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Application of Aza-type iso-cryptolepine derivatives in prevention and treatment of agricultural plant diseases

A technology of isoftenine and semenine, which is applied in the field of medicinal chemistry and can solve the problems of an alarming growth rate of resistance and the like

Inactive Publication Date: 2020-11-17
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] At present, chemical agents are mostly used to control plant fungal diseases in agricultural production, but the resistance increases at an alarming rate during the long-term single use of drugs

Method used

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  • Application of Aza-type iso-cryptolepine derivatives in prevention and treatment of agricultural plant diseases
  • Application of Aza-type iso-cryptolepine derivatives in prevention and treatment of agricultural plant diseases
  • Application of Aza-type iso-cryptolepine derivatives in prevention and treatment of agricultural plant diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the synthesis of target compound A-0

[0019]

[0020] The synthetic method of compound A-0 of the present invention is carried out according to the following reaction formula:

[0021]

[0022] Synthesis of target compound A-0: 2-(2 bromophenyl)benzimidazole (1mmol), sodium azide (2mmol), cuprous iodide (0.2mmol), p-toluenesulfonic acid (2mmol), tert Add butyl hydroperoxide (1mmol) into a 50mL round-bottomed flask, then add an appropriate amount of N,N-dimethylacetamide (DMA), reflux at 130°C for 10h under nitrogen protection, cool to room temperature after reaction, add dichloro 50mL of methane was extracted several times with brine and water, the organic layer was taken, spin-dried, and purified by column chromatography to obtain it (refer to the literature for the synthesis method: Eur.J.Org.Chem., 2017, 514-522).

[0023] Yield: 67.5%; light yellow powdery solid; m.p.: 228.3-230.6°C; 1 H NMR (400MHz, Chloroform-d 6 )δ9.15(s,1H),8.68(dd,J=7.9,...

Embodiment 2

[0024] Embodiment 2: the synthesis of target compound A-1

[0025]

[0026] The synthetic method of compound A-1 of the present invention is carried out according to the following reaction formula:

[0027]

[0028] The synthesis of target compound A-1: ​​get 2-(2-bromophenyl) benzimidazole derivative (2mmol), guanidine hydrochloride (3mmol), cuprous iodide (5mol%) and potassium phosphate (6mmol) respectively Add 7 mL of DMF to a 50 mL round-bottomed flask, blow nitrogen gas three times, exhaust the air, reflux at 100°C for 16 h, and monitor the reaction by TLC. After the reaction was completed, cool to room temperature, dissolve with 50mL of dichloromethane, add 150mL of saturated sodium chloride solution for extraction three times, then wash the organic phase with water, collect the organic layer, evaporate to dryness under reduced pressure, and dissolve with petroleum ether-ethyl acetate The system was purified by silica gel column chromatography to obtain . (Refer ...

Embodiment 3

[0030] Embodiment 3: the synthesis of target compound A-2

[0031]

[0032] The synthesis method is the same as in Example 2, only replacing guanidine hydrochloride with amidine hydrochloride.

[0033] Yield: 48.0%; pale yellow powdery solid; m.p.: 200.0-202.3°C; 1 H NMR (400MHz, DMSO-d 6 )δ8.40(dd, J=7.9,1.6Hz,1H),7.92(d,J=8.0Hz,1H),7.66(ddd,J=8.5,7.0,1.7Hz,1H),7.58–7.51(m ,2H),7.46(s,2H),7.40-7.35(m,1H),3.18(s,3H). 13C NMR (101MHz, DMSO-d6) δ148.90, 146.96, 145.11, 144.31, 132.27, 128.63, 125.52, 124.82, 124.24, 123.63, 122.80, 119.52, 115.12, 114.79, 19.12 / z: CESI m 15 h 11 N 3 : 234.14[M+H] + .

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Abstract

The invention discloses application of any compound of Aza-type iso-cryptolepine derivatives A0-A38 in prevention and treatment or resisting of agricultural plant diseases. Antibacterial activity testresults show that the compounds have certain inhibitory activity on six plant diseases, namely phyllosticta of corn, sclerotinia rot of rape, rhizoctonia solani, gray mold of tomatoes, rice blast andgray mold of cotton, and the inhibitory activity of a part of the compounds on germs is superior to the inhibitory activity of azoxystrobin; so the compounds can be developed as bactericides.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and discloses a new application of "Aza" type isolophylline derivatives, and specifically relates to the use of derivatives A-0 to A-38 in the prevention and treatment of pointomyces maize, rape sclerotinia, Application in plant diseases caused by tomato gray mold, rhizoctonia solani, rice blast, cotton wilt. Background technique [0002] At present, chemical agents are mostly used to prevent and control plant fungal diseases in agricultural production, but the resistance increases at an alarming rate during the long-term single use of drugs. Benzimidazoles, triazoles and methoxyacrylates, known as the three milestones in the field of agricultural antimicrobials, are currently facing severe resistance problems. However, the demand for antibacterial drugs in current agricultural production is increasing day by day. Therefore, the development of new pesticides with high efficiency, low toxicity ...

Claims

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Application Information

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IPC IPC(8): A01N43/90A01P3/00C07D487/04
CPCA01N43/90C07D487/04
Inventor 刘映前李俊采王仁轩朱佳凯赵中敏周锐孙钰燕银芳彭静文
Owner LANZHOU UNIVERSITY
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