CN105481762B - A kind of cinnamic acid pyridine ethyl ester type compound and purposes - Google Patents
A kind of cinnamic acid pyridine ethyl ester type compound and purposes Download PDFInfo
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- CN105481762B CN105481762B CN201610051586.3A CN201610051586A CN105481762B CN 105481762 B CN105481762 B CN 105481762B CN 201610051586 A CN201610051586 A CN 201610051586A CN 105481762 B CN105481762 B CN 105481762B
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- 0 *C1C=C(*)C=C[C@]1C=CC(Cl)=O Chemical compound *C1C=C(*)C=C[C@]1C=CC(Cl)=O 0.000 description 3
- BXGYBSJAZFGIPX-UHFFFAOYSA-N OCCc1ccccn1 Chemical compound OCCc1ccccn1 BXGYBSJAZFGIPX-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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses the cinnamic acid 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 cinnamic acid 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.103130663 A of CN disclose a kind of cinnamic acid diethylaminoethanol ester class compound
Application as plant growth regulator.103719082 B of CN disclose a kind of cinnamide compound as plant growth
The application of conditioning agent, can be widely applied to plant and promotes seed sprouting, promoting root growth, volume increase, degeneration-resistant and upgrading.
In the prior art, cinnamic acid 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 cinnamic acid 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 cinnamic acid pyridine ethyl ester type compound and its salt of a kind of structure shown in formula I：
In formula：X is H, Y H；X is Cl, Y Cl；The salt is inorganic acid salt or acylate.
Compound of formula I and its salt can be made by following reaction：
X, Y are as defined above in formula；AH is citric acid, lactic acid, oxalic acid or p-aminobenzene sulfonic acid.Cinnamic acid exists shown in Formula II
React 2-4h in suitable solvent under 10 DEG C to reflux temperature with thionyl chloride, decompression steams solvent and excessive protochloride
Sulfone, is made cinnamoyl chloride shown in formula III；Obtained acyl chlorides is added to appropriate solvent solution-forming, -10 DEG C of stirrings of temperature control -10 DEG C
Under be added drop-wise to and be dissolved in by two pyridine ethanols in the solution that appropriate solvent is made into, the hydrochloride of compound of formula I is made；By the chemical combination
Thing hydrochloride is soluble in water, is neutralized with saturated sodium carbonate solution, and compound of formula I is made；Compound of formula I and inorganic acid or organic acid
The inorganic acid or acylate of compound of formula I are made by reaction with same mole.
Solvent is selected from dichloromethane, benzene, toluene, ethyl acetate.
Since part compound of formula I is water-insoluble liquid at room temperature, ingress of air easy oxidation discoloration, and be inconvenient to make
With pretending when being used for plant growth regulator and to occur usually in the form of inorganic acid salt or acylate.Inorganic acid refer to hydrochloric acid,
Phosphoric acid or nitric acid, organic acid refer to citric acid, lactic acid, oxalic acid or p-aminobenzene sulfonic acid.
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, is substantially better than DA-6 (being shown in Table 1) at wheat seed rudiment, aspect of taking root, after apple tree foliage spray, is improving yield
Meanwhile appearance and interior quality also significantly improve.The compound of the present invention can be realized with relatively low use cost and protrusion
Plant growth regulating activity achievees the purpose that crops are significantly increased production, and has good market development prospect and commodity development valency
Value.
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.
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, Formulas I a compounds (X=H, Y=H)
(1) synthesis of cinnamoyl chloride
14.8g (0.1mol) cinnamic acid, 150mL toluene, 14.3g (0.12mol) are sequentially added in 250mL three-necked flasks
Thionyl chloride, is stirred at room temperature lower dropwise addition 0.2mL n,N-Dimethylformamide, temperature rising reflux 2h.TLC monitoring reactions are completed, revolving
Go out solvent and excessive thionyl chloride, obtain 16.1g pale yellowish oil liquid, yield 96.4%.
(2) synthesis of cinnamic acid 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 20.0g (0.12mol) cinnamoyl chlorides obtained above and 50mL ethyl acetate composition is added dropwise, be added dropwise
Finish, reaction 2h is stirred at room temperature；Filter, filter cake washs with appropriate ethyl acetate, dry white solid 26.7g, yield
92.1%.
(3) synthesis of cinnamic acid pyridine ethyl ester
Formulas I a compound hydrochlorides 29.0g (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 23.5g, yield 92.9%.
Formulas I a compounds1H NMR (500MHz, DMSO-d6), δ (ppm)：3.115-3.140 (t, 2H, CH2), 4.525-
4.550 (t, 2H, CH2), 6.369-6.401 (d, 1H, CH), 7.130-7.152 (t, 1H, Ar-H), 7.233-7.248 (d, 2H,
Ar-H), 7.353-7.369 (d, 2H, Ar-H), 7.713 (s, 2H, Pyridyl-H), 7.582-7.614 (d, 1H, CH),
7.855-7.872 (d, 1H, Pyridyl-H), 8.497-8.503 (d, 1H, Pyridyl-H).
The preparation of example 2, Formulas I a compounds (X=H, Y=H) citrate
9.6g (0.05mol) citric acids and 80mL methanol, stirring and dissolving, under stirring are sequentially added into 250mL reaction bulbs
The mixed liquor of 12.7g (0.05mol) cinnamic acid pyridine ethyl ester (Formulas I a compounds) and 20mL methanol is slowly added dropwise, drop finishes, after
Continuous stirring 0.5h, dry white solid 22.1g, yield about 99.1%.
The lactate, oxalates or sulfanilate of cinnamic acid pyridine ethyl ester can similarly be made.
The synthesis of example 3, Formulas I b compounds (X=Cl, Y=Cl)
According to the method for embodiment 1, compound Ib2,4- dichloro meat can be made by changing cinnamic acid into 2,4- dichloro-cinnamic acids
Cinnamic acid pyridine ethyl ester and 2,4- dichloro-cinnamic acid pyridine ethyl ester citrates.
The fusing point of Formulas I b compounds is 69.5 DEG C -71.2 DEG C.1H NMR (500MHz, DMSO-d6), δ (ppm)：3.113-
3.137 (t, 2H, CH2), 4.526-4.551 (t, 2H, CH2), 6.668-6.700 (d, 1H, CH), 7.230-7.252 (t, 1H,
Ar-H), 7.331-7.348 (d, 1H, Ar-H), 7.452-7.4969 (d, 1H, Ar-H), 7.723 (s, 2H, Pyridyl-H),
7.772-7.804 (d, 1H, CH), 7.955-7.972 (d, 1H, Pyridyl-H), 8.499-8.506 (d, 1H, Pyridyl-H).
Formulation examples
The preparation of example 4,5% cinnamic acid, two pyridine ethyl ester citrate aqua
5g cinnamic acid 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% cinnamic acid pyridine ethyl ester citrate aqua.
The preparation of example 5,5%2,4- dichloro-cinnamic acid pyridine ethyl ester citrate aquas
5g2,4- dichloro-cinnamic acids pyridine ethyl ester citrate and 88g water are separately added into 250mL beakers, stirring is molten
Solution, adds 3g Tween 80s, 4g alkyl glycosides, is sufficiently stirred 0.5h, obtains 5%2,4- cinnamic acid pyridine ethyl ester citric acid brine
Agent.
The preparation of example 6,5%2,4- dichloro-cinnamic acid pyridine ethyl ester microemulsions
5g2,4- dichloro-cinnamic acid pyridine ethyl esters and 10g ethyl acetate, 5g AEO-7 are separately added into 250mL beakers
With 20g agriculture breast 500#, 60g water is stirring evenly and then adding into, is sufficiently stirred 0.5h, obtain 5%2,4- cinnamic acid pyridine ethyl ester micro emulsions
Agent.
The preparation of example 7,10%2,4- dichloro-cinnamic acid pyridine ethyl ester citrate DA-6 aquas
5g2,4- dichloro-cinnamic acid pyridine ethyl esters citrate, 5g DA-6 and 70g are separately added into 250mL beakers
Water, stirring and dissolving, adds 10g alkyl glycosides, 10g agriculture breast 1601#, is sufficiently stirred 0.5h, obtains 10%2,4- dichloro-cinnamic acid pyrroles
Pyridine ethyl ester citrate DA-6 aquas.
Biological activity determination
Example 8, Seeds Germination Tests
Carried out using paper bed sproutung method.Respectively by Formulas I a compounds citrate, Ib compounds citrate and DA-6 (rivers
5% aqua Nan Zhengshi) is configured to, is diluted with distilled water into concentration respectively as 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/
The plant growth regulator solution of mL and 120 μ g/mL.The wheat seed that Seed size is uniform, full is selected, uses hypochlorite solution
After being sterilized to seed, soaked seed in beaker with above-mentioned dilution and cultivate 8h, often handle 100 seeds, 3 repetitions, processing
Seed is uniformly placed in the culture dish of double-layer filter paper afterwards, is maintained a certain distance between seed, is well placed after seed
25 DEG C of insulation vernalization processing in complete intelligent climate box are put it into, during which periodically to add distilled water makes filter paper keep moistening, urges
The germination of each processing is observed between sprouting stage, radicel length is standard about with the 1/2 of seed length, and each culture dish is counted after 24h
Middle wheat seed germination percentage, is compared with the DA-6 of same concentrations and clear water (CK), while calculates each dilution germination promotion rate,
As a result it is 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 9, the root experiment of seed soaking growth-promoting
Formulas I a compounds citrate, Ib compounds 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 20 wheats, seed, is uniformly placed on by 3 repetitions after processing
On the paper bed of moistening, maintained a certain distance between seed, to ensure that seed fully absorbs moisture, when putting bed, embryo portion is upwards and court
To the same side, it is well placed seed and puts it into progress vernalization processing 24h in complete intelligent climate box afterwards, during which periodically to add steaming
Distilled water makes paper bed keep moistening.Treat that wheat main root exposes 2mm or so, by its kind in the solid medium solidified, then
It is put into complete intelligent climate box and is cultivated.It is high with kind of calliper main root, stem after 40h, and make detailed record.With same concentrations
DA-6 and clear water processing (CK) compare, 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 10, 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 cinnamic acid pyridine ethyl ester type compound and its salt of a kind of structure shown in formula I,
In formula：X is H, Y H；X is Cl, Y Cl.
2. the salt of cinnamic acid pyridine ethyl ester type compound according to claim 1, it is characterised in that the salt is nothing
Machine hydrochlorate or acylate, inorganic acid salt refer to hydrochloride, phosphate or nitrate, and acylate refers to citrate, lactate, grass
Hydrochlorate or sulfanilate.
3. the purposes of cinnamic acid pyridine ethyl ester type compound according to claim 1 and its salt, it is characterised in that be used 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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