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Application of 4-(benzofuran-5-yl)-2-phenzyl aminothiazole as bactericide

A technology of anilinothiazole and benzofuran, which is applied in the direction of fungicides, applications, and biocides, and can solve problems such as high toxicity

Inactive Publication Date: 2013-06-12
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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  • Application of 4-(benzofuran-5-yl)-2-phenzyl aminothiazole as bactericide
  • Application of 4-(benzofuran-5-yl)-2-phenzyl aminothiazole as bactericide
  • Application of 4-(benzofuran-5-yl)-2-phenzyl aminothiazole as bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 4-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)-5-methyl-2-(2-methoxyanilino)thiazole to prepare

[0018]

[0019] 1) Preparation of 1-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)acetone

[0020] Under an ice-water bath, add 35.6 g of 7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran, 19.4 g of propionyl chloride, 30.7 g of aluminum trichloride and 150 mL of nitrobenzene, and mix After stirring for 5 h, TLC monitored the reaction to the end point. The reaction solution was poured into ice water, separated into layers, the solvent was evaporated, and recrystallized from ethanol / water to obtain 34.3 g of a light yellow solid with a yield of 73.1%. m.p.74.4~75.5℃.

[0021] 2) Preparation of 2-bromo-1-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)acetone

[0022] 11.0 g of 1-(7-methoxy-2,2-dimethyl-2,3-dihydro-5-benzofuryl)acetone and 100 mL of ethanol, heating, stirring, when the temperature rises to 60 ℃ , add 22.4 g of copper bromide in batches, heat pr...

Embodiment 2

[0026] Preparation of 4-(benzofuran-5-yl)-2-anilinothiazole (Ⅰ)

[0027]

[0028] I

[0029] Wherein, R is selected from: C 1 ~C 2 Alkyl, C 3 ~C 4 Straight chain alkyl or branched chain alkyl; R 1 From: H, C 1 ~C 2 Alkyl, C 3 ~C 4 Straight-chain alkyl or branched-chain alkyl; X is selected from: 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy, 3-ethoxy, 4-ethoxy, 2-trifluoromethoxy, 3-trifluoromethoxy, 4-trifluoromethoxy.

[0030] 4-(benzofuran-5-yl)-2-phenylaminothiazole was prepared according to the method of Example 1 or according to the Chinese invention patent [ZL 201010553848.9 and CN102603726A]].

Embodiment 3

[0032] Determination of the fungicidal activity of 4-(benzofuran-5-yl)-2-anilinothiazole

[0033] 1 Test purpose

[0034] The toxicity of the new compound to various pathogenic bacteria was determined indoors at the tested concentration, and its bactericidal activity was preliminarily evaluated.

[0035] 2 Test conditions

[0036] 2.1 Test target

[0037] Rapeseed Sclerotia sclerotiorum (Sclerotonia sclerotiorum), strains are stored in the refrigerator (4 ~ 8 ℃), 2-3 days before the test inoculated from the slant of the test tube into the petri dish, cultivated at a suitable temperature for the test. The experimental medium was potato agar (PDA).

[0038] 2.2 Culture conditions

[0039] The culture conditions of the tested target and the target after the test are temperature 25 ± 5°C, relative humidity 65 ± 5%

[0040] 2.3 Instruments and equipment

[0041] Beakers, pipettes, graduated cylinders, petri dishes, autoclaves, constant temperature biochemical incubators, etc....

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Abstract

The invention discloses an application of 4-(benzofuran-5-yl)-2-phenzyl aminothiazole as shown in the chemical structural formula I for preparing bactericide for killing sclerotinia sclerotiorum, wherein R is selected from C1-C2 alkyl, C3-C4 straight chain alkyl or branch chain alkyl; R1 is selected from H, C1-C2 alkyl, C3-C4 straight chain alkyl or branch chain alkyl; X is selected from 2-methoxyl, 3-methoxyl, 4-methoxyl, 2-ethoxyl, 3-ethoxyl, 4-ethoxyl, 2-trifluoromethoxyl, 3-trifluoromethoxyl and 4-trifluoromethoxyl.

Description

technical field [0001] The present invention relates to the application of compounds, specifically 4-(alkoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-anilinothiazole in the preparation of rapeseed sclerotia The application of fungicides for germs. 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 8-10 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. Therefore, the world's new pesticide creation companies shift part of their ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/78A01P3/00
Inventor 胡艾希林定戴明崇罗先福叶姣欧晓明
Owner HUNAN UNIV
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