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Application of a class of 1,2,3-triazole-5-amide compounds as agricultural fungicides

A technology of amide compounds and agricultural fungicides, applied in class 1, can solve problems such as poor safety, weak work foundation, and late start

Active Publication Date: 2019-02-15
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the weak foundation and late start of my country's new pesticide creation work, the main varieties in the current market have been controlled by foreign multinational pesticide companies for a long time, resulting in the prevention and control of many major crop pests that have always relied on low activity, large dosage, many residues, and poor safety. pesticide

Method used

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  • Application of a class of 1,2,3-triazole-5-amide compounds as agricultural fungicides
  • Application of a class of 1,2,3-triazole-5-amide compounds as agricultural fungicides
  • Application of a class of 1,2,3-triazole-5-amide compounds as agricultural fungicides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 2-chloro-N-(1-(4-chlorophenyl)-1,2,3-triazole-5)benzamide (compound 1)

[0018]

[0019] Dissolve 2-chlorobenzoic acid in SOCl 2 Reflux at 80°C for 120 minutes, and distill under reduced pressure to remove excess SOCl 2 , Get o-chlorobenzoyl chloride. Under the condition of -78℃ and nitrogen protection, 2mmol of n-butyl lithium was added dropwise to 2mL of dry tetrahydrofuran, and then 2mmol of dry acetonitrile was slowly added dropwise. After stirring for 5 minutes, the substituted 4-chloro dissolved in 2mL of tetrahydrofuran Phenyl azide (2mmol) was slowly added dropwise into the reaction flask, returned to normal temperature and stirred for 120 minutes. After the reaction, purified by silica gel column to obtain 4-chlorophenyl-5-amino-1,2,3-triazole . Take 1 mL of o-chlorobenzoyl chloride, add 1 mmol 4-chlorophenyl-5-amino-1,2,3-triazole, add a small amount of NaH under ice bath, stir at room temperature overnight, and purify by silica gel col...

Embodiment 2

[0020] Example 2: Preparation of 2-chloro-N-(1-(4-fluorophenyl)-1,2,3-triazole-5)benzamide (compound 2)

[0021]

[0022] The preparation method is the same as in Example 1. Replace 4-chlorophenyl azide with 4-fluorophenyl azide to prepare the target compound. The product is a white powder with a yield of 62.3%. m.p.141.3-141.5℃. 1 H NMR(600MHz, DMSO-d 6 )δ10.96(s, 1H), 8.04(s, 1H), 7.69-7.65(m, 2H), 7.56-7.51(m, 4H), 7.44(dd, J=7.6, 1.8Hz, 1H). ESI -MS m / z: 317.07(C 15 H 11 ClFN 4 O, [M+H] + ).

Embodiment 3

[0023] Example 3: Preparation of 2-chloro-N-(1-(3,4-dichlorophenyl)-1,2,3-triazole-5)benzamide (compound 3)

[0024]

[0025] The preparation method is the same as in Example 1. Replace 4-chlorophenyl azide with 3,4-dichlorophenyl azide to prepare the target compound. The product is a white powder with a yield of 60.1%. m.p.155.1-155.5℃. 1 H NMR(600MHz, DMSO-d 6 )δ11.07(s, 1H), 8.07(s, 1H), 8.02(d, J=2.4Hz, 1H), 7.91(d, J=8.6Hz, 1H), 7.67(dd, J=8.6, 2.4 Hz, 1H), 7.60-7.55 (m, 2H), 7.53 (td, J=7.7, 1.5 Hz, 1H), 7.48-7.44 (m, 1H). ESI-MS m / z: 367.04 (C 15 H 10 Cl 3 N 4 O, [M+H] + ).

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Abstract

The invention relates to the field of organic chemistry and agricultural pharmacology and discloses a derivative containing a 1,2,3-triazole-5-amide structure and a preparation method and application thereof. The 1,2,3-triazole-5-amide compound is characterized in that the general formula of the compound is as shown in the specification. In the formula, R1 is selected from groups as shown in the specification and R2 is selected from groups as shown in the specification. The compound has a good antibacterial activity to phytopathogen and can be used as an agricultural fungicide for plant disease control.

Description

Technical field [0001] The invention relates to the synthesis of a class of 1,2,3-triazole-5-amide compounds and their application as fungicides in the prevention and control of plant diseases. Background technique [0002] Pesticides are an indispensable means of production to ensure stable and high yields in agriculture. Their innovative level and leading ability are of irreplaceable significance for food, food and ecological safety. Due to the weak foundation of the creation of new pesticides in my country and the late start, the main varieties in the current market have long been constrained by foreign multinational pesticide companies, resulting in the prevention and control of many major crop pests that have been dependent on low activity, large dosage, large residue, and poor safety. pesticide. Therefore, finding and developing new pharmaceuticals with independent intellectual property rights with high efficiency, low toxicity, strong selectivity and good environmental com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/04C07D401/12C07D403/12A01N43/647A01P3/00
CPCA01N43/647C07D249/04C07D401/12C07D403/12
Inventor 叶永浩王兴严威李天喜
Owner NANJING AGRICULTURAL UNIVERSITY