Pyrazol bi-amide compounds containing 1,2,3-thiadiazole and synthetic method and application thereof

A technology of pyrazole bisamides and thiadiazoles, applied in the field of pyrazole bisamides and their synthesis, can solve the problems of weak lipophilicity and strong hydrophilicity, and achieve good armyworm killing activity and room for modification and transformation The effect of large size and reasonable and easy synthesis method

Inactive Publication Date: 2015-11-11
CHINA AGRI UNIV
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  • Description
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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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  • Pyrazol bi-amide compounds containing 1,2,3-thiadiazole and synthetic method and application thereof
  • Pyrazol bi-amide compounds containing 1,2,3-thiadiazole and synthetic method and application thereof
  • Pyrazol bi-amide compounds containing 1,2,3-thiadiazole and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1N-(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] Add 7.5mL (183.78mmol) fuming nitric acid into a 50mL three-necked flask, slowly add 8.4mL (170.57mmol) of fuming sulfuric acid dropwise under ice bath, control the system temperature below 5°C during the dropping process, 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, 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] Add 10g (54mmol) of 3-ethyl-4-nitro-1H-pyrazole-5-carboxylic acid and 51mL (702mmol) of thionyl chloride into a 100mL three-necked flask, heat to reflux for 4h, after the reaction is complete, remove the unreacted mixture under reduced pressure ...

Embodiment 2

[0050] Example 2N-(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) N,3-diethyl-4-nitro-1H-pyrazole-5-carboxamide Preparation Reference Example 1: white solid, yield: 41.01%, m.p.150-152°C. 1 HNMR (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) The preparation of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride refers to Example 1;

[0055] (5) N-(3-ethyl-5-(ethylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide The preparation reference example 1: white solid, yield: 73.78%, m.p.196~197 ℃; 1 HNMR (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), 3.39~3.42(q, J=7.2Hz, ...

Embodiment 3

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

[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 HNMR (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) The preparation of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride refers to Example 1;

[0061] (5) N-(3-ethyl-5-(n-propylcarbamoyl)-1H-pyrazol-4-yl)-4-methyl-1,2,3-thiadiazole-5-methanol The preparation of amides refers to Example 1: white solid, yield: 93.83%, m.p.186~187°C; 1 HNMR (CH 3 OH-d 4 , ppm): 0.93~0.98(t, J=7.4Hz, 3H), 1.23~1.2...

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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 Applications(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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