CN102127106A - Dichlorodiphenyl-stannane complex and preparation method and application thereof - Google Patents
Dichlorodiphenyl-stannane complex and preparation method and application thereof Download PDFInfo
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- CN102127106A CN102127106A CN2010106150659A CN201010615065A CN102127106A CN 102127106 A CN102127106 A CN 102127106A CN 2010106150659 A CN2010106150659 A CN 2010106150659A CN 201010615065 A CN201010615065 A CN 201010615065A CN 102127106 A CN102127106 A CN 102127106A
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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
The present invention relates to a kind of phenylbenzene tindichloride title complex and preparation method thereof, and this compound is as herbicide applications.
Background technology
Hydrazone compound is the product that the reaction dehydration is eliminated in hydrazides and aldehydes or ketones generation nucleophilic addition(Adn) again.The acylhydrazone compounds is owing to exist the Schiff base (CH=N) and amido linkage (CONH-) isoreactivity group in the molecular structure, has weeding mostly, biological activitys such as sterilization combine formed organotin acylhydrazone title complex with acylhydrazone and have more obvious weeding activity with organo-tin compound.Further investigation to this compounds is one of current agricultural chemicals circle focus, and this shows that this compounds has the wide development prospect, but does not at present screen or develop the compound that a kind of weeding activity height, cost are low, be applicable to scale operation and use.
Summary of the invention
At above-mentioned prior art, the invention provides the hydrazone compound that a kind of weeding activity height, cost are low, be applicable to scale operation and use: phenylbenzene tindichloride title complex, and the preparation method and the application thereof of this compound are provided.
The present invention is achieved by the following technical solutions:
A kind of phenylbenzene tindichloride title complex, structural formula is as follows:
The preparation method of described phenylbenzene tindichloride title complex is: the 2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone, the sodium ethylate of 1～1.5mmol, the phenylbenzene tindichloride of 1～1.5mmol and the methyl alcohol of 20～30ml that add 1mmol in flask, under 60～70 ℃ of temperature, stirring and refluxing 6～7 hours, cool to room temperature, rotary evaporation obtains yellow solid; With dichloromethane-ethanol recrystallization (methylene dichloride and alcoholic acid volume ratio are 2: 1～1: 1), obtain the yellow transparent crystal, be phenylbenzene tindichloride title complex.
Its reaction formula is as follows:
Described phenylbenzene tindichloride title complex has good weeding activity to barnyard grass grass, lady's-grass, radish and rape, can be used as weedicide and uses.
Organotin coordination compound molecular formula of the present invention is C
70H
52Cl
2N
6O
4Sn
3Molecular weight is 1468.24, have higher weeding activity, can be used to prepare the weedicide of removing barnyard grass grass, lady's-grass, radish and rape, when specifically using, can use as effective constituent separately, also can mix as weedicide and on agricultural or gardening, use with other agricultural chemicals.Compare with the weedicide that generally uses at present, characteristics such as organotin complex of the present invention has weeding activity height, fat-soluble good, water-soluble height, cost is low, the preparation method is simple are for the exploitation weedicide provides new way.
Embodiment
The present invention is further illustrated below in conjunction with embodiment:
Embodiment 1: preparation phenylbenzene tindichloride title complex: 2-hydroxyl-1-naphthalene-3 pyridine carbonylhydrazone, the sodium ethylate of 1.0mmol, the Dibutyltin oxide of 1.0mmol and the methyl alcohol of 20ml that add 1.0mmol in flask, 65 ± 1 ℃ of stirring and refluxing 7 hours, cool to room temperature, rotary evaporation obtains yellow solid; With dichloromethane-ethanol recrystallization (methylene dichloride and alcoholic acid volume ratio are 1: 1), obtain the yellow transparent crystal, be organotin coordination compound, productive rate 75%.
Through Infrared spectroscopy and nuclear magnetic resonance spectroscopy, the result is as follows:
Infrared spectra (KBr, cm
-1): 1610 (m, C=N), 1590 (s, C=N-N=C), 564 (w, Sn-O), 475 (m, Sn-N).
1H nuclear-magnetism (CDCl
3, ppm): δ 8.88 (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);
13C-NMR (CDCl
3, ppm): 163.7 (CH=N), 163.89 (CO-N), 152.1,150.3,137.2,126.3,123.9 (pyridine-C), and 135.1,132.4,129.1,128.0,126.8,126.6,123.9,118.4 (naph-C), 137.5,128.8, (Ph-C)
Ultimate analysis: calculated value C
70H
52Cl
2N
6O
4Sn
3: C, 52.26; H, 3.57; N, 5.73%; Measured value C, 52.35; H, 5.51; N, 5.66%.
Embodiment 2: preparation phenylbenzene tindichloride title complex: 2-hydroxyl-1-naphthalene-3 pyridine carbonylhydrazone, the sodium ethylate of 1.2mmol, the Dibutyltin oxide of 1.5mmol and the methyl alcohol of 30ml that add 1.0mmol in flask, 65 ± 1 ℃ of stirring and refluxing 7 hours, cool to room temperature, rotary evaporation obtains yellow solid; With dichloromethane-ethanol recrystallization (methylene dichloride and alcoholic acid volume ratio are 2: 1), obtain the yellow transparent crystal, be organotin coordination compound, productive rate 78%.
Embodiment 3: preparation phenylbenzene tindichloride title complex: 2-hydroxyl-1-naphthalene-3 pyridine carbonylhydrazone, the sodium ethylate of 1.5mmol, the Dibutyltin oxide of 1.0mmol and the methyl alcohol of 30ml that add 1.0mmol in flask, 50 ± 1 ℃ of stirring and refluxing 6 hours, cool to room temperature, rotary evaporation obtains yellow solid; With dichloromethane-ethanol recrystallization (methylene dichloride and alcoholic acid volume ratio are 2: 1), obtain the yellow transparent crystal, be organotin coordination compound, productive rate 70%.
Test example: adopt national novel pesticide initiative biological activity determination standard method-Plating, target compound is carried out indoor weeding activity screening and estimates, be the screening target by selecting monocotyledons barnyard grass grass, lady's-grass and dicotyledons radish, rape for use.At sectional area 64cm
2The plastic tub alms bowl in quantitatively the dress soil pressure is flat, place Stainless steel basin, choose full seed, seed of the same size, divide single, double cotyledon plant to divide the alms bowl sowing, respectively account for 1/3 of alms bowl area, cover the thick fine earth of 1cm, add water to upper layer of soil from plastic tub alms bowl bottom and soak into, place hot-house culture, material to be tried grows to required leaf age to be handled; Soil treatment before examination material sowing the carrying out next day seedling, unifacial leaf examination material grow to 1 heart stage of 1 leaf, dicotyledonous examination material grow to 2 leaf periods and carry out seedling after cauline leaf handle; Accurately take by weighing sample, adding a little emulsification with suitable solvent dissolving back is blank with clear water, dimethyl formamide and the Tween-80 of equivalent respectively: handle the examination material and place hot-house culture; Handling range estimation overground part growing state after 15 days, is the contrast medicament with the fenoxaprop, tests it respectively to monocotyledons (lady's-grass, barnyard grass grass), the long inhibiting rate long of dicotyledons (little lamb's-quarters, rape) root with stem, and calculation formula is as follows:
Handle repressed grade with each group of appearance method investigation, grade scale is as follows: E level: unrestraint; D level: 10～29%; C level: 30～49%; B level: 50～79%; A level: 80～100%.The investigation result record sees the following form:
Experimental result shows that compound that general formula represents is better than stem to the inhibition effect of the root of plant, and along with increasing progressively of concentration, inhibiting rate also increases progressively.Compound is to the good weeding activity that has of barnyard grass grass, lady's-grass, radish sclerotium, and wherein the inhibiting rate to the stem of lady's-grass reaches 86.5%.
Claims (3)
1. phenylbenzene tindichloride title complex, structural formula is as follows:
2. the preparation method of the described phenylbenzene tindichloride of claim 1 title complex, it is characterized in that: the 2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone, the sodium ethylate of 1～1.5mmol, the phenylbenzene tindichloride of 1～1.5mmol and the methyl alcohol of 20～30ml that in flask, add 1mmol, under 60～70 ℃ of temperature, stirring and refluxing 6～7 hours, cool to room temperature, rotary evaporation obtains yellow solid; Use the dichloromethane-ethanol recrystallization, obtain the yellow transparent crystal, be phenylbenzene tindichloride title complex; Wherein, methylene dichloride and alcoholic acid volume ratio are (2: 1)～(1: 1).
3. the described phenylbenzene tindichloride of claim 1 title complex is as herbicide applications.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718794A (en) * | 2012-07-09 | 2012-10-10 | 聊城大学 | Dihydrazone Schiff base tindiphenyl (IV) coordinate complex and preparation method and application thereof |
| CN103044482A (en) * | 2013-01-22 | 2013-04-17 | 聊城大学 | Dibutyltin coordination compound and preparation method and application thereof |
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| WO2003078386A1 (en) * | 2002-03-19 | 2003-09-25 | Unisearch Limited | Naphthylsemicarbazone, naphthylhydrazone, naphthylthiosemicarbazone, and naphthylthiohydrazone compounds and therapeutic use thereof |
| CN101434616A (en) * | 2008-11-17 | 2009-05-20 | 聊城大学 | Organotin Schiff base coordination compound, as well as preparation method and application thereof |
| CN101475583A (en) * | 2008-11-17 | 2009-07-08 | 聊城大学 | Dibutyl tin dichloride schiff alkali coordination compound, as well as preparation method and application thereof |
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2010
- 2010-12-30 CN CN 201010615065 patent/CN102127106B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003078386A1 (en) * | 2002-03-19 | 2003-09-25 | Unisearch Limited | Naphthylsemicarbazone, naphthylhydrazone, naphthylthiosemicarbazone, and naphthylthiohydrazone compounds and therapeutic use thereof |
| CN101434616A (en) * | 2008-11-17 | 2009-05-20 | 聊城大学 | Organotin Schiff base coordination compound, as well as preparation method and application thereof |
| CN101475583A (en) * | 2008-11-17 | 2009-07-08 | 聊城大学 | Dibutyl tin dichloride schiff alkali coordination compound, as well as preparation method and application thereof |
Non-Patent Citations (3)
| Title |
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| 《Chinese J. Struct. Chem.》 20101215 CUI Ji-Chun等， Synthesis, Characterization and Crystal Structure of a Trinuclear Diorganotin(IV) Complex with N'-acetylsalicylhydrazide 第1784-1787页 1-3 第29卷, 第12期 * |
| CUI JI-CHUN等，: "Synthesis, Characterization and Crystal Structure of a Trinuclear Diorganotin(IV) Complex with N’-acetylsalicylhydrazide", 《CHINESE J. STRUCT. CHEM.》, vol. 29, no. 12, 15 December 2010 (2010-12-15), pages 1784 - 1787 * |
| K.Y. EL-BARADIE等，: "Synthesis and Characterization of Pd(II) and Ru(III) Complexes with Arylidene Derivatives of Picolinic,Nicotinic and Isonicotinic Acids Hydrazides", 《EGYPT. J. CHEM.》, vol. 37, no. 5, 31 December 1994 (1994-12-31), pages 442 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718794A (en) * | 2012-07-09 | 2012-10-10 | 聊城大学 | Dihydrazone Schiff base tindiphenyl (IV) coordinate complex and preparation method and application thereof |
| CN103044482A (en) * | 2013-01-22 | 2013-04-17 | 聊城大学 | Dibutyltin coordination compound and preparation method and application thereof |
| CN103044482B (en) * | 2013-01-22 | 2015-08-19 | 聊城大学 | A kind of dibutyl tin coordination compound and preparation method thereof and application |
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