New 2,4-diphenyloxazoline compounds, and synthesis method and acaricidal activity thereof

A technology of diphenyloxazoline and compound is applied in the field of 2,4-diphenyloxazoline new compound, synthesis and its acaricidal activity, and can solve problems such as poor quick effect and the like

Inactive Publication Date: 2012-09-19
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The quick-acting agent is poor, but it has a long-term effect of killing eggs and killing larvae and nymphs

Method used

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  • New 2,4-diphenyloxazoline compounds, and synthesis method and acaricidal activity thereof
  • New 2,4-diphenyloxazoline compounds, and synthesis method and acaricidal activity thereof
  • New 2,4-diphenyloxazoline compounds, and synthesis method and acaricidal activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Synthesis of m-tert-butylanisole (I-1)

[0040] Add 30 g of m-chloro-tert-butylphenol, 160 g (10%) NaOH and 150 mL of benzene into a 500 mL four-neck flask, heat to 70° C., and continue stirring for 1 h. After cooling to 65°C, 22.8 g of dimethyl sulfate was added dropwise. The dropwise addition was completed within 1 hour, and the temperature was kept for 1.5 hours to 4 hours, followed by TLC until the end of the reaction. Cool to 20°C, let stand, separate the organic layer, extract the water layer with benzene (30mL×2), combine the organic layers, and remove the solvent by rotary evaporation. Distilled at 68-72° C. / 267 Pa, 33.3 g of a light yellow transparent liquid was obtained, and the yield was 92%.

[0041] (2) Synthesis of 3-nitro-2,6-difluorobenzoic acid (I-2)

[0042] (1) Preparation of mixed acid: slowly add concentrated sulfuric acid (120 g) into concentrated nitric acid (53 g) under the condition of an ice-water bath. Mix well and cool for later use. ...

Embodiment 2

[0055] Example 2: 2,3-difluoro-N-[3-((4-(2-ethoxy-4-tert-butyl)-phenyl)-4,5-dihydro-1,3-oxa Synthesis of azole-2-yl)-2,4-difluorophenyl]-pyridine-4-carboxamide (2a)

[0056] Add 1.87g of compound I-7 (0.6mmol), 1.26g of triethylamine and 20mL of dry tetrahydrofuran (THF) into a 100mL four-necked flask, and cool to 0°C. Dissolve 1.17g of 2,3-difluoropyridine-4-carbonyl chloride (0.66mmol) in 3mL of tetrahydrofuran, and slowly drop it into a four-necked flask. After the dropwise addition was completed, stir for 3 h, then return to room temperature, and track the reaction by TLC. After the reaction, the reaction liquid was desolvated and separated by column chromatography (silica gel 200-300 mesh), the yield: 65%. 1 H NMR (300MHz, CDCl 3 )δ10.77(s, 1H), 8.19(dd, J=5.0, 1.4Hz, 1H), 7.99(td, J=9.0, 5.8Hz, 1H), 7.69(t, J=4.9Hz, 1H), 7.35(td, J=9.2, 1.6Hz, 1H), 7.20(d, J=8.0, 1H), 6.97(m, 2H), 5.53(dd, J=10.4, 8.4Hz, 1H), 4.84(dd, J=10.4, 8.4Hz, 1H), 4.13(m, 3H), 1.34(t, J=6.9Hz...

Embodiment 3

[0057] Example 3: 2,4-difluoro-N-[3-((4-(2-ethoxy-4-tert-butyl)-phenyl)-4,5-dihydro-1,3-oxa Synthesis of azole-2-yl)-2,4-difluorophenyl]-pyridine-3-carboxamide (2b)

[0058] Add 1.87g of compound I-7 (0.6mmol), 1.26g of triethylamine and 20mL of dry tetrahydrofuran (THF) into a 100mL four-necked flask, and cool to 0°C. 1.17g of 2,4-difluoropyridine-3-carbonyl chloride (0.66mmol) was dissolved in 3mL of tetrahydrofuran, and slowly dropped into a four-necked flask. After the dropwise addition was completed, stir for 3 h, then return to room temperature, and track the reaction by TLC. After the reaction, the reaction solution was desolvated and separated by column chromatography (silica gel 200-300 mesh), yield: 70%. 1 H NMR (400MHz, CDCl 3 )δ8.67(m, 1H), 8.30(m, 2H), 7.27(m, 1H), 6.97(m, 4H), 5.60(ddd, J=12.0, 10.4, 8.5Hz, 1H), 4.87(dt , J=10.5, 8.1Hz, 1H), 4.13(m, 4H), 1.43(t, J=6.9, 5.8Hz, 3H), 1.33(s, 9H).

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Abstract

The invention relates to new 2,4-diphenyloxazoline compounds, and a synthesis method and acaricidal activity thereof. The structure of the compounds provided by the invention has certain similarities with that of the existing acaricide Etoxazole, and is disclosed as a structural formula I, wherein R1 is a substituent pyridyl group or substituent phenyl group. The synthesis method comprises the following steps: by using meta-tert-butyl phenol, 2,6-difluorobenzoic acid and chloroacetaldehyde dimethyl acetal as the initial raw materials, carrying out etherification, nitrification, amidation, condensation, Friedel-Craft reaction, cyclization, catalytic hydrogenation, amidation and the like to obtain the compounds. Most of the compounds have acaricidal activity. The inhibition rates of the compound 2a and the compound 2g with the test concentration of 100mg / L for carminespider mite eggs are respectively 100% and 95%.

Description

technical field [0001] The present invention relates to the synthetic method of 2,4-diphenyloxazoline novel compounds and its acaricidal activity, specifically relates to a class of 2,4-diphenyloxazoline derivatives and the preparation of such compounds Intermediates and synthesis methods and the acaricidal activity of such compounds. technical background [0002] Etoxazole is a brand-new acaricide with a special structure developed by Sumitomo Chemical Co., Ltd. in Japan. The Chinese common name is etoxazole, the English common name is etoxazole, and the chemical name is (RS)-5-tert-butyl- 2-[2-(2,6-Difluorophenyl)-4,5-dihydro-1,3-oxazol4-yl]ethoxybenzene. Melting point: 101.5-102.5°C, the pure product is white crystal powder. Its structural formula is as follows: [0003] [0004] etoxazole [0005] Etoxazole has high ovicidal and larvicidal activity against various spider mites such as vegetable spider mites, citrus spider mites, apple spider mites, and pear spider...

Claims

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Application Information

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IPC IPC(8): C07D263/06C07D401/12A01N43/76A01P7/02
Inventor 李玉峰卜洪忠马鸿飞魏云郝春燕石洁庾金良
Owner NANJING UNIV OF TECH
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