Pyrazole-containing bishydrazide compound and preparation method and application thereof

A technology of pyrazole bishydrazide and compound, which is applied to pyrazole bishydrazide-containing compounds and the fields of preparation and application thereof, and can solve the problems of few bishydrazide compounds and the like

Active Publication Date: 2015-05-20
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although the wide range of biological activities of bishydrazide compounds has attracted more and more attention, and the research on it has become more and more in-depth. There are few reports on the compounds

Method used

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  • Pyrazole-containing bishydrazide compound and preparation method and application thereof
  • Pyrazole-containing bishydrazide compound and preparation method and application thereof
  • Pyrazole-containing bishydrazide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 1-(2-Ethyl-phenyl)-5-methyl-1 H- Preparation of pyrazole-4-carboxylic acid chloride

[0022] Add 0.46g (0.002mol) 1-(2-ethyl-phenyl)-5-methyl-1 to a 50mL one-necked flask H- Pyrazole-4-carboxylic acid and 1.428 g (0.012 mol) SOCl 2 , react at room temperature for 1 h, and then reflux for 2 h. After the reaction, remove excess thionyl chloride to obtain a light yellow transparent liquid, which is sealed and stored for future use.

Embodiment 2

[0023] Example 2 Preparation of the target product

[0024] Add 4-methylphenoxyacetylhydrazide (0.0018 mol), (Et) 3 N, ethyl acetate (10 mL), and then Example 1. Add the mixed solution of acid chloride and ethyl acetate dropwise into the reaction flask, stir overnight at room temperature, solids are precipitated, and monitor by pointing a plate. After the raw materials are completely reacted, suction filter and wash to obtain a light-colored solid powder, namely the product. Melting point 241-243 o C, yield 63%.

[0025] of the compound 1 H NMR and ESI-MS data are as follows:

[0026] 1 H NMR (CDCl 3 , d / ppm)δ 1.08 (t, J =7.6Hz, 3H ,CH 3 ), 2.31(s, 3H, CH 3 ), 2.34 (q, J =7.6Hz, 2H, CH 2 ), 2.37(s, 3H, CH 3 ), 4.66 (s, 2H, OCH 2 ), 6.88 (d, J =9.6Hz, 2H, Ph-H), 7.13 (d, J =8.3Hz, 2H, Ph-H), 7.17 (d, J =7.7Hz, 1H, Ph-H), 7.32 (t, J =8.2Hz, 1H, Ph-H), 7.40 (d, J =6.9Hz, 1H, CONH), 7.46 (t, J =7.0Hz, 1H, Ph-H), 7.95 (s, 1H, CH), 8.32 (s, 1H, Ph-H), 9.01 (d, ...

Embodiment 3

[0027] Example 3 Preparation of the target product

[0028] Add 2-nitrophenoxyacetylhydrazide (0.0018 mol), (Et) 3 N. Ethyl acetate (10 mL), then drop the mixed solution of acid chloride and ethyl acetate into the reaction flask, stir at room temperature overnight, there is solid precipitation, spot plate monitoring, after the raw materials are completely reacted, suction filtration, washing, to obtain Light yellow solid powder, the product, melting point 179-182 o C, yield 91%.

[0029] of the compound 1 H NMR and ESI-MS data are as follows:

[0030] δ 1.08 (t, J =7.6Hz, 3H,CH 3 ), 2.35(q, J =7.6Hz, 2H, CH 2 ), 2.31(s, 3H, CH 3 ), 4.85(s, 2H, OCH 2 ), 7.10(d, J =7.8Hz, 1H, Ph-H), 7.19(t, J =8.0Hz, 2H, Ph-H), 7.32 (t, J =7.6Hz, 1H, Ph-H), 7.40 (d,J =7.8Hz, 1H,Ph-H ), 7.46 (t, J =7.5Hz, 1H, Ph-H), 7.68 – 7.61 (m, 1H, Ph-H), 7.95 (s, 1H, CH), 8.06 (s, 1H, Ph-H), 8.08 (s, 1H, CONH), 9.34 (d , J = 4.0 Hz, 1H, CONH). ESI-MS: 424[M+H].

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Abstract

The invention relates to a pyrazole-containing bishydrazide compound and a preparation method and application thereof. According to the bishydrazide compound and the preparation method and application thereof, disclosed by the invention, the bishydrazide compound has the structure represented by a formula (I) shown in description, wherein R represents substituted phenyl; a benzene ring of the substituted phenyl is monosubstituted or polysubstituted, and each substituent is independently selected from C1-C10 alkyl, halogen or nitro. The bishydrazide compound disclosed by the invention is simple in preparation and has excellent weeding activity and can be used as a weedicide.

Description

technical field [0001] The invention relates to a pyrazole-containing bishydrazide compound and a preparation method and application thereof. Background technique [0002] Bihydrazide compounds have been developed into a class of insect growth regulators due to their wide range of biological activities, low toxicity, high sensitivity and unique mode of action, such as commercialized hydrazine and tebufenozide. Compared with traditional organic synthetic pesticides, at the same time, due to the control of pests, the destruction of ecological balance, and the resistance of pests, "insect growth regulators" (IGRS) came into being. Its mechanism of action is to interfere with the development, molting and reproduction of insects. , and safe for humans, livestock, natural enemies of pests and the environment. At the same time, it also has great potential in drug treatment. So far, there have been many reports on the anti-tumor and anti-malarial effects of bishydrazide compounds....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/14A01P13/00
CPCA01N43/56C07D231/14
Inventor 谭成侠何海琴贡云芸史建俊刘幸海翁建全
Owner HUAWEI TEHCHNOLOGIES CO LTD
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