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Pyrazolo-3-carboxamide analogs and their preparation and application

A formamide, pyrazolo technology, applied in the field of organic compounds, can solve the problems of poor stability, difficult synthesis, complex chemical structure and the like

Active Publication Date: 2019-05-17
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

People once thought of using natural ecdysone as a pesticide, but due to its complex chemical structure, difficult synthesis, poor stability and other reasons, it encountered great difficulties in practical application.

Method used

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  • Pyrazolo-3-carboxamide analogs and their preparation and application
  • Pyrazolo-3-carboxamide analogs and their preparation and application
  • Pyrazolo-3-carboxamide analogs and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: N-(3-methoxyphenyl)-2-phenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxamide (I2)

[0035] Step 1: Preparation of ethyl 2-oxocyclopentyl acetylacetonate

[0036] Add 2.05g of sodium to 100ml of absolute ethanol, after the sodium is dissolved, heat and keep at 40°C for 1h. Cool to 0°C, slowly add dropwise a mixture of 17.5g (0.12mol) diethyl oxalate and 10.0g (0.12mol) cyclopentanone, and stir for 4h at a temperature lower than 4°C. Add 100ml of ice water, adjust the pH to 2 with 36.5% hydrochloric acid, extract with dichloromethane, dry and filter the organic phase, and remove the solvent to obtain 10.0g of yellow liquid with a yield of 45%.

[0037] Step 2: Preparation of 2-phenyl-2,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylic acid

[0038] Add 0.69g (0.005mol) of phenylhydrazine hydrochloride and 10ml of ethanol to a 100ml three-necked flask, add an appropriate amount of triethylamine under stirring to adjust the pH to 7, and slowly add 1.0g (...

Embodiment 2

[0043] Example 2: N-(4-tert-butylphenyl)-2-phenyl-4,5,6,7-tetrahydrocyclohexane[c]pyrazole-3-carboxamide (I3)

[0044] Step 1: Preparation of Ethyl 2-Oxycyclohexylacetylacetonate

[0045] Add 2.05g of sodium to 100ml of absolute ethanol, after the sodium is dissolved, heat and keep at 40°C for 1h. Cool to 0°C, slowly dropwise add a mixture of 14.6g (0.10mol) diethyl oxalate and 10.0g (0.10mol) cyclohexanone, and stir for 4h at a temperature lower than 4°C. Add 100ml of ice water, adjust the pH to 2 with 36.5% hydrochloric acid, extract with dichloromethane, dry and filter the organic phase, and remove the solvent to obtain 9.6g of yellow liquid with a yield of 48%.

[0046] Step 2: Preparation of 2-phenyl-4,5,6,7-tetrahydrocyclohexane[c]pyrazole-3-carboxylic acid

[0047] Add 0.69g (0.005mol) of phenylhydrazine hydrochloride and 10ml of ethanol to a 100ml three-necked flask, add an appropriate amount of triethylamine under stirring to adjust the pH to 7, and slowly add 1.0g ...

Embodiment 3

[0052] Example 3: N-(4-tert-butylphenyl)-2-phenyl-2,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxamide (I5)

[0053] Step 1: Preparation of Ethyl 2-Oxycycloheptylacetylacetonate

[0054] Add 2.05g of sodium to 100ml of absolute ethanol, after the sodium is dissolved, heat and keep at 40°C for 1h. Cool to 0°C, slowly add dropwise a mixture of 13.0g (0.09mol) diethyl oxalate and 10.0g (0.09mol) cycloheptanone, and stir for 4h at a temperature lower than 4°C. Add 100ml of ice water, adjust the pH to 2 with 36.5% hydrochloric acid, extract with dichloromethane, dry and filter the organic phase, and precipitate from the solvent to obtain 12.7g of dark red viscous liquid, with a yield of 67.1%.

[0055] Step 2: Preparation of 2-phenyl-2,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxylic acid

[0056] Add 0.69g (0.005mol) of phenylhydrazine hydrochloride and 10ml of ethanol to a 100ml three-necked flask, add an appropriate amount of triethylamine to adjust the pH to 7 while ...

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Abstract

The invention provides a pyrazolo-cyclo-3-carboxamide analog. The pyrazolo-cyclo-3-carboxamide analog has a structure shown in the general formula I. In the formula I, n is an integer of 1-3, R1 represents C1-C10 alkyl, cyclopropyl, cyclohexyl or phenyl, hydrogen in the phenyl can be replaced by one or more of halogens, a cyano group, C1-C10 alkyl and C1-C10 alkoxy group. The pyrazolo-cyclo-3-carboxamide analog is designed according to active conformation of a bishydrazide compound, has obvious effects of killing agricultural pests and can be used as a pesticide in agriculture.

Description

technical field [0001] The invention belongs to the field of organic compounds, and in particular relates to a heterocyclic organic compound, its preparation and application. Background technique [0002] The molting and metamorphosis characteristics of insect growth and development are strictly regulated by ecdysone. Insect ecdysone is secreted by insect prothymus and is an endogenous hormone. When juvenile hormone is present, it mainly plays a role in molting. By disrupting the normal growth and development of insects, it can cause the death of individual insects, the demise of the population or weaken the viability of insects. [0003] Natural insect ecdysone was first isolated and purified from the pupa of calliphora by Adolf Butenandt and Peter Karlson in 1954. So far, more than 15 ecdysones have been extracted from insects and their structures have been identified, and most of them have very similar structures. In 1966, Nakanishi Koji et al. isolated ponasterone A, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/54A01N43/56A01P7/04
CPCA01N43/56C07D231/54
Inventor 杨新玲邓希乐张莉迟鸣袁德凯胡雪萍米益铎
Owner CHINA AGRI UNIV
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