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Oxazoline compound with 4-phenyl para-position containing thioether and derivative structure thereof, preparation and application as pest and mite killing agent

A technology of oxazolines and compounds, which is applied in the field of oxazolines compounds, can solve problems such as human body and environmental damage, and achieve excellent killing and activity effects

Active Publication Date: 2016-02-24
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

my country is a large agricultural country, and the prevention and control of crop diseases and insect pests directly affects the yield of food. However, while traditional insecticides kill pests, they will also cause great harm to the human body and the environment.

Method used

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  • Oxazoline compound with 4-phenyl para-position containing thioether and derivative structure thereof, preparation and application as pest and mite killing agent
  • Oxazoline compound with 4-phenyl para-position containing thioether and derivative structure thereof, preparation and application as pest and mite killing agent
  • Oxazoline compound with 4-phenyl para-position containing thioether and derivative structure thereof, preparation and application as pest and mite killing agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of compound Ia-1:

[0024]5.0g (16.1mmol) of compound f, 40mL of dichloromethane, 40mL of water, 1.9g (16.1mmol) of potassium bromide and 1.33g (8.05mmol) of potassium bromate were successively added into a 250mL single-necked bottle. Control the temperature in an ice-water bath at 0°C, add 20 mL of a solution containing 6.1 mL of concentrated hydrochloric acid dropwise, react for 25 hours, monitor the completion of the reaction by TLC, separate the liquids, and wash the organic phase with sodium carbonate solution and sodium bicarbonate solution until it is nearly colorless, and then use The aqueous phase was extracted with dichloromethane, and the combined organic phases were washed with sodium chloride solution, anhydrous NaSO 4 Dry, filter with suction, and spin dry to obtain a white solid, which is recrystallized from toluene and petroleum ether to obtain the product g, a total of 3.5 g, with a yield of 55.9%. Melting point: 127-128°C. ...

Embodiment 2

[0026] Embodiment 2: the synthesis of compound Ia-2~Ia-23:

[0027] Compounds Ia-2 to Ia-23 were synthesized by the method shown in Example 1.

[0028] Compound Ia-2

[0029] Pale yellow solid, yield 57%. Melting point: 92-94°C. 1 HNMR (400MHz, CDCl 3 )δ7.91(d, J=8.0Hz, 1H), 7.76(d, J=8.0Hz, 1H), 7.48(d, J=8.4Hz, 2H), 7.46-7.41(m, 3H), 7.32( d, J=8.4Hz, 2H), 7.00(t, J=8.0Hz, 2H), 5.46(dd, J=10.4, 8.4Hz, 1H), 4.81(dd, J=10.4, 8.4Hz, 1H), 4.61(s, 2H), 4.29(t, J=8.4Hz, 1H); 13 CNMR (100MHz, CDCl 3 )δ166.3, 161.2 (dd, J=254.8, 6.0Hz), 157.7, 153.2, 141.4, 135.8, 135.4, 132.5 (t, J=10.4Hz), 129.6, 127.1, 126.1, 124.3, 121.6, 121.0, 112.0 (dd, J=22.8, 2.6Hz), 107.2 (t, J=17.4Hz), 74.7, 70.0, 37.4; HRMS(ESI)calcdforC 23 h 17 f 2 N 2 OS 2 [M+H] + 439.0745, found 439.0751.

[0030] Compound Ia-3

[0031] Yellow solid, yield 71%. Melting point: 110-112°C. 1 HNMR (400MHz, CDCl 3 )δ7.62(d, J=7.6Hz, 1H), 7.48(d, J=8.0Hz, 2H), 7.46-7.40(m, 2H), 7.32(d, J=8.0Hz, 2H), 7.24- ...

Embodiment 3

[0072] Embodiment 3: the synthesis of compound Ib-1:

[0073] Add 2-(2,6-difluorophenyl)-4-(4-((naphthalene-2-ylsulfur)methyl)phenyl)-4,5-dihydrooxazole Ia- 14 (0.5g, 1.16mmol), 20mL of dichloromethane, 1.25mL of trifluoroacetic acid was added under stirring at room temperature, 0.5mL of 30% hydrogen peroxide was added in batches, the reaction was carried out at room temperature, and the reaction progress was tracked by TLC. Add 1.5 g of sodium bisulfite to decompose excess hydrogen peroxide, and stir at room temperature for 1 h. Add 20 mL of water, separate the layers, extract the aqueous phase with 2×20 mL of dichloromethane, combine the organic phases, wash with 15 mL of water and 15 mL of brine in turn, and dry over anhydrous sodium sulfate. Filtration, precipitation, crude silica gel column chromatography [eluent is petroleum ether (60-90°C) and ethyl acetate = 4:1], to obtain 0.49g of white solid, yield 90%, melting point: 157-159°C . 1 HNMR (400MHz, CDCl 3 )δ8.23 (s...

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PUM

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Abstract

The present invention relates to an oxazoline compound with a 4-phenly para-position containing a structure of thioether, sulphone, sulfilimine and sulfoximine represented by a formula (I), and preparation for the compound and an application of the compound as a pest and mite killing agent. The compound represents a novel and simple pest and mite killing agent structure type with simple preparation, a broad spectrum and high efficiency. The oxazoline compound with the 4-phenly para-position containing the structure of thioether, sulphone, sulfilimine and sulfoximine is used as a novel pest and mite killing agent which can perfectly prevent and control oriental armyworms, cotton bollworms, ostrinia nubilalis, and mosquito larvae, and can perfectly prevent and control mite eggs and baby mites of carmine spider mites. The formula (I) is shown in the description, wherein R' can be cyano, nitryl, trifluoroformoxyl or formamido; R'' can be hydrogen, cyano, nitryl, trifluoroformoxyl or formamido; and R can be heterocycle (substituted heterocycle), aryl (substituted aryl) or alkyl (branched aryl).

Description

technical field [0001] The present invention relates to a new class of oxazoline compounds containing sulfide, sulfone, sulfoxide, sulfimine, and sulfoximine structures in the para-position of 4-phenyl, as well as their preparation and application in the control of insects and mites. Pesticide technology field. Background technique [0002] Agricultural pests and harmful mites are very harmful to fruit trees, vegetables, tea trees and other crops. They are prone to develop resistance to insecticides and acaricides, especially mites are a kind of worldwide harmful organisms. With their strong reproductive ability and The extremely short growth cycle can quickly produce resistance to acaricides, which can harm more than 150 kinds of crops and cause great losses to agricultural and forestry production every year. Pesticides can prevent the occurrence of pests and diseases very well, and ensure that the output of food can meet the growing needs of human beings, so the use of pe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/10C07D413/12C07D417/12A01N43/76A01N43/78A01N43/824A01P7/04A01P7/02
CPCA01N43/76A01N43/78C07D263/10C07D413/12C07D417/12A01N43/82
Inventor 汪清民于秀玲刘玉秀王兹稳
Owner NANKAI UNIV
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