N-substituted phenyl-benzothiazolone-3-formamide derivative

A technology of benzothiazolone and formamide, applied in biocides, chemicals for biological control, biocides, etc.

Active Publication Date: 2012-11-21
山东盛世共青茶业有限公司
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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 biological activity of N-substituted phenyl-benzothiazolone-3-carboxamide derivatives

Method used

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  • N-substituted phenyl-benzothiazolone-3-formamide derivative
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  • N-substituted phenyl-benzothiazolone-3-formamide derivative

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Embodiment 1

[0023] The synthesis of embodiment 1N-phenyl-benzothiazolone-3-carboxamide

[0024] Benzothiazolone (1.52 g, 10 mmol) and triethylamine (1 mmol) were dissolved in 20 mL of dichloromethane and stirred. Under cooling in an ice bath, phenylisocyanate (12 mmol) was added dropwise. After the dropwise addition was completed, the reaction was carried out at 0-3°C. The reaction was tracked and monitored by TLC. After the reaction was completed for 10 hours, the reaction solution was concentrated, and the residue was recrystallized with 10 mL of absolute ethanol to obtain white crystals, that is, N-phenyl-benzene And thiazolone-3-carboxamide. The melting point is 162-164°C, and the yield is 86.0%.

[0025] of the compound 1 H NMR and IR are as follows,

[0026] 1 H NMR (DMSO-d 6 , 500MHz) δ: 7.11~7.59 (m, 9H, -Ph), 8.92 (s, 1H, -NH); IR (KBr) v: 3311, 1719, 1670, 1551, 1503, 1439, 1267cm -1 .

Embodiment 2

[0027] The synthesis of embodiment 2N-phenyl-6-chloro-benzothiazolone-3-carboxamide

[0028] 6-Chloro-benzothiazolone (1.87 g, 10 mmol) and 4-dimethylaminopyridine (1 mmol) were dissolved in 30 mL of toluene and stirred. Under cooling in an ice bath, phenylisocyanate (12 mmol) was added dropwise. After the dropwise addition was completed, the reaction was carried out at 0-3°C, and the reaction was followed and monitored by TLC. After the reaction was completed for 12 hours, the reaction liquid was concentrated, and the residue was recrystallized with 15 mL of n-hexane to obtain white crystals, namely N-phenyl-6-chloro -Benzothiazolone-3-carboxamide. The melting point is 182-184°C, and the yield is 84.0%.

[0029] of the compound 1 H NMR and IR are as follows,

[0030] 1 H NMR (DMSO-d 6 , 500MHz) δ: 7.02~7.99 (m, 8H, -Ph), 10.08 (s, 1H, -NH); IR (KBr) v: 3268, 1731, 1642, 1479, 1391, 1300, 1259cm -1 .

Embodiment 3

[0031] The synthesis of embodiment 3N-p-tolyl-benzothiazolone-3-carboxamide

[0032] Benzothiazolone (1.52 g, 10 mmol) and pyridine (1 mmol) were dissolved in 30 mL of dichloromethane and stirred. Under cooling in an ice bath, p-tolyl isocyanate (12 mmol) was added dropwise. After the dropwise addition was completed, the reaction was carried out at 3 to 5°C, and the reaction was followed and monitored by TLC. After the reaction was completed for 10 hours, the reaction solution was concentrated, and the residue was recrystallized with 10 mL of ethyl acetate to obtain white crystals, namely, N-p-tolyl- Benzothiazolone-3-carboxamide. The melting point is 173-175°C, and the yield is 82.0%.

[0033] of the compound 1H NMR and IR are as follows,

[0034] 1 H NMR (DMSO-d 6 , 500MHz) δ: 2.29 (s, 3H, -CH3), 7.09~8.38 (m, 8H, -Ph), 8.88 (s, 1H, -NH);

[0035] IR (KBr) v: 3298, 1729, 1668, 1569, 1547, 1439, 1288cm -1 .

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Abstract

The invention discloses an N-substituted phenyl-benzothiazolone-3-formamide derivative, a preparation method thereof and applications of the derivative used as an insecticide and a bactericidal agent. The new N-substituted phenyl-benzothiazolone-3-formamide derivative has simple preparation method, can be applied to the insecticide and the bactericidal agent and has higher insecticidal activity and bacteriostatic action.

Description

(1) Technical field [0001] The invention relates to an N-substituted phenyl-benzothiazolone-3-carboxamide derivative and its preparation method and application. (2) Background technology [0002] Because heterocyclic compounds have a wide range of biological activities, coupled with their low toxicity, high efficiency, and environmental friendliness, they have become a hot spot in the development of pesticides today. Among heterocyclic compounds, fused heterocyclic compounds with extremely high biological activity have received great attention. As an important member of the fused heterocyclic ring system, benzothiazole has a wide range of biological activities and plays an important role in the creation of new pesticides. According to literature reports, in terms of agriculture, benzothiazole and its derivatives have insecticidal, bactericidal, antiviral, herbicidal, plant growth regulation and other activities. For example, in 1987, the high-efficiency herbicide mefenacet...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/68A01N47/38A01P7/04A01P7/02A01P3/00
Inventor 翁建全刘幸海谭成侠曹耀艳
Owner 山东盛世共青茶业有限公司
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