Application of a substituted benzothiazole C2 amide alkylation derivative as a fungicide

A technology of benzothiazole and amide alkyl, which is applied in the application field of substituted benzothiazole C2 amide alkylated derivatives as fungicides, can solve problems such as no literature reports in biological activity research, and achieve good inhibitory activity, The effect of mild reaction conditions

Active Publication Date: 2019-11-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The series of substituted benzothiazole C2 amide alkylated derivatives designed and synth

Method used

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  • Application of a substituted benzothiazole C2 amide alkylation derivative as a fungicide
  • Application of a substituted benzothiazole C2 amide alkylation derivative as a fungicide
  • Application of a substituted benzothiazole C2 amide alkylation derivative as a fungicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Derivative Ia ((R)n=H, R 1 =H) Synthesis

[0027] Weigh benzothiazole (0.5mmol, 67mg), K 2 S 2 o 8 (1mmol, 0.27g) and Eosin Y (0.0025mmol, 1.6mg) were placed in a 25mL Schlenk reaction tube, then N,N-dimethylformamide (87.5mmol, 6.4g) was added, and placed in a 15W LED white light Reaction under irradiation, stirring reaction at room temperature, tracking and monitoring the reaction process with TLC, after 20h, the reaction was completed, the reaction solution was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent was sherwood oil / ethyl acetate with a volume ratio of 1:1 ester) to obtain a yellow oil, the derivative Ia. Yield 68%.

[0028] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0029] 1 H NMR (CDCl 3,500MHz)δ8.19(s,1H),7.99-8.03(t,J=7.5Hz,1H),7.85-7.90(m,1H),7.46-7.53(m,1H),7.37-7.44(m, 1H), 4.94(s, 2H), 3.07(s, 3H); 13 C NMR (CDCl 3 , 125MHz) δ166.2, ...

Embodiment 2

[0030] Example 2 Derivatives Ib ((R)n=5-chloro, R 1 =H) Synthesis

[0031] Weigh 5-chlorobenzothiazole (0.5mmol, 85mg), K 2 S 2 o 8 (1mmol, 0.27g) and Eosin Y (0.0035mmol, 2.3mg) were placed in a 25mL Schlenk reaction tube, then N,N-dimethylformamide (87.5mmol, 6.4g) was added, and placed in a 15W LED white light lamp Reaction under irradiation, stirring reaction at room temperature, tracking and monitoring the reaction process with TLC, after 20h, the reaction was completed, the reaction solution was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent was sherwood oil / ethyl acetate with a volume ratio of 1:1 ester) to obtain a yellow oil, the derivative Ib. Yield 58%.

[0032] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0033] 1 H NMR (CDCl 3 ,500MHz)δ8.20(s,1H),8.01(dd,J=8.5,2.0Hz,1H),7.78-7.83(m,1H),7.38-7.44(m,1H),4.93(s,2H) ,3.10(s,3H); 13 C NMR (CDCl 3 , 125MHz) δ168.3...

Embodiment 3

[0034] Example 3 Derivatives Ic ((R)n=6-OMe, R 1 =H) Synthesis

[0035] Weigh 6-methoxybenzothiazole (0.5mmol, 83mg), K 2 S 2 o 8 (1mmol, 0.27g) and Eosin Y (0.0035mmol, 2.3mg) were placed in a 25mL Schlenk reaction tube, then N,N-dimethylformamide (87.5mmol, 6.4g) was added, and placed in a 15W LED white light lamp Reaction under irradiation, stirring reaction at room temperature, tracking and monitoring the reaction process with TLC, after 20h, the reaction was completed, the reaction solution was concentrated to remove the solvent, and the concentrated solution was separated by column chromatography (eluent was sherwood oil / ethyl acetate with a volume ratio of 1:1 ester) to obtain a yellow oil, the derivative Ic. Yield 71%.

[0036] of the compound 1 H NMR and 13 C NMR analysis data are described below,

[0037] 1 H NMR (CDCl 3 ,500MHz)δ8.16(s,1H),7.86(dd,J=9.0,6.5Hz,1H),7.30(dd,J=7.5,2.5Hz,1H),7.07(m,1H),4.87(s ,2H),3.85(s,3H),3.04(s,3H); 13 C NMR (CDCl 3 , 12...

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Abstract

The invention discloses application of a substituted benzothiazole C2 amide alkylation derivative as a fungicide. The structure of the derivative is shown as a formula (I). In the formula (I), a substitute R1 is hydrogen or C1-C5 alkyl; H on a benzothiazole ring is monosubstituted, polysubstituted or unsubstituted by a substituent R, with the C2 site of the benzothiazole ring is not substituted bythe R; n is an integer of 0 to 4, and represents the number of the substituents R on the benzothiazole ring; when the n is 0, indicating that H on the benzothiazole ring is not substituted; when then is 1, indicating that the H on the benzothiazole ring is monosubstituted by the substituent R; when the n is 2 to 4, indicating that H on the benzothiazole ring is polysubstituted by the substituents R, with the substituents R at different substation positions being same or different; the substituent R is hydrogen, C1-C5 alkyl, C1-C2 alkoxyaryl, or halogen. The derivative has good inhibitory effects on fungi causing wheat scab, corn southern leaf blight, cucumber anthracnose and rice sheath blight disease.

Description

technical field [0001] The invention relates to the application of a substituted benzothiazole C2 amide alkylated derivative as a fungicide. Background technique [0002] As a very important class of nitrogen-containing fused heterocyclic compounds, benzothiazole and its derivatives have attracted much attention due to their wide range of biological activities. Wide range of applications. It has insecticidal (Phytoparasitica, 2016, 44 (1): 115-124), bactericidal (Pestic. Biochem. Phys., 2019, 154: 7-16), herbicidal (Pest Manag. Sci., 2019, 75(1):262-269), antiviral (Chin.J.Org.Chem., 2007, 27, 279) and other activities; in the field of medicine, it has anticancer (J.Heterocyclic.Chem., 2019, 56(4) : 1437-1457), hypoglycemic (Bioorg.Chem., 2019, 83: 6-19), anti-inflammatory (Acta Pol. Pharm., 2009, 66(4): 387-392) and other activities. At present, a variety of compounds containing benzothiazole structures have been successfully developed into commercial agents, such as fun...

Claims

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Application Information

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IPC IPC(8): A01N43/78A01P3/00
CPCA01N43/78
Inventor 翁建全徐雯秀戴小强刘幸海
Owner ZHEJIANG UNIV OF TECH
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