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Bis-(1, 3, 4-thiadiazole) derivative as well as preparation method and application thereof

A technology of thiadiazoles and compounds, applied in the field of bis-class derivatives and their preparation, can solve problems such as copper poisoning and red spider induction

Pending Publication Date: 2022-07-29
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to long-term and intensive use, its resistance continues to increase, causing spider mites, copper poisoning and other prominent problems

Method used

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  • Bis-(1, 3, 4-thiadiazole) derivative as well as preparation method and application thereof
  • Bis-(1, 3, 4-thiadiazole) derivative as well as preparation method and application thereof
  • Bis-(1, 3, 4-thiadiazole) derivative as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0059] The preparation method of the bis-(1,3,4-thiadiazole) compound of the present invention comprises the following steps:

[0060] First, after completely dissolving hypophosphite in water and concentrated hydrochloric acid, put into dithiourea, and directly heat, stir and reflux for 15-20 hours. Washing with water, draining and drying in an infrared oven to obtain 2-amino-5-mercapto-1,3,4-thiadiazole; with the intermediate 2-amino-5-thio-1,3,4-thiadiazole Diazole as raw material, add 2-amino-5-sulfanyl-1,3,4-thiadiazole to the aqueous solution of sodium hydroxide, stir to dissolve all the raw materials, slowly add various dialdehyde solutions, and at room temperature The reaction was carried out for 1-2 hours, then dilute hydrochloric acid was added to adjust the pH value of the system to neutrality, and finally the precipitated solid was vacuum filtered, sucked dry, and dried at 100°C.

[0061] Wherein, the concentration of the sodium hydroxide aqueous solution is 5-20%...

Embodiment 1

[0086] Example 1 Preparation of intermediate 2-amino-5-mercapto-1,3,4-thiadiazole

[0087]In a 500 ml clean three-necked flask, add 50 ml of water and 100 ml of concentrated hydrochloric acid, and 1.5 g of calcium hypophosphite as a catalyst. After stirring and dissolving, slowly add 30 g of dithiourea to the three-necked flask, and heat to 100°C. Carry out reflux reaction, stir and reflux for 15 hours, after the reaction is completed, after the reaction system is cooled to room temperature, crystals are precipitated, and the precipitated crystals are subjected to suction filtration with a glass funnel and then dried under infrared oven conditions to obtain Intermediate 2 -Amino-5-mercapto-1,3,4-thiadiazole 18.35g, the melting point is 230-232°C, the content is 95-97%, and the yield is 87.07%.

Embodiment 2

[0088] Example 2 Preparation of N,N-ethylene-bis(2-amino-5-mercapto-1,3,4-thiadiazole) (1T) compound

[0089] Weigh 5 g (37.54 mmol) of the intermediate 2-amino-5-sulfanyl-1,3,4-thiadiazole into a 250 mL beaker, slowly add 10-20% aqueous sodium hydroxide solution to the beaker, After stirring to dissolve all the raw materials, slowly add 40% glyoxal solution to the beaker, react at 25-30 ° C for 5-6 hours, then add dilute hydrochloric acid to adjust the pH value of the system to neutrality, and finally remove the precipitated The solid was vacuum filtered, sucked dry, and dried at 100°C to obtain 8.73 g of N,N-ethylene-bis-(2-amino-5-mercapto-1,3,4-thiadiazole) compound, The melting point is 129-131°C, the content is 93-95%, and the yield is 79.53%. 1 HNMR (500MHz, DMSO-d 6 )δ13.28(s,-SH,2H),8.22(s,-NH,2H),3.47(t,J=1.36Hz,- (CH 2 ) -,4H). 13 C NMR (100MHz, DMSO-d 6 )δ184(s),164.2(s),48.7(s).HRMS(ESI)m / z for C 6 H 8 N 6 NaS 4 [M+Na] + calcd 314.97431, found: 314.977...

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Abstract

The invention relates to the field of chemical engineering and pesticides, and mainly relates to a bactericide for preventing and treating bacterial diseases such as rice bacterial leaf blight, rice bacterial leaf streak, citrus canker, citrus yellow shoot, tomato bacterial wilt, tobacco bacterial wilt, peach tree shot hole, cabbage black rot, cabbage soft rot, muskmelon bacterial angular leaf spot and watermelon bacterial fruit rot. The effective chemical name of the N, N-n-bis-(2-amino-5-sulfydryl-1, 3, 4-thiadiazole) is N, N-n-bis-(2-amino-5-sulfydryl-1, 3, 4-thiadiazole), and the chemical structure is shown in the specification. The preparation disclosed by the invention is effective to bacteria of crops; the bactericidal composition has a good prevention and treatment effect on plant bacterial diseases such as rice bacterial leaf blight, rice bacterial leaf streak, citrus canker, citrus yellow shoot, tomato bacterial wilt, tobacco bacterial wilt, peach tree shot hole, cabbage black rot, cabbage soft rot, muskmelon bacterial angular leaf spot and watermelon bacterial fruit rot, and especially has a good prevention and treatment effect on plant bacterial diseases such as rice bacterial leaf blight, rice bacterial leaf streak, citrus canker, citrus yellow shoot disease, tomato bacterial wilt, tobacco bacterial wilt, peach tree shot hole.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to bis-(1,3,4-thiadiazole) derivatives and a preparation method and application thereof. Background technique [0002] Plant bacterial disease is the third largest type of plant disease after fungal and viral diseases caused by bacteria infecting plants. Bacterial diseases such as rice bacterial blight, rice bacterial leaf spot, citrus canker, tobacco bacterial wilt and tomato bacterial wilt are all important worldwide diseases. In recent years, with the changes of crop cultivation system and environmental climate in my country, rice bacterial wilt, rice bacterial leaf spot, citrus canker, citrus yellow dragon disease, tomato bacterial wilt, tobacco bacterial wilt, peach tree perforation Bacterial diseases of crops, such as black rot of cabbage, soft rot of cabbage, bacterial angular spot of melon and bacterial fruit rot of watermelon, tend to occur more heavily in my country. This kind o...

Claims

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Application Information

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IPC IPC(8): C07D285/135A01N43/824A01P1/00
CPCC07D285/135A01N43/82A01P1/00
Inventor 宋宝安李洪德李建专王建胡德禹韦春乐王荣华
Owner GUIZHOU UNIV
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