CN102127013B - 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof - Google Patents
2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof Download PDFInfo
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- CN102127013B CN102127013B CN201010615088XA CN201010615088A CN102127013B CN 102127013 B CN102127013 B CN 102127013B CN 201010615088X A CN201010615088X A CN 201010615088XA CN 201010615088 A CN201010615088 A CN 201010615088A CN 102127013 B CN102127013 B CN 102127013B
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- naphthalene
- pyridinecarbonylhydrazone
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- herbicide
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Abstract
The invention discloses 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone of which structural formula is shown as below. The preparation method comprises the following steps: adding 10mmol of 3-picolinyl hydrazide and 20-30ml of methanol in a flask, refluxing and stirring to ensure that the hydrazide is completely dissolved, then adding 10mmol of 2-hydroxyl-1-naphthoic aldehyde to generate yellow precipitate instantly, reacting for 2-3 hours, cooling to the room temperature, performing suction filtering to obtain a hydrazone crude product; and then using the mixed solvent of absolute alcohol of which volume is 1:1 and N, N-dimethylformamide to recrystalliza and obtain yellow crystals; then washing with ethanol, and drying to obtain the pure product. The 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone has higher herbicidal activity and can be used to prepare a herbicide for killing Echinochloa crusgalli, Digitaria sanguinalis, radish and rape. The product of the invention is characterized by high herbicidal activity, good liposolubility, high water solubility, low cost, simple preparation method and the like and a new way is provided for the development of the herbicide.
Description
Technical field
The present invention relates to 2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone 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, pyrazoles formyl hydrazine and arone reaction synthetic acylhydrazone compounds have weeding activity and bacteriostatic activity, also existing report.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 filter out the compound that a kind of weeding activity is high, cost is low, be applicable to scale operation and use at present.
Summary of the invention
To above-mentioned prior art, the invention provides the hydrazone compound that a kind of weeding activity is high, cost is low, be applicable to scale operation: 2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone, and the preparation method of this compound is provided.
The present invention realizes through following technical scheme:
2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone, structural formula is following:
The preparation method of 2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone is: in flask, add the 3-pyridine formyl hydrazine of 10mmol, the methyl alcohol of 20～30ml, refluxing and stirring is all dissolved hydrazides; 2-hydroxyl-1-the naphthaldehyde that adds 10mmol again; There is yellow mercury oxide to generate immediately, reacted 2～3 hours, be cooled to room temperature; Suction filtration gets the thick product of acylhydrazone; Using volume ratio then is 1: 1 absolute ethyl alcohol and the mixed solvent recrystallization of DMF, gets yellow crystals; Use washing with alcohol then, the constant weight that vacuum-drying is thought highly of is put in oven dry, promptly gets pure article.
Its reaction formula is following:
2-hydroxyl of the present invention-1-naphthalene-3-pyridine carbonylhydrazone has good weeding activity to barnyard grass grass, lady's-grass, radish and rape, can be used as weedicide and use.
2-hydroxyl of the present invention-1-naphthalene-3-pyridine carbonylhydrazone molecular formula is C
17H
13N
3O
2Molecular weight is 291.30; 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 hydrazone compound 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
Below in conjunction with embodiment the present invention is further described:
Embodiment: in flask, add the 3-pyridine formyl hydrazine of 10mmol, the methyl alcohol of 20～30ml, refluxing and stirring is all dissolved hydrazides; 2-hydroxyl-1-the naphthaldehyde that adds 10mmol again has yellow mercury oxide to generate immediately, reacts 2～3 hours; Be cooled to room temperature, suction filtration gets the thick product of acylhydrazone.Using volume ratio is 1: 1 absolute ethyl alcohol and the mixed solvent recrystallization of DMF, gets yellow crystals.Use washing with alcohol then, the constant weight that vacuum-drying is thought highly of is put in oven dry, promptly gets pure article.Productive rate is: 80%.
Through IR spectroscopy and nuclear magnetic resonance spectroscopy, the result is following:
Ir spectra (KBr, cm
-1): υ (OH), 3380, υ (C=O), 1701, υ (C=N), 1655.
1The H nuclear-magnetism (d1-DMSO, ppm): δ 7.63-9.17 (m, 4H, C
5H
4N-), 7.21-7.86 (m, 6H, C
10H
6-), 5.00 (s, 1H ,-OH), 8.00 (s, 1H ,-NH), 8.10 (s, 1H, CH=N).
13The C nuclear-magnetism (d1-DMSO, ppm): δ 163.0 (C=O), 153.7,148.2,138.0,130.7,125.1 (C
5H
4N-), 158.8,135.1,132.4,129.1,128.0,126.8,126.6,123.9,118.4,108.6 (C
10H
6-OH) 143.0 (N=CH).
Ultimate analysis: calculated value C
17H
13N
3O
2: C, 70.09; H, 4.50; N, 14.42%; Measured value C, 70.15; H, 4.45; N, 14.37%.
Test Example: adopt national novel pesticide initiative biological activity determination standard method-Plating; Target compound 2-hydroxyl-1-naphthalene-3-pyridine carbonylhydrazone is carried out indoor weeding activity screening and estimates, be the screening target through 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 treating 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, use suitable solvent dissolving back to add a little emulsification and be blank with clear water, N 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 following:
Handle repressed grade with each group of appearance method investigation, grade scale is following: 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 the compound that general formula is represented has good result to dicotyledons, along with the increase of concentration, the inhibiting rate of root and stem is also increased.Concerning monocotyledons, along with the increase of concentration, to the inhibiting rate of root increase slower, and to the inhibiting rate of stem increase very fast; Concerning dicotyledons, along with the increase of concentration, to the inhibiting rate of stem increase very fast, to the inhibiting rate of root increase slower.
Claims (1)
1.2-hydroxyl-the 1-naphthalene-the 3-pyridine carbonylhydrazone is as herbicide applications, structural formula is following:
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010615088XA CN102127013B (en) | 2010-12-30 | 2010-12-30 | 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof |
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| CN201010615088XA CN102127013B (en) | 2010-12-30 | 2010-12-30 | 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof |
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| CN102127013A CN102127013A (en) | 2011-07-20 |
| CN102127013B true CN102127013B (en) | 2012-05-23 |
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| CN106198476B (en) * | 2016-07-29 | 2019-02-19 | 贵州大学 | A kind of couple of Mg2+And Ga3+The recognition methods of reagent with highly selective identification function |
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Non-Patent Citations (4)
| Title |
|---|
| K.Y.El-Baradie et al..Synthesis and characterization of Pd(II) and Ru(III) complexes with arylidene derivatives of picolinic, nicotinic and isonicotinic acids hydrazides.《Egypt.J.Chem.》.1994,第37卷(第5期),441-456. * |
| Medicinal Chemistry Letters》.2005,第16卷(第1期),31-35. * |
| Patricia Melnyk et al..Design, synthesis and in vitro antimalarial activity of an acylhydrazone library.《Bioorganic & * |
| PatriciaMelnyketal..Design synthesis and in vitro antimalarial activity of an acylhydrazone library.《Bioorganic & Medicinal Chemistry Letters》.2005 |
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