Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Carboxyl acylamide compound and its preparing method and use

A technology of carboxamides and compounds is applied in the field of carboxamide fungicides and their preparation, and can solve the problems of unfriendly environment of fungicides, toxic and side effects of humans and animals, etc.

Active Publication Date: 2006-05-24
NANKAI UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, some of these fungicides are not friendly to the environment, have toxic and side effects on humans and animals, and long-term use will cause obvious resistance to strains

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Carboxyl acylamide compound and its preparing method and use
  • Carboxyl acylamide compound and its preparing method and use
  • Carboxyl acylamide compound and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1: Preparation of (Rc, Ss)-(1-hydroxymethyl-2-methylsulfoxide ethyl)-5-methylpyrazine-2-amide (I-1)

[0098] In a 50 mL round-bottomed flask, add (Rc, Ss)-2-amino-3- Methylsulfoxide propanol (0.5mmol, 92mg, the compound was prepared according to the literature J.Org.Chem.1981,46,5408-5413), dicyclohexylcarbodiimide (114mg, 0.55mmol), 1- Hydroxybenzotriazole (5 mg), stirred at room temperature for 24 hours. After the solvent was removed under reduced pressure, 123 mg of white solid was obtained by column chromatography, with a yield of 80.9%; 1 H NMR (400MHz, D 2 O) δ8.97(s, 1H, Py), 8.56(s, 1H, Py), 4.64(m, 1H, NHCH), 4.08 and 3.91(AB spectrum, d, J=14.0Hz, 2H, SOCH 2 S), 3.80 (m, 2H, CH 2 OH), 3.31-3.18 (m, 2H, SOCH 2 CH), 2.60(s, 3H, PyCH 3 ), 2.21(s, 3H, SCH 3 ); 13 C NMR (100MHz, D 2 O+CD 3 OD-d 4 )δ 165.84, 158.08, 144.34, 142.12, 141.60, 63.03, 54.77, 52.52, 46.95, 20.74, 16.19.

Embodiment 2

[0099] Example 2: Preparation of (Rc, Rs)-(1-hydroxymethyl-2-methylsulfoxide ethyl)-5-methylpyrazine-2-amide (I-2)

[0100] In a 50 mL round-bottomed flask, add (Rc, Rs)-2-amino-3- Methylsulfoxide propanol (0.5mmol, 92mg, the compound was prepared according to the literature J.Org.Chem.1981,46,5408-5413), dicyclohexylcarbodiimide (114mg, 0.55mmol), 1- Hydroxybenzotriazole (5 mg), stirred in an ice-water bath for 24 hours. After the solvent was removed under reduced pressure, 112 mg of a colorless oil was obtained by column chromatography, with a yield of 73.6%; 1 H NMR (300MHz, D 2 O) δ8.99 (s, 1H, Py), 8.60 (s, 1H, Py), 4.63 (m, 1H, NHCH), 4.16 and 3.96 (AB spectrum, d, J=13.9Hz, 2H, SOCH 2 S), 3.85 (m, 2H, CH 2 OH), 3.44 and 323 (ABpart of ABX spectrum, 8 lines, J AB =13.7Hz,J AX =8.7Hz,J BX =5.1Hz, 2H, SOCH 2 CH), 2.63(s, 3H, PyCH 3 ), 2.27(s, 3H, SCH 3 ); 13 C NMR (75.5MHz, D 2 O+CD 3 OD-d 4 )δ 166.47, 159.04, 145.30, 143.01, 142.58, 63.60, 55.80, 53.08, 48.62,...

Embodiment 3

[0101] Example 3: Preparation of (Sc, Ss)-(1-hydroxymethyl-2-methylsulfoxide ethyl)-5-methylpyrazine-2-amide (I-3)

[0102] In a 50 mL round-bottomed flask, (Sc, Ss)-2-amino-3- Methylsulfoxide propanol (0.5mmol, 92mg, the compound was prepared according to the literature J.Org.Chem.1981,46,3273-3283), dicyclohexylcarbodiimide (114mg, 0.55mmol), 1- Hydroxybenzotriazole (5 mg), stirred at room temperature for 24 hours. After the solvent was removed under reduced pressure, 131 mg of a colorless oil was obtained by column chromatography, with a yield of 73.6%; 1 H NMR (300MHz, D 2 O) δ9.01 (s, 1H, Py), 8.61 (s, 1H, Py), 4.67 (m, 1H, NHCH), 4.18 and 3.98 (AB spectrum, d, J=13.9Hz, 2H, SOCH 2 S), 3.86(d, J=5.2Hz, 2H, CH 2 OH), 3.46 and 3.25 (AB part of ABX spectrum, 8 lines, J AB =13.7Hz,J AX =8.7Hz,J BX =5.1Hz, 2H, SOCH 2 CH), 2.65(s, 3H, PyCH 3 ), 2.29 (s, 3H, SCH 3 ); 13 C NMR (75.5MHz, D 2 O+CD 3 OD-d 4 )δ 165.53, 158.03, 144.26, 142.00, 141.52, 62.57, 54.75, 51.99...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a carboxyl amide compound and its nontoxic salt, obtained by reaction of two compounds at 0-40 deg.C, where one compound contains 5-methyl pyrazine-2-radical, 5-methyl urea pyrilamine-1-methylene, urea pyrilamine-4-radical, coumarin-3-radical, 5-bromofuran-2-radical, quinoxaline-6-radical, 3-hydroxyl quinoxaline-2-radical, (thiophene -2-) or (indole-3-) or (imidazole-4-) ethylene, benzotriazole-5- radical, benzoimidazole-5-radical, (benzoimidazole-2-)ethyl, (2-amino thiazole-5-) or (2, 5-dioxyimidazoline-4-) methylene, or (benzo dioxypentane-5-) ethylene; and the other compound contains C1-8 alkyl, C1-8 oxyalkyl, aryl, or heteroatomic radical. It can be used to prepare disinfectant.

Description

technical field [0001] The invention relates to a carboxamide fungicide compound and a preparation method thereof. Background technique [0002] Since Von Schmeling discovered systemic wisterin in 1966, carboxamide fungicides have experienced more than 30 years of development. Carboxamide fungicides are still widely used in agriculture due to the slow rate of development of resistance using these fungicides. A lot of commercial carboxamide fungicides have been reported, such as Vitavax, Mebenil, Metsulfovax, Methfuroxam, Flutolanil, Triflumazid. [0003] [0004] However, some of these fungicides are not friendly to the environment, have toxic and side effects on humans and animals, and long-term use will cause obvious resistance to strains. Therefore, designing and synthesizing fungicides with high efficiency, low toxicity, broad spectrum, high selectivity, low residue and low resistance is an urgent problem in the current pesticide research. Contents of the inventi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D241/24C07D209/04C07D233/54C07D235/04C07D239/26C07D241/44C07D249/18C07D277/02C07D307/68
Inventor 席真程晓峰王勇曹力强陈文彬
Owner NANKAI UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com