Dichlorodiphenyl-stannane complex and preparation method and application thereof

A technology of diphenyltin dichloride and complexes, which is applied in the direction of botany equipment and methods, tin organic compounds, applications, etc., can solve the problems of low cost, unscreened or developed herbicidal activity, etc., and achieve low cost, Simple preparation method and high water solubility

Inactive Publication Date: 2011-07-20
LIAOCHENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In-depth research on this type of compound is one of the hot spots in the pesticide industry today, which shows that this type of compound has broad d...

Method used

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  • Dichlorodiphenyl-stannane complex and preparation method and application thereof
  • Dichlorodiphenyl-stannane complex and preparation method and application thereof
  • Dichlorodiphenyl-stannane complex and preparation method and application thereof

Examples

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Embodiment 1

[0013] Example 1: Preparation of diphenyltin dichloride complex: add 1.0mmol of 2-hydroxy-1-naphthalene-3-pyridylhydrazone, 1.0mmol of sodium ethoxide, and 1.0mmol of dibutyltin oxide to the flask and 20ml of methanol, stirred and refluxed at 65±1°C for 7 hours, cooled to room temperature, and rotovaped to obtain a yellow solid; recrystallized with dichloromethane-ethanol (the volume ratio of dichloromethane to ethanol is 1:1), to obtain The yellow transparent crystal is an organotin coordination compound, and the yield is 75%.

[0014] Through infrared spectrum analysis and NMR analysis, the results are as follows:

[0015] Infrared spectrum (KBr, cm -1 ): 1610 (m, C=N), 1590 (s, C=N-N=C), 564 (w, Sn-O), 475 (m, Sn-N).

[0016] 1 H NMR (CDCl 3 , ppm): δ8.88 (2H, m, N=CH), 7.26-9.23 (8H, m, pyridine-H), 7.08-7.21 (12H, m, naph-H); 6.89-7.06 (30H, m , Ph-H); 13 C-NMR (CDCl 3 , ppm): 163.7 (CH=N), 163.89 (CO-N), 152.1, 150.3, 137.2, 126.3, 123.9 (pyridine-C), 135.1, 132.4...

Embodiment 2

[0018] Example 2: Preparation of diphenyltin dichloride complex: add 1.0mmol of 2-hydroxy-1-naphthalene-3-pyridylhydrazone, 1.2mmol of sodium ethoxide, and 1.5mmol of dibutyltin oxide to the flask and 30ml of methanol, stirred and refluxed at 65±1°C for 7 hours, cooled to room temperature, and rotovaped to obtain a yellow solid; recrystallized with dichloromethane-ethanol (the volume ratio of dichloromethane to ethanol is 2:1), to obtain The yellow transparent crystal is an organotin coordination compound, and the yield is 78%.

Embodiment 3

[0019] Example 3: Preparation of diphenyltin dichloride complex: add 1.0mmol of 2-hydroxy-1-naphthalene-3-pyridylhydrazone, 1.5mmol of sodium ethoxide, and 1.0mmol of dibutyltin oxide to the flask and 30ml of methanol, stirred and refluxed at 50±1°C for 6 hours, cooled to room temperature, and rotovaped to obtain a yellow solid; recrystallized with dichloromethane-ethanol (the volume ratio of dichloromethane to ethanol is 2:1), to obtain The yellow transparent crystal is an organotin coordination compound, and the yield is 70%.

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Abstract

The invention discloses a dichlorodiphenyl-stannane complex of which structural formula is shown as below. The preparation method comprises the following steps: adding 1mmol of 2-hydroxyl-1-naphthalene-3-pyridinecarboxamide, 1-1.5mmol of sodium ethoxide, 1-1.5mmol of dichlorodiphenyl-stannane and 20-30ml of methanol in a flask, stirring and refluxing at 60-70 DEG C for 6-7h, cooling to the room temperature, performing rotary evaporation to obtain yellow solid; and using dichloromethane-ethanol to recrystallize and obtain yellow transparent crystals, namely the dichlorodiphenyl-stannane complex. The organotin complex of the invention has higher herbicidal activity, can be used to prepare a herbicide for killing Echinochloa crusgalli, Digitaria sanguinalis, radish and rape. Compared with the common herbicide, the organotin complex of the invention is characterized by high herbicidal activity, good liposolubility, high water solubility, low cost, simple preparation method and the like, thus a new way is provided for the development of the herbicide.

Description

technical field [0001] The invention relates to a diphenyltin dichloride complex, a preparation method thereof, and an application of the compound as a herbicide. Background technique [0002] Acylhydrazone compounds are products of nucleophilic addition of hydrazides to aldehydes or ketones followed by elimination of water loss. Acylhydrazone compounds have active groups such as Schiff base (-CH=N) and amide bond (-CONH-) in their molecular structure, and most of them have biological activities such as herbicide and bactericide. They are formed by combining acylhydrazone with organotin compounds The organotinylhydrazone complexes have more obvious herbicidal activity. In-depth research on this type of compound is one of the hot spots in the pesticide industry today, which shows that this type of compound has broad development prospects, but there is no screening or development of a herbicidal activity, low cost, suitable for large-scale production and use. compound of. ...

Claims

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Application Information

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IPC IPC(8): C07F7/22A01N59/16A01P13/00
Inventor 尹汉东魏新庭李静
Owner LIAOCHENG UNIV
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