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Alkynyl thiofuran compound and its prepn and application

An alkynyl thiophene and compound technology, applied in the field of alkynyl thiophene compounds, can solve the problems of failure to popularize and apply, limited application value, low cost and the like

Inactive Publication Date: 2006-08-02
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
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  • Alkynyl thiofuran compound and its prepn and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: 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 the protection of nitrogen, add 0.0325g (0.0001mol) of palladium acetate ), cuprous iodide 0.038g (0.0002mol) and triphenylphosphine 0.0786g (0.0003mol). The temperature was raised and refluxed for 4h, and a large amount of salt was produced. Cool to room temperature, filter, and wash the remaining solid with benzene; combine the filtrate, distill under reduced pressure to remove the solvent, and recrystallize with ethanol to obtain 13.26 g of 2,5-bis(thiophen-2-ylethynyl) as pale yellow flake 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....

Embodiment 2

[0053] Example 2: Preparation of 2,5-diphenylethynylthiophene

[0054] -40℃, 16gNaNH 2 Add to 200mL liquid ammonia, add 20.4kg phenylacetylene, and pass N 2 Protect, add 24.2g dibromothiophene in ether solution, heat to -30℃ with stirring, stop stirring after 1h, let stand overnight, add NH 4 Cl, heated to recover ammonia gas, filtered, washed with ether solution, removed ether, and dried to obtain a yellow solid, recrystallized from ethanol, 22.5 g of pale yellow flake solid, with a yield of 80%. mp 75.8-76.7°C. 1 H NMR (500MHz): 87.1539 (s, 2H, thiophene-H), 7.32-7.53 (m, 10H, Ph-H). 13 C NMR: δ 82.34, 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-diynylthiophene compounds, 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 meta-ethynylpyridine and 24.2g (0.1mol) of 2,5-dibromothiophene, add 100ml of anhydrous triethylamine, stir under the protection of nitrogen, add 0.065g (0.0002mol) of palladium acetate, Cuprous iodide 0.076g (0.0004mol) and triphenylphosphine 0.1572g (0.0006mol). The temperature was raised and refluxed for 4h, and a large amount of salt was produced. Cool to room temperature, filter, and wash the remaining solid with benzene; combine the filtrate and distill off the solvent under reduced pressure to obtain 21 g of 1-pyridin-3-yl-2-(5-bromothiophen-2-yl)acetylene as a solid, 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, add 100ml of anhydrous triethylamine , Stirring under the protection of nitrogen, add 0.0325g (0.0001mol) of palladium acetate, 0...

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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 present invention relates to an alkynyl thiophene compound, and also relates to a preparation method of the compound and a pesticide composition using the compound as an active ingredient for controlling agricultural pests, pests, pathogenic bacteria, weeds or human and animal health pests. Background technique [0002] There are many scientific evidences that some plants in nature can inhibit the harm of other species through light-induced toxic reactions, and the concept of photosensitizers as insecticides developed based on this has proved extremely valuable in application. Relevant information is available in "Journal of Xi'an Union University" 2001, Volume 4, Issue 2, page 5, "Chemical Progress" 1999, Volume 11, Issue 4, page 341, "Journal of South China Agricultural University" 1995, Volume 16, No. 1 Issue page 127, "Insect Biochemistry and Molecular Biology" 2000, Volume 30, page 915 provides a detailed review. Such insecticides generally produce...

Claims

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Application Information

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