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1, 2, 3-triazole hydrazide or amide compound as well as preparation method and application thereof

A compound and composition technology, applied in 1 field, can solve the problems of reduced potency, complicated situation of multidrug-resistant microbial strains, increased number of infections, etc.

Active Publication Date: 2021-04-02
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, chemical pesticides are still the main helpers in the control of plant microbial diseases, however, the gradual decrease in efficacy, especially the resistance of pathogenic microorganisms, has been plagued by people and led to an increase in the number of infections
In addition, the emergence and multiplication of multidrug-resistant microbial strains complicates the situation

Method used

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  • 1, 2, 3-triazole hydrazide or amide compound as well as preparation method and application thereof
  • 1, 2, 3-triazole hydrazide or amide compound as well as preparation method and application thereof
  • 1, 2, 3-triazole hydrazide or amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the preparation of intermediate 2 (4-(azidomethyl) methyl benzoate)

[0055] The raw material 4-bromomethylbenzoic acid methyl ester (5.00g, 21.83mmol) and sodium azide (7.10g, 0.11mol) were added in a 100mL reaction flask, and 14mL N,N-dimethylformamide ( DMF), heated to 60°C for 4 hours to stop the reaction, extracted with ethyl acetate, washed with saturated ammonium chloride three to four times, dried over anhydrous sodium sulfate, and precipitated to obtain 4.12 g of a colorless oil, with a yield of 98.80% .

Embodiment 2

[0056] Example 2: Preparation of intermediate 3 (4-((4-(2-chlorophenyl)-1H-1,2,3-triazol-1-yl)methyl)methyl benzoate)

[0057]Intermediate 2 (4.0g, 20.92mmol) and 1-chloro-2-ethynylbenzene (2.60g, 19.02mmol) were dissolved in 10 mLTHF, then 10mL of water was added to the system, and anhydrous copper sulfate (0.48g , 1.90mmol) and sodium ascorbate (0.75g, 3.80mmol) were dissolved in 8mL of water and added dropwise to the above system, reacted at room temperature for 14 hours, then stopped the reaction, precipitated, dissolved in water, then extracted with dichloromethane, anhydrous Drying over sodium sulfate, precipitation, and separation by column chromatography gave 6.24 g of a white solid with a yield of 99.39%. Its NMR data are: 1 H NMR (500MHz, CDCl 3 ) δ8.23 (dd, J=7.9, 1.7Hz, 1H, 2-Cl-phenyl-H), 8.15 (s, 1H, triazole-H), 8.03-8.00 (m, 2H, benzene-H), 7.40(dd, J=8.0, 1.3Hz, 1H, 2-Cl-phenyl-H), 7.36-7.33(m, 2H, benzene-H), 7.33-7.31(m, 1H, 2-Cl-phenyl- H), 7.24 (ddd, J...

Embodiment 3

[0058] Example 3: Preparation of intermediate 4 (4-((4-(2-chlorophenyl)-1H-1,2,3-triazol-1-yl)methyl)benzoic acid)

[0059] Intermediate 3 (4.30g, 13.12mmol) was dissolved in 20mL of tetrahydrofuran, and then 20mL of water dissolved in KOH (1.10g, 19.68mmol) was added to the system, and heated to 55°C for 3 hours to stop the reaction and desolvate. The pH was adjusted to 3-4 with dilute hydrochloric acid, a large amount of solids were precipitated, and filtered by suction to obtain 3.85 g of white solids, with a yield of 93.39%. Its NMR data are: 1 H NMR (400MHz, DMSO-d6) δ13.04(s, 1H, -COOH), 8.82(s, 1H, triazole-H), 8.09(dd, J=7.8, 1.8Hz, 1H, 2-Cl-phenyl -H), 7.96(d, J=8.3Hz, 2H, benzene-H), 7.56(dd, J=7.9, 1.3Hz, 1H, 2-Cl-phenyl-H), 7.4 8-7.44(m, 2H , benzene-H), 7.44 (d, J=2.5Hz, 1H, 2-Cl-phenyl-H), 7.41-7.35 (m, 1H, 2-Cl-phenyl-H), 5.80 (s, 2H, CH 2 ); 13 C NMR (101MHz, DMSO-d 6 )δ167.4, 143.3, 141.3, 131.0, 130.8, 130.7, 130.3, 130.0, 129.5, 128.4, 128.0, 125.2, 53....

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Abstract

The invention relates to 1, 2, 3, -triazole hydrazide or amide compounds as well as a preparation method and application thereof. The compound has a structure as shown in a general formula (I) which is described in the specification. On the basis of methyl 4-bromomethyl benzoate, a 1, 2, 3-triazole structure is introduced through a substitution reaction and a cycloaddition reaction, and then phenylhydrazine or aniline groups are introduced to the 1, 2, 3-triazole structure to synthesize a series of 1, 2, 3-triazole compounds containing hydrazide or amide groups; the compound has a good inhibition effect on fusarium graminearum, botryosphaeria dothidea, rhizoctonia solani, xanthomonas oryzae pv. Oryzae, xanthomonas axonopodis pv. Citri, xanthomonas axonopodis pv. Actinidia and the like.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 1,2,3-triazole hydrazide or amide compound containing a substituted phenyl group and a benzylidene structure, and a preparation method and application thereof. Background technique [0002] As the population continues to grow, food security has once again become a rigid requirement. Among the many factors contributing to food shortages, plant microbial diseases lead to drastic reductions in crop quality and yields. Pathogenic fungi, such as Botrytis botrytis, Rhizoctonia solani, Dragon fruit anthracnose and wheat gibberella are the most destructive plant parasites, causing serious diseases on various crops; followed by pathogenic bacteria, These include the notorious bacterial blight of rice, canker of citrus, and bacterial canker of kiwifruit. At present, chemical pesticides are still the main helpers in the control of plant microbial diseases, however, the gradu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/06A01N43/647A01N43/84A01P1/00A01P3/00
CPCC07D249/06A01N43/647A01N43/84Y02A50/30
Inventor 王培义丁月龙周卿张玲吉庆田
Owner GUIZHOU UNIV
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