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Preparation method of thiophene-1, 3, 4-oxadiazole carboxamide compound, product and application thereof

A technology of oxadiazole carboxamide and thiophene carboxyl hydrazide is applied in the field of pesticide synthesis and achieves the effects of easy availability of raw materials, simple preparation method and easy control of reaction conditions

Inactive Publication Date: 2021-08-06
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there is no report on the use of thiophene-linked 1,3,4-oxadiazole carboxamides as agricultural fungicides

Method used

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  • Preparation method of thiophene-1, 3, 4-oxadiazole carboxamide compound, product and application thereof
  • Preparation method of thiophene-1, 3, 4-oxadiazole carboxamide compound, product and application thereof
  • Preparation method of thiophene-1, 3, 4-oxadiazole carboxamide compound, product and application thereof

Examples

Experimental program
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preparation example Construction

[0043] Schematic view of the preparation method of thiophene 1,3,4-malodazoleamide compounds of the present invention figure 1 , Including the following steps:

[0044] (1) 2-thiochloric acid was esterified by esterification of 2-thiophene;

[0045] (2) 2-thiophene carbide for a hydrazine, 2-thiophene hydrazide (1);

[0046] (3) 2-thiophene hydrazide and oxalyl monochloride reactively forms a bisamide intermediate (2);

[0047] (4) Disoxamide intermediate (2) is reacted with trichloroside, resulting in thiophene 1,3,4-malodoxazole (3);

[0048] (5) thiophene 1,3,4-oxazoleate and the substituted benzylamine reaction synthesis thiophene 1,3,4-malodazoleamamide.

Embodiment 1

[0050] Preparation of thiophene 1,3,4-malodazole ester

[0051] 2-thiochloric acid (6.41 g, 50 mmol) was added to 250 mL of single-mouth bottle, and 100 mL of methanol and catalytic amount of concentrated sulfuric acid (0.5 g, 5 mmol) were added, increased to reflow temperature, reaction for 6 h, TLC detection, reaction, cooling To room temperature, the saturated sodium hydrogencarbonate solution was added dropwise to pH = 7, and ethyl acetate was added (50 ml × 3), combined with the organic layer, washed with brine (100 ml × 2), dried over anhydrous sodium sulfate. Filtration, dissolve the oil 6g.

[0052]6 g of the 6 g of the oil was dissolved in 60 ml of ethanol, and 85% hydrazine (7.94 g, 211 mmol) was added, and the reflux reaction was 5 h, the TLC detection raw material reaction was complete, cooled, rotated to remove most of ethanol, precipitate solid, and filtered Wash (10 mL × 3), dried 2-thiophene hydrazide.

[0053] 2-thiophene hydrazide (0.99 g, 7.0 mmol) was dissolved...

Embodiment 2

[0056] Preparation of thiophene 1,3,4-oxazoleamide

[0057]

[0058] 4-chlorobenzylamine (1.2 mmol) was added to a solution of an intermediate thiophene 1,3,4-oxagnectate (1.0 mmol) 10 ml of DMF, temperature rising to 80 ° C reaction for 2 h, TLC monitoring the feedstock reaction The system is cooled to room temperature, poured into ice water (50 mL), stirring, stirring solid, filtration, drying after drying, crystallization N- (4-chlorophenyl) -5-thiophene-2 - Base - [1,3,4] malodazole-2-formamide (I-1): white solid; yield, 53.3%, MP183.6-185.9 ° C; 1H NMR (600 MHz, DMSO-D6) Δ9. 91 (t, j = 6.1Hz, 1H), 8.03 (D, J = 4.9 Hz, 1H), 7.93 (D, J = 3.6Hz, 1H), 7.40 (Q, J = 8.6Hz, 4H), 7.33 ( T, J = 4.0Hz, 1H), 4.48 (D, J = 6.2 Hz, 2H) .13C NMR (150MHz, DMSO-D6) δ161.36, 157.78, 153.04, 137.31.42, 129.31.62, 131.42, 129.33, 128.95, 128.26 123.58, 41.89.

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Abstract

The invention discloses a preparation method of a thiophene-1, 3, 4-oxadiazole formamide compound, a product and application thereof. 2-thiophenecarboxylic acid is subjected to methyl esterification and hydrazinolysis reaction to synthesize 2-thiophenecarboxylic acid hydrazine, then the 2-thiophenecarboxylic acid hydrazine and oxalyl chloride monomethyl ester are subjected to amidation reaction to obtain a bisamide intermediate, the bisamide intermediate and phosphorus oxychloride are subjected to cyclization reaction to prepare thiophene-1, 3, 4-oxadiazole formate, and then the thiophene-1, 3, 4-oxadiazole formate and substituted benzylamine are subjected to one-step reaction to synthesize the thiophene-linked 1, 3, 4-oxadiazole carboxamide compound. The compound has a good prevention effect on sclerotinia sclerotiorum and alternaria solani under an in-vitro condition, and can be used for preventing and treating fungal diseases of agricultural or forestry plants. The preparation method of the compound is simple and convenient, the yield is high, and the product property is stable.

Description

Technical field [0001] The present invention belongs to the field of pesticide synthesis, and is specifically involved in the preparation method and product of a class of thiophene 1,3,4-malodazolamide compounds and their applications. Background technique [0002] Since the commodity of ferrite in 1966, the succinate dehydrogenase inhibitor has been developed for nearly 60 years, which is the first batch of commercial fungicides containing amide. The mechanism of action of succinate dehydrogenate is based on the interruption of the mitochondrial tricarboxylic acid cycle and the breathing chain. [0003] The main structure of the succinate dehydrogenase inhibitor contains an amide group, as a commonly used fungicide, the number of varieties accounts for considerable proportion, but such bactericides are used for a period of time, the disease will It produces resistance, therefore requires continuous invention of new and improved compounds with bactericidal activity to meet the ne...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04C07D413/14A01N43/824A01P3/00
CPCC07D413/04C07D413/14A01N43/82
Inventor 谷文杨子辉孙月刘青松王石发孙雪宝孙露陈霖霖
Owner NANJING FORESTRY UNIV
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