CN111362817A - Preparation and application of plant growth regulator caprylic-N, N-diethylaminoethyl ester salt - Google Patents
Preparation and application of plant growth regulator caprylic-N, N-diethylaminoethyl ester salt Download PDFInfo
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- CN111362817A CN111362817A CN202010155473.4A CN202010155473A CN111362817A CN 111362817 A CN111362817 A CN 111362817A CN 202010155473 A CN202010155473 A CN 202010155473A CN 111362817 A CN111362817 A CN 111362817A
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- diethylaminoethyl
- diethylaminoethyl ester
- caprylic acid
- plant growth
- growth regulator
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- NIWZVGDDVLDDTA-UHFFFAOYSA-N 2-(diethylamino)ethyl octanoate Chemical class CCCCCCCC(=O)OCCN(CC)CC NIWZVGDDVLDDTA-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- -1 caprylic acid-N, N-diethylaminoethyl ester citrate Chemical compound 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 27
- KNPDHVNBUQKSNW-UHFFFAOYSA-N 2-(diethylamino)ethyl octanoate hydrochloride Chemical compound CCCCCCCC(=O)OCCN(CC)CC.Cl KNPDHVNBUQKSNW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 5
- 239000003337 fertilizer Substances 0.000 claims description 51
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 30
- 238000003756 stirring Methods 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 230000001965 increasing effect Effects 0.000 description 15
- 241000219109 Citrullus Species 0.000 description 12
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 12
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- 241000557833 Hua gabonii Species 0.000 description 10
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- 150000001875 compounds Chemical class 0.000 description 5
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229930002875 chlorophyll Natural products 0.000 description 2
- 235000019804 chlorophyll Nutrition 0.000 description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 2
- 230000035558 fertility Effects 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 230000029553 photosynthesis Effects 0.000 description 2
- 238000010672 photosynthesis Methods 0.000 description 2
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- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- 241000167854 Bourreria succulenta Species 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- OORIKNJWZHTXDC-UHFFFAOYSA-N CCCC(CC)C(CC)(C(=O)OCC)N Chemical compound CCCC(CC)C(CC)(C(=O)OCC)N OORIKNJWZHTXDC-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 240000001008 Dimocarpus longan Species 0.000 description 1
- 208000035240 Disease Resistance Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
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- 240000009088 Fragaria x ananassa Species 0.000 description 1
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- 244000068988 Glycine max Species 0.000 description 1
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- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 108090000913 Nitrate Reductases Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
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- 235000010721 Vigna radiata var radiata Nutrition 0.000 description 1
- 235000011469 Vigna radiata var sublobata Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
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- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fertilizers (AREA)
Abstract
The invention discloses a preparation method of a plant growth regulator caprylic acid-N, N-diethylaminoethyl ester salt, which comprises the following steps of preparing caprylic acid-N, N-diethylaminoethyl ester hydrochloride, wherein the utilized reaction chemical formula is as follows; step two, neutralizing with alkali and extracting to obtain caprylic acid-N, N-diethylaminoethyl ester; and step three, preparing the caprylic acid-N, N-diethylaminoethyl ester citrate by using a solvent method or a solvent-free method. When in use, the caprylic acid-N, N-diethylaminoethyl ester hydrochloride and the caprylic acid-N, N-diethylaminoethyl ester citrate can be sprayed, irrigated and sprayed on agricultural products, economic crops and fruits. The octanoic acid-N, N-diethylaminoethyl ester salt is prepared by reaction at low temperature, raw materials are easy to obtain and low in price, the synthesis method is simple and safe, the yield is high, the use of solvents is reduced in the salt forming process, the cost is saved, the reaction time is short, the efficiency and the energy are high, and the method is suitable for industrial production.
Description
Technical Field
The invention relates to the field of chemical industry and agriculture, in particular to a preparation method and application of a plant growth regulator caprylic-N, N-diethylaminoethyl ester salt.
Background
A plant growth regulator commonly used in the prior art is DA-6, also known as diethyl aminoethyl hexanoate, which is a high-efficiency plant growth regulator with broad-spectrum effect. It can increase the activity of plant peroxidase and nitrate reductase, increase chlorophyll content, accelerate photosynthesis, promote division and elongation of plant cell, promote root growth and regulate nutrient balance in vivo.
In modern agriculture, plant growth regulators are widely applied to grain crops, economic crops, fruit trees, vegetables, flowers, edible fungi and the like, and the low-concentration use of the plant growth regulators can greatly improve the yield of the crops and obviously improve the quality of products. The synthesis method of the plant growth regulator mainly comprises a solid acid catalysis method, a non-acid catalyst catalysis method and the like. Wherein, the solid acid catalysis method has higher yield, but the catalyst is fussy to prepare, and the production process is complicated; the yield of the organic acid catalytic method is not very high, and the salt formed by the catalyst and the diethylaminoethanol is mutually soluble with a reaction system, so that the post-treatment difficulty is high; tetrabutyl phthalate used in the non-acid catalyst catalytic method report is expensive and has high cost.
Green chemistry is an important research area for the development of chemical science in the 21 st century. Green chemistry utilizes a series of principles to reduce or eliminate the adaptation and production of harmful substances in the design, production and application of chemical products. Many plant growth regulators have volatile organic compounds in their production, which when released into the atmosphere will cause harmful fumes, while solvent-free systems eliminate the emission of harmful fumes, which has the most significant advantages for human health and the environment, and is one of the green chemical research directions.
Disclosure of Invention
Aiming at the improvement and improvement of the prior art, the invention provides a plant growth regulator caprylic acid-N, N-diethylaminoethyl ester salt, which is characterized in that the caprylic acid-N, N-diethylaminoethyl ester salt can react at low temperature and normal pressure without high pressure or high heat reaction, the raw materials for preparing the caprylic acid-N, N-diethylaminoethyl ester salt which is the plant growth regulator are easy to obtain, the price is low, the synthesis method is safe, the yield is high, the efficiency and the energy are high, in addition, the zero emission can be realized in the application, and the plant growth regulator is suitable for industrial production and large-scale agricultural application.
The technical scheme adopted by the invention is as follows:
a preparation method of a plant growth regulator octanoic acid-N, N-diethylaminoethyl ester salt is characterized by comprising the following steps:
step one, preparing caprylic acid-N, N-diethylaminoethyl ester hydrochloride, wherein the reaction chemical formula of the caprylic acid-N, N-diethylaminoethyl ester hydrochloride is as follows;
step two, neutralizing with alkali and extracting to obtain caprylic acid-N, N-diethylaminoethyl ester;
step three, preparing caprylic acid-N, N-diethylaminoethyl ester citrate by using a solvent method or a solvent-free method; the chemical formula is as follows:
wherein, the intermediate product of caprylic acid-N, N-diethylaminoethyl ester hydrochloride in the step one and caprylic acid-N, N-diethylaminoethyl ester citrate finally obtained in the step three can be used as plant growth regulators for application.
Further, the specific method comprises the following steps: adding diethylaminoethanol into a three-neck flask, dissolving the diethylaminoethanol into dichloromethane, adding a certain catalyst, stirring and cooling the mixture in a low-temperature cold trap, dropwise adding octanoyl chloride when the temperature is reduced to 0 ℃, and controlling the dropwise adding temperature to be-10-20 ℃. After the dropwise addition is finished, reacting at low temperature for 1-3 hours, stirring at 40-60 ℃ for 2-6 hours, stopping the reaction, cooling and discharging, and vacuumizing to remove a small amount of solvent to obtain the octanoic acid-N, N-diethylaminoethyl ester hydrochloride with high purity.
Wherein the mass ratio of the octanoyl chloride to the N, N-diethylaminoethanol is 1: 1.0-1.5.
Further, the specific method of the second step is to neutralize hydrochloric acid in caprylic acid-N, N-diethylaminoethyl ester hydrochloride with alkali and extract with ethyl acetate to obtain caprylic acid-N, N-diethylaminoethyl ester.
And further, in the third step, a solvent method is utilized to prepare the caprylic acid-N, N-diethylaminoethyl ester citrate, and specifically, citric acid is dissolved in a solvent, the caprylic acid-N, N-diethylaminoethyl ester is dropwise added after the citric acid is dissolved, stirring is continued until the dropwise addition is finished, the stirring is stopped when solids are separated out, and then the solvent is removed through reduced pressure suction filtration to obtain white powder of the caprylic acid-N, N-diethylaminoethyl ester citrate.
And further, preparing the caprylic acid-N, N-diethylaminoethyl ester citrate by a solvent-free method in the third step, specifically, heating the caprylic acid-N, N-diethylaminoethyl ester to 140 ℃, adding citric acid while stirring until the citric acid is dissolved, stopping heating, and continuing stirring until caprylic acid-N, N-diethylaminoethyl ester salt solid powder is formed.
The application of caprylic acid-N, N-diethylaminoethyl ester salt as plant growth regulator in preparing agricultural products, industrial crops and fruits is disclosed.
Further, the caprylic acid-N, N-diethyl aminoethyl ester salt is mixed with a water-soluble fertilizer to be sprayed.
Further, the octanoic acid-N, N-diethyl amino ethyl ester salt compound fertilizer is sprayed.
Further, the mass ratio of the caprylic acid-N, N-diethylaminoethyl ester salt in use is 0.0001-10%.
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
(1) the octanoic acid-N, N-diethylaminoethyl ester salt is prepared by reaction at low temperature, raw materials are easy to obtain and low in price, the synthesis method is simple and safe, the yield is high, the use of solvents is reduced in the salt forming process, the cost is saved, the reaction time is short, the efficiency and the energy are high, and the method is suitable for industrial production;
(2) the caprylic acid-N, N-diethylaminoethyl ester citrate is easily degraded by the action of enzyme in soil and is not easily fixed by the soil, so that the activity of soil microorganisms is not influenced or the soil microorganisms can be decomposed by the microorganisms, and the hazard to the soil environment is not caused;
(3) the caprylic acid-N, N-diethylaminoethyl citrate can improve the water absorption capacity of the root system, promote rooting and is beneficial to improving the stress resistance of plants, such as drought resistance, cold resistance, saline-alkali resistance, disease resistance and the like; after the leaves are treated by the caprylic-N, N-diethylaminoethyl citrate, the number of pores of the leaves is reduced, the transpiration rate is reduced, and the drought resistance can be improved;
(4) the caprylic-N, N-diethylaminoethyl citrate has a regulating effect on the growth of crops, can promote the growth of roots, stems and leaves of plants, promote the reproductive growth (namely the growth of flowers and fruits) of the plants, and improve the fruit setting rate of the plants. The tillering and spike increasing yield can be promoted, the chlorophyll content is increased after the application, the leaf color is dark green, the photosynthesis is enhanced, the leaf blade is thickened, and the root system is developed;
(5) the invention is a novel broad-spectrum efficient plant growth regulator, can greatly improve the yield of crops by using at low concentration, can be used in combination with water-soluble fertilizers and compound fertilizers, obviously improves the quality of products, can be used singly, can promote the growth of roots, thicken stems and leaves of plants, and improve the quality and stress resistance, can make the crops resistant to drought and waterlogging, prevent the crops from overgrowing and lodging, resist salt and alkali, and can be used for cash crops, grain crops, fruit trees, vegetables, flowers, edible fungi and the like.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The octanoic acid-N, N-diethylaminoethyl ester salt as plant growth regulator is synthesized through low temperature reaction and can form octanoic acid-N, N-diethylaminoethyl ester hydrochloride, octanoic acid-N, N-diethylaminoethyl ester tartrate, octanoic acid-N, N-diethylaminoethyl ester salicylate and octanoic acid-N, N-diethylaminoethyl ester citrate according to the type of the used raw material acid in the salt forming process, wherein the octanoic acid-N, N-diethylaminoethyl ester salt with plant growth regulating effect has the following nuclear magnetic data:
1H-NMR(400MHz，CDCl3)δ：4.36(t，2H)，2.97(t，2H)，2.89(m，4H)，2.32(t， 2H)，1.66(m，2H)，1.14-1.33(m，14H)，0.88(t，3H)；13C-NMR(400MHz，CDCl3)δ： 173.2，62.4，54.2，49.7，49.7，33.9，31.8，29.2，29.2，25.3，22.8，14.2，13.1， 13.1。
in order to facilitate the application of the plant growth regulator in agriculture, octanoic acid-N, N-diethylaminoethyl ester salt is generally adopted to form different preparations for product production, and the preparation types can be emulsifier, aqua, emulsion powder and powder, wherein the powder comprises soluble powder or wettable powder; the different types of preparations can also be used in combination with water-soluble fertilizers, compound fertilizers and biochemical regulators or can be used independently.
If the caprylic acid-N, N-diethylaminoethyl ester salt is compounded and applied with water soluble fertilizer, compound fertilizer and biochemical regulator, the fertilizer comprises the following components in percentage by weight: 0.0001-10% of caprylic-N, N-diethylaminoethyl ester salt and 85-99.9% of auxiliary agent; the auxiliary agent is a solvent and a synergist, and comprises the following components in percentage by weight: comprises 55-95% of deionized water, 5-10% of solvent and 5-10% of synergist.
When the caprylic acid-N, N-diethylaminoethyl ester salt is used alone, the mass ratio of the caprylic acid-N, N-diethylaminoethyl ester salt is 0.0001-10%.
The caprylic-N, N-diethylaminoethyl ester salt can be suitable for grain crops such as wheat, corn, rice, cotton, peanut, soybean and garlic, can also be applied to economic crops such as tea, tobacco, rape, tomato, mung bean, flowers, traditional Chinese medicinal materials and lawns, and fruit crops such as longan, loquat, plum, strawberry, banana, cherry, mango, kiwi fruit, peach and watermelon.
Example 1
The preparation of N, N-diethylaminoethyl caprylate hydrochloride as plant growth regulator includes the following steps:
adding 200 g of diethylaminoethanol into a three-neck flask, dissolving the diethylaminoethanol into dichloromethane, stirring and cooling the mixture in a low-temperature cold trap, adding 10g of sodium bicarbonate, dropping 250 g of octanoyl chloride when the temperature is reduced to 0 ℃, wherein the dropping time is 1 hour, and the dropping temperature is controlled to be-10-20 ℃; reacting at low temperature for two hours, stirring at normal temperature for three hours, stopping stirring, and removing the solvent to obtain the caprylic acid-N, N-diethylaminoethyl ester hydrochloride.
Example 2
Adding 100 g of diethylaminoethanol into a three-neck flask, stirring and cooling in a low-temperature cold trap, dropping 150 g of octanoyl chloride when the temperature is reduced to 0 ℃, wherein the dropping time is 1 hour, and the dropping temperature is controlled to be-10-20 ℃. Reacting at low temperature for 3 hours, stirring at 40-60 ℃ for 2 hours, stopping stirring, discharging, and slightly cooling to obtain white solid of caprylic acid-N, N-diethylaminoethyl ester hydrochloride.
Example 3
The preparation of N, N-diethylaminoethyl caprylate citrate as plant growth regulator includes the following steps:
step one, preparing caprylic acid-N, N-diethylaminoethyl ester hydrochloride: adding 200 g of diethylaminoethanol into a three-neck flask, dissolving the diethylaminoethanol into dichloromethane, stirring and cooling the mixture in a low-temperature cold trap, dropping 280 g of octanoyl chloride when the temperature is reduced to 0 ℃, wherein the dropping time is 1 hour, and the dropping temperature is controlled to be-10-20 ℃. Reacting at low temperature for two hours, stirring at normal temperature for three hours, stopping stirring, and removing the solvent to obtain the caprylic acid-N, N-diethylaminoethyl ester hydrochloride.
Step two, neutralizing and extracting by alkali to obtain caprylic acid-N, N-diethylaminoethyl ester: preferably, the acid salt of the octanoic acid-N, N-diethylaminoethyl ester salt obtained in the first step is neutralized with an aqueous sodium hydrogencarbonate solution as a base and extracted with ethyl acetate to obtain octanoic acid-N, N-diethylaminoethyl ester in a yield of 92%.
Step three, preparing caprylic acid-N, N-diethylaminoethyl ester citrate by a solvent method: dissolving 80 g of citric acid in a certain amount of solvent, dropwise adding 80 g of caprylic-N, N-diethylaminoethyl ester after dissolving, continuing stirring until the dropwise adding is finished, stopping stirring when solid is separated out, and removing the solvent by reduced pressure suction filtration to obtain white powder of caprylic-N, N-diethylaminoethyl ester citrate.
Wherein the solvent can be any one of benzene, toluene, xylene, chloroform, dichloromethane and acetone.
Example 4
Preparation of the plant growth regulator caprylic-N, N-diethylaminoethyl ester citrate was based on steps one and two of example 3, but step three used a solvent-free method to prepare caprylic-N, N-diethylaminoethyl ester citrate: namely, 100 g of caprylic acid-N, N-diethylaminoethyl ester is heated to 140 ℃, 80 g of citric acid is added under stirring until the citric acid is dissolved, the heating is stopped, and the stirring is continued until solid powder of caprylic acid-N, N-diethylaminoethyl ester citrate is formed.
Example 5
The application of a plant growth regulator caprylic-N, N-diethylaminoethyl ester citrate:
in particular to an application of octanoic acid-N, N-diethylaminoethyl ester citrate and a macroelement water soluble fertilizer in irrigation planting of tomatoes, which comprises the following steps:
the method comprises the steps of raising seedlings in a hole tray in a greenhouse, then selecting tomato seedlings with uniform sizes, transplanting the tomato seedlings to a field for planting, wherein the row spacing is 50cm, the plant spacing is 30cm, the planting soil is common vegetable garden soil, the fertility is medium, NPK compound fertilizer (N-P-K is 19-19-19) is applied as base fertilizer and applied at one time, and the management during the test period is the same as the management of the common field cultivation.
The experiment was set up with 3 treatment items, 2 control items, 3 replicates per treatment item, 20m per cell2The random block design is adopted,the design groupings are as follows:
processing T1: water soluble fertilizer +30ppm caprylic acid-N, N-diethylaminoethyl ester citrate;
processing T2: water soluble fertilizer +50ppm caprylic-N, N-diethylaminoethyl citrate:
processing T3: water soluble fertilizer +50ppm DA-6:
control CK 1: singly applying a water-soluble fertilizer:
control CK 2: applying clear water blank control:
the concentration of the water soluble fertilizer used in the test is 500 times diluted, and the water soluble fertilizer is treated for 3 times in the seedling stage, the full-bloom stage and the fruiting stage of the tomato.
And randomly selecting 10 plants for data acquisition every time, counting the number of the tomatoes in the first inflorescence and the second inflorescence, and measuring the single fruit weight and the single plant yield of the tomatoes. And (3) measuring each index, and performing related statistical analysis on the test data by adopting DPS (data processing System) and Excel software to obtain data of the influence of different treatments on the tomato initial fruit characters in the following table 1:
as can be seen from Table 1, compared with the clear water control CK2, the single application of the water-soluble fertilizer CK1 has a promoting effect on the number of the first inflorescence and the second inflorescence of the tomatoes, and the growth rates are respectively 9.72% and 5.05%. The water-soluble fertilizer is compounded with caprylic-N, N-diethylaminoethyl citrate, the water-soluble fertilizer has a promoting effect on the tomato fruit numbers of the first inflorescence and the second inflorescence at 30ppm and 50ppm, and compared with a clear water control CK2, the water-soluble fertilizer has obvious difference, and the growth rates are respectively (46.76% and 22.71%) and (50.93% and 27.13%); compared with the comparison CK1 of single water-soluble fertilizer application, the growth promoter has obvious promotion effect on the number of first inflorescences, the growth rate reaches more than 30%, and the promotion effect on the number of second inflorescences is about 15%. The water-soluble fertilizer is compounded with DA-6, the effect of promoting the tomato fruiting numbers of the first inflorescence and the second inflorescence of the tomato is shown, compared with the clear water control CK2, the growth rates are respectively 12.04% and 8.20%, but compared with the single water-soluble fertilizer control CK1, the effect is not obvious.
In addition, data were also obtained for the effect of different treatments on tomato yield in table 2, as follows:
as can be seen from Table 2, compared with the clear water control CK2, the single application of the water-soluble fertilizer CK1 has a promoting effect on the number of tomato single plants and the yield, and the growth rates are 8.10% and 10.48% respectively. The water-soluble fertilizer is compounded with caprylic-N, N-diethylaminoethyl citrate, and at 30ppm and 50ppm, the accelerating effect on the number of tomato single plants and the yield is obvious compared with the clear water control CK2, and the growth rates are respectively (17.27% and 23.38%) and (27.53% and 33.06%): compared with a control CK1 that only applies water soluble fertilizer, the fertilizer also has obvious yield increasing effect, wherein at 50ppm, the yield of a single tomato plant is increased by more than 20%. The water-soluble fertilizer is compounded with DA-6, so that the effect of promoting the fruiting number and the yield of each tomato plant is not obvious compared with the effect of singly applying the water-soluble fertilizer by using CK1 as a control.
The experiment shows that the single fertilization can increase the number and the yield of the tomato fruits to a certain extent, but the increase effect is relatively small, and the caprylic-N, N-diethylaminoethyl citrate and the fertilizer are compounded for use, so that the tomato fruit number and the yield are obviously promoted, especially the initial stage fruit number of the tomato is increased more, wherein the promotion effect on the first inflorescence fruit number is more obvious, the increase rate is more than 30 percent, and the promotion effect on the second inflorescence fruit number is about 15 percent; at 50ppm, the yield of the tomato single plant is increased by more than 20 percent. The effect of increasing the tomato yield is not obvious when DA-6 is used together with a fertilizer.
Compared comprehensively, the caprylic-N, N-diethylaminoethyl citrate has great potential in increasing the fertilizing effect of the tomatoes, can further achieve the effect of increasing the yield on the basis of single fertilization and yield increase, and has the effect obviously superior to that of DA-6.
Example 6
The application of a plant growth regulator caprylic-N, N-diethylaminoethyl ester citrate:
particularly, the experiment of the influence of the matched application of the caprylic acid-N, N-diethylaminoethyl citrate and the fertilizer on the growth of the garlic comprises the following specific steps:
common vegetable garden soil is selected, the fertility is uniform, and 10kg of soil is filled in each flowerpot; selecting garlic seeds with consistent sizes; sowing 10 garlic in each pot, and performing normal field management;
4 groups of treatment items and 2 groups of comparison items are set, each treatment item is set with 3 repetitions, each cell has 10 pots, and a random block design is adopted, wherein the items are as follows:
treatment 1: fertilization +30ppm caprylic-N, N-diethylaminoethyl citrate;
and (3) treatment 2: fertilizing with 50ppm caprylic-N, N-diethylaminoethyl citrate;
and (3) treatment: fertilization +30 ppmDA-6:
and (4) treatment: fertilization +50ppm DA-6:
control CK 1: single fertilization;
control CK 2: blank control;
fertilizing 10g each time for each pot plant, spraying pesticide while fertilizing, treating for 2 times in seedling stage, and spacing 1 month between two times;
at the garlic sprout harvest stage, 4 plants per pot were selected and plant height, stem thickness and individual plant weight were investigated. The indexes are measured, the test data are subjected to relevant statistical analysis by adopting DPS and Excel software, and the influence of the octanoic acid-N, N-diethylaminoethyl ester citrate and fertilizer in the garlic growth is obtained as shown in the following table:
as can be seen from the table, compared with the control without fertilization, the fertilization has obvious promotion effect on the height of the garlic plant and the weight average of the single plant, the growth rate is 10.01 percent and 14.30 percent, and the influence on the stem thickness of the garlic is not great; the octanoic acid-N, N-diethylaminoethyl ester citrate is applied with fertilizer at a set concentration, has remarkable promoting effects on the height, stem thickness and weight average of a single garlic plant, has the growth rates of (14.04%, 15.45% and 56.87%) and (14.40%, 11.48% and 35.14%) compared with a non-fertilization control group, and also has the promoting effects on the height, stem thickness and weight of the single garlic plant compared with a fertilization control group, wherein the growth rate of the weight of the single garlic plant reaches more than 20%, even 40%. The DA-6 has the promoting effect on the height, stem thickness and weight average of a single garlic plant when the set concentration is matched with a fertilizer, compared with a non-fertilization control group, the growth rates are respectively (0.16%, 9.20% and 23.52%) and (6.78%, 5.11% and 20.05%), compared with a fertilization control group, the promoting effect on the stem thickness and the weight of the single garlic plant is not obvious, and the height of the garlic plant is even slightly lower than that of a single fertilization situation.
The experiment shows that the fertilization can promote the height and the weight of a single garlic plant, but has little influence on the stem thickness of the garlic, the octanoic acid-N, N-diethylaminoethyl ester citrate is matched with the fertilizer to obviously promote the weight-average performance of the height, the stem thickness and the single garlic plant of the garlic plant, and compared with the fertilization control, the growth rate of the single weight of the garlic sprout reaches more than 20 percent, even 40 percent. Compared with a single fertilization control, the DA-6 has no obvious promotion effect on the stem thickness and the plant weight of the garlic and even slightly inhibits the plant height of the garlic when being applied with the fertilizer.
Compared comprehensively, the octanoic acid-N, N-diethylaminoethyl ester citrate and the compound fertilizer are applied in a matching way, so that the fertilization effect can be improved, the fertilizer utilization rate can be improved, the yield increase effect can be further achieved on the basis of single fertilization and yield increase, and the effect is obviously superior to that of DA-6.
Example 7
The application of a plant growth regulator caprylic-N, N-diethylaminoethyl ester citrate:
in particular to an experiment for the influence of caprylic acid-N, N-diethylaminoethyl ester citrate on the growth of watermelons
In the test, under the premise of ensuring that the total nutrient content of the base fertilizer and the topdressing fertilizer is the same, 2 different treatment items and 1 control item are set, and each cell is 45m2Each treatment was 3 replicates.
Processing T1: water soluble fertilizer +30ppm caprylic acid-N, N-diethylaminoethyl ester citrate,
processing T2: 30ppm octanoic acid-N, N-diethylaminoethyl ester citrate,
control CK: clear water blank control.
After field planting, 60 plants are reserved in each cell, 880 plants are planted per mu, spraying treatment is carried out for 1 time in the seedling stage, the vine pulling stage and the fruit setting stage, and other field management measures are consistent. Measuring the length of a main vine in the flowering period of the watermelon; the watermelon fruits are picked uniformly according to the subdistricts after being ripe, 10 fruits are picked at random in each subdistrict, the average single watermelon quality is calculated, the yield of each 667 square meters of the watermelon is converted by multiplying the average single watermelon quality by the watermelon number, and the recorded data are shown in the following table:
as can be seen from the table, 2 treatment items had a certain promotion effect on the growth and yield of watermelon as compared with the control item. The promoting effect of the 2 treatment items on the main vine length of the watermelon in the flowering period is that the growth rate is 7.61 percent and 3.46 percent respectively compared with the control item, and the difference is obvious compared with the control item. According to the measured weight of a single fruit multiplied by the number of melons per mu, the yield per mu is converted, 2 treatment items have promotion effects on the yield of the watermelons, and compared with a control item, the yield is 9.82% and 3.40%, wherein the yield increasing effect of the T1 water soluble fertilizer and 30ppm caprylic acid-N, N-diethylaminoethyl ester citrate is better, the yield is increased by 370 kg/mu and is 9.82% compared with the control item.
The test shows that 2 treatment items have certain promotion effect on the growth vigor and the yield of the watermelon, the yield increasing effect of the water soluble fertilizer and 30ppm of caprylic acid-N, N-diethylaminoethyl ester citrate in the 2 treatment items is better, the yield is increased by 370 kg/mu compared with a control, and the yield is increased by 9.82%. Test results show that the effect of the water-soluble fertilizer in combination is better than the effect of the caprylic acid-N, N-diethyl aminoethyl citrate in single use, the fertilizer effect can be exerted to a greater extent in combination, the yield is improved, and the economic benefit is increased.
Example 8
The application of octanoic acid-N, N-diethylaminoethyl ester hydrochloride as plant growth regulator includes:
particularly, the experiment of the influence of the caprylic acid-N, N-diethylaminoethyl ester hydrochloride on the growth of rice is as follows:
the test is carried out by random block arrangement, 333.5m per cell2Repeat 3 times. Rice with the same batch sowing, transplanting, same management and consistent growth potential is selected as a test material.
In the field test, stem and leaf spraying treatment is adopted, the concentration of caprylic-N, N-diethylaminoethyl ester hydrochloride is set to 30ppm and 50ppm2, clear water is set as a reference CK, the fertilizer is sprayed for 1 time after the rice is transplanted and seedlings are delayed, and the fertilizer is sprayed for 1 time in the heading and grouting period. The plant height and harvest time are investigated in the maturation period, the grain number, thousand grain weight and yield of each ear are investigated, and the influence of caprylic-N, N-diethylaminoethyl ester hydrochloride on the plant height and yield of rice is recorded, as shown in the following table:
as can be seen from the table, caprylic acid-N, N-diethylaminoethyl ester hydrochloride shows a promoting effect on the plant height of rice at 20ppm and 40ppm, and the growth rates are 2.27% and 10.07% respectively compared with the control item, wherein at 40ppm, the difference is significant compared with the control item; compared with the control item, the 2 treatment items increase the grain number of the rice per ear by 0.1 and 0.4, the thousand kernel weight by 0.7g and 0.9g, and the yield per mu is respectively 4.46 percent and 6.56 percent in terms of yield per mu, wherein the yield per mu reaches 39.4kg at 40 ppm.
Test results show that the caprylic-N, N-diethylaminoethyl ester hydrochloride with the concentration of 20ppm and 40ppm has promotion effects on growth vigor and yield of rice, wherein the effect on the rice is better at 40ppm, the difference is obvious compared with a control, the acre growth rate is 6.56%, and the acre yield is 39.4 kg.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principles of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A preparation method of a plant growth regulator caprylic-N, N-diethylaminoethyl ester salt is characterized by comprising the following steps:
step one, preparing caprylic acid-N, N-diethylaminoethyl ester hydrochloride, wherein the reaction chemical formula of the caprylic acid-N, N-diethylaminoethyl ester hydrochloride is as follows;
step two, neutralizing with alkali and extracting to obtain caprylic acid-N, N-diethylaminoethyl ester;
step three, preparing caprylic acid-N, N-diethylaminoethyl ester citrate by using a solvent method or a solvent-free method; the chemical formula is as follows:
wherein, the intermediate product of caprylic acid-N, N-diethylaminoethyl ester hydrochloride in the step one and the caprylic acid-N, N-diethylaminoethyl ester citrate finally obtained in the step three can be used as plant growth regulators for application.
2. The preparation method of the N, N-diethylaminoethyl octanoate as a plant growth regulator according to claim 1, wherein the specific method in step one comprises: adding diethylaminoethanol into a three-neck flask, dissolving the diethylaminoethanol into dichloromethane, adding a certain catalyst, stirring and cooling the mixture in a low-temperature cold trap, dropwise adding octanoyl chloride when the temperature is reduced to 0 ℃, and controlling the dropwise adding temperature to be-10-20 ℃. After the dropwise addition is finished, reacting at low temperature for 1-3 hours, stirring at 40-60 ℃ for 2-6 hours, stopping the reaction, cooling and discharging, and vacuumizing to remove a small amount of solvent to obtain the octanoic acid-N, N-diethylaminoethyl ester hydrochloride with high purity.
3. The preparation method of the octanoic acid-N, N-diethylaminoethyl ester salt as a plant growth regulator according to claim 2, wherein the mass ratio of octanoyl chloride to N, N-diethylaminoethanol is 1: 1.0 to 1.5.
4. The method for preparing N, N-diethylaminoethyl octanoate as a plant growth regulator according to claim 1, wherein the second step is carried out by neutralizing hydrochloric acid in N, N-diethylaminoethyl octanoate hydrochloride with a base and extracting with ethyl acetate to obtain N, N-diethylaminoethyl octanoate.
5. The method for preparing caprylic acid-N, N-diethylaminoethyl ester salt as a plant growth regulator according to claim 1, wherein the preparation method comprises dissolving citric acid in a solvent, dropwise adding caprylic acid-N, N-diethylaminoethyl ester after dissolving, continuing stirring until dropwise adding is completed, stopping stirring when solids are precipitated, and removing the solvent by vacuum filtration to obtain white powder of caprylic acid-N, N-diethylaminoethyl ester citrate.
6. The preparation of N, N-diethylaminoethyl caprylate as a plant growth regulator according to claim 1, wherein the preparation of N, N-diethylaminoethyl caprylate citrate is carried out in step three by a solvent-free method, wherein the N, N-diethylaminoethyl caprylate citrate is heated to 140 ℃, citric acid is added while stirring until the citric acid is dissolved, the heating is stopped, and the stirring is continued until solid powder of the N, N-diethylaminoethyl caprylate is formed.
7. Use of N, N-diethylaminoethyl octanoate as a plant growth regulator for agricultural products, commercial crops and fruits, wherein the N, N-diethylaminoethyl octanoate as claimed in claim 1 is used.
8. The use of N, N-diethylaminoethyl octanoate as a plant growth regulator in accordance with claim 7, wherein the N, N-diethylaminoethyl octanoate is diluted alone into an aqueous solution for spraying.
9. The use of N, N-diethylaminoethyl caprylate as a plant growth regulator according to claim 7, wherein the mixed fertilizer of N, N-diethylaminoethyl caprylate is sprayed.
10. The use of an N, N-diethylaminoethyl octanoate as a plant growth regulator according to claim 8 or 9, wherein the N, N-diethylaminoethyl octanoate is used at a mass ratio of 0.0001% to 10%.
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| CN113068696A (en) * | 2021-04-19 | 2021-07-06 | 张�林 | Preparation method and application of mixed fatty acid ester and salt thereof |
| CN113754550A (en) * | 2021-09-22 | 2021-12-07 | 郑州郑氏化工产品有限公司 | Compound for improving fertilizer absorption and utilization efficiency and preparation method and application thereof |
| CN114982757A (en) * | 2022-05-09 | 2022-09-02 | 郑州尼采生物科技有限公司 | Method for preparing ester or tertiary amine plant growth regulator aqueous solution |
| CN115968883A (en) * | 2022-12-07 | 2023-04-18 | 郑州郑氏化工产品有限公司 | Composition containing 5-aminolevulinic acid and nicotinamide ester and application thereof |
| CN115968883B (en) * | 2022-12-07 | 2024-06-28 | 郑州郑氏化工产品有限公司 | Composition containing 5-aminolevulinic acid and amine ester and application thereof |
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| CN113754550A (en) * | 2021-09-22 | 2021-12-07 | 郑州郑氏化工产品有限公司 | Compound for improving fertilizer absorption and utilization efficiency and preparation method and application thereof |
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| JPH01290606A (en) * | 1988-05-17 | 1989-11-22 | Nitto Baion Kk | Plant growth promoter and production thereof |
| CN111362818A (en) * | 2020-03-06 | 2020-07-03 | 河南福联生物科技有限公司 | Preparation and application of butyric acid-N, N-diethylaminoethyl ester salt serving as plant growth regulator |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113068696A (en) * | 2021-04-19 | 2021-07-06 | 张�林 | Preparation method and application of mixed fatty acid ester and salt thereof |
| CN113754550A (en) * | 2021-09-22 | 2021-12-07 | 郑州郑氏化工产品有限公司 | Compound for improving fertilizer absorption and utilization efficiency and preparation method and application thereof |
| CN113754550B (en) * | 2021-09-22 | 2024-03-22 | 郑州郑氏化工产品有限公司 | Compound for improving fertilizer absorption and utilization efficiency and preparation method and application thereof |
| CN114982757A (en) * | 2022-05-09 | 2022-09-02 | 郑州尼采生物科技有限公司 | Method for preparing ester or tertiary amine plant growth regulator aqueous solution |
| CN115968883A (en) * | 2022-12-07 | 2023-04-18 | 郑州郑氏化工产品有限公司 | Composition containing 5-aminolevulinic acid and nicotinamide ester and application thereof |
| CN115968883B (en) * | 2022-12-07 | 2024-06-28 | 郑州郑氏化工产品有限公司 | Composition containing 5-aminolevulinic acid and amine ester and application thereof |
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