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Novel hydrazide derivatives as well as preparation method and application thereof

A technology of hydrazide derivatives and derivatives, which is applied in the field of synthesis of agricultural chemical insecticides, can solve the problems of increased consumer costs and reduced productivity, and achieve excellent insecticidal activity, improved fat solubility, and broad application prospects

Inactive Publication Date: 2014-01-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Invertebrate pest damage to growing and stored crops can cause significant reductions in productivity and consequently increased costs to consumers

Method used

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  • Novel hydrazide derivatives as well as preparation method and application thereof
  • Novel hydrazide derivatives as well as preparation method and application thereof
  • Novel hydrazide derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 3-Bromo-N-tert-butyl-1-(3-chloro-2-pyridyl)-N'-(4-trifluoromethylbenzoyl)-1H-pyrazole-5-carboxhydrazide (derivatized Synthesis of Item 01):

[0045] Step A: Preparation of N’-tert-butyl-4-trifluoromethyl benzohydrazide

[0046] Add 4-trifluoromethylbenzoic acid (0.57g, 3mmol), SOCl in a 100mL round bottom flask 2 , Reflux, reduce excess SOCl 2 , The crude acid chloride is obtained, and it is added dropwise to a mixture of a suitable amount of tert-butylhydrazine hydrochloride, sodium hydroxide, dichloromethane and water. After dropping, react at room temperature, add ethyl acetate, separate the organic layer, and the organic layer After desolvation, the title compound was obtained, 0.57 g of white powder, mp 77-78°C.

[0047] Step B: Preparation of 3-bromo-N-tert-butyl-1-(3-chloro-2-pyridinyl)-N'-(4-trifluoromethylbenzoyl)-1H-pyrazole-5- Formyl hydrazide

[0048] Add 3-bromo-1-(3-chloro-2-pyridyl)-1H-biazole-5-carboxylic acid (0.30g, 1.00mm0l), oxalyl chloride and dichloromet...

Embodiment 2

[0050] N'-(2-Amino-5-chloro-3-methylbenzoyl)-3-bromo-N-tert-butyl-1-(3-chloro-2-pyridyl)-1H-pyrazole-5 -Synthesis of formyl hydrazide (derivative 17)

[0051] Step A: Preparation of 2-amino-3-methyl-5-chlorobenzoic acid

[0052] Dissolve 2-amino-3-methylbenzoic acid (15.10g, 100mmol) in DMF, add excess NCS to it, heat, cool, and pour into 500mL ice water. A brown-red solid appears. Filter and dry to obtain the title compound. 12.3g.

[0053] Step B: Preparation of N’-tert-butyl-2-amino-3-methyl-5-chlorobenzohydrazide

[0054] Add 2-amino-3-methyl-5-chlorobenzoic acid (0.56g, 3mmol), SOCl in a 100mL round bottom flask 2 , Reflux, reduce excess SOCl 2 , To obtain crude acid chloride, add dropwise to a mixture of tert-butylhydrazine hydrochloride, sodium hydroxide, dichloromethane and water under cooling in an ice-water bath, react at room temperature, add 100 mL of ethyl acetate, and separate the organic layer After the organic layer was desolvated, the title compound was obtained, 0....

Embodiment 3

[0058] N-[2-(2-(3-Bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formyl)-2-(tert-butyl)hydrazinocarbonyl)-4 -Chloro-6-methylphenyl] the synthesis of methyl carbamate (derivative 45)

[0059] Add N'-(2-amino-5-chloro-3-methylbenzoyl)-3-bromo-N-tert-butyl-1-(3-chloro-2-pyridine to a 100mL single-necked round bottom flask Base)-1H-pyrazole-5-carboxhydrazide (0.32g, 0.6mmol), triethylamine and dichloromethane, add acetyl chloride dropwise, after dropping, stir at room temperature, after the reaction is over, add ethyl acetate, divide The organic layer was separated, and after the organic layer was desolvated, the title compound was obtained, 0.14 g white powder, mp264-265°C.

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PUM

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Abstract

The invention relates to novel hydrazide derivatives as well as a preparation method and application thereof. The novel hydrazide derivatives have a general formula as shown in the specification, wherein each group is as shown in the claim 1. The novel hydrazide derivatives provided by the invention are improved in insecticidal activity while the previous compound lipid solubility thereof is improved; the derivatives have excellent insecticidal activity; instantly after the derivatives are applied, insects can lose control on muscle and stop eating, and are obviously shrank and paralyzed; at last, the insects can be caused to die, and in the meantime, abnormal ecdysis of insects also can be induced; the novel hydrazide derivatives are very effective especially for lepidoptera pests such as mythimna separata, plutella xylostella and asparagus caterpillar, and thus are pesticides having wide application prospect.

Description

Technical field [0001] The invention involves the synthesis technology of agricultural chemical pesticides, especially a type of derivatives and their preparation methods and applications. Background technique [0002] The prevention and control of vertebrates is extremely important among high planting efficiency.The damage to crops growing and storing crops of vertebrates of vertebrates will cause significant reduction in productivity and therefore leading to increased consumer costs.At the same time, the prevention and treatment of pests is also important in forests, animal husbandry, vice, fishing and public health.Although there are some new pest control agents on the market, due to the continuous expansion of the market, the resistance of pests, the life of the drug, and the increasing importance to the people's environmental ecology, scientists need to continue to study, and then develop more effective and more effective and more effective and more effective.Low -cost, low ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCC07D401/04A01N43/56
Inventor 李正名周蕴赟刘辰周莎狄凤娟熊丽霞王宝雷李玉新赵毓
Owner NANKAI UNIV
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