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Ether bond-containing oxazoline derivative, design synthesis and application thereof in prevention and treatment of phytophagous mites

A technology of oxazolines and derivatives, applied in the directions of botanical equipment and methods, applications, acaricides, etc., can solve the problem that insects cannot form epidermis, etc.

Pending Publication Date: 2021-04-09
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Scientific research on the specific target is currently divided into two categories, one supports sulfonylurea receptors, while the other believes that it directly acts on chitin synthase, which is still controversial, but it is certain that B Methazole affects the synthesis of chitin, thereby causing insects to fail to form new cuticles and die (J.Insect.Physiol., 1978, 24, 827-831)

Method used

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  • Ether bond-containing oxazoline derivative, design synthesis and application thereof in prevention and treatment of phytophagous mites
  • Ether bond-containing oxazoline derivative, design synthesis and application thereof in prevention and treatment of phytophagous mites
  • Ether bond-containing oxazoline derivative, design synthesis and application thereof in prevention and treatment of phytophagous mites

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of C

[0024] Add A (15.3g, 110mmol), B (15.2g, 100mmol), NBS (19.6g, 110mmol), 125mL of CH 2 Cl 2 . Concentrated sulfuric acid (6.5 mL, 120 mmol) was slowly added dropwise to the system under ice-bath stirring, and the stirring was continued under ice-bath. The reaction was monitored by TLC (PE / EA=4 / 1), and the reaction was completed after stirring at room temperature for 8 hours. Dichloromethane and saturated sodium thiosulfate solution were added to separate the layers, and the aqueous phase was extracted three times with dichloromethane. After combining the organic phases, they were washed once with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried and filtered over anhydrous sodium sulfate, and concentrated under reduced pressure to remove dichloromethane. After column chromatography with PE / EA=6 / 1, 33.4 g of light yellow solid was obtained, the yield was 86%, and the melting point was 128-129°C.

[...

Embodiment 2

[0026] Embodiment 2: the synthesis of D

[0027] The synthesized substrate C (19.4 g, 50 mmol) was added into a 100 mL single-necked bottle, and 30 mL of methanol was added to dissolve it. Sodium methoxide (2.97 g, 55 mmol) was added with stirring in an ice-water bath. Stir at room temperature. The reaction was monitored by TLC (PE / EA=4 / 1), and the reaction was completed after 5 min. Methanol was spun off, water and dichloromethane were added to separate the layers, and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were washed once with water and once with saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to remove dichloromethane. After spin-drying, 12.8 g of light yellow solid D was obtained, with a yield of 83%. The melting point is 64-65°C.

[0028] 1 H NMR (400MHz, DMSO-d 6 )δ7.73-7.62(m, 1H), 7.47(d, J=7.8Hz, 2H), 7.34(d, J=8.0Hz, 2H), 7.30(t, J=8.4Hz, 2...

Embodiment 3

[0029] Embodiment 3: F-1, F-2, the synthesis of F-3

[0030] Substrate D (0.31g, 1mmol), sodium alkoxide (0.51g, 1.0mmol) and 10mL dry THF were added to a 100mL single-necked flask to dissolve, and refluxed under the protection of argon. The reaction was monitored by TLC (PE / EA=4 / 1), and the reaction was completed after 2 hours. Water and dichloromethane were added to separate layers, the aqueous phase was extracted with dichloromethane 3 times, the combined organic phases were washed 2 times with water, washed 1 time with saturated sodium chloride, dried over anhydrous sodium sulfate, solvent extraction, column chromatography (PE / EA = 6 / 1).

[0031] Colorless transparent oily liquid, yield 67%. 1 H NMR (400MHz, DMSO-d 6 )δ7.76-7.61 (m, 1H), 7.44-7.21 (m, 6H), 5.50 (dd, J=10.0, 8.0Hz, 1H), 4.86 (dd, J=10.0, 8.8Hz, 1H), 4.42 (s, 2H), 4.20(t, J=8.4Hz, 1H), 3.30(s, 3H). 13 C NMR (100MHz, DMSO-d 6 )δ160.2 (dd, J=253.2, 6.1Hz), 155.8, 141.2, 137.6, 133.5, 127.8, 126.4, 112.3...

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PUM

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Abstract

The invention relates to an oxazoline compound containing an ether bond structure as shown in a general formula F, preparation and application thereof in prevention and treatment of phytophagous mites. The compound represents a novel and concise acaricide structure type. The oxazoline derivatives F-2, F-3, F-5, F-6 and F-19 disclosed by the invention show higher tetranychus cinnabarinus killing activity than etoxazole.

Description

technical field [0001] The invention relates to oxazoline derivatives containing ether bonds and their preparation and application in preventing and treating herbivorous mites, belonging to the technical field of agricultural protection. Background technique [0002] Due to the influence of pathogens, insects and other pests and mites, global agricultural production has suffered great damage (J.Agric.Food.Chem., 2018, 66(34), 8898-8913). Plant phytophagous mites are common harmful mites in agricultural production. They not only eat plants, but also act as a medium for the transmission of plant pathogens and viruses, which severely reduces the yield of many important economic crops, thus causing great harm to agricultural production (Pestic. Biochem. Physiol., 2015, 121, 12-21). [0003] Nowadays, the control methods for phytophagous mites are mainly chemical control. There are many types of acaricides developed on the market. Through the research on the mechanism of action,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/14C07D413/12A01N43/76A01P7/02
CPCC07D263/14C07D413/12A01N43/76
Inventor 汪清民张钰刘玉秀王兹稳李永强陈仕林
Owner NANKAI UNIV
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