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

A technology of oxazoline insects and aldoxime ethers, which is applied in the field of pesticides, can solve the problems of environmental pollution resistance, harm, and destruction of ecological balance, and achieve excellent activity against spider mite cinnabarinus

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

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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 ha

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of compound 1:

[0028] Add 10 g (32 mmol) of compound f and 60 mL of glacial acetic acid into a 250 mL three-necked flask, and stir at room temperature to form a light yellow solution. The ice-salt bath was lowered to -10°C, and 7 mL of concentrated sulfuric acid was slowly added dropwise, keeping the temperature at -10-5°C during the dropwise addition, and the dropwise addition was completed in 1 hour. 6.46g (65mmol) of chromium trioxide ground into powder was added in batches, and the reaction was continued for 6 hours. The reaction solution was poured into 300 mL of ice-water mixture, extracted with ethyl acetate (100 mL×5), and the organic layers were combined. Wash once with a large amount of water, saturated sodium hydrogen acid acid and saturated brine, and dry with anhydrous magnesium sulfate.

[0029] The solvent was spun off under reduced pressure to obtain a black residue, which was added with 30 mL of methanol and 10 mL of conc...

Embodiment 2

[0032] Embodiment 2: the synthesis of compound 2~11:

[0033] Compounds 2-11 were synthesized by the method shown in Example 1.

[0034] Compound 2

[0035] Oily liquid, the yield is 57.5%. 1 H NMR (400MHz, CDCl 3 )δ8.12(s, 1H), 7.60(d, J=8.0Hz, 2H), 7.48-7.41(m, 1H), 7.35(d, J=8.0Hz, 2H), 7.01(t, J=8.0 Hz, 2H), 6.10-6.00(m, 1H), 5.48(dd, J 1 =10.4Hz,J 2 =8.4Hz, 1H), 5.36(dd, J 1 =17.2Hz,J 2 =1.6Hz, 1H), 5.26(dd, J 1 =10.4Hz,J 2 =1.2Hz, 1H), 4.83(dd, J 1 =10.4Hz,J 2 =8.4Hz, 1H), 4.68(d, J=5.6Hz, 2H), 4.28(t, J=8.0Hz, 1H).HRMS(ESI): Calcd.for C 19 h 16 f 2 N 2 o 2 Na[M+Na] + 365.1072; found 365.1075.

[0036] Compound 3

[0037] Oily liquid, yield 47.0%. 1 H NMR (300MHz, CDCl 3 )δ8.13(s, 1H), 7.62(d, J=8.1Hz, 2H), 7.49-7.39(m, 1H), 7.36(d, J=8.1Hz, 2H), 7.01(t, J=8.1 Hz, 2H), 5.49 (dd, J 1 =10.2Hz,J 2 =8.2Hz, 1H), 4.83(dd, J 2 =10.2Hz,J 1 =8.2Hz, 1H), 4.78(d, J=2.1Hz, 2H), 4.27(t, J=8.1Hz, 1H), 2.51(t, J=2.4Hz, 1H).HRMS(ESI): Calcd. for C 19 h 14 f ...

Embodiment 3

[0054] Example 3: 4-phenyl para-position containing aldoxime ether structure Insecticidal activity of oxazoline compounds 1-11 against armyworm (M.separate), Culex acuti (C.pipiens), cotton bollworm (H.armigera) and corn borer (P.nubilalis):

[0055] The measurement procedure is as follows:

[0056] Viability test of oriental armyworm

[0057] The experimental method of oriental armyworm: dipping method, after configuring the desired concentration, immerse the leaves with a diameter of about 5-6cm in the liquid medicine for 5-6 seconds, take them out, put them on absorbent paper to dry, and put them in the designated place. Insert 10 3rd instar larvae into the petri dish, put them into an insect culture room at 27±1°C and observe the results after 3-4 days.

[0058] Mosquito larva activity test

[0059] Experimental method of mosquito larvae: Culex amphipitus subspecies light-coloured, normal population raised indoors. Weigh about 5 mg of the test compound into a penicill...

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Abstract

The invention relates to a 4-phenyl para-aldoxime 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-aldoxime 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 4-phenyl para-position containing aldoxime ether structure The oxazoline compound and its preparation and application in controlling insects, mites, fungi and grasses belong to the technical field of pesticides. Background technique [0002] As we all know, chemical pesticides have always played an important role in the integrated pest control system, and will continue to be a very valuable method in the future for a period of time, playing an important role in human health care and ensuring high crop yields. played an indelible role. 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 di...

Claims

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Application Information

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IPC IPC(8): C07D263/10A01N43/76A01P7/02A01P7/04A01P3/00A01P13/00
Inventor 汪清民李永强刘玉秀郑彦龙魏朋韦兴存李朝杰马巧巧
Owner NANKAI UNIV
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