2,4-disubstituted thiazolines derivatives, preparing method and application thereof

A compound and thienyl technology, which is applied to 2,4-disubstituted thiazoline derivatives and the fields of their preparation and application, can solve the problem that the action level and duration of action are not completely satisfactory and the like

Inactive Publication Date: 2008-09-17
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the levels of action and/or duration of action of these compounds in the prior art are not entirely satisfacto

Method used

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  • 2,4-disubstituted thiazolines derivatives, preparing method and application thereof
  • 2,4-disubstituted thiazolines derivatives, preparing method and application thereof
  • 2,4-disubstituted thiazolines derivatives, preparing method and application thereof

Examples

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example 1

[0029] The synthesis of example 1,2-furyl-4-methyl-thiazoline (CAU-FB-1)

[0030] Into a 50 mL round bottom flask was added 1.12 g (10 mmol) furan-2-carboxylic acid and 2 mL SOCl 2 , refluxed for 4 hours, and the excess SOCl was evaporated under reduced pressure with a rotary evaporator 2 , without further purification to give furan-2-yl chloride, which was then added with 10 mL of CH 2 Cl 2 stand-by. Add 50 mL of dichloromethane and 4 mL of triethylamine (Et 3 N) and 0.72g (10mmol) alaninol, cooled to 0°C in an ice bath, added dropwise the dichloromethane solution of the above-mentioned furan-2-acyl chloride within 30min under continuous rapid stirring, stirred at room temperature for 4 hours after dropping, and removed by rotary evaporator. solvent to obtain N-(1-methyl-2-hydroxyl) ethyl-2-furanamide; then add 50mL toluene, 5mL triethylamine (Et 3 N) and 3.33g (15mmol) of phosphorus pentasulfide, refluxed for 6 hours, cooled, poured out the supernatant, washed twice wit...

Embodiment 2

[0039] Embodiment 2, the preparation of compound CAU-FB series emulsifiable concentrate preparation

[0040] Add compound CAU-FB-1110mg in the 100mL volumetric flask, use the emulsifier (the emulsifier is polyoxyalkylene alkyl aryl ether) with mass percentage composition to be 12%, the mass percentage content to be 1% penetrant (penetrant The agent is dissolved in xylene solution of alkyl aryl sulfonate), and then the above-mentioned xylene solution is used to dilute to obtain the emulsifiable concentrate preparation containing compound CAU-FB-110.01%.

Embodiment 3

[0041] The antifungal activity determination of embodiment 3, CAU-FB series compound

[0042] Experimental method: In vitro growth rate assay was used.

[0043] Bacteriostatic solution: In the experiment, each compound of CAU-FB 1-15 was prepared into a 5000mg / L bacteriostatic solution with acetone.

[0044] Strains:

[0045]Rhizoctonia solani kühn, Phytophthora parasitica Dast, Sclerotinia sclerotiorum (Lib) de Bary, Pythium melon should be: (Pythiumaphanidermatum), Fulvia fulva (Cooke) Cif.), Fusarium oxysporum Schl.f.sp. Vasinfectum (Atk). Snyd & Hans..), Pyricularia oryzae Cav., Phomopsis asparagi (sacc .) Bubak), Macrophoma kawatsukaiHara.

[0046] Preparation of fungal block: Transfer the above-mentioned fungi to a PSA plate under aseptic conditions, place Sclerotinia sclerotiorum in a 23-25°C incubator, and cultivate the rest of the plant pathogenic fungi in a 27-28°C incubator until the hyphae are uniform Overgrown the PSA plate, and then made a bacterial block wit...

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Abstract

The invention provides a kind of 2,4-disubstituted thiazoline derivatives, a preparation method and application thereof. The derivatives are shown in formula (I), wherein R<1> represents 2-furyl, 2-thienyl, 2-pyrrolyl, 2-indyl or 3-indyl; and R<2> represents methyl, isopropyl, isobutyl, benzyl or phenyl. The preparation method includes allowing acyl chloride and amino alcohol to react to obtain amide compound; and performing cyclic reaction to obtain the compound of the formula (I). The bioactivity experiment indicates that the 2,4-disubstituted thiazoline derivatives (CAU-FB series compound) have a certain inhibiting effect on various fungus, especially CAU-FB11 displays an inhibiting rate of 100% at a concentration of 50mg/l.

Description

technical field [0001] The invention relates to 2,4-disubstituted thiazoline derivatives and their preparation method and application. Background technique [0002] The thiazoline ring is a structural unit with important physiological activities. Some thiazoline compounds have been synthesized for agricultural purposes such as insecticide, acaricide, nematicide and fungicide, and have low toxicity to plants and the ecological environment, and are environmentally friendly and environmentally friendly. However, the levels of action and / or duration of action of these compounds in the prior art are not entirely satisfactory in various fields of application, especially when used against certain organisms or at low application concentrations. Therefore, there is an urgent need to develop plant insecticides with high activity, long duration and wide range of action. The existing structure types are generally phenyls with different substituents at the 2-position of thiazoline, and...

Claims

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Application Information

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IPC IPC(8): C07D417/04A01N43/78A01P3/00
Inventor 傅滨程学明肖玉梅李舟郑中博
Owner CHINA AGRI UNIV
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