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Carboxyl acylamide compound and its preparing method and use

A technology of carboxamides and compounds, which is applied in the field of carboxamide fungicide compounds and their preparation, and can solve the problems of human and animal side effects and unfriendly fungicides, etc.

Active Publication Date: 2009-01-14
NANKAI UNIV
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  • 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

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  • 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

[0096] Example 1: Preparation of (Rc, Ss)-(1-hydroxymethyl-2-methylsulfoxide ethyl)-5-methylpyrazine-2-amide (I-1)

[0097] 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

[0098] Example 2: Preparation of (Rc, Rs)-(1-hydroxymethyl-2-methylsulfoxide ethyl)-5-methylpyrazine-2-amide (I-2)

[0099]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 3.23 (ABpart of ABX spectrum, 8 lines, J AB =1 3.7Hz,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....

Embodiment 3

[0100] Example 3: Preparation of (Sc, Ss)-(1-hydroxymethyl-2-methylsulfoxide ethyl)-5-methylpyrazine-2-amide (I-3)

[0101] 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...

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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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/24C07D239/26C07D307/68C07D241/44C07D209/04C07D233/54C07D249/18C07D235/04C07D277/02A01N43/48A01N43/64A01N43/72A01P3/00
Inventor 席真程晓峰王勇曹力强陈文彬
Owner NANKAI UNIV
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