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A kind of 2,5-disubstituted-1,3,4-oxadiazole derivative and its application

A technology of oxadiazole and derivatives, applied in the field of pesticides, can solve problems such as the reduction of the sensitivity of pest populations, and achieve the effect of alleviating the problem of drug resistance

Inactive Publication Date: 2018-10-12
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, it should be pointed out that due to the long-term and large-scale use of existing insecticides, the sensitivity of pest populations to pesticides has decreased, making the resistance problems faced by many current insecticide varieties increasingly prominent, and more novel structures have been developed. Insecticide varieties become an important way to solve the problem of resistance

Method used

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  • A kind of 2,5-disubstituted-1,3,4-oxadiazole derivative and its application
  • A kind of 2,5-disubstituted-1,3,4-oxadiazole derivative and its application
  • A kind of 2,5-disubstituted-1,3,4-oxadiazole derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Compound I-1:: 2-[5-(3-bromo-1-(3-chloro-pyridin-2-yl)-1H-pyrazole)]-5-(2-chlorophenoxymethylene)- 1,3,4-oxadiazole

[0023]

[0024] (1) Take 5.5mmol of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid III, 3mL of thionyl chloride and 7mL of toluene and add them into a reflux condenser and a thermometer In a 25mL three-necked flask, heat up to 50-80°C for 4-5 hours, then distill off excess thionyl chloride and toluene to obtain 3-bromo-1-(3-chloropyridin-2-yl)- 1H-pyrazole-5-formyl chloride III-1, directly used in the next step reaction;

[0025] (2) In a 50mL round bottom flask, add 5mmol intermediate 4-chlorophenoxyalkyl hydrazide II, 3mmol K 2 CO 3 , 20mL of dichloromethane, the intermediate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride III-1 was added dropwise under stirring at room temperature, after the addition was completed, the reaction was tracked by TLC. Stir at room temperature for 0.5-3h, filter with suction, wash wi...

Embodiment 2

[0069] Compound I-7: 2-[5-(3-bromo-1-(3-chloro-pyridin-2-yl)-1H-pyrazole)]-5-(2,4-dichlorophenoxymethylene )-1,3,4-oxadiazole

[0070]

[0071] (1) Take 5.5mmol of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid III, 3mL of thionyl chloride and 7mL of toluene and add them into a reflux condenser and a thermometer In a 25mL three-necked flask, heat up to 50-80°C for 4-5 hours, then distill off the remaining thionyl chloride and toluene to obtain 3-bromo-1-(3-chloropyridin-2-yl)- 1H-pyrazole-5-formyl chloride III-1, directly used in the next step reaction;

[0072] (2) Add 5mmol intermediate 2,4-dichlorophenoxyalkylhydrazide II, 3mmol K to a 50mL round bottom flask 2 CO 3 , 20mL of dichloromethane, the intermediate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride III-1 was added dropwise under stirring at room temperature, after the addition was completed, the reaction was tracked by TLC. Stir at room temperature for 0.5-3h, filter with suct...

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Abstract

The invention discloses a 2,5-disubstituted-1,3,4-oxadiazole derivative as shown in a general formula I which is described in the specification. In the formula I, R is halogen, hydrogen, a nitro group, a methyl group, a methoxy group or a trifluoromethyl group; R<1> is a methyl group, an ethyl group or hydrogen; R<2> is a trifluoromethyl group, chlorine or bromine; and R<4> is halogen or hydrogen. The compound has substantial inhibitory effect on armyworms and can be used an effective component of a pesticide.

Description

technical field [0001] The invention relates to a 2,5-disubstituted-1,3,4-oxadiazole derivative and an active component with insecticidal effect, which are used in the field of insecticides. Background technique [0002] In recent decades, heterocyclic compounds have attracted widespread attention from pesticide workers due to their high biological activity, and many commercial pesticides containing pyrazole and pyridine heterocycles have been continuously reported. Such as the herbicides Azimsulfuron, Pyrazolate, and Nipyraclofen; the insecticides Fenpyroximate, Chlorantraniliprole, and Nipyramide (Cyantraniliprole) etc. and fungicide pyraclostrobin (Pyraclostrobin) etc. In addition, oxadiazole heterocyclic compounds often have good biological activity, and have extensive research and important applications in the creation of new pesticides, and many commercial pesticides have also been developed. Such as the herbicide oxadiazone and the insecticide oxadiazone. [0003] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14A01N43/824A01P7/04
CPCA01N43/82C07D413/14
Inventor 王威宁斌科李秉擘王列平张晓光薛超
Owner XIAN MODERN CHEM RES INST
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