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A distyryl-containing succinate dehydrogenase inhibitor and its preparation method and application

A technology of succinate dehydrogenase and distyryl, which is applied in the field of pesticide and organic chemistry, can solve problems such as resistance, achieve good bactericidal activity, and prevent gray mold

Active Publication Date: 2021-06-08
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

Method used

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  • A distyryl-containing succinate dehydrogenase inhibitor and its preparation method and application
  • A distyryl-containing succinate dehydrogenase inhibitor and its preparation method and application
  • A distyryl-containing succinate dehydrogenase inhibitor and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0023]

[0024] 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

[0026] Preparation of (E)-4-(4-(2-thienyl)-1,3,4-oxadiazole)styryl)benzoic acid

[0027]

[0028] 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

[0030] Preparation of (E)-(4-(2-thienyl)-1,3,4-oxadiazol-2-yl)styryl)benzoyl)-L-leucine

[0031]

[0032] 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- Acid, stirred at room temperature for 5-7 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-leucine, yield 63.0%. Melting point(mp), 195-197℃; 1 H NMR (400MHz, DMSO-d 6 )δ8.59(d, J=7.9Hz, CONH, 1H), 8.09(d, J=8.2Hz, Th-H, 2H), 8.01–7.92(m, Ph-H, 4H), 7.87(d, J=8.2Hz, Ph-H, 2H), 7.76(d, J=8.1Hz, ...

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Abstract

The invention relates to the fields of pesticide and organic chemistry, and discloses a distyryl-containing succinate dehydrogenase inhibitor, its preparation method and application. The inhibitor has a structure represented by formula (I). The inhibitor of the invention has good bactericidal activity and can effectively prevent and treat Botrytis cinerea.

Description

technical field [0001] The invention relates to the fields of pesticide and organic chemistry, in particular to a distyryl-containing compound and its preparation method and application. Background technique [0002] Succinate dehydrogenase, also known as succinate ubiquinone reductase, also known as mitochondrial respiratory chain complex II, is a key enzyme involved in the tricarboxylic acid cycle, which can catalyze the oxidation of succinate to fumarate and the reduction of ubiquinone to ubiquinol It is one of the most promising agricultural fungicide targets at present. [0003] Succinate dehydrogenase fungicides targeting succinate dehydrogenase are a class of compounds with similar action mechanisms and resistance mechanisms newly classified by the Fungicide Resistance Action Committee, and have become the most important class of fungicides at present Variety. It mainly inhibits the respiration of fungi by binding to the ubiquinone reducing site of succinate dehydro...

Claims

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Application Information

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Patent Type & Authority Patents(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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