Gamma-aryl substituted chiral triazole bactericides and their synthesis process

A triazole and chiral technology, applied in the field of chiral triazole compounds and their synthesis, can solve problems such as rare reports, achieve simple separation and purification, good product yield and enantioselectivity, and simple and easy synthesis method row effect

Inactive Publication Date: 2007-08-22
HUAZHONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the widely used broad-spectrum, high-efficiency azole fungicides are still sold in the form of racemates, and they have shown good antibacterial activity against many plant pathogenic bacteria. The research on the antibacterial activity of their chiral pure isomers, At present, there are few reports at home and abroad

Method used

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  • Gamma-aryl substituted chiral triazole bactericides and their synthesis process
  • Gamma-aryl substituted chiral triazole bactericides and their synthesis process
  • Gamma-aryl substituted chiral triazole bactericides and their synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Under nitrogen protection, 20 ml of anhydrous tetrahydrofuran solution of D-(-)-camphorsultam (1a) (10.76 g, 50 mmol) was added dropwise to 40 ml of sodium hydride (2.4 g, 100 mmol). mL of anhydrous tetrahydrofuran solution, react at room temperature for 1 hour, then drop cinnamoyl chloride (10.0 g, 60 mmol) in 20 mL of tetrahydrofuran solution into the reaction flask. After reacting at room temperature for 24 hours, 20 ml of ice water was added to terminate the reaction, extracted with diethyl ether (3×40 ml), the organic phase was washed with water, and anhydrous MgSO 4 Drying, concentration under reduced pressure, recrystallization from a mixed solution of ethyl acetate and petroleum ether (volume ratio 1:1) yielded 15.75 g of white solid product 2a, with a yield of 91.2%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 0.99 (s, 3H), 1.21 (s, 3H), 1.36-1.48 (m, 2H), 1.91-1.93 (m, 3H), 2.12-2.21 (m, 2H), 3.49 (d , J=14.0Hz, 1H), 3.56(d, J=14.0Hz, 1H), 4.0(dd, 1H), 7.17(d, J=...

Embodiment 2

[0033] Except that L-(+)-camphorsultam (1b) was used instead of D-(-)-camsylsultam, other conditions were the same as in Example 1. The obtained 2b, 3b, 4b, 5b, 6b are as follows:

[0034] 2b: 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 0.99 (s, 3H), 1.21 (s, 3H), 1.36-1.48 (m, 2H), 1.91-1.93 (m, 3H), 2.12-2.21 (m, 2H), 3.49 (d , J=14.0Hz, 1H), 3.56(d, J=14.0Hz, 1H), 4.0(dd, 1H), 7.17(d, J=15.2Hz, 1H), 7.38-7.43(m, 3H), 7.56 -7.60(m, 2H), 7.80(d, J=15.2Hz, 1H).

[0035] 3b: 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 0.81 (t, 3H), 0.96 (s, 3H), 1.17 (s, 3H), 1.12-1.35 (m, 6H), 1.59-1.65 (m, 2H), 1.84-1.88 (m , 3H), 2.01(m, 2H), 3.06(m, 2H), 3.22(m, 1H), 3.40(d, J=14.0Hz, 1H), 3.48(d, J=13.6Hz, 1H), 3.80 (dd, 1H), 7.19(m, 3H), 7.27(m, 2H).

[0036] 4b: 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 0.82 (t, 3H), 1.10-1.29 (m, 4H), 1.57-1.64 (m, 2H), 1.81 (m, 2H), 1.92-1.97 (m, 1H), 2.67 (m , 1H), 3.45-3.53 (m, 2H), 7.17 (m, 3H), 7.29 (m, 2H).

[0037] 5b: 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 0.8...

Embodiment 3

[0040] (1) Raw material, operation and condition are the same as embodiment 1 step (1).

[0041] (2) Under the protection of nitrogen, add compound 2a (3.45 g, 10 mmol) and 50 ml of anhydrous tetrahydrofuran into a dry three-necked flask, and add the freshly prepared ether solution of n-EtMgBr (24 mmol 20 ml), after the dropwise addition was completed, the stirring reaction was continued at -78°C for 3 hours, the temperature was raised to -40°C, and the reaction was terminated with saturated aqueous ammonium chloride solution, extracted with ether, and the organic phase was washed with saturated brine, anhydrous MgSO 4 It was dried, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain 1.97 g of the product N-(3'R)-3'-phenylpentanoylcamphorane-10,2-sultam (3a), with a yield of 52.5%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 0.78 (t, 3H), 0.96 (s, 3H), 1.17 (s, 3H), 1.31-1.36 (m, 2H), 1.57-1.69 (m, 2H), 1.84-1.89 (m , 3H), 2.01(m, 2H), 2.9...

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Abstract

The present invention relates to one kind of gamma-aryl substituted chiral triazole compound and its synthesis process. The compound in the structure as shown features the chiral center introduced to the gamma position of triazole. It is obtained through a chiral assistant camphor sultam induced asymmetrical process, and the process has high product yield and high antipodal selectivity.

Description

technical field [0001] The invention relates to a class of γ-aryl substituted chiral triazole compounds and a synthesis method thereof. Background technique [0002] In the past 20 years, people have been extremely active in the research on nitrogen heterocyclic fungicides. In the late 1960s, West German Bayer and Belgian Janssen first reported the fungicidal activity of 1-substituted azole derivatives. In the early 1970s, azole The high-efficiency bactericidal properties of these compounds have attracted great attention from the international pesticide industry, and the development and application of triazole agricultural chemicals have developed rapidly. Triazole compounds are important systemic fungicides, and dozens of products have been developed. In 1990, triazole fungicides accounted for 10% of fungicides. In addition, triazole plant growth regulators, insecticides, and acaricides are scattered in various literatures, which provide broad application prospects for 1,2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08A01N43/653A01P3/00
Inventor 刘盛华曹秀芳余广鳌陆文昌刘芳
Owner HUAZHONG NORMAL UNIV
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