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Alkynyl thiofuran compound and its prepn and application

A technology of alkynyl thiophene and compounds, which is applied in the field of alkynyl thiophene compounds, and can solve problems such as failure to promote application, limited application value, and low activity

Inactive Publication Date: 2008-11-12
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are many kinds of photofrens with insecticidal activity, but they have not been popularized due to different shortcomings.
Most of the photosensitive pigments that entered the application research in the early stage are dye compounds, such as erythrosin B, which are relatively low in cost, but their activity is much lower than that of polythiophene photosensitive pigments such as α-T in outdoor applications.
However, the synthesis cost of α-T and other polythiophene photosensitizers is relatively high, which limits its application value.

Method used

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  • Alkynyl thiofuran compound and its prepn and application
  • Alkynyl thiofuran compound and its prepn and application
  • Alkynyl thiofuran compound and its prepn and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the preparation of 2,5-bis (thiophen-2-ylethynyl) thiophene

[0052] Weigh 10.8g (0.1mol) of 2-ethynylthiophene and 12.1g (0.05mol) of 2,5-dibromothiophene, add 100ml of anhydrous diethylamine, stir under nitrogen protection, add 0.0325g (0.0001mol) of palladium acetate ), cuprous iodide 0.038g (0.0002mol) and triphenylphosphine 0.0786g (0.0003mol). Heated and refluxed for 4h, a large amount of salt was produced. Cool to room temperature, filter, and wash the residual solid with benzene; combine the filtered solution, distill off the solvent under reduced pressure, and recrystallize with ethanol to obtain 13.26 g of 2,5-bis(thiophen-2-ylethynyl) in light yellow flaky crystals Thiophene has a melting point of 113.8-114.3°C. 1 HNMR (500MHz): δ7.3410(d, J=5.05Hz, 2H, thiophene-H), 7.3135(d, J=3.45Hz, 2H, thiophene-H), 7.305(d, J=8.8Hz, 2H, thiophene-H), 7.1578 (s, 2H, thiophene-H). 13 C NMR: δ85.84, 87.51, 122.65, 124.65, 127.24, 128.04, 131.99, 13253. EI...

Embodiment 2

[0053] Embodiment 2: the preparation of 2,5-diphenylethynylthiophene

[0054] -40℃, 16gNaNH 2 Add to 200mL liquid ammonia, add 20.4kg of phenylacetylene, pass through N2 protection, add 24.2g of dibromothiophene in ether solution, stir, heat up to -30°C, stop stirring after 1h, let stand overnight, add NH 4 Cl, heat up to recover ammonia, filter, wash with ether, remove ether, and dry to obtain a yellow solid, recrystallized from ethanol, 22.5 g of light yellow flake solid, yield 80%. mp 75.8-76.7°C. 1 H NMR (500MHz): δ7.1539 (s, 2H, thiophene-H), 7.32-7.53 (m, 10H, Ph-H). 13 C NMR: δ82.34, 94.12, 122.73, 124.78, 128.44, 128.69, 131.55, 131.83. EIMS m / z (%): 284 (M + , 100), 158(3), 142.05(21).

[0055] To synthesize asymmetric 2,5-diynylthiophenes, the reaction formula is as follows:

[0056]

Embodiment 3

[0057] Example 3: Preparation of 2-pyridine-3-ethynyl-5-p-methoxyphenylethynylthiophene:

[0058] Weigh 10g (0.097mol) of m-ethynylpyridine and 24.2g (0.1mol) of 2,5-dibromothiophene, add 100ml of anhydrous triethylamine, stir under nitrogen protection, add 0.065g (0.0002mol) of palladium acetate, Cuprous iodide 0.076g (0.0004mol) and triphenylphosphine 0.1572g (0.0006mol). Heated and refluxed for 4h, a large amount of salt was produced. Cool to room temperature, filter, and wash the residual solid with benzene; combine the filtered solution, and distill off the solvent under reduced pressure to obtain 21 g of 1-pyridin-3-yl-2-(5-bromothiophen-2-yl)acetylene with a melting point of 128°C.

[0059] Weigh 6.6g (0.05mol) of p-methoxyphenylacetylene and 13.2g (0.05mol) of 1-pyridin-3-yl-2-(5-bromothiophen-2-yl)acetylene, and add 100ml of anhydrous triethylamine , stirred under the protection of nitrogen, and added 0.0325 g (0.0001 mol) of palladium acetate, 0.038 g (0.0002 mol)...

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Abstract

The present invention provides alkynyl thiofuran compound as shown in the general expression (I), and its preparation process and the application of its pesticide composition in controlling farm pest, germ, weed and pest to human and animal.

Description

technical field [0001] The invention relates to an alkynyl thiophene compound, a preparation method of the compound and a pesticide composition using the compound as an active ingredient for controlling agricultural pests, harmful mites, pathogenic bacteria, weeds or human and animal hygiene pests. Background technique [0002] There are many scientific arguments to prove that some plants in nature can inhibit the damage of other species through light-induced toxic reactions, and the concept of photosensitizers developed on this basis as insecticides has proven to be of great application value. Relevant information has been published in "Journal of Xi'an United University", Vol. Issue page 127, "Insect Biochemistry and Molecular Biology" 2000, volume 30, page 915, has been reviewed in detail. Such pesticides generally work by generating singlet oxygen or other active free radicals after being excited by light. These singlet oxygen and free radicals can attack the biofilm, D...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/10A01N43/10A01P7/02A01P13/00
Inventor 徐汉虹吴仁海
Owner SOUTH CHINA AGRI UNIV