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N-(thiazol-2-yl)-2-[4-(pyridin-2-oxy)phenoxy]amide derivatives

A technology of amide derivatives and phenoxy, applied in biocides, chemicals for biological control, biocides, etc., can solve the problem of no research and development reports on the herbicidal activity of amide derivatives

Inactive Publication Date: 2017-12-05
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (R)-N-(thiazol-2-yl)-2-[4-(pyridine-2-oxyl)phenoxy]amide derivatives have no research and development reports

Method used

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  • N-(thiazol-2-yl)-2-[4-(pyridin-2-oxy)phenoxy]amide derivatives
  • N-(thiazol-2-yl)-2-[4-(pyridin-2-oxy)phenoxy]amide derivatives
  • N-(thiazol-2-yl)-2-[4-(pyridin-2-oxy)phenoxy]amide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of (R)-N-(4-tert-butylthiazol-2-yl)-2-[4-(3-chloro-5-trifluoromethylpyridine-2-oxy)phenoxy]propionamide

[0035]

[0036] 1mmol 4-tert-butyl-2-aminothiazole, 1.0mmol triethylamine, catalytic amount of 4-dimethylaminopyridine (DMAP), 20mL dichloromethane, ice bath, add 2.0mmol(R)-2-[ 4-(3-Chloro-5-trifluoromethylpyridin-2-oxy)phenoxy]propionyl chloride in dichloromethane, drip in about 15min, and react at room temperature for 1h; the organic layer is washed with water and saturated brine , Dry, desolventize, the crude product is subjected to column chromatography [V Petroleum ether :V Ethyl acetate =7:1~5:1] to obtain a yellow solid (R)-N-(4-tert-butylthiazol-2-yl)-2-[4-(3-chloro-5-trifluoromethylpyridine-2) -Oxy)phenoxy]propionamide 0.398g, mp 52~55°C, yield 70.1%, 1 HNMR(400MHz, CDCl 3 )δ: 1.30(s, 9H, 3×CH 3 ), 1.68(d, J=6.8Hz, 3H, CH 3 ), 4.89 (q, J = 6.8 Hz, 1H, CH), 6.59 (s, 1H, 5-H, thiazole), 7.04 (d, J = 9.0 Hz, 2H, C 6 H 4 2,6-H), 7.14(d, J=9.0Hz, 2...

Embodiment 2

[0038] Preparation of (R)-N-(4-tert-butylthiazol-2-yl)-2-[4-(5-chloro-3-fluoropyridin-2-oxy)phenoxy]propionamide

[0039]

[0040] The preparation method is the same as in Example 1, 1.0mmol 4-tert-butyl-2-aminothiazole and 2.0mmol (R)-2-[4-(5-chloro-3-fluoropyridin-2-oxy)phenoxy]propane Reaction with acid chloride for 2h; obtain orange solid (R)-N-(4-tert-butylthiazol-2-yl)-2-[4-(5-chloro-3-fluoropyridin-2-oxy)phenoxy] Propionamide 0.30g, mp57~60℃, yield 66.5%, 1 H NMR(400MHz, CDCl 3 )δ: 1.30(s, 9H, 3×CH 3 ), 1.67(d, J=7.0Hz, 3H, CH 3 ), 4.87 (q, J = 7.0 Hz, 1H, CH), 6.58 (s, 1H, thiazole 5-H), 7.01 (d, J = 9.0 Hz, 2H, C 6 H 4 2,6-H), 7.13(d, J=9.0Hz, 2H, C 6 H 4 3,5-H), 7.51(dd, J 1 =9.0Hz, J 2 =2.0Hz, 1H, C 5 H 2 N 4-H), 7.87 (d, J = 2.0 Hz, 1H, C 5 H 2 N 6-H), 9.63 (s, 1H, CONH).

Embodiment 3

[0042] (R)-N-(4-tert-butyl-5-nitrothiazol-2-yl)-2-[4-(3-chloro-5-trifluoromethylpyridine-2-oxy)phenoxy ]Preparation of propionamide

[0043]

[0044] The preparation method is the same as in Example 1, 1.0mmol 4-tert-butyl-5-nitro-2-aminothiazole and 2.0mmol (R)-2-[4-(3-chloro-5-trifluoromethylpyridine-2- Oxy)phenoxy]propionyl chloride, react for 3.5h to obtain (R)-N-(4-tert-butyl-5-nitrothiazol-2-yl)-2-[4-(3-chloro -5-Trifluoromethylpyridine-2-oxy)phenoxy]propionamide 0.37g, mp63~66℃, yield 68.0%, 1 HNMR(400MHz, CDCl 3 )δ: 1.46(s, 9H, 3×CH 3 ), 1.70(d, J=6.8Hz, 3H, CH 3 ), 4.95 (q, J = 6.8 Hz, 1H, CH), 7.05 (d, J = 9.0 Hz, 2H, C 6 H 4 2,6-H), 7.17(d, J=9.0Hz, 2H, C 6 H 4 3,5-H), 7.99(s, 1H, C 5 H 2 N6-H), 8.27(s, 1H, C 5 H 2 N 4-H), 9.66 (s, 1H, CONH).

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Abstract

The present invention relates to a class of (R)-N-(thiazol-2-yl)-2-[4-(pyridin-2-oxy)phenoxy]amide derivatives having a chemical structure formula represented by a formula (I) and salts thereof, wherein R is selected from C1-C2 alkyl, C3-C4 linear chain alkyl, or C3-C4 branched chain alkyl, R1 is selected from hydrogen, trifluoromethyl, C1-C2 alkyl, C3-C4 linear chain alkyl or C3-C4 branched chain alkyl, R2 is selected from hydrogen, C1-C2 alkyl, C3-C4 linear chain alkyl or C3-C4 branched chain alkyl, nitro, carboxy, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl and tert-butoxycarbonyl, Y1 is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine or iodine, and Y2 is selected from hydrogen, trifluoromethyl, C1-C2 alkyl, fluorine, chlorine, bromine or iodine. According to the present invention, the (R)-N-(thiazol-2-yl)-2-[4-(pyridin-2-oxy)phenoxy]amide derivatives and the salts thereof can be used for preparing weeding agents.

Description

Technical field [0001] The invention relates to a class of new compounds and their uses, specifically N-(thiazol-2-yl)-2-[4-(pyridine-2-oxy)phenoxy]amide derivatives and their use in the preparation of herbicides In the application. Background technique [0002] 4-aryloxy)phenoxy carboxylic acid derivatives have good biological activity [2-(4-aryloxy)phenoxy)alkanamide and its applications, Chinese invention patent, ZL201310041239.9, authorized on May 14, 2014 ; 2-[4-(Benzoxazole-2-oxy)phenoxy]alkanamide and its application, Chinese invention patent, ZL201310040974.8, authorized 20148.13; N-picolyl / methoxy-2- The medical use of phenoxyamide, Chinese invention patent, ZL201310437071.3, authorized on October 22, 2014; the medical use of N-thiazolmethyl / methoxy-2-phenoxyamide, ZL201310437111.4, authorized on 2015.5.13] ; Among them, aryloxyphenoxypropionic acid derivatives have more than 20 commercial varieties in agricultural herbicides [DE2640730, DE3004770, US4713109, EP0302203...

Claims

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Application Information

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IPC IPC(8): C07D417/12A01N43/78A01P13/00
Inventor 胡艾希杨子辉元科阳叶姣伍智林
Owner HUNAN UNIV
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