Benzoyl urea compound containing urethane group structure as well as preparation method and insecticidal application of benzoyl urea compound

A carbamate-based, benzoylurea technology, applied in the field of benzoylurea compounds, to achieve the effects of completely novel structure, wide insecticidal activity, and excellent insecticidal activity

Inactive Publication Date: 2015-11-25
TIANJIN AGRICULTURE COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, there are no literature reports on the synthesis and insecticidal activity of 2,6-dihalobenzoyl-4-(N-substituted phenylcarbamate) urea derivatives

Method used

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  • Benzoyl urea compound containing urethane group structure as well as preparation method and insecticidal application of benzoyl urea compound
  • Benzoyl urea compound containing urethane group structure as well as preparation method and insecticidal application of benzoyl urea compound
  • Benzoyl urea compound containing urethane group structure as well as preparation method and insecticidal application of benzoyl urea compound

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Experimental program
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Effect test

Embodiment 12

[0016] Embodiment 12, the preparation of 6-difluorobenzoyl-4-hydroxyphenylurea

[0017] Slowly add the acetonitrile solution of 3.0g 2,6-difluorobenzoyl isocyanate dropwise to the acetonitrile solution of 1.8g p-aminophenol and 0.2g triethylamine, stir at room temperature overnight, and use dichloromethane:methanol=10:1 The column obtained 4.5 g of 2,6-difluorobenzoyl-4-hydroxyphenylurea as a gray solid, yield 93.8%, melting point: 160.0-162.0°C. 1 HNMR (400MHz, DMSO): δ11.36(brs, 1H), 9.99(brs, 1H), 7.61(m, 1H), 7.33(d, J=8.5Hz, 2H), 7.25(t, J=8.2Hz , 2H), 6.73(d, J=8.8Hz, 2H), 6.02(s, 1H).

Embodiment 22

[0018] Embodiment 22, Preparation of 6-difluorobenzoyl-4-(N,N-diisopropylcarbamate phenyl)urea

[0019] After stirring 0.5g of 2,6-difluorobenzoyl-4-hydroxyphenyl urea, 1.0g of potassium carbonate in acetonitrile and aqueous solution at room temperature for 0.5 hours, slowly drop in 0.4g of triphosgene in acetonitrile solution, and react again for 0.5 hours and slowly A solution of 0.4 g of diisopropylamine in acetonitrile was added dropwise, and the reaction was stopped after 0.5 hours. After the reaction solution was washed twice with water, the organic phase was dried with anhydrous sodium sulfate, solvent removal, petroleum ether: ethyl acetate = 5: 1 silica gel column chromatography, the above product was obtained as a white solid 0.4 g, yield 55.6%, melting point: 208-209 ℃. 1 HNMR (400MHz, CDCl 3 ): δ10.41(s, 1H), 7.89(s, 1H), 7.50-7.56(m, 3H), 7.05-7.14(m, 4H), 3.98-4.12(m, 2H), 1.33-1.35(m , 12H).

Embodiment 32

[0020] Embodiment 32, the preparation of 6-difluorobenzoyl-4-(piperidine formic acid phenyl) urea

[0021] After stirring 0.5g of 2,6-difluorobenzoyl-4-hydroxyphenyl urea, 1.0g of potassium carbonate in acetonitrile and aqueous solution at room temperature for 0.5 hours, slowly add dropwise 0.4g of triphosgene in acetonitrile solution, and react again for 0.5 hours and slowly A solution of 0.5 g of piperidine in acetonitrile was added dropwise, and the reaction was stopped after 0.5 hours. After the reaction solution was washed twice with water, the organic phase was dried with anhydrous sodium sulfate, precipitated, petroleum ether: ethyl acetate = 2:1 silica gel column chromatography, and the above product was obtained as a white powdery solid 0.1 g, yield 14.5%, melting point: 212 -215°C. 1 HNMR (400MHz, DMSO): δ11.44(s, 1H), 10.19(s, 1H), 7.63(m, 1H), 7.56(d, J=7.6Hz, 2H), 7.26(m, 2H), 7.10 (d, J = 7.9 Hz, 2H), 3.50-3.60 (m, 2H), 3.45-3.55 (m, 2H), 1.55-1.59 (m, 6H).

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Abstract

The invention relates to a benzoyl urea compound containing a urethane group structure as well as a preparation method and an insecticidal application of the benzoyl urea compound. The general formula of the benzoyl urea compound is shown by a formula (I), wherein X and X' represent hydrogen and halogen atoms respectively and independently; R3 represents hydrogen, halogen atoms, C1-10 alkyl and C1-10 halogenated alkyl; and R1 and R2 represents hydrogen, C1-10 alkyl or cycloalkyl, C1-10 halogenated alkyl, aryl and substituted aryl respectively and independently. The corresponding compound provided by the invention is a new compound with excellent insecticidal activity and is used for control of crop insects.

Description

technical field [0001] The invention relates to a benzoylurea compound containing a carbamate group structure, a preparation method and an insecticidal application. Background technique [0002] US3450747 and US3748356 disclose benzoyl phenyl urea compounds and their insecticidal activity; CN102690241A discloses benzoyl urea compounds containing isoxazole structures and their preparation and application; US475113, US4497822 and US4666942 disclose Sulfuryl, arylthio and N-thiocarbamate alkyl ester benzoyl phenyl urea derivatives and their insecticidal activity; CN1891686A discloses the preparation and preparation of N-thioaminobenzoyl phenyl urea compounds application. Therefore, exploring the introduction of a carbamate group structure on the B ring of benzoylurea and testing its biological activity has important theoretical and practical value. [0003] However, there are no literature reports on the synthesis and insecticidal activity of 2,6-dihalobenzoyl-4-(N-substitute...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/54C07C273/18C07D295/205A01N47/34A01P7/04
Inventor 黄治强张婧王丹婷赵毓石军朱华玲卜路霞王远宏骆建霞
Owner TIANJIN AGRICULTURE COLLEGE
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