CN105777618B - A kind of methyl α-naphthyl acetate pyridine ethyl ester type compound and purposes - Google Patents
A kind of methyl α-naphthyl acetate pyridine ethyl ester type compound and purposes Download PDFInfo
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- CN105777618B CN105777618B CN201610051979.4A CN201610051979A CN105777618B CN 105777618 B CN105777618 B CN 105777618B CN 201610051979 A CN201610051979 A CN 201610051979A CN 105777618 B CN105777618 B CN 105777618B
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- naphthyl acetate
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- 0 *C(Cc1c(cc(cc2)-c3cc(cccc4)c4c(CC(O)=O)c3)c2ccc1)=O Chemical compound *C(Cc1c(cc(cc2)-c3cc(cccc4)c4c(CC(O)=O)c3)c2ccc1)=O 0.000 description 1
- DSVAZLXLRDXHKO-UHFFFAOYSA-N O=C(Cc1cccc2c1cccc2)Cl Chemical compound O=C(Cc1cccc2c1cccc2)Cl DSVAZLXLRDXHKO-UHFFFAOYSA-N 0.000 description 1
- NLCIKAVSWMZQEF-UHFFFAOYSA-N O=C(Cc1cccc2c1cccc2)OCCc1ccccn1 Chemical compound O=C(Cc1cccc2c1cccc2)OCCc1ccccn1 NLCIKAVSWMZQEF-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N OC(Cc1cccc2c1cccc2)=O Chemical compound OC(Cc1cccc2c1cccc2)=O PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- General Health & Medical Sciences (AREA)
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- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses the methyl α-naphthyl acetate pyridine ethyl ester type compound and its salt of a kind of structure shown in formula I：
Description
The invention belongs to plant growth regulator field in pesticide for technical field, and in particular to a kind of methyl α-naphthyl acetate pyridine second
Base ester type compound and purposes.
Background technology plant growth regulator major control seed germination and dormancy, hestening rooting, regulation and control plant strain growth,
Flower and fruit thinning, enhancing resistance (disease-resistant, drought resisting, salt resistance, cold-resistant), in agricultural production and income, improve quality etc. performance
Important effect, increasingly attracts attention in Ensuring Food Safety, food security aspect plant growth regulator.
The plant growth regulator of Chinese commodity mainly has：Methyl α-naphthyl acetate, heteroauxin, gibberellin, ethephon (CEPHA),2-(chloroethyl) phosphonic acid, 6- benzyl ammonia
Base purine (6-BA), forchlorfenuron, increase production of amines, DA-6 (diethylamino ethanol caproate citrate) etc., belong to China and independently know
It is seldom to know the kind of property right, and there is the deficiencies of function is single, security is poor, therefore develop the plant growth tune of highly effective and safe
Section agent new varieties have the function that positive.103636602 B of CN disclose a kind of naphthaleneacetamide class compound and its salt is used as planting
The purposes of thing growth regulator, can be widely used for the taking root of the crops such as grain, cotton, fruit and vegetable or plant, strong sprout, increasing yield and improving quality.It is domestic
Document report methyl α-naphthyl acetate triazole alcohol ester and methyl α-naphthyl acetate olefin conversion ester have the activity (Li Jun of significant inducing soybean seedling rooting
Triumphant, Tan Tangfeng, Xu Hanhong, wait the synthesis of naphthylacetic acid derivants and its measure Hua Zhong Agriculture University journal of bioactivity,
2008,27(2):208-212)。
In the prior art, methyl α-naphthyl acetate pyridine ethyl ester type compound as described in the present invention and its plant growth regulating are lived
Property is not disclosed.
The content of the invention
The object of the present invention is to provide a kind of promotion seed sprouting, hestening rooting, increase upgrading, plant safe and convenient to use
Thing growth regulator, specifically a kind of methyl α-naphthyl acetate pyridine ethyl ester type compound, survive available for crop is agriculturally improved
Rate and promotion crop yield upgrading.
Technical scheme is as follows：
The present invention provides the methyl α-naphthyl acetate pyridine ethyl ester type compound and its salt of a kind of structure shown in formula I：
The salt is inorganic acid salt or acylate.
Compound of formula I and its salt can be made by following reaction：
AH is citric acid, lactic acid, oxalic acid or p-aminobenzene sulfonic acid.Methyl α-naphthyl acetate is in suitable solvent with thionyl chloride 10
DEG C to 2-4h is reacted under reflux temperature, decompression steams solvent and excessive thionyl chloride, and naphthalene chloroacetic chloride is made；By obtained acyl chlorides
Add appropriate solvent solution-forming, be added drop-wise under -10 DEG C of stirrings of temperature control -10 DEG C and appropriate solvent is dissolved in by 2- pyridine ethanols is made into
Solution in, be made compound of formula I hydrochloride；The hydrochloride is soluble in water, neutralized with saturated sodium carbonate solution, formula is made
Compound I；The inorganic acid salt or organic acid of the compound are made with inorganic acid or organic acid by reaction with same mole for compound of formula I
Salt.
Solvent is selected from dichloromethane, benzene, toluene, ethyl acetate.
Inorganic acid refers to hydrochloric acid, phosphoric acid or nitric acid, and acylate refers to citric acid, lactic acid, oxalic acid or p-aminobenzene sulfonic acid.In order to
Improve the dissolubility of the compound and beneficial to plant absorption, when the compound is into salt, inorganic acid or organic acid and the compound are equal
It is to be matched according to equimolar.
The compounds of this invention and its salt as plant growth regulator in use, can be used alone, also can be with other work
Property material is applied in combination, to improve the comprehensive performance of product.
Present invention additionally comprises the plant growth regulator composition of compound of formula I and its salt as active component, the combination
Thing includes compound of formula I and its salt as active component and agriculturally acceptable carrier.
The compound of the present invention can be used in the form of preparation：Compound of formula I and its salt be dissolved in as active component or
It is scattered in carrier or solvent, adds suitable surfactant and aqua, missible oil, microemulsion, aqueous emulsion, suspending agent etc. is made.
The advantages and positive effects of the present invention：
Compound of formula I and its salt have simple synthetic method, cost is low, effective ingredient consumption is small, safe and convenient to use etc.
Advantage.Substantial amounts of experiment proves：DA-6 (being shown in Table 1) is substantially better than at wheat seed rudiment, aspect of taking root, is sprayed in wheat growth stage
Spill, rate of growth is up to more than 15%；After apple tree foliage spray, while yield (volume increase 15%) is improved, appearance and inherence
Quality also significantly improves；Also there is the effect of similar with great Jiang for cucumber.The compound of the present invention can be realized to be made with relatively low
Achieve the purpose that crops are significantly increased production with cost and prominent plant growth regulating activity, before there is good market development
Scape and commodity development value.
It should be appreciated that in scope defined by the claims of the present invention, various conversion and change can be carried out.
Embodiment
Following synthesis example, formulation examples and raw test result can be used to further illustrate the present invention, but not mean that
The limitation present invention.
Synthesize example
The synthesis of example 1, compound of formula I
(1) synthesis of naphthalene chloroacetic chloride
20.8g (0.1mol) Nafusaku is added into 250mL three-necked flasks, adds suitable quantity of water, heating makes its dissolving, while hot
It is acidified with concentrated hydrochloric acid (36%), adjusts pH to 2~3, cooled down, filtered, obtain methyl α-naphthyl acetate white solid, is dried, obtain white solid
18.2g, yield 97.8%.
Added into 50mL three-necked flasks and sequentially add 18.6g (0.1mol) methyl α-naphthyl acetate, 150mL toluene, 14.3g
(0.12mol) thionyl chloride, is stirred at room temperature lower dropwise addition 0.2mL n,N-Dimethylformamide, temperature rising reflux 2h.TLC monitoring reactions
Complete, rotate out solvent and excessive thionyl chloride, obtain 19.6g pale yellowish oil liquid, yield 95.6%.
(2) synthesis of methyl α-naphthyl acetate pyridine ethyl ester hydrochloride
12.3g (0.1mol) 2- pyridine ethanols, 150mL ethyl acetate, ice salt bath are sequentially added into 250mL three-necked flasks
Under the conditions of stir the lower solution that 24.6g (0.12mol) naphthalene chloroacetic chlorides obtained above and 50mL ethyl acetate toluene composition is added dropwise,
It is added dropwise, reaction 2h is stirred at room temperature；Filter, filter cake washs with appropriate ethyl acetate, dry white solid 30.3g, yield
92.4%.
(3) synthesis of methyl α-naphthyl acetate pyridine ethyl ester
Compound of formula I hydrochloride 32.8g (0.1mol) obtained above, 150mL water are added into 250mL reaction bulbs, is stirred
Mix dissolving, add 100mL dichloromethane, be stirred at room temperature lower dropwise addition be made into by 15.9g (0.15mol) sodium carbonate and 80mL water it is molten
Liquid, drop finish, and continue to stir 0.5h, stratification, separates lower floor's organic phase, is washed twice with water (30mL × 2), organic phase nothing
Aqueous sodium persulfate is dried, and is rotated out methylene chloride, is obtained pale yellowish oil liquid 27.4g, yield 94.2%.
Compound of formula I1H NMR (500MHz, DMSO-d6), δ (ppm)：3.015-3.041 (t, 2H, CH2), 4.088
(s, 2H, CH2), 4.433-4.460 (t, 2H, CH2), 7.103-7.1199 (d, 1H, Pyridyl-H), 7.178-7.202 (t,
1H, Pyridyl-H), 7.344-7.448 (m, 2H, Ar-H), 7.501-7.558 (m, 2H, Ar-H), 7.587-7.618 (t, 1H,
Pyridyl-H), 7.835-7.877 (t, 2H, Ar-H), 7.920-7.936 (d, 1H, Pyridyl-H), 8.489-8.498 (d,
1H, Ar-H).
The preparation of example 2, compound of formula I citrate
9.6g (0.05mol) citric acids and 80mL ethanol, stirring and dissolving, under stirring are sequentially added into 250mL reaction bulbs
The mixed liquor of 14.6g (0.05mol) methyl α-naphthyl acetate pyridine ethyl ester (compound of formula I) and 20mL ethanol is slowly added dropwise, drop finishes, and continues
0.5h is stirred, rotates out solvent, dry white solid 24.0g, yield 99.2%.
The lactate, oxalates or sulfanilate of methyl α-naphthyl acetate pyridine ethyl ester can similarly be made.
Formulation examples
The preparation of example 3,5% methyl α-naphthyl acetate pyridine ethyl ester citrate aqua
5g methyl α-naphthyl acetate pyridine ethyl esters and 90g water are separately added into 250mL beakers, stirring and dissolving, adds 5g alkyl sugar
Glycosides, is sufficiently stirred 0.5h, obtains 5% methyl α-naphthyl acetate pyridine ethyl ester citrate aqua.
The preparation of example 4,10% methyl α-naphthyl acetate pyridine ethyl ester citrate aqua
10g methyl α-naphthyl acetate pyridine ethyl esters and 80g water are separately added into 250mL beakers, stirring and dissolving, adds 3g 1601#
With 7g Tween 80s, 0.5h is sufficiently stirred, obtains 10% methyl α-naphthyl acetate pyridine ethyl ester citrate aqua.
The preparation of example 5,5% methyl α-naphthyl acetate pyridine ethyl ester microemulsion
5g methyl α-naphthyl acetate pyridine ethyl esters and 10g ethyl acetate are separately added into 250mL beakers, stirring and dissolving, adds 5g
AEO-9 and 20g Nongru-700 #, are stirring evenly and then adding into 60g water, are sufficiently stirred 0.5h, obtain 5% methyl α-naphthyl acetate pyridine ethyl ester micro emulsion
Agent.
The preparation of example 6,10% methyl α-naphthyl acetate pyridine ethyl ester citrate DA-6 aquas
5g methyl α-naphthyl acetate pyridine ethyl esters citrate, 5g DA-6 and 70g water are separately added into 250mL beakers, stirring is molten
Solution, adds 10g alkyl glycosides, 10gEL-40, is sufficiently stirred 0.5h, obtains 10% methyl α-naphthyl acetate pyridine ethyl ester citrate DA-6
Aqua.
Biological activity determination
Example 7, Seeds Germination Tests
Carried out using paper bed sproutung method.Compound of formula I citrate and DA-6 (Henan Zheng Shi) are configured to 5% respectively
Aqua, is diluted with distilled water into plant of the concentration for 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL respectively
Growth regulating agent solution.The wheat seed that Seed size is uniform, full is selected, after being sterilized with hypochlorite solution to seed,
Soaked seed in beaker with above-mentioned dilution and cultivate 8h, often handle 100 seeds, seed, is uniformly placed on by 3 repetitions after processing
Have in the culture dish of double-layer filter paper, maintained a certain distance between seed, be well placed seed and put it into complete intelligent weather afterwards
25 DEG C of insulation vernalization processing in case, during which periodically to add distilled water makes filter paper keep moistening, and each processing is observed during vernalization
Germination, radicel length are standard about with the 1/2 of seed length, and wheat seed germination percentage in each culture dish is counted after 24h, with
The DA-6 and clear water (CK) of same concentrations are compared, while calculate each dilution germination promotion rate, as a result as shown in table 1 below.
1 wheat seed germinating experimental data of table
By 1 test data of table as it can be seen that the germination percentage that formula Compound I is respectively handled is superior to contrast agents DA-6, more
It is significantly better than clear water processing (CK).
Example 8, the root experiment of seed soaking growth-promoting
Compound of formula I citrate and DA-6 (Henan Zheng Shi) are configured to 5% aqua respectively, it is dilute with distilled water respectively
It is interpreted into plant growth regulator solution of the concentration for 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL.Select
Uniform, the full wheat seed of Seed size, after being sterilized with hypochlorite solution to seed, with above-mentioned dilution in beaker
Seed soaking culture 8h, often handles 20 wheats, seed, is uniformly placed on the paper bed of moistening, between seed by 3 repetitions after processing
Maintain a certain distance, to ensure that seed fully absorbs moisture, when putting bed embryo portion upward towards the same side, be well placed seed it
After put it into complete intelligent climate box and carry out vernalization processing 24h, during which periodically to add distilled water makes paper bed keep moistening.Treat
Wheat main root exposes 2mm or so, by its kind in the solid medium solidified, is then placed in complete intelligent climate box and carries out
Culture.It is high with kind of calliper main root, stem after 40h, and make detailed record.Made with the DA-6 of same concentrations and clear water processing (CK)
Control, it is as a result as shown in table 2 below.
The seed soaking growth-promoting root experimental data of table 2
The compounds of this invention reaches wheat seed soaking rush rooting efficiency in 30 μ g/mL concentration it can be seen from the result of table 2
To optimal, DA-6 is significantly better than.
Embodiment 9, field control effectiveness test
3 processing are set altogether to apple experiment, the suitable bough of new upper 3 growth potentials of Gala apple tree of each processing selection into
OK, experiment takes strain at random, and tree-plot, 3 repetitions, respectively spray one in red fuji apple young fruit period and fruit expanding period respectively
Secondary, foliage-spray clear water after harvest, measures the index of quality of apple respectively as compareing, wherein, VCContent is using routine 2,6-
Dichloropheno-lindophenol method measures, and soluble sugar content is measured using conventional anthrone colorimetry, and the results are shown in Table 3.
3 apple quality test data of table
To sum up data, it can be seen that compound of formula I of the invention has remarkable result at germination, aspect of taking root, excellent
In contrast agents (DA-6)；After carrying out foliage-spray to apple, appearance and interior quality are also shown while apple production is improved
Writing improves, it can be deduced that compound of the invention is a kind of plant growth regulator of excellent combination property.
Claims (4)
1. the methyl α-naphthyl acetate pyridine ethyl ester type compound and its salt of a kind of structure shown in formula I,
2. the salt of compound of formula I according to claim 1, it is characterised in that the salt is inorganic acid salt or organic acid
Salt, inorganic acid salt refer to hydrochloride, phosphate or nitrate, and acylate refers to citrate, lactate, oxalates or p-aminophenyl
Sulfonate.
3. the purposes of compound of formula I according to claim 1 and its salt, it is characterised in that as plant growth regulator.
4. a kind of plant growth regulator composition, contain compound of formula I described in claim 1 or its salt as active component
With acceptable carrier in agricultural or forestry.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610051979.4A CN105777618B (en) | 2016-01-26 | 2016-01-26 | A kind of methyl α-naphthyl acetate pyridine ethyl ester type compound and purposes |
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| CN106748979B (en) * | 2017-01-19 | 2019-06-18 | 青岛科技大学 | A kind of 2,4,6- trichlorophenyl pyridine ethyl ether plant growth regulator |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446013A (en) * | 1991-11-07 | 1995-08-29 | Hoechst Aktiengesellschaft | 2-alkyl-or-aryl-substituted-2-(pyrimidinyl-or-traizinyl-oxy(or-thio))-acotic acid derivatives, process for preparation, and use as herbicides or plant-growth regulators |
| CN103636602A (en) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators |
-
2016
- 2016-01-26 CN CN201610051979.4A patent/CN105777618B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446013A (en) * | 1991-11-07 | 1995-08-29 | Hoechst Aktiengesellschaft | 2-alkyl-or-aryl-substituted-2-(pyrimidinyl-or-traizinyl-oxy(or-thio))-acotic acid derivatives, process for preparation, and use as herbicides or plant-growth regulators |
| CN103636602A (en) * | 2013-12-26 | 2014-03-19 | 青岛科技大学 | Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators |
Non-Patent Citations (2)
| Title |
|---|
| Preparation of some alkenoic acid derivatives as new plant growth regulators;Kayed A. Abu Safieh等;《Res Chem Intermed》;20130625;第41卷;1863-1872 * |
| 水果中常用植物生长调节剂的研究进展;史晓梅等;《食品工业科技》;20121231;第33卷(第4期);第417-422、426页 * |
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