Benzophenone hydrazone sulfonylurea compound and its preparation method and use

A technology for benzophenone hydrazone sulfonylurea and compound, which is applied in the field of new benzophenone hydrazone sulfonylurea compounds and achieves the effects of excellent application prospect, high product purity and strong poisoning effect

Inactive Publication Date: 2015-06-24
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there are no research reports on the use of benzophenone hydrazone as a leading structure and the application of sulfonylurea active functional groups for structural modification and the insecticidal and acaricidal activities of such compounds

Method used

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  • Benzophenone hydrazone sulfonylurea compound and its preparation method and use
  • Benzophenone hydrazone sulfonylurea compound and its preparation method and use
  • Benzophenone hydrazone sulfonylurea compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of N-methylsulfonyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-keto]semicarbazone (6a)

[0025] Synthesis of raw material benzophenone hydrazone precursor (5): Dissolve 0.1mmol of phenol in 100mL of dry dichloroethane, quickly weigh and add 1.5mmol of anhydrous aluminum trichloride, heat to about 70°C in an oil bath, 0.1 mmol of 4-chlorobenzoyl chloride was added dropwise to the reaction liquid, and stirring was continued for 2 hours after the dropwise addition was completed. Cooled, poured into 100mL of ice water, extracted three times with dichloromethane, separated the organic phase, dried with anhydrous sodium sulfate, evaporated the solvent under reduced pressure, and recrystallized with anhydrous methanol to obtain 4-chloro-4- Hydroxybenzophenones (3). Dissolve 0.05mmol of 4-chloro-4-hydroxybenzophenone in 50mL of dry dichloromethane, drop into 0.05mL of pyridine, control the temperature at 0°C, add 0.06mmol of trifluoromethanesulfonic anhydride...

Embodiment 2

[0034] Synthesis of N-naphthalenesulfonyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-keto]semicarbazone (6b)

[0035] The experimental procedure is the same as in Example 1, except that methyl is replaced by naphthyl. The detection data of the product obtained from the reaction are as follows: Yield: 55%; Melting point: 198-200°C; 1 H NMR (400MHz, DMSO-d 6 )δ:7.21(d,J=8.4Hz,1H,Ar-H),7.27(d,J=8.0Hz,1H,Ar-H),7.39-7.47(m,4H,Ar-H),7.59( d,J=8.4Hz,2H,Ar-H),7.65-7.74(m,3H,Ar-H),7.91(d,J=8.8Hz,1H,Ar-H),8.05(d,J=7.2 Hz,1H,Ar-H),8.14(d,J=8.8Hz,1H,Ar-H),8.23(d,J=8.0Hz,1H,Ar-H),9.55(s,1H,-CONHSO 2 -);MS-ESI m / z:612.3[M+H] + .

Embodiment 3

[0037] Synthesis of N-p-fluorobenzoyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6c)

[0038] The experimental procedure is the same as in Example 1, except that p-fluorophenyl is used instead of methyl. The detection data of the product obtained from the reaction are as follows: Yield: 48%; Melting point: 209-210°C; 1 H NMR (400MHz, DMSO-d 6 )δ:7.21(d,J=8.4Hz,1H,Ar-H),7.29(d,J=8.4Hz,1H,Ar-H),7.37-7.50(m,7H,Ar-H),7.59( d,J=8.4Hz,1H,Ar-H),7.66(d,J=8.4Hz,1H,Ar-H),7.91-7.97(m,1H,Ar-H),9.24(s,1H,- CONHSO 2 -);MS-ESI m / z:579.9[M+H] + .

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Abstract

The invention relates to a novel benzophenone hydrazone sulfonylurea compound and its preparation method and use in preparation of insecticides and acaricides.

Description

technical field [0001] The invention relates to a novel benzophenone hydrazone sulfonylurea compound, a preparation method of the compound, and an application thereof in preparing insecticides and acaricides. Background technique [0002] In 1973, the DuPont Company of the United States reported for the first time the excellent insecticidal activity of some benzophenone hydrazone compounds with simple structures (Middleton W.J., Chadds F, (DuPont). US3732307), because these compounds have simple preparation, excellent activity, and With the characteristics of broad spectrum and low toxicity, this kind of compound has attracted the interest of many pesticide companies and scientific researchers. BASF, Sumitomo, DuPont, Bayer and other foreign companies have successively reported a large number of derivatives of benzophenone hydrazone structure with pesticide biological activity, and have successively developed commercial varieties such as insecticide hydrazone and metaflumizo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/55C07C311/61C07C303/40A01N47/34A01P7/02A01P7/04
Inventor 刘映前乌丹闫莉婷李中榜南祥杨柳吴小兵宋子龙朱高翔
Owner LANZHOU UNIVERSITY
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