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Preparation method and application of 1,2,3-thiadiazole pyrazole oxime ether compounds

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

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 method and application of 1,2,3-thiadiazole pyrazole oxime ether compounds
  • Preparation method and application of 1,2,3-thiadiazole pyrazole oxime ether compounds
  • Preparation method and application of 1,2,3-thiadiazole pyrazole oxime ether compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of compound Ia (R in general formula II 1 4-C (CH 3 ) 3 , R in formula III 2 for CH 3 )

[0032] In a reaction flask, add 5 mmol of compound II, 5.5 mmol of compound III, 10 mmol of anhydrous cesium carbonate and 60 mL of DMF, and heat to 90° C. for 20 h. Heating was stopped, cooling, suction filtration, the mother liquor was rotary evaporated to dryness, and the obtained residue was separated by silica gel column chromatography with petroleum ether / ethyl acetate (V:V=15:1) as the eluent to obtain the target compound Ia. rate 71.4%; 1 HNMR (400MHz, CDCl 3 ): δ7.78(s, 1H, CH=N), 7.31(d, J=8.8Hz, 2H, Ar-H), 6.80(d, J=8.4Hz, 2H, Ar-H), 5.22(s ,2H,CH 2 ),3.59(s,3H,N-CH 3 ),2.65(s,3H,CH 3 ),2.38(s,3H,CH 3 ),1.30(s,9H,-C(CH 3 ) 3 ).

Embodiment 2

[0034] The synthesis of compound Ib (R in the general formula II 1 4-OCF 3 , R in formula III 2 for CH 3 )

[0035] In a reaction flask, add 5 mmol of compound II, 9 mmol of compound III, 10 mmol of DIPEA and 60 mL of DMSO, and heat to 90° C. for 15 h. Heating was stopped, cooled, the mother liquor was rotary evaporated to dryness, and the obtained residue was separated by silica gel column chromatography with petroleum ether / ethyl acetate (V:V=15:1) as the eluent to obtain the target compound Ib with a yield of 65.3%. ; 1 H NMR (400MHz, CDCl 3 ): δ7.80(s, 1H, CH=N), 7.19(d, J=8.4Hz, 2H, Ar-H), 6.91(d, J=9.2Hz, 2H, Ar-H), 5.20(s ,2H,CH 2 ),3.63(s,3H,N-CH 3 ),2.67(s,3H,CH 3 ),2.39(s,3H,CH 3 ).

Embodiment 3

[0037] The synthesis of compound Ic (R in the general formula II 1 is 4-F, R in formula III 2 for CH 3 )

[0038] In a reaction flask, add 5 mmol of compound II, 7.5 mmol of compound III, 10 mmol of potassium carbonate and 60 mL of acetonitrile, and heat to reflux for 20 hours. Heating was stopped, cooled, filtered, and the mother liquor was rotary evaporated to dryness, and the resulting residue was separated by silica gel column chromatography with petroleum ether / ethyl acetate (V:V=25:1) as eluent to obtain the target compound Ic. The yield was 60.5%; 1 HNMR (400MHz, CDCl 3 ):δ7.76(s,1H,CH=N),6.96-7.00(m,2H,Ar-H),6.82-6.85(m,2H,Ar-H),5.20(s,2H,CH 2 ),3.59(s,3H,N-CH 3),2.64(s,3H,CH 3 ),2.35(s,3H,CH 3 ).

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Abstract

The invention relates to a preparation method and an application of 1,2,3-thiadiazole pyrazole oxime ether compounds. The preparation method comprises the following step: condensing parazole-containing hydroxyl oxime (II) with substituted substituent 5- chloromethyl-1,2,3- thiadiazole (III) to obtain the 1,2,3-thiadiazole pyrazole oxime ether compounds. The 1,2,3-thiadiazole pyrazole oxime ether compounds I have effective prevention and control effects on harmful insects and can be used for preparing pesticides in the fields such as agriculture and gardening.

Description

technical field [0001] The invention belongs to the field of pesticides, and specifically relates to a 1,2,3-thiadiazole-containing pyrazole oxime ether compound, a preparation method and an application. 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 1,2,3-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 1,2,3-thiadiazole ring through oxime ether is expected to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A01N47/02A01N43/828A01P7/04A01P7/02
CPCA01N43/82C07D417/12
Inventor 戴红石玉军何海兵李钰王森林李刚李阳方源
Owner NANTONG UNIVERSITY
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