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A class of pyrazole bisamide compounds containing 1,2,3-thiadiazole and its synthesis method and application

A technology of pyrazole bisamide and thiadiazole is applied in the field of pyrazole bisamide compounds and their synthesis, which can solve the problems of weak lipophilicity and strong hydrophilicity, achieve good armyworm killing activity and room for modification and modification. Large, novel structure

Inactive Publication Date: 2017-12-22
CHINA AGRI UNIV
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  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the principle of pesticide screening, the normal range of the hydrophobic constant (logP, ester-water partition coefficient) of pesticide molecules is [0,5], but the biheterocyclic skeleton of the current biheterocyclic compound contains multiple N atoms and two amide bonds Structure, so lipophilicity is weak, hydrophilicity is strong

Method used

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  • A class of pyrazole bisamide compounds containing 1,2,3-thiadiazole and its synthesis method and application
  • A class of pyrazole bisamide compounds containing 1,2,3-thiadiazole and its synthesis method and application
  • A class of pyrazole bisamide compounds containing 1,2,3-thiadiazole and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 N-(3-ethyl-5-(methylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide

[0038] (1) 3-Ethyl-4-nitro-1H-pyrazole-5-carboxylic acid

[0039] In the 50mL there-necked flask, add 7.5mL (183.78mmol) fuming nitric acid, slowly add 8.4mL (170.57mmol) of fuming sulfuric acid dropwise under the ice bath, control the temperature of the system to be lower than 5°C during the dropwise addition, and add 3- Ethyl-1H-pyrazole-5-carboxylic acid 7.0g (50mmol), reacted at 60°C for 18h, cooled to room temperature, poured the reaction solution into 100g of ice, a white precipitate appeared, suction filtered, and dried to obtain 6.64g of white solid, Yield: 71.78%, m.p.150~152℃;

[0040] (2) N-methyl-3-ethyl-4-nitro-1H-pyrazole-5-carboxamide

[0041] 10g (54mmol) of 3-ethyl-4-nitro-1H-pyrazole-5-carboxylic acid and 51mL (702mmol) of thionyl chloride were added to a 100mL there-necked flask, heated to reflux for 4h, the reaction was completed, and the unreacted ...

Embodiment 2

[0050] Example 2 N-(3-ethyl-5-(ethylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide

[0051] (1) The preparation of 3-ethyl-4-nitro-1H-pyrazole-5-carboxylic acid refers to Example 1;

[0052] (2) Preparation of N,3-diethyl-4-nitro-1H-pyrazole-5-carboxamide Reference Example 1: white solid, yield: 41.01%, m.p.150~152°C. 1 H NMR (CDCl 3 ,ppm): 1.28~1.35(m, 6H), 2.99~3.07(q, J=7.4Hz, 2H), 3.52~3.61(m, 2H), 9.04(s, 1H), 12.20(s, 1H); MS:210.8[M-H] － ;

[0053] (3) The preparation of N,3-diethyl-4-amino-1H-pyrazole-5-carboxamide refers to Example 1;

[0054] (4) Refer to Example 1 for the preparation of 4-methyl-1,2,3-thiadiazole-5-formyl chloride;

[0055] (5) N-(3-ethyl-5-(ethylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide The preparation of the reference Example 1: white solid, yield: 73.78%, m.p.196 ~ 197 ℃; 1 H NMR (CH 3 OH-d 4 ,ppm):1.18~1.23(t,J=7.2Hz,3H),1.24~1.29(t,J=7.6Hz,3H),2.71~2.78(q,J=7.6Hz,2H),2.94(s, 3H),3.39~3....

Embodiment 3

[0056] Example 3 N-(3-ethyl-5-(n-propylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-methyl amide

[0057] (1) The preparation of 3-ethyl-4-nitro-1H-pyrazole-5-carboxylic acid refers to Example 1;

[0058] (2) Reference Example 1 for the preparation of 3-ethyl-N-n-propyl-4-nitro-1H-pyrazole-5-carboxamide: white solid, yield: 73.00%, m.p.132~134°C; 1 H NMR (DMSO, ppm): 0.87~0.92 (t, J=7.4Hz, 3H), 1.20~1.25 (t, J=7.5Hz, 3H), 1.47~1.54 (m, 2H), 2.86~2.94 (q , J=7.5Hz, 2H), 3.19(m, 2H), 8.50(s, 1H); MS: 227.1[M+H] + ;

[0059] (3) The preparation of 3-ethyl-N-n-propyl-4-amino-1H-pyrazole-5-carboxamide refers to Example 1;

[0060] (4) Refer to Example 1 for the preparation of 4-methyl-1,2,3-thiadiazole-5-formyl chloride;

[0061] (5) N-(3-ethyl-5-(n-propylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-methyl For the preparation of amide, refer to Example 1: white solid, yield: 93.83%, m.p.186~187°C; 1 H NMR (CH 3 OH-d 4 , ppm): 0.93~0.98 (t, J=7.4Hz, ...

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a pyrazol bi-amide compound containing 1,2,3-thiadiazole and a synthetic method and application thereof. The compound has a structure of a general formula I shown in the specification. When the compound is prepared, firstly, a 4-amino pyrazole intermediate and a 1,2,3-thiadiazole formyl chloride intermediate are synthesized; secondly, the 4-amino pyrazole intermediate and the 1,2,3-thiadiazole formyl chloride intermediate are condensed according to a conventional condensation reaction condition, and then the compound of the general formula I can be synthesized. The compound has the superior mosquito larva killing activity and certain armyworm killing activity, and part of the compound has the anti-tobacco mosaic virus activity and bactericidal activity. The compound is novel in structure and large in space of modification and improvement, the preparing method is reasonable and practical, the compound can serve as a pesticide activity lead for deep studying, can serve as mosquitocide to be applied and has potential production and application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a class of pyrazole bisamide compounds containing 1,2,3-thiadiazole and its synthesis method and application. Background technique [0002] Fungal diseases are the most serious diseases among plant diseases, endangering the production of food, fruits, vegetables and horticulture, and the damage is serious. Apple ring disease, also known as rough skin, black rot, water rot, fruit rot, ring brown rot or verrucous rough skin, is a serious hazard and occurs in large areas of orchards in northern my country. Shandong, Henan, and Beijing are most at risk. The disease becomes serious with the increase of tree age. The incidence rate of fruit trees aged 11 to 17 years is 78.7%, and the disease index is 53.8; it often occurs together with dry rot and anthracnose, which is a major threat to fruit production. There is a tendency to spread and increase, and the curren...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/12A01N43/828A01P7/04A01P1/00A01P3/00
CPCA01N43/82C07D417/12
Inventor 袁德凯刘艳红张景朋徐高飞
Owner CHINA AGRI UNIV
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