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Sterilizing agent containing 1, 3, 4-oxadiazole cyclodistyrene amide as well as preparation method and application thereof

A technology of oxadiazole ring stilbene amide and fungicide, which is applied in the field of 1,3,4-oxadiazole ring stilbene amide compound and its preparation, and can solve the problems of difficult removal of by-products, high temperature, and resistance to Sexual problems and other problems, to achieve a good effect of prevention and treatment

Active Publication Date: 2018-07-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such fungicides have serious resistance problems due to long-term use
In addition, the traditional synthesis method of 1,3,4-oxadiazole group requires higher temperature and dehydrating agent, and the generated by-products are not easy to remove

Method used

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  • Sterilizing agent containing 1, 3, 4-oxadiazole cyclodistyrene amide as well as preparation method and application thereof
  • Sterilizing agent containing 1, 3, 4-oxadiazole cyclodistyrene amide as well as preparation method and application thereof
  • Sterilizing agent containing 1, 3, 4-oxadiazole cyclodistyrene amide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of (E)-4-(4-(2-thienyl)-1,3,4-oxadiazole)styryl)benzoic acid methyl ester

[0019]

[0020] Dissolve 1.13 g (3.0 mmol) of 4-(5-thienyl)-1,3,4-oxadiazol-2-yl)benzyl diethyl phosphate and 3.0 mmol of methyl p-formylbenzoate in 20 mL In N,N-dimethylformamide (DMF), after half an hour of reaction at room temperature, slowly add 10 mL of ethanol solution containing 0.41 g (3.6 mmol) of potassium tert-butoxide (t-BuOK) dropwise, and continue the reaction at room temperature for 6 hours; Add 20 mL of distilled water to the mixture, cool, filter and wash, dry by infrared, and recrystallize the crude product from a mixed solvent of dimethyl sulfoxide (DMSO) / water to obtain a light yellow solid (E)-4-(4-(2-thienyl) -1,3,4-oxadiazole) styryl) methyl benzoate, yield 79%.

Embodiment 2

[0022] Preparation of (E)-4-(4-(2-thienyl)-1,3,4-oxadiazole)styryl)benzoic acid

[0023]

[0024] Add 3mmol (E)-methyl 4-(4-(2-thienyl)-1,3,4-oxadiazole)styryl)benzoate into 40mL of 1M aqueous sodium hydroxide solution, stir and reflux at 80°C. After the reaction was complete, 10 mL of 1M hydrochloric acid aqueous solution was added, the reaction system was extracted twice with ethyl acetate, and the resulting organic layer was washed with anhydrous Na 2 SO 4 After drying, the yellow solid (E)-4-(4-(2-thienyl)-1,3,4-oxadiazole)styryl)benzoic acid was obtained in a yield of 75.4%. Melting point(mp), 333-335℃; 1 HNMR (400MHz, DMSO-d6) δ12.91 (s, COOH, 1H), 8.07 (d, J=8.0Hz, Th-H, 2H), 7.96 (d, J=7.5Hz, Ph-H, 4H) , 7.85(d, J=8.1Hz, Ph-H, 2H), 7.75(d, J=8.0Hz, Ph-H, 2H), 7.48(s, CH=CH, 2H), 7.32(t, J= 4.3Hz, Th-H, 1H); 13 C NMR (101MHz, DMSO-d6) δ167.46, 163.76, 160.78, 141.38, 140.65, 132.12, 131.00, 130.45, 130.29, 130.24, 130.18, 129.20, 128.05, 127.49, 127.267, 124.7 ...

Embodiment 3

[0026] Preparation of (E)-(4-(2-thienyl)-1,3,4-oxadiazol-2-yl)styryl)benzoyl)-L-methionine

[0027]

[0028] Dissolve 0.374g (1mmol) (E)-4-(4-(2-thienyl)-1,3,4-oxadiazole)styryl)benzoic acid in 15mL DMF, add 0.135g (1mmol ) 1-hydroxybenzotriazole (HOBt), 0.192g (1mmol) 1-ethyl-(3-dimethylaminopropyl) carbodiimide (EDCI) reacted at room temperature for 2 hours and then added 1mmol L-formazol Thionine, stirred at room temperature for 6 hours. After the reaction was completed, 30 mL of distilled water was added, filtered with suction, and washed with 0.5 M hydrochloric acid solution / methanol. The crude product was recrystallized from a mixed solvent of absolute ethanol / dimethyl sulfoxide (DMSO) to obtain (E)-(4-(2-thienyl)-1,3,4-oxadiazol-2-yl as a yellow solid ) styryl) benzoyl) -L-methionine, yield 61.5%. Melting point(mp), 228-230℃; 1 H NMR (400MHz, DMSO-d 6 )δ12.68 (s, COOH, 0H), 8.66 (d, J = 7.7Hz, CONH, 1H), 8.09 (d, J = 8.0Hz, Th-H, 2H), 7.99–7.93 (m, Ph- H, 4H), ...

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Abstract

The invention relates to the field of agricultural pharmacology and organic chemistry, and discloses a sterilizing agent containing 1, 3, 4-oxadiazole cyclodistyrene amide as well as a preparation method and application thereof. The sterilizing agent has the structure shown in the formula (I). The sterilizing agent has the characteristic of high efficiency and low toxicity, and has a good prevention and treatment effect on botrytis cinerea and colletotrichum. The formula (I) is shown in the description.

Description

technical field [0001] The invention relates to the fields of pesticide and organic chemistry, in particular to a stilbene amide compound containing a 1,3,4-oxadiazole ring and its preparation method and application. Background technique [0002] Among the fungicides that have been commercialized or are being developed in the new era, heterocyclic compounds have attracted people's attention in the process of pesticide and drug design, development and synthesis. Five-membered heterocyclic compounds have different biological activities and are widely used in the fields of medicine and pesticides. 1,3,4-oxadiazole is a kind of nitrogen-containing heterocyclic active group with a wide range of biological activities. Studies have shown that 1,3,4-oxadiazole has a wide range of biological activities, such as antibacterial, anti-tuberculosis, Anti-inflammatory, anti-cancer, anti-convulsant, analgesic, sedative-hypnotic, anesthetic and insecticidal activities. In addition, the com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04A01N43/824A01P3/00
CPCA01N43/82C07D413/04
Inventor 何道航文岚
Owner SOUTH CHINA UNIV OF TECH
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