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N-[(dihydrobenzofuran-7-yloxyl)alkyl]-2-aryloxy amide derivatives

A technology of aryloxyamide and dihydrobenzene, which is applied in the directions of biocides, chemicals for biological control, biocides, etc., can solve the problem that the herbicidal activity of 2-aryloxyamide derivatives is not reported, etc.

Active Publication Date: 2017-11-24
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The herbicidal activity of N-[(dihydrobenzofuran-7-oxyl)alkyl]-2-aryloxyamide derivatives has not been reported

Method used

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  • N-[(dihydrobenzofuran-7-yloxyl)alkyl]-2-aryloxy amide derivatives
  • N-[(dihydrobenzofuran-7-yloxyl)alkyl]-2-aryloxy amide derivatives
  • N-[(dihydrobenzofuran-7-yloxyl)alkyl]-2-aryloxy amide derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of 2-(2,2-dimethyl-2,3-benzofuran-7-oxyl)ethylamine

[0029]

[0030] 3.0g of phthalimide and 30mL of ethanol, stirred by magnetic force, slowly added dropwise to 10mL of ethanol containing 1.71g of KOH, after dropping, refluxed, TLC detected that the reaction of the raw materials was complete, reacted for 2.0h, cooled, filtered with suction, and dried to obtain Potassium salt of phthalimide as white solid, yield 90.3%.

[0031] 50mL DMF, 0.025mol potassium salt of phthalimide, 0.10mol 1,2-dibromoethane, 0.5g TBAB, react at 70°C for 2.0h, cool to room temperature, pour into ice water, extract with ethyl acetate , washed with water, dried, desolvated, and left to stand overnight, 5.11 g of colorless solid N-(2-bromoethyl)phthalimide was precipitated, m.p.80-83°C, yield 80.5%.

[0032] 1.0mmol furanol, 2.0mmol K 2 CO 3 , catalytic amount PEG-200, 20mL DMF, add 1.5mmol N-(2-bromoethyl)phthalimide DMF solution dropwise under stirring, react at 70°C for 3.0...

Embodiment 2

[0036] Preparation of 3-(2,2-dimethyl-2,3-benzofuran-7-oxyl)propylamine

[0037]

[0038] 50mLDMF, 0.025mol potassium salt of phthalimide, 0.10mol 1,3-dibromopropane and 0.5g TBAB, react at 70°C for 2.0h; cool to room temperature, pour into ice water, extract with ethyl acetate, wash with water , dried, precipitated, and left to stand overnight, 5.91 g of white solid N-(3-bromopropyl)phthalimide was precipitated, m.p.70-73°C, yield 88.3%.

[0039] 1.0mmol furanol, 2.0mmol K 2 CO 3 , catalytic amount PEG-200, 20mL DMF, stirred, 0.402g (1.5mmol) N-(3-bromopropyl)phthalimide DMF solution was added dropwise, reacted at 70°C for 2.0h, cooled, poured into ice In water, pump. Filter and dry to obtain light yellow solid 2-(3-(2,2-dimethyl-2,3-dihydrobenzofuran-7-oxyl)propyl)isoindoline-1,3-di Ketone 0.29g, m.p.83~86℃, yield 82.8%; 1 H NMR (400MHz, CDCl 3 )δ: 1.45(s, 6H, 2×CH 3 ), 2.15~2.22 (m, 2H, CCH 2 C), 2.98(s, 2H, CH 2 ), 3.87(t, J=6.8Hz, 2H, NCH 2 ), 4.11(t, J=6.8Hz...

Embodiment 3

[0042] Preparation of 4-(2,2-Dimethyl-2,3-benzofuran-7-oxyl)butylamine

[0043]

[0044] 50mLDMF, 0.025mol potassium salt of phthalimide, 0.10mol 1,4-dibromobutane and 0.5g TBAB, react at 70°C for 2.0h; cool to room temperature, pour into ice water, extract with ethyl acetate, After washing with water, drying, desolvation, and standing overnight, 5.82 g of white solid N-(4-bromobutyl)phthalimide was precipitated, m.p.78-81°C, yield 82.5%.

[0045] 0.164g furanol, 0.276g K 2 CO 3 , a catalytic amount of PEG-200 and 20ml DMF, stirred, 0.42g N-(4-bromobutyl)phthalimide DMF solution was added dropwise, reacted at 70°C for 2.0h, cooled, poured into ice water, stirred, Suction filtration and drying gave white solid 2-(4-(2,2-dimethyl-2,3-dihydrobenzofuran-7-oxyl)butyl)isoindoline-1,3-di Ketone 0.287g, m.p.64~67℃, yield 78.7%. 1 H NMR (400MHz, CDCl 3 )δ: 1.49(s, 6H, 2×CH 3 ), 1.85~1.91 (m, 4H, CH 2 CH 2 ), 3.00 (s, 2H, CH 2 ), 3.74(t, J=4.4Hz, NCH 2 ), 4.08(t, J=4.4Hz, O...

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Abstract

The invention discloses N-[( dihydrobenzofuran-7-yloxyl)alkyl]-2-aryloxy amide derivatives which are represented as a structural formula I and a structural formula II, and in the structural formula I or II, R is selected from a group consisting of H, C1-C2 alkyl, C3-C4 linear alkyl and C3-C4 branched alkyl; n is selected from a group consisting of 1,2,3,4,5 and 6; Y<1> is selected from a group consisting of H, C1-C2 alkyl, F, Cl, Br and I; Y<2> is selected from a group consisting of H, C1-C2 alkyl, F, Cl, Br, I, trifluoromethyl and trifluoroethyl; and Y<3> is selected from a group consisting of H, C1-C2 alkyl, F, Cl, Br and I. The invention also provides an application of the N-[(dihydrobenzofuran-7-yloxyl)alkyl]-2-aryloxy amide derivatives to preparing herbicides.

Description

technical field [0001] The present invention relates to a class of novel compounds and their preparation methods and applications, specifically N-[(dihydrobenzofuran-7-oxyl)alkyl]-2-aryloxyamide derivatives and their preparation methods and Application in the preparation of herbicides. 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. Kim et al. [US20030096706, 2003-5-22; J Agr FoodChem, 2007, 55(14): 5416-5422] from Korea Chemical Technology Research ...

Claims

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Application Information

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