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A class of furan-linked 1,3,4-oxadiazole carboxamide compounds and its preparation method and application

A technology for oxadiazole carboxamide and amine compounds, which is applied in the field of pesticide synthesis and achieves the effects of novel molecular structure, easy control of reaction conditions, and easy availability of raw materials

Active Publication Date: 2022-01-07
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 furan-linked 1,3,4-oxadiazole carboxamides as agricultural fungicides

Method used

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  • A class of furan-linked 1,3,4-oxadiazole carboxamide compounds and its preparation method and application
  • A class of furan-linked 1,3,4-oxadiazole carboxamide compounds and its preparation method and application
  • A class of furan-linked 1,3,4-oxadiazole carboxamide compounds and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Preparation of furan-linked 1,3,4-oxadiazole methyl ester:

[0060] Take 2-furancarboxylic acid (5.62g, 50mmol) in a 250mL single-necked bottle, add 100mL of methanol and a catalytic amount of concentrated sulfuric acid (5mmol), after the addition is complete, heat up to reflux temperature, react for 6h, TLC detection, after the reaction is complete, cool to room temperature, Under stirring, add saturated sodium bicarbonate solution dropwise to pH=7, add ethyl acetate for extraction (50mL×3), combine the organic layers, wash with saturated brine (100mL×2), dry over anhydrous sodium sulfate, suction filter, remove 6.2 g of 2-furanoic acid ester was dissolved as an oil.

[0061] Dissolve 6.2g of the oily 2-furanoate in 60mL of ethanol, then add 85% hydrazine hydrate (9.22g, 245mmol), after the addition is complete, reflux for 6h, TLC detects that the reaction of the raw materials is complete, cool, and remove most of the mixture by rotary concentration Ethanol, a solid p...

Embodiment 2

[0065] Preparation of furan-linked 1,3,4-oxadiazole carboxamide

[0066] Furan-linked 1,3,4-oxadiazole carboxamide derivatives (I-1)

[0067]

[0068] 4-Chlorobenzylamine (1.2mmol) was added to the 10mL DMF solution in which the intermediate furan-linked 1,3,4-oxadiazole methyl ester (1.0mmol) was dissolved, and the temperature was raised to 80°C for 5 hours, and the reaction of the raw materials was monitored by TLC. , the system was cooled to room temperature, poured into ice water (50mL), the solid was precipitated under stirring, suction filtered, and the crude product was recrystallized with petroleum ether / ethanol mixed solvent after drying to obtain the target compound N-(4-chlorobenzyl)-5 -furan-2-yl-[1,3,4]oxadiazole-2-carboxamide (I-1): yellow solid; yield, 85.1%, m.p.136.5-138.5°C; 1H NMR (600MHz, DMSO- d6) δ9.91(t, J=6.1Hz, 1H), 8.12(s, 1H), 7.48(d, J=3.5Hz, 1H), 7.41(d, J=8.5Hz, 2H), 7.37(d ,J=8.5Hz,2H),6.84(dd,J1=3.5Hz,J2=1.7Hz,1H),4.47(d,J=6.2Hz,2H).13C NMR...

Embodiment 3

[0070]

[0071] 4-Fluorobenzylamine (1.2mmol) was added to 10mL of DMF solution in which the intermediate furan-linked 1,3,4-oxadiazole methyl ester (1.0mmol) was dissolved, and the temperature was raised to 80°C for 5 hours. TLC monitored that the reaction of the raw materials was complete. , the system was cooled to room temperature, poured into ice water (50mL), the solid was precipitated under stirring, suction filtered, and the crude product was recrystallized with petroleum ether / ethanol mixed solvent after drying to obtain the target compound N-(4-fluorobenzyl)-5 -furan-2-yl-[1,3,4]oxadiazole-2-carboxamide (I-2): white solid; yield, 84.4%, m.p.137.1-139.5°C; 1H NMR (600MHz, DMSO- d6) δ9.90(t, J=6.0Hz, 1H), 8.12(s, 1H), 7.48(d, J=3.5Hz, 1H), 7.39(dd, J1=8.4Hz, J2=5.7Hz, 2H ), 7.17(t, J=8.9Hz, 2H), 6.84(t, J1=3.8Hz, J2=1.7Hz, 1H), 4.46(d, J=6.2Hz, 2H).13C NMR(150MHz, DMSO) δ161.80(d, J=241.0Hz), 158.28, 158.09, 153.41, 148.15, 138.61, 135.04(d, J=2.9Hz), 130.02(d, J=8...

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Abstract

The invention discloses a class of furan-linked 1,3,4-oxadiazole carboxamide compounds and a preparation method and application thereof. Formic acid ester carries out hydrazinolysis reaction, makes 2-furyl hydrazide; 2-furyl hydrazide is reacted with oxalyl monomethyl chloride to generate a bisamide intermediate; the bisamide intermediate is reacted with phosphorus oxychloride to prepare Furanyl 1,3,4-oxadiazole carboxylate is obtained; furyl 1,3,4-oxadiazole carboxylate is reacted with substituted benzylamine to synthesize furanal 1,3,4-oxadiazole carboxamide. The compound has good control effect on tomato cinerea, rape sclerotinia and tomato early blight under in vitro conditions, and can be used to prevent and control agricultural or forestry plant fungal diseases. The preparation method of the compound is simple, the yield is high, and the product has stable properties.

Description

technical field [0001] The invention belongs to the technical field of pesticide synthesis, and in particular relates to a class of furan-linked 1,3,4-oxadiazole carboxamide compounds and a preparation method and application thereof. Background technique [0002] Succinate dehydrogenase inhibitors have been in development for nearly 60 years since carboxyl was commercialized in 1966, and were the first commercial fungicides containing amides. At present, 23 fungicides of this type have been commercialized, and the Fungicide Resistance Action Committee has classified the varieties of amide fungicides. In terms of sales, in 2016, the global sales of succinate dehydrogenase inhibitors (SDHIs) fungicides were US$1.691 billion, accounting for 3.0% of the global pesticide market of US$56.452 billion, accounting for US$15.268 billion of fungicides (including 11.1% of the non-crop fungicides) market. The global sales of succinate dehydrogenase inhibitors had the highest compound g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/04A01N43/824A01P3/00
CPCC07D413/04A01N43/82
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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