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Preparation and application of bispyrazole carboxamide derivative to the control of rice black streaked dwarf disease

A technology of bispyrazole amides and derivatives, applied in the field of bispyrazole amide compounds, can solve problems such as few reports of antiviral activity

Inactive Publication Date: 2015-03-11
ANHUI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the reports on the activity of pyrazole amide compounds mainly focus on insecticidal, bactericidal, acaricidal, and herbicidal, but there are fewer reports on antiviral activity.

Method used

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  • Preparation and application of bispyrazole carboxamide derivative to the control of rice black streaked dwarf disease
  • Preparation and application of bispyrazole carboxamide derivative to the control of rice black streaked dwarf disease
  • Preparation and application of bispyrazole carboxamide derivative to the control of rice black streaked dwarf disease

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Embodiment one: the synthesis of compound 1:

[0020]

[0021] In the three-necked flask, add 30mL of water and 3.6g (0.025mol) of phenylhydrazine hydrochloride, stir well at room temperature, slowly add an appropriate amount of sodium carbonate to adjust the pH of the system to 7-8, and then dropwise add ethyl acetoacetate dissolved in 10mL of ethanol 3.3 mL (0.026 mol) of the ester was heated slowly to 65° C. under a nitrogen-tight condition and stirred for 5 h. The reaction was traced by TLC. After the reaction was completed, it was cooled, and the crude product a was obtained by suction filtration. DMF and POCl 3 Mix in an ice bath for 30 minutes, then dissolve the above solid a in the above mixture, and heat to 70-80°C for 5 hours. After cooling to room temperature, pour into ice water, filter with suction and wash with water, and dry to obtain solid b. Dissolve solid b in water, heat to 70-80°C, add potassium permanganate solution dropwise under stirring, con...

Embodiment 2

[0024] Embodiment two: the synthesis of compound 2:

[0025]

[0026] Synthetic method is the same as embodiment one. Step 4 is synthesized by replacing phenylhydrazine hydrochloride with p-chlorophenylhydrazine hydrochloride. The target compound was obtained as white crystals. Yield 78%, m.p.171-172°C; 1 H NMR (400MHz, CDCl 3 )δ8.12(s,1H),7.55-7.43(m,9H),2.65(s,3H).MS(ESI): 438.68(C 21 h 14 Cl 2 N 6 O,[M+H] + ).Anal.Calcd for C 21 h 14 Cl 2 N 6 O: C, 57.68; H, 3.23; N, 19.22; Found: C, 57.72; H, 3.81; N, 21.11.

Embodiment 3

[0027] Embodiment three: the synthesis of compound 3:

[0028]

[0029] Synthetic method is the same as embodiment one. Step 4 is synthesized by replacing phenylhydrazine hydrochloride with p-methylphenylhydrazine hydrochloride. The target compound was obtained as white crystals. Yield 62%, m.p.123-125℃; 1 H NMR (400MHz, CDCl 3 )δ8.12(s,1H),7.63-7.41(m,9H),2.66(s,3H),2.42(s,3H).MS(ESI):418.02(C 22 h 17 ClN 6 O,[M+H] + ).Anal.Calcd for C 22 h 17 ClN 6 O: C, 63.39; H, 4.11; N, 20.16; Found: C, 63.71; H, 4.42; N, 21.22.

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Abstract

Preparation and application of bispyrazole carboxamide derivative to the control of rice black streaked dwarf disease. The invention discloses a bispyrazole carboxamide compound, which is synthesized by using carboxamide structure as the core, and introducing bispyrazole ring. The invention also discloses the preparation method of the bispyrazole carboxamide compound and application of the compound to the control of rice black streaked dwarf disease. The invention has the advantages that through the preliminary bioassay, the synthesized target compound has good activity on rice black streaked dwarf virus.

Description

technical field [0001] The invention relates to a class of bispyrazole amide compounds and a preparation method and application thereof. Background technique [0002] Since Knott discovered that antipyrine containing a pyrazole ring has slow and lasting antipyretic and analgesic effects in 1883 and Thampson discovered that 2-pyrazol-5-one can inhibit growth in 1946, pyrazole compounds have been used as a class of compounds containing Nitrogenous heterocyclic compounds have attracted extensive attention due to their high biological activity. Due to low toxicity, high efficiency and variable substituents on the pyrazole ring, pyrazole compounds have broad research and development prospects in the fields of medicine and pesticides. [0003] As a branch of pyrazole compounds, pyrazole amide compounds have a wide range of biological activities, and relevant reports have been reported in aspects such as insecticide, bactericide, herbicide and acaricide. For example, the fipronil ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/40A01N43/56A01P1/00
CPCA01N43/56C07D231/40
Inventor 操海群吕献海廖敏肖金晶褚明杰
Owner ANHUI AGRICULTURAL UNIVERSITY
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