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Chiral alkane oxazinone compounds and their use as fungicides

A technology of butan and oxazinone, which is applied in the field of pesticides and can solve the problems of less research

Active Publication Date: 2020-10-13
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The natural product drimenal has shown good inhibitory effect on Botrytis cinerea and Potato infestans (Jochen M.Scher et al..Phytochemistry, 2004, 65, 2583-2588), but literature research found that this type of compound is not effective in the field of pesticides. There are few studies on it, we found that chiral 8-hydroxyl-butane sesquiterpene amides have good antibacterial activity (Chinese invention patent, application number 201610762193.3; application publication number CN106397254A; Eur.J.Med. Chem.2017, 136, 114-121.)

Method used

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  • Chiral alkane oxazinone compounds and their use as fungicides
  • Chiral alkane oxazinone compounds and their use as fungicides
  • Chiral alkane oxazinone compounds and their use as fungicides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: (4aR, 6aS, 10aS, 10bS)-4a,7,7,10a-tetramethyldecalin-3H-naphtho[1,2-e][1,3]oxazine-3- Ketone synthesis

[0044]

[0045] The first step: the synthesis of ((+)-sclareolide) of sclareolide;

[0046] The natural product sclareol (-)-sclareol (10.0g, 32.4mmol, 1.0equiv) was dissolved in 200mL of anhydrous acetone, the system was placed in an ice bath, and 60mL of acetic anhydride was added thereto; Potassium manganate powder (30.7 g, 194.5 mol, 6 equiv). The system was gradually returned to room temperature, magnetically stirred, and thin layer chromatography (TLC) was used to track and detect the reaction process. After the raw material was consumed, an aqueous solution of sodium carbonate (20.0g / 150mL) was slowly added therein to quench the reaction, continued to stir for 0.5 hours, filtered, and the acetone was distilled off under reduced pressure to obtain the mixture of sclareolactone and licorane carboxylic acid. mixture.

[0047] 2N aqueous sodium h...

Embodiment 2

[0053] Example 2: (4aR, 6aS, 10aS, 10bS)-2-benzyl-4a,7,7,10a-tetramethyldecalin-3H-naphthyl[1,2-e][1,3] Synthesis of Oxazin-3-one

[0054]

[0055] Weigh the chiral alkoxazinone compound D (265 mg, 1.0 mmol, 1.0 equiv) and dissolve it in N, N-dimethylformamide solution (2 mL), add NaH (60% dispersion in mineral oil , 0.080g, 2.0mmol, 2.0equiv) and stirred the reaction at this temperature for 30 minutes, then added benzyl chloride (0.145mL, 1.2mmol, 1.2equiv), reacted under room temperature, thin layer chromatography (TLC) tracking detection reaction process. After the reaction was completed, the temperature was lowered to room temperature, and then water was added dropwise to quench the reaction. Add saturated ammonium chloride solution to neutralize to pH about 7, then extract with ethyl acetate 3 times (3x20mL), wash the organic phase with water in turn, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, evaporate under reduced pressure Remove the ...

Embodiment 3

[0058]

[0059] Weigh chiral alkane oxazinone compound D (432mg, 1.6mmol, 1.0equiv) in a 50mL eggplant-shaped bottle, add dichloromethane solution (4mL), add methanol (250μL) in turn, trichloroisocyanuric acid (370mg, 1.6mmol, 1.0equiv), stirring reaction at room temperature for 4 hours (TLC monitors the reaction is complete), then flash silica gel column chromatography to obtain compound (4aR, 6aS, 10aS, 10bS)-2-chloro -4a,7,7,10a-Tetramethyldecalin-3H-naphthyl[1,2-e][1,3]oxazin-3-one, white solid, yield 96.4%, melting point 140.3- 140.7 (℃). 1 H NMR (400MHz, CDCl 3 ): δ3.71-3.63 (m, 1H, CH 2 N), 3.60 (dd, J=10.5, 6.1Hz, 1H, CH 2 N), 2.03(dt, J=12.9, 3.2Hz, 1H, CH-9), 1.97(dd, J=12.3, 6.1Hz, 1H), 1.77(d, J=14.2Hz, 1H), 1.63(ddd , J=25.6, 13.1, 7.5Hz, 3H), 1.48(dd, J=16.6, 6.1Hz, 3H), 1.43(s, 3H, CH 3 ), 1.36-1.24(m, 2H), 1.19(td, J=13.4, 3.7Hz, 1H), 1.09(dd, J=12.3, 3.5Hz, 1H), 1.01(dd, J=12.4, 1.9Hz, 1H), 0.91(s, 3H, CH 3 ), 0.90 (s, 3H, CH 3 ), 0.82 (s, 3H, CH 3...

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Abstract

The invention relates to chiral drimane oxazinone compounds and a use thereof as a bactericide. The chemical formula of the compounds is represented by a formula (I) as shown in the description, wherein the stereoscopic configuration of a site 8 is R or S.

Description

technical field [0001] The invention relates to a new class of chiral alkoxazinone compounds and their use as fungicides; in particular, the application of these compounds in the prevention and control of agricultural fungal diseases and bacterial diseases belongs to the technical field of pesticides. Background technique [0002] As an indispensable and important material for agricultural production, pesticides play a very important role in controlling plant diseases, insect pests and weeds, regulating plant growth, and stable and high yield of crops. According to the statistics of the Food and Agriculture Organization of the United Nations, the annual loss caused by diseases in the world is more than 11%. For example, the annual loss caused by potato late blight is about 6.7 billion US dollars in the world, and the annual loss caused by rice blast can feed 60 million people in the world. The annual cost of mildew in the United States is as high as $3 billion. On the other...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/12A01N43/86A01P1/00A01P3/00
CPCA01N43/86C07B2200/07C07D265/12
Inventor 李圣坤李挡挡张莎莎宋泽华王国通张璐臧传丽
Owner NANJING AGRICULTURAL UNIVERSITY
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