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A kind of 1,2,4-oxadiazole insecticide containing o-benzoylsulfonylimide group

A technology based on benzoylsulfonimide and oxadiazole, which is applied in the direction of insecticides, biocides, fungicides, etc., and can solve the problems of undisclosed insecticides

Active Publication Date: 2021-05-18
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, the compound of general formula I as shown in the present invention and its use as agricultural and forestry pesticides have not been disclosed

Method used

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  • A kind of 1,2,4-oxadiazole insecticide containing o-benzoylsulfonylimide group
  • A kind of 1,2,4-oxadiazole insecticide containing o-benzoylsulfonylimide group
  • A kind of 1,2,4-oxadiazole insecticide containing o-benzoylsulfonylimide group

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020] The preparation of example 1, general formula I compound

[0021] (1) Synthesis of intermediate 2,2-difluoroethanolsulfonate

[0022] Add 0.12mol (9.84g) 2,2-difluoroethanol, 0.125mol (12.63g) triethylamine, 100mL ethyl acetate as solvent to a 250mL three-necked flask, place the reaction flask in an ice-water bath, stir, and Dilute 0.121mol (13.85g) of methanesulfonyl chloride with 50mL of ethyl acetate, and slowly add it dropwise into the reaction flask. After the dropwise addition of methanesulfonyl chloride, react in an ice-water bath for one hour, filter with suction, keep the organic phase, and distill under reduced pressure to obtain 18.7 g of light yellow oily liquid 2,2-difluoroethanolsulfonate, with a yield of 97.4% , proceed directly to the next reaction.

[0023]

[0024] (2) Synthesis of 2-(2,2-difluoroethoxy)benzonitrile

[0025]

[0026] Add 0.1mol (11.9g) of salicylonitrile, 0.105mol (14.49g) of potassium carbonate, and 100mL of DMF into a 250mL ...

example 2

[0041] Example 2, insecticidal activity assay

[0042] Dissolve the compound of general formula I in aqueous sodium hydroxide solution, then dilute it with 1‰ Tween 80 aqueous solution, and prepare 50 ml of the test solution with the required concentration.

[0043] The bioactivity of the compounds synthesized in this paper was determined by leaf invasion method. Taking diamondback moth (Plutella xylostellaLinnaeus) and beet armyworm (Beet armyworm) as test objects, they were divided into two groups, and a blank control was set up. Select cabbage leaves with consistent growth and dip them in the prepared medicine for 10 seconds, take out the dried medicine solution with tweezers, and spread them on a clean plate in order. After drying, the leaves were transferred to petri dishes that had been sorted and contained moisture filter paper, and 30 2-year-old beet armyworms with similar growth conditions were implanted in each petri dish, and placed in a constant temperature incuba...

example 3

[0050] Example 3, bactericidal activity assay

[0051] Dissolve the compound of general formula I in aqueous sodium hydroxide solution, then dilute it with 1‰ Tween 80 aqueous solution, and prepare 50 ml of the test solution with the required concentration.

[0052] The bactericidal effect of the compounds was determined by plate method. Four mycelia of rice sheath blight (Rhizoctonia solani), pepper anthracnose fungus (Colletotrichum capsici), wheat scab fungus (Gibberella zeae) and rose mildew fungus were used as test objects, divided into four groups, and a blank control was set. Draw 1mL of the drug solution, pour it into a sterile Erlenmeyer flask that has melted the sterilized medium in advance, shake it well, and then pour it into 3 petri dishes with a diameter of 9cm to make a drug-containing solution with a concentration of 50μg / L. The plate was set up to repeat the experiment 3 times, and the same treatment without drug was used as a blank control. The above-cultiv...

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Abstract

The invention discloses a 1,2,4-oxadiazole compound containing o-benzoylsulfonimide group and its synthesis method and application. Its general structural formula is shown in formula I: In the formula: R is selected from 2,2‑Difluoroethyl or ethyl. The compound of general formula I has excellent insecticidal activity and certain bactericidal effect, and can be used for the prevention and control of agricultural or forestry plant pests and diseases.

Description

technical field [0001] The invention belongs to the field of pesticides and insecticides, and in particular relates to a 1,2,4-oxadiazole insecticide containing an o-benzoylsulfonimide group. Background technique [0002] In 2013, Monsanto developed a new type of high-efficiency nematicide thiophene and phenyl-substituted oxadiazole compound Tioxazafen (compound II), which has a new mechanism of action and exerts its drug effect by interfering with the activity of nematode ribosomes (Slomczynska U, South M S, Bunkers G J, et al. Tioxazafen: A New Broad-Spectrum Seed Treatment Nematicide [M], Discovery and Synthesis of Crop Protection Products, 2015.). Literature [Idoux J P, Gibbsrein K S, Gupton J T, et al.Synthesis and insecticidal activity of some 2,5-(fluoroalkoxyphenyl)-1,3,4-oxadiazoles and their N,N'-dibenzoylhydrazine precursors[J]. Journal of Chemical&EngineeringData, 1988,33(3):385-388.] reported a series of oxadiazole compounds containing halogenated alkoxyphenyl,...

Claims

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Application Information

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IPC IPC(8): C07D417/06A01N43/836A01P7/04A01P3/00
CPCA01N43/82C07D417/06
Inventor 许良忠孙鉴昕王明慧胡娆崔焕奇
Owner QINGDAO UNIV OF SCI & TECH
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