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Preparation and application of compound containing 1,3,4-thiadiazole parazole oxime ether

A technology of thiadiazole pyrazole oxime and ether compounds, which is applied in the field of pesticides to achieve excellent control effects

Inactive Publication Date: 2014-11-19
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice

Method used

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  • Preparation and application of compound containing 1,3,4-thiadiazole parazole oxime ether
  • Preparation and application of compound containing 1,3,4-thiadiazole parazole oxime ether
  • Preparation and application of compound containing 1,3,4-thiadiazole parazole oxime ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of compound Ia (R in the general formula II 1 for H)

[0034]

[0035] In a 50 ml single-necked bottle, add 25 ml of acetonitrile, 5 mmol of compound II, 5.2 mmol of compound III, and 10 mmol of potassium carbonate, and reflux for 18 hours. The reaction was monitored by TLC. After the reaction was completed, it was cooled, suction filtered, and the solvent was evaporated to dryness. The resulting solid was separated by silica gel column chromatography (200-300 mesh) to obtain a white solid product Ia with a yield of 75.2%; 1 H NMR (500MHz, CDCl 3 ):δ7.82(s,1H,CH=N),7.32–7.35(m,2H,Ar-H),7.11–7.14(m,1H,Ar-H),6.91(d,J=7.5Hz, 2H,ArH),5.17(s,2H,CH 2 ), 4.57 (q, J=7.0Hz, 2H, CH 2 ),3.63(s,3H,N-CH 3 ),2.41(s,3H,Ar-CH 3 ), 1.47(t, J=7.0Hz, 3H, CH 3 ).

Embodiment 2

[0037] The synthesis of compound Ib (with reference to the synthesis of Ia, R in the general formula II 1 4-OCH 3 )

[0038] In a 50 ml single-necked bottle, add 25 ml of DMSO, 5 mmol of compound II, 5.5 mmol of compound III, and 10 mmol of diisopropylethylamine, and react at 90° C. for 15 hours. The reaction was monitored by TLC. After the reaction was completed, it was cooled and the solvent was evaporated to dryness. The resulting solid was separated by silica gel column chromatography (200-300 mesh) to obtain a white solid product Ib with a yield of 80.3%; 1 H NMR (500MHz, CDCl 3 ): δ7.79(s,1H,CH=N),6.84(s,4H,Ar-H),5.18(s,2H,CH 2 ), 4.56 (q, J=6.5Hz, 2H, CH 2 ),3.79(s,3H,OCH 3 ),3.62(s,3H,N-CH 3 ),2.39(s,3H,Ar-CH 3 ), 1.46(t, J=6.5Hz, 3H, CH 3 ).

Embodiment 3

[0040] The synthesis of compound Ic (with reference to the synthesis of Ia, R in the general formula II 1 for 3-Cl)

[0041]In a 50 ml single-necked bottle, add 25 ml of N,N-dimethylformamide, 5 mmol of compound II, 5.5 mmol of compound III, and 10 mmol of cesium carbonate, and react at 90°C for 12 hours. The reaction was monitored by TLC. After the reaction was completed, it was cooled, suction filtered, and the solvent was evaporated to dryness. The resulting solid was separated by silica gel column chromatography (200-300 mesh) to obtain a white solid product Ic, with a yield of 60.5%; 1 HNMR (500MHz, CDCl 3 ): δ7.82(s,1H,CH=N),7.22–7.26(m,1H,Ar-H),7.09(d,J=8.0Hz,1H,ArH),6.89(s,1H,ArH) ,6.79(d,J=8.5Hz,1H,ArH),5.14(s,2H,CH 2 ), 4.56 (q, J=7.0Hz, 2H, CH 2 ),3.61(s,3H,N-CH 3 ),2.38(s,3H,Ar-CH 3 ), 1.45(t, J=7.0Hz, 3H, CH 3 ).

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PUM

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Abstract

The invention relates to preparation and application of a compound (I) which is as shown in the specification and contains 1,3,4-thiadiazole parazole oxime ether. The compound is prepared by condensing pyrazol-containing hydroxamic (II) and substituted 5-ethyoxyl-1,3-4-thiadiazole (III). The compound containing 1,3,4-thiadiazole parazole oxime ether has an effective prevention and control effect on harmful insects. The compound can be used for preparing insecticides in the fields such as the agriculture industry and the gardening industry.

Description

technical field [0001] The invention belongs to the field of pesticides, in particular to a 1,3,4-thiadiazole-containing pyrazole oxime ether compound, a preparation method and application thereof. Background technique [0002] Pest control has always been the core field of pesticide scientific research, and the widespread use of insecticides has enabled most pests to be effectively controlled. However, with the continuous expansion of the application scale of pesticides, the problem of resistance to traditional pesticides has become increasingly prominent, coupled with the continuous emergence of new pests and diseases, making the continued research and development of new pesticides an inevitable choice. [0003] Pyrazole ring and 1,3,4-thiadiazole ring are commonly found in insecticides, acaricides and fungicides, and are active building blocks for the design of pesticide compounds. Linking pyrazole ring and 1,3,4-thiadiazole ring through oxime ether is expected to obtain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A01N43/824A01P7/04A01P7/02
CPCA01N43/82C07D417/12
Inventor 戴红石玉军李钰何海兵曹宇锋王森林李刚张轶
Owner NANTONG UNIVERSITY
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