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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
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  • 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

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  • 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).

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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

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Application Information

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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
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