple to prepare and cheap and easily available in raw materials, and are expected to be developed into novel bactericides.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and discloses a new application of 2-position modified benzimidazole derivatives, and specifically relates to the use of benzimidazole derivatives Y-0 to Y-12 in the prevention and treatment of Phytophthora maize, Botrytis cinerea, Botrytis cinerea, Application in plant diseases caused by Sclerotinia sclerotiorum, rice blast, Rhizoctonia solani and cotton wilt. Background technique [0002] Under the contradiction of increasing global food demand and gradually decreasing arable land area, the contribution of pesticides to ensuring the stable and high yield of crops is obvious to all. According to statistics, plant fungal diseases cause about 10% reduction in the yield of major crops in the world every year, and the economic losses amount to hundreds of billions of dollars. At present, chemical reagents are mostly used to prevent and control plant fungal diseases in agricultural production, but...

Claims

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Application Information

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IPC IPC(8): A01N43/52A01N43/54A01P3/00C07D235/12C07D405/06C07D403/04C07D405/14
CPCA01N43/52A01N43/54C07D235/12C07D403/04C07D405/06C07D405/14
Inventor 刘映前王仁轩李俊采杨程杰陈永甲彭静文尹晓丹燕银芳
Owner LANZHOU UNIVERSITY
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