4-phenyl para-alcohol oxime ether-containing oxazoline compound and preparation and application in controlling insects, mites, bacteria and weeds

A technology of alcohol oxime ether and oxazoline, which is applied in the field of oxazoline compounds, can solve the problems of destroying ecological balance, environmental pollution resistance, and polluting the environment, and achieve low toxicity, good environmental compatibility, and wide biological spectrum Effect

Active Publication Date: 2015-09-16
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, human and animal poisoning, environmental pollution, and "three R" problems caused by chemical pesticides are becoming more and more serious (Pestic.Sci.1998, 54, 300-322. ; Pesticides, 2009, 48 (9), 625~628.), have brought serious harm to mammals and other non-target organisms, caused environmental pollution and even destroyed ecological balance, which requires that the direction of plant protection today is to protect harmful organisms regulation, not blindly "kill (-cide)"

Method used

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  • 4-phenyl para-alcohol oxime ether-containing oxazoline compound and preparation and application in controlling insects, mites, bacteria and weeds
  • 4-phenyl para-alcohol oxime ether-containing oxazoline compound and preparation and application in controlling insects, mites, bacteria and weeds
  • 4-phenyl para-alcohol oxime ether-containing oxazoline compound and preparation and application in controlling insects, mites, bacteria and weeds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of Compound 1:

[0026] In a 250 mL single-neck flask, 5.0 g (16.1 mmol) of compound f, 40 mL of dichloromethane, 40 mL of water, 1.9 g (16.1 mmol) of potassium bromide, and 1.33 g (8.05 mmol) of potassium bromate were sequentially added. Control the temperature in an ice-water bath to 0℃, add dropwise 20 mL of a solution containing 6.1 mL of concentrated hydrochloric acid, and react for 25 hours. TLC monitors the completion of the reaction and separates the layers. The organic phase is washed with sodium carbonate solution and sodium bicarbonate solution until it is close to colorless, and then used Extract the aqueous phase with dichloromethane, combine the organic phases and wash with sodium chloride solution, anhydrous MgSO 4 It was dried, filtered with suction, and spin-dried to obtain a white solid, which was recrystallized with toluene and petroleum ether to obtain the product g, 3.5 g in total, with a yield of 55.9%. Melting point: 127-128°C. 1...

Embodiment 2

[0028] Example 2: Synthesis of Compounds 2-11:

[0029] Compounds 2-11 were synthesized using the method shown in Example 1.

[0030] Compound 2

[0031] Yellow thick liquid with a yield of 40%. 1 H NMR(400M, CDCl 3 )7.46-7.41(m, 1H), 7.36(d, J=8.0Hz, 2H), 7.32(d, J=8.0Hz, 2H), 7.00(t, J=8.4Hz, 2H), 5.52-5.42( m, 1H), 5.05 (s, 2H), 4.85-4.78 (m, 1H), 4.32-4.28 (m, 1H), 2.50 (t, J=6.2, 2H), 2.24-2.15 (m, 2H), 1.64-1.66 (m, 4H), 1.59-1.61 (m, 2H). HRMS (ESI): Calcd.for C 22 H 22 F 2 N 2 O 2 H[M+H] + 385.1722; found385.1722.

[0032] Compound 3

[0033] Light yellow liquid, the yield was 46.4%. 1 H NMR(400MHz, CDCl 3 )δ7.46-7.41(m, 1H), 7.37(d, J=8.0Hz, 2H), 7.32(d, J=8.0Hz, 2H), 7.00(t, J=8.0Hz, 2H), 5.47( dd, J = 10.4, 8.0 Hz, 1H), 5.06 (s, 2H), 4.81 (dd, J = 10.4, 8.4 Hz, 1H), 4.30 (t, J = 8.4 Hz, 1H), 2.59-2.54 (m , 2H), 2.38-2.34 (m, 2H), 1.73-1.56 (m, 8H). HRMS (MALDI): Calcd.for C 21 H 20 F 2 N 2 O 2 [M+H] + 399.1879; found399.1875.

[0034] Compound 4

[0035] Yellow thick liquid...

Embodiment 3

[0050] Example 3: 4-phenyl para-position of oxazoline compounds containing alcohol oxime ether structure 1-11 to armyworm (M. separate), Culex pipiens (C.pipiens), and cotton bollworm (H. armigera) And the insecticidal activity of corn borer (P.nubilalis):

[0051] The measurement procedure is as follows:

[0052] Activity Test of Oriental Armyworm

[0053] The experimental method of the oriental armyworm: the leaf dipping method, after configuring to the required concentration, immerse the leaf with a diameter of about 5-6cm in the liquid medicine for 5-6 seconds, take it out, dry on absorbent paper, and place it in the designated In the petri dish, insert 10 3rd instar larvae, put them in the insect breeding room at 27±1℃ and observe the results after 3-4 days.

[0054] Viability test of mosquito larvae

[0055] The experimental method of mosquito larvae: Culex pipiens pallens, a normal population raised indoors. Weigh about 5 mg of the test compound into a penicillin vial, add 5 m...

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Abstract

The invention relates to a 4-phenyl para-alcohol oxime ether-containing oxazoline compound as shown in the general formula (I), preparation of the compound and an application of the compound in pesticides. The compound represents a novel concise, wide-spectral and high-efficiency insecticidal anti-mite bactericidal herbicide structure type. When used as a novel insecticidal anti-mite bactericidal herbicide, the 4-phenyl para-alcohol oxime ether-containing oxazoline compound can greatly control oriental armyworm, cotton bollworm, corn borer, plutella xylostella, beet armyworm and mosquito larvae, can greatly control Tetrangychus cinnabarinus, can greatly inhibit ten pathogenic bacteria including cucumber fusarium wilt, Cercospora arachidicola, Physalospora piricola Nose, Alternaria solani, Fusarium graminearumt, late blight of potato, sclerotinia sclerotioru, Botrytis cinerea, rice sheath blight and phytophthora capsici, and can control and eliminate weeds including rape, amaranth, barnyard grass and crab grass, wherein the meaning of R is as shown in the specification.

Description

Technical field [0001] The invention relates to a new type of oxazoline compound containing alcohol oxime ether structure at the para-position of 4-phenyl group and its preparation and application in the prevention and control of insects, mites, fungi and grasses, belonging to the technical field of pesticides. Background technique [0002] As we all know, chemical pesticides have always occupied an important position in the integrated prevention and control system of diseases, pests and weeds, and will continue to be a very valuable method in the prevention and control of diseases, pests and weeds for a period of time, and play a role in human health and ensuring high crop yields. Has an indelible effect. However, human and animal poisoning, environmental pollution, and the "three R" problems caused by chemical pesticides are residue, resistance and resurgence (Pestic.Sci.1998,54,300-322. ; Pesticides, 2009, 48(9), 625~628.), which have caused serious harm to non-target organis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/14A01N43/76A01P7/04A01P7/02A01P3/00A01P13/00
CPCA01N43/76C07D263/14
Inventor 汪清民刘玉秀李永强李朝杰马巧巧韦兴存郑彦龙魏朋
Owner NANKAI UNIV
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