5-[2-(Benzylimino)thiazole-4-yl]benzofuranol ether and its application in preparation of pesticide

A technology of benzylimino and furan phenol ether, which can be applied to compounds and their application fields and can solve problems such as high toxicity

Inactive Publication Date: 2011-11-23
HUNAN UNIV
View PDF3 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Carbamate pesticides have high activity and are widely used, but they are highly toxic. Therefore, it is necessary to develop alternative products with lower toxicity and better activity to meet market demand

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 5-[2-(Benzylimino)thiazole-4-yl]benzofuranol ether and its application in preparation of pesticide
  • 5-[2-(Benzylimino)thiazole-4-yl]benzofuranol ether and its application in preparation of pesticide
  • 5-[2-(Benzylimino)thiazole-4-yl]benzofuranol ether and its application in preparation of pesticide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(2-hydroxy-3,5-dichlorobenzylidene Preparation of amino)thiazole

[0038] (1) Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)acetone

[0039] 0.02mol 1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)acetone, 80ml ethanol, stirred and refluxed, 0.04mol copper bromide was added in batches, After reacting for about 1 hour, the reaction solution was filtered while it was hot, the solvent was recovered by distillation, dissolved in ethyl acetate, washed with dilute acid, filtered, the filtrate was washed with water, separated, dried, and recrystallized from ethanol to obtain 2-bromo-1-(7-methoxy -2,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)acetone, yield 97.9%, melting point 75-76°C.

[0040] (2) Preparation of 5-methyl-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole

[0041] 0.017mol 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)acetone, 0.0...

Embodiment 2

[0044] Example 2 5-methyl-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(2-hydroxyl-3,5 -Preparation of dibromobenzimino)thiazole

[0045] 5-methyl-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole and 2-hydroxy-3,5- Dibromobenzaldehyde is fed in a molar ratio of 1:1.1, ethanol is used as a solvent, stirred, and piperidine is catalyzed for 5.5 hours at 30°C; 5-methyl-4-(7-methoxy-2,2-dimethyl -2,3-dihydrobenzofuran-5-yl)-2-(2-hydroxy-3,5-dibromobenzimino)thiazole; yield 31.8%, melting point 122~123°C; 1 H NMR (CDCl 3 , 400MHz), δ: 1.55(s, 6H, 2×CH 3 ), 2.59 (s, 3H, CH 3 ), 3.10 (s, 2H, CH 2 ), 3.93 (s, 3H, CH 3 O), 7.04(s, 2H, C 6 h 2 ), 7.56 (d, J=2.4Hz, 1H, C 6 h 2 , 6-H), 7.79 (d, J=2.4Hz, 1H, C 6 h 2 , 4-H), 9.17 (s, 1H, N=CH), 13.35 (s, 1H, OH).

Embodiment 3

[0046] Example 3 5-methyl-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(2-hydroxyl-5-bromo Preparation of benzimino)thiazole

[0047] 5-methyl-4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole and 2-hydroxy-5-bromobenzene Formaldehyde is fed in a molar ratio of 1:1.1, ethanol is used as a solvent, stirred, and piperidine is catalyzed for 7.0 hours at 30°C; 5-methyl-4-(7-methoxy-2,2-dimethyl-2 is obtained, 3-dihydrobenzofuran-5-yl)-2-(2-hydroxy-5-bromobenzimino)thiazole; yield 63.2%, melting point 145~147°C; 1 H NMR (CDCl 3 , 400MHz), δ: 1.55(s, 6H, 2×CH 3 ), 2.58 (s, 3H, CH 3 ), 3.10 (s, 2H, CH 2 ), 3.94 (s, 3H, CH 3 O), 6.94(d, J=8.8Hz, 1H, C 6 h 3 3-H), 7.05(s, 2H, C 6 h 2 ), 7.49 (dd, J 1 =8.8Hz,J 2 = 2.4Hz, 1H, C 6 h 2 , 4-H), 7.57 (d, J=2.4Hz, 1H, C 6 h 2 , 6-H), 9.13 (s, 1H, N=CH), 12.34 (s, 1H, OH).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to view more

Abstract

The invention discloses 5-[2-(Benzylimino)thiazole-4-yl]benzofuranol or aryl ether as shown in the chemical structure formula I, wherein X is selected from chlorine, fluorine, hydroxyl, methoxy, ethoxy, nitro, dimethylamino, sulfonic, methylsulfonyl amino, sulfamoyl, 2-chlorine-5-nitro, 3-ethyl-4-hydroxy, 3,4-dimethoxy, 2,4-dichloro, 2-hydroxy-5-bromine, 2-hydroxy-5-iodine, 2-hydroxy-5-chlorine, 2,4-difluoro, 2-hydroxy-3,5-difluoro, 2-hydroxy-3,5-dichloro, 2-hydroxy-3,5-dibromo or 2-hydroxy-3,5-diiodo; R is selected from H, C1-C2 alkyl, C3-C4 linear alkyl or branched alkyl; and R1 is selectedfrom H, C1-C2 alkyl, C3-C4 linear alkyl or branched alkyl. An application of 5-[2-(Benzylimino)thiazole-4-yl] benzofuranol or aryl ether in the preparation of a pesticide.

Description

technical field [0001] The present invention relates to a class of compounds and applications thereof, specifically 5-[2-(benzimino)thiazol-4-yl]furan phenol ether, i.e. 4-(7-hydroxyl / alkoxyl-2,2-dimethyl -2,3-Dihydrobenzofuran-5-yl)-2-benziminothiazole and its use for the preparation of insecticides. Background technique [0002] Furanol (chemical name 2,2-dimethyl-2,3-dihydrobenzofuranphenol) is an important intermediate in the production of large-tonnage carbamate pesticides such as carbofuran, haoanwei and carbofuran. Carbamate pesticides have high activity and are widely used, but they are more toxic. Therefore, it is necessary to develop alternative products with lower toxicity and better activity to meet the market demand. As we all know, it takes 8 to 10 years to develop a new pesticide variety. In addition, there are many data and projects required for the registration of new pesticide varieties, and the cost is hundreds of millions of dollars. There are already i...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A01N43/78A01P7/04A01P7/02
Inventor 胡艾希沈芳欧晓明杨林涛
Owner HUNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap