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2-aryloxy carboxylic acid(dihydrobenzofuran-7-phenoxyl)alkyl ester

A technology of aryloxycarboxylic acid and dihydrobenzene, which is applied in biocides, plant growth regulators, animal husbandry and other directions, can solve the problem that 2-aryloxycarboxylic acid herbicidal activity is not reported and the like

Active Publication Date: 2016-11-23
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The herbicidal activity of 2-aryloxycarboxylic acid (dihydrobenzofuran-7-oxyl) alkyl ester has not been reported

Method used

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  • 2-aryloxy carboxylic acid(dihydrobenzofuran-7-phenoxyl)alkyl ester
  • 2-aryloxy carboxylic acid(dihydrobenzofuran-7-phenoxyl)alkyl ester
  • 2-aryloxy carboxylic acid(dihydrobenzofuran-7-phenoxyl)alkyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-oxyl)ethanol

[0027]

[0028] 10mmol furanol, 40mmol 2-chloroethanol, 20mmol K 2 CO 3 React with 0.5mmol PEG-200, 20mL ethanol, 70°C for 10.0h. TLC detection, the reaction is complete, cooling, filtering to remove K 2 CO 3 , the filtrate was desolvated, the residue was dissolved in 40mL of dichloromethane, the organic layer was washed with water and dried, and the desolvated dark green solid 2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-oxo Base) ethanol, m.p.42~45 ℃, yield 93.2%; 1 H NMR (400MHz, CDCl 3 )δ: 1.41(s, 6H, 2×CH 3 ), 2.93 (s, 2H, CH 2 ), 3.80~3.83 (m, 2H, OCH 2 ), 4.03~4.05 (m, 2H, CH 2 ), 6.66~6.71 (m, 3H, C 6 h 3 ).

Embodiment 2

[0030] Preparation of 3-(2,2-Dimethyl-2,3-dihydrobenzofuran-7-oxyl)propanol

[0031]

[0032] Operation is with embodiment 2, 0.84g (5.1mmol) furan phenol and 2.84g (20.4mmol) 3-bromopropanols, 1.41g (10.2mmol) K 2 CO 3 , and reacted for 7.0h to obtain 0.94g of light green solid 3-(2,2-dimethyl-2,3-dihydrobenzofuran-7-oxyl)propanol 6b, m.p.52~55℃, yield 83.2 %; 1 H NMR (400MHz, CDCl 3 )δ: 1.49(s, 6H, 2×CH 3 ), 2.00~2.07 (m, 2H, CH 2 ), 3.02(s, 2H, CH 2 ), 3.84~3.88 (m, 2H, OCH2 ), 4.18~4.22 (m, 2H, CH 2 ), 6.75~6.80 (m, 3H, C 6 h 3 ).

Embodiment 3

[0034] Preparation of 4-(2,2-Dimethyl-2,3-dihydrobenzofuran-7-oxyl)butanol

[0035]

[0036] 0.164g (1.0mmol) furanol and 0.43g (4.0mmol) 4-chlorobutanol, 0.276g (2.0mmol) K 2 CO 3 , catalytic amount of TBAB, 20mL acetone, reflux for 12.0h, cooling, suction filtration, drying, precipitation, crude product through column chromatography [V 石油醚 :V 乙酸乙酯 =5:1] Column chromatography yielded 0.18 g of white solid 4-(2,2-dimethyl-2,3-dihydrobenzofuran-7-oxyl)butanol, m.p.62-65°C, yield 76.2%; 1 H NMR (400MHz, CDCl 3 )δ: 1.50(s, 6H, 2×CH 3 ), 1.73~1.78 (m, 2H, CH 2 ), 1.86~1.93 (m, 2H, CH 2 ), 3.01 (s, 2H, CH 2 ), 3.71(t, J=6.4Hz, 2H, OCH 2 ), 4.09(t, J=6.4Hz, 2H, CH 2 ), 6.73~6.76 (m, 3H, C 6 h 3 ).

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Abstract

The invention discloses 2-aryloxy carboxylic acid(dihydrobenzofuran-7-phenoxyl)alkyl ester shown as the chemical structural formula I and the chemical structural formula II (please see the formula I and the formula II in the specification). R is selected from hydrogen, C1-C2 alkyl, C3-C4 linear chain alkyl and C3-C4 branch alkyl, n is selected from 1, 2, 3, 4, 5 and 6, and Z is selected from CH and N; Y<1> is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine and iodine; Y<2> is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoro ethyl and cyano; Y<3> is selected from hydrogen, C1-C2 alkyl, fluorine, chlorine, bromine and iodine. 2-aryloxy carboxylic acid(dihydrobenzofuran-7-phenoxyl)alkyl ester aims at being applied to preparing a herbicide.

Description

technical field [0001] The present invention relates to a class of novel compounds and their preparation method and application, specifically 2-aryloxycarboxylic acid (dihydrobenzofuran-7-oxyl) alkyl ester and its preparation method and herbicide preparation Applications. Background technique [0002] 4-Aryloxyphenoxyalkanoic acid derivatives have a wide range of biological activities, and aryloxyphenoxypropionic acid derivatives are their typical representatives, and there are more than 20 commercial varieties in agricultural herbicides [DE2640730, DE3004770 , US4713109, EP302203, JP54022371, EP4414, US 20030096706]. The main mode of action of 4-aryloxyphenoxy carboxylic acid derivatives is to inhibit plant acetyl-CoA carboxylase, thereby affecting the synthesis of plant fatty acids and causing plant death to achieve the purpose of weeding. Liu Li et al. [Modern Pesticides, 2006,5(4):21-23] selected 2-cyano-3-(2-hydroxyethylamino)-3-ethyl p-methylphenylacrylate and 2-[4 ...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07D307/86A01N43/60A01N43/40A01N43/12A01P13/00
CPCA01N43/12A01N43/40A01N43/60C07D307/86C07D405/12
Inventor 胡艾希杨子辉叶姣李永红
Owner HUNAN UNIV
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