CN113754550B - Compound for improving fertilizer absorption and utilization efficiency and preparation method and application thereof - Google Patents
Compound for improving fertilizer absorption and utilization efficiency and preparation method and application thereof Download PDFInfo
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- CN113754550B CN113754550B CN202111107957.2A CN202111107957A CN113754550B CN 113754550 B CN113754550 B CN 113754550B CN 202111107957 A CN202111107957 A CN 202111107957A CN 113754550 B CN113754550 B CN 113754550B
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- diethylaminoethanol
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- 239000003337 fertilizer Substances 0.000 title claims abstract description 82
- 150000001875 compounds Chemical class 0.000 title claims abstract description 71
- 238000010521 absorption reaction Methods 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title abstract description 12
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229940049920 malate Drugs 0.000 claims abstract description 36
- HCJFRRRPNUMIET-UHFFFAOYSA-N 1-(diethylamino)ethyl octanoate Chemical compound C(CCCCCCC)(=O)OC(C)N(CC)CC HCJFRRRPNUMIET-UHFFFAOYSA-N 0.000 claims abstract description 35
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000003756 stirring Methods 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000003973 irrigation Methods 0.000 claims abstract description 13
- 230000002262 irrigation Effects 0.000 claims abstract description 13
- 238000005507 spraying Methods 0.000 claims abstract description 12
- 238000011010 flushing procedure Methods 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 230000032050 esterification Effects 0.000 claims abstract description 9
- 238000005886 esterification reaction Methods 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims abstract description 8
- 239000001630 malic acid Substances 0.000 claims abstract description 8
- 235000011090 malic acid Nutrition 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 8
- 239000000843 powder Substances 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 125000005474 octanoate group Chemical group 0.000 claims description 4
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 42
- 240000008042 Zea mays Species 0.000 abstract description 21
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 21
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 20
- 235000005822 corn Nutrition 0.000 abstract description 20
- 244000105624 Arachis hypogaea Species 0.000 abstract description 17
- 235000020232 peanut Nutrition 0.000 abstract description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract description 13
- 229910052700 potassium Inorganic materials 0.000 abstract description 13
- 239000011591 potassium Substances 0.000 abstract description 13
- 235000010469 Glycine max Nutrition 0.000 abstract description 11
- 238000010992 reflux Methods 0.000 abstract description 11
- 244000068988 Glycine max Species 0.000 abstract description 10
- 235000017060 Arachis glabrata Nutrition 0.000 abstract description 9
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 9
- 235000018262 Arachis monticola Nutrition 0.000 abstract description 9
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 abstract description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052796 boron Inorganic materials 0.000 abstract description 8
- 239000000618 nitrogen fertilizer Substances 0.000 abstract description 8
- 239000011701 zinc Substances 0.000 abstract description 8
- 229910052725 zinc Inorganic materials 0.000 abstract description 8
- 240000008067 Cucumis sativus Species 0.000 abstract description 7
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract description 7
- 239000011733 molybdenum Substances 0.000 abstract description 6
- 229910052750 molybdenum Inorganic materials 0.000 abstract description 6
- 239000002686 phosphate fertilizer Substances 0.000 abstract description 6
- 238000004821 distillation Methods 0.000 abstract description 3
- 238000012360 testing method Methods 0.000 description 41
- 238000011282 treatment Methods 0.000 description 27
- 230000000694 effects Effects 0.000 description 23
- 235000013339 cereals Nutrition 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- 229960002446 octanoic acid Drugs 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 7
- 229930002875 chlorophyll Natural products 0.000 description 7
- 235000019804 chlorophyll Nutrition 0.000 description 7
- 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 7
- 235000015097 nutrients Nutrition 0.000 description 7
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000013461 design Methods 0.000 description 5
- 230000001737 promoting effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- QJZYHAIUNVAGQP-UHFFFAOYSA-N 3-nitrobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2(C(O)=O)[N+]([O-])=O QJZYHAIUNVAGQP-UHFFFAOYSA-N 0.000 description 3
- 108090000913 Nitrate Reductases Proteins 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 239000004021 humic acid Substances 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 230000035764 nutrition Effects 0.000 description 3
- 235000011837 pasties Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001057636 Dracaena deremensis Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- GVYLWCPUAAZCES-UHFFFAOYSA-N ethanol;octanoic acid Chemical compound CCO.CCCCCCCC(O)=O GVYLWCPUAAZCES-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- MMDJDBSEMBIJBB-UHFFFAOYSA-N [O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[NH6+3] Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[NH6+3] MMDJDBSEMBIJBB-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- -1 diethyl aminoethyl octanoate Chemical compound 0.000 description 1
- VJVHVCGQROIJFW-UHFFFAOYSA-N diethyl(1-hydroxyethyl)azanium;octanoate Chemical compound CC[NH+](CC)C(C)O.CCCCCCCC([O-])=O VJVHVCGQROIJFW-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000003501 hydroponics Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000013332 literature search Methods 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 108010034764 nitric acid reductase Proteins 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000011895 specific detection Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Fertilizers (AREA)
Abstract
The invention belongs to the technical field of fertilizer synergism, and particularly relates to a compound for improving fertilizer absorption and utilization efficiency, which is diethylaminoethanol caprylate malate, and a preparation method thereof, comprising the following steps: (1) Carrying out reflux water diversion reaction on octanoic acid and N, N-diethylaminoethanol in the presence of an organic solvent and an esterification catalyst, and carrying out reduced pressure distillation to obtain diethylaminoethanol octanoate; (2) The diethylaminoethanol octanoate and malic acid are put into a reactor, heated under stirring and crystallized into white solid powder. The compound is used as a fertilizer synergist, can promote the absorption and utilization of nitrogen fertilizer, phosphate fertilizer and zinc fertilizer by corn by applying at the bottom of the seedling stage of corn or by flushing in a large bell mouth stage, can promote the absorption and utilization of potassium fertilizer, boron fertilizer and molybdenum fertilizer by peanut by spraying on the leaf surfaces of the early flowering stage of peanut, can promote the absorption of nitrogen fertilizer and phosphate fertilizer by seedlings by water planting in the seedling stage of cucumber, can promote the absorption and utilization of nitrogen by functional leaves by drip irrigation in the seedling stage of soybean, and can improve the yield and protein content of seeds.
Description
Technical Field
The invention belongs to the technical field of fertilizer synergism, and particularly relates to a compound for improving fertilizer absorption and utilization efficiency, and a preparation method and application thereof.
Background
From the national conditions of China, the national grain safety strategy under the new situation is implemented, the national grain safety is guaranteed, the national grain is basically cultivated, the technology is on the way, and the yield-increasing potential of the grain needs to be excavated by the technology. The potential of high-tech yield increase is needed to be exerted, and the popularization and application of new varieties, new machines and new technologies are well promoted. The technology for improving the absorption and utilization of the fertilizer is one of the irreplaceable supporting directions for guaranteeing the grain safety, and the development of the fertilizer synergist with high productivity, low cost, stable effect, safety and environmental protection is also a popular research in the field of novel fertilizers in recent two years.
According to the invention, a series of novel compounds possibly having biological activity are designed and synthesized according to the structure-activity relationship by researching the molecular structural characteristics of plant endogenous substances and PGR having biological activity, and then the novel compounds, namely the diethylaminoethanol caprylate malate, which are novel compounds for promoting the absorption and utilization of nutrition by plants are successfully screened out by combining with the multi-directional development technical researches of promoting the absorption of nutrition by plants, improving the assimilation efficiency of plant nutrients, improving the soil environment and the like. Proved by experiments in recent two years, the compound fertilizer has synergism on absorption and utilization of the fertilizer through various treatment modes such as water culture, bottom application, flushing application, drip irrigation, leaf surface spraying and the like, and the synthesis and application literature report of the diethylaminoethanol caprylate malate are not found through the literature search in the prior art.
In view of the above, an object of the present invention is to provide a compound that improves the absorption and utilization efficiency of a fertilizer.
Disclosure of Invention
The present inventors found that, in screening a novel compound having biological activity, the compound diethylaminoethanol caprylate malate has a remarkable synergistic effect on absorption and utilization of fertilizers, thereby completing the present invention.
In order to achieve the aim of the invention, the invention adopts the following technical scheme: a compound for improving the absorption and utilization efficiency of fertilizer, the chemical name of which is diethylaminoethanol caprylate malate, has the structural formula:
further, the preparation method of the compound for improving the absorption and utilization efficiency of the fertilizer comprises the following steps:
(1) Reflux-separating octanoic acid and N, N-diethylaminoethanol with the molar ratio of 1:1-2 at the temperature of 110-145 ℃ in the presence of an organic solvent and an esterification catalyst for reaction for 3-10 hours until the mole number of separated water is equal to the mole number of the octanoic acid put into the reaction kettle, filtering the solid esterification catalyst, distilling the organic solvent and the excessive N, N-diethylaminoethanol under reduced pressure, sleeving the reaction kettle substrate on the next batch for use, and continuously distilling the reaction kettle substrate under reduced pressure by using a vacuum pump to obtain yellowish liquid diethylaminoethanol octanoate;
(2) And (3) placing the diethylaminoethanol octoate and the malic acid in a molar ratio of 1:1 into a reactor, heating to 50-80 ℃ under stirring, and gradually crystallizing to obtain white solid powder, thus obtaining the diethylaminoethanol octoate malate.
Further, in the step (1), the organic solvent is toluene or xylene, and the mass ratio of the organic solvent to the octanoic acid is 1-2:1.
Further, in the step (1), the esterification catalyst is concentrated sulfuric acid, sulfamic acid, phosphotungstic acid or strong acid ion resin, and the dosage of the esterification catalyst is 1.0-4.2% of the mass of octanoic acid.
Further, the compound is applied to fertilizer synergism as a fertilizer synergist, and aims to improve the absorption and utilization efficiency of crops to fertilizers.
Further, the application mode of the compound is bottom application, drip irrigation, flushing, foliar spraying or water planting.
Further, the effective dosage of the compound is 10-200 g/mu, preferably 40-60 g/mu.
Further, the effective amount of the compound for drip irrigation is 2-40 g/mu, preferably 5-10 g/mu.
Further, the effective dosage of the compound for flushing is 10-100 g/mu, preferably 20-40 g/mu.
Further, the effective dosage of the compound for foliar spraying is 5-100 mg/L, preferably 20-60 mg/L.
Further, the effective amount of the compound for water culture is 1-20 mg/L, preferably 2.5-5 mg/L.
In the invention, the preparation principle of the compound diethyl aminoethyl octanoate malate is shown as the following formula:
the invention has the beneficial effects that:
1. the invention provides a compound diethyl aminoethyl octanoate malate which can improve the absorption and utilization efficiency of fertilizer, and the compound is used as a fertilizer efficiency synergist.
2. The compound of the invention, namely the diethylaminoethanol caprylate malate, is prepared by two-step reaction, has simple preparation process and low cost, the total molar yield of the two steps reaches 85.0-94.9%, the used solvent can be recovered and reused, the three wastes are less discharged, no pollution is generated, and the invention belongs to a green environment-friendly process and is suitable for industrial production.
3. The compound diethyl caprylate ethanol ester malate prepared by the invention is used as a fertilizer synergist, and can promote the absorption and utilization of nitrogenous fertilizer, phosphate fertilizer and zinc fertilizer by corn after being applied at the bottom of the seedling stage of corn or being applied in a large bell mouth stage.
4. The compound diethyl aminoethyl octanoate malate prepared by the invention is used as a fertilizer synergist, and can effectively promote the absorption and utilization of potassium fertilizer, boron fertilizer and molybdenum fertilizer by peanuts through the foliar spraying treatment in the early flowering stage of the peanuts.
5. The compound caprylic acid diethylaminoethanol ester malate prepared by the invention is used as a fertilizer synergist, and can effectively promote the absorption of nitrogenous fertilizer and phosphate fertilizer by seedlings in the water planting treatment of cucumber seedlings.
6. The compound diethyl caprylate ethanol ester malate prepared by the invention is used as a fertilizer synergist, and can effectively promote the absorption and utilization of nitrogen by functional leaves during the drip irrigation treatment of soybean seedlings, and improve the yield of seeds and the protein content.
Detailed Description
In order to make the technical purpose and technical solution of the present invention more clear, the technical solution of the present invention will be further described with reference to specific embodiments, and the described embodiments are only some embodiments, but not all embodiments of the present invention. All other embodiments, which can be made by those skilled in the art without making any inventive effort, are intended to be within the scope of the present invention.
Example 1
A preparation method of a compound (diethylaminoethanol octanoate malate) for improving the absorption and utilization efficiency of a fertilizer comprises the following steps: the method comprises the following steps:
(1) 144g (1 mol) of octanoic acid, 117g (1 mol) of N, N-diethylaminoethanol, 6.0g of concentrated sulfuric acid and 144g of toluene are added into a 1000ml four-neck flask provided with a reflux water diversion device, stirring and heating are carried out to 110 ℃ for reflux reaction for 10 hours until 18g (1 mol) of water is separated, the solvent toluene (recycled) and excessive N, N-diethylaminoethanol are firstly distilled out under preliminary reduced pressure, and then the kettle substrate is continuously distilled by using a vacuum pump to obtain 207g of light yellow oily liquid diethylaminoethanol octanoate with the yield of 85.0 percent;
(2) And mixing and stirring the diethylaminoethanol octoate and 114g of malic acid with the molar ratio of 1, heating to 50 ℃, enabling the system to become pasty under stirring, and then slowly cooling and crystallizing to form salt to obtain 321g of the diethylaminoethanol octoate malate which is a white powdery solid product, wherein the yield is 100%.
Example 2
A preparation method of a compound (diethylaminoethanol octanoate malate) for improving the absorption and utilization efficiency of a fertilizer comprises the following steps: the method comprises the following steps:
(1) 144g (1 mol) of octanoic acid, 234g (2 mol) of N, N-diethylaminoethanol, 6.0g of concentrated sulfuric acid and 288g of toluene are added into a 1000ml four-neck flask provided with a reflux water diversion device, stirring and heating are carried out to 130 ℃ for reflux reaction for 5 hours until 18g (1 mol) of water is separated, the solvent toluene (recycled) and excessive N, N-diethylaminoethanol are firstly distilled out under preliminary reduced pressure, and then the kettle substrate is continuously distilled by using a vacuum pump to obtain 218g of light yellow oily liquid diethylaminoethanol octanoate with the yield of 89.6%;
(2) And then, the diethylaminoethanol octanoate and 120g of malic acid with the molar ratio of 1 are mixed and stirred, heated to 60 ℃, the system is firstly changed into paste under stirring, and then slowly cooled and crystallized into salt, thus obtaining 338g of the solid diethylaminoethanol octanoate malate with the yield of 100 percent.
Example 3
A preparation method of a compound (diethylaminoethanol octanoate malate) for improving the absorption and utilization efficiency of a fertilizer comprises the following steps: the method comprises the following steps:
(1) 144g (1 mol) of octanoic acid, 176g (1.5 mol) of N, N-diethylaminoethanol, 6.0g of sulfamic acid and 288g of toluene are added into a 1000ml four-neck flask provided with a reflux water diversion device, stirring and heating are carried out to 125 ℃ for reflux reaction for 7 hours until 18g (1 mol) of water is separated, the solvent toluene (recycled) and excessive N, N-diethylaminoethanol are firstly distilled off under preliminary reduced pressure, and then the kettle substrate is continuously distilled by using a vacuum pump to obtain 215g of light yellow oily diethylaminoethanol octanoate with the yield of 88.3 percent;
(2) And then mixing and stirring the diethylaminoethanol octanoate and 118.5g of malic acid with the molar ratio of 1, heating to 65 ℃, enabling the system to become pasty under stirring, and then slowly cooling and crystallizing to form salt to obtain 333.5g of the solid diethylaminoethanol octanoate malate which is white powder, wherein the yield is 100%.
Example 4
A preparation method of a compound (diethylaminoethanol octanoate malate) for improving the absorption and utilization efficiency of a fertilizer comprises the following steps: the method comprises the following steps:
(1) 144g (1 mol) of octanoic acid, 176g (1.5 mol) of N, N-diethylaminoethanol, 5.0g of strongly acidic ionic resin and 288g of toluene are added into a 1000ml four-neck flask provided with a reflux water diversion device, stirring and heating are carried out to 120 ℃ for reflux reaction for 8 hours until 18g (1 mol) of water is separated, stirring is stopped, resin is removed by filtration (recycling), the filtrate is firstly subjected to preliminary reduced pressure distillation to remove solvent toluene (recycling) and excessive N, N-diethylaminoethanol (recycling), and then a kettle substrate is continuously distilled by a vacuum pump to obtain 226g of light yellow oily liquid diethylaminoethanol octanoate with the yield of 92.8 percent;
(2) And then mixing and stirring the diethylaminoethanol octanoate and 124.5g of malic acid with the molar ratio of 1, heating to 70 ℃, enabling the system to become pasty under stirring, and then slowly cooling and crystallizing to form salt to obtain 350.5g of the solid diethylaminoethanol octanoate malate which is white powder, wherein the yield is 100%.
Example 5
A preparation method of a compound (diethylaminoethanol octanoate malate) for improving the absorption and utilization efficiency of a fertilizer comprises the following steps: the method comprises the following steps:
(1) 144g (1 mol) of octanoic acid, 176g (1.5 mol) of N, N-diethylaminoethanol, 1.5g of phosphotungstic acid and 288g of dimethylbenzene are added into a 1000ml four-neck flask provided with a reflux water diversion device, stirring and heating are carried out to 145 ℃ for reflux reaction for 3 hours until 18g (1 mol) of water is separated, stirring is stopped, phosphotungstic acid is filtered and removed (recycling is carried out), the filtrate is firstly subjected to preliminary reduced pressure distillation to obtain solvent dimethylbenzene (recycling) and excessive N, N-diethylaminoethanol (recycling), and then a kettle substrate is continuously distilled by using a vacuum pump to obtain 231g of light yellow oily liquid diethylaminoethanol octanoate with the yield of 94.9 percent;
(2) And then mixing and stirring 127g of diethyl aminoethyl octanoate and 1 time of malic acid, heating to 80 ℃, firstly changing the system into paste under stirring, and then slowly cooling and crystallizing to form salt to obtain 358g of white powdery solid product diethyl aminoethyl octanoate malate with 100 percent of yield.
In order to further test the practical effect of the compound provided by the invention for improving the absorption and utilization of crop fertilizers, the inventor adopts a method of indoor biological measurement and field test, and combines different application modes of bottom application, leaf surface spraying, drip irrigation, flushing, water planting and the like to make practical test effect evaluation.
Test example 1 influence of the Compound of the present invention on the absorption and utilization of corn fertilizer (flushing)
Test crop: corn
Test site: zhongmue county eight sentry town Ding Liucun
Test treatment: the bottom-applied compound fertilizer is 19-19-19 compound fertilizer, and simultaneously, 50g of zinc sulfate and the compound prepared in the example 1 with different contents are applied according to 20kg of compound fertilizer (19-19-19) per mu and additional fertilizer in the corn large bell mouth period. And measuring plant height, stem thickness and chlorophyll content 7d after the medicine, collecting leaves in the growing stage, measuring the content of elements such as nitrogen, phosphorus, potassium, zinc and the like by sending inspection to the academy of agricultural science in Henan province, and measuring the yield and thousand seed weight in the harvesting stage.
Test agent test design:
the test results are as follows:
(1) Effect of each treatment on corn plant height, stem thickness and chlorophyll content
As can be seen from the data in the table, compared with the single application of the fertilizer, the compound of the invention, namely the diethylaminoethanol caprylate malate, prepared by the example 1 with different contents has different promotion effects on morphological indexes such as corn plant height, stem thickness, chlorophyll content and the like by being treated as a fertilizer synergist.
(2) Effect of each treatment on nitrogen, phosphorus, potassium and zinc element content of corn leaves
As shown in the data of the table, compared with the single application of fertilizer, the compound of the invention, namely the diethylaminoethanol caprylate malate, prepared in the embodiment 1 of the invention is used as a fertilizer synergist to treat the corn leaves in the growing period, and has remarkable promotion effect on the contents of nitrogen, phosphorus and zinc elements, especially on trace element zinc. However, the potassium content is not greatly influenced, and the analysis is caused by different requirements of the corn on nitrogen, phosphorus, potassium and zinc in a large bell mouth period, the requirement of the corn on the potassium in a jointing period, a large bell mouth period and a flowering period is relatively less, and the requirement of the corn on the potassium in a flowering period is greatly improved.
(3) Effect of treatments on corn yield and thousand kernel weight
As can be seen from the data in the table above, compared with the single application of fertilizer, the compound diethyl aminoethyl octanoate malate prepared in the embodiment 1 of the invention has certain promotion effect on corn yield and thousand grain weight by being treated as a fertilizer synergist, and especially by being treated with 2 and 3, the increase rate reaches 18.59% and 23.75% respectively.
Test example 2 influence of the Compound prepared according to the invention on the absorption and utilization of peanut fertilizers (spraying)
Test crop: peanut
Test site: zhongmue county eight sentry town Ding Liucun
Test treatment: the method comprises the steps of taking 0.5% urea, 0.5% monopotassium phosphate, 0.1% boron and 0.005% ammonium molybdate as base fertilizers, carrying out spraying treatment on leaves in an early flowering phase by matching with the compound prepared in example 2 with different concentrations, measuring chlorophyll content 7d after the pesticide, recording the needle-down number of peanuts, collecting functional leaves in a full-growth period, and measuring nitrogen, phosphorus, potassium, boron and molybdenum content by inspection by the national academy of agricultural science in Henan province. Yield and quality were measured at the time of harvest.
Test agent test design:
the test results are as follows:
(1) Effect of each treatment on chlorophyll content and needle count of peanut
As can be seen from the data in the table, compared with the single application of the fertilizer, the compound of the invention, namely the diethylaminoethanol caprylate malate, prepared by the concentration example 2 has different degrees of promotion effects on the chlorophyll content of peanuts by being treated as a fertilizer synergist, and meanwhile, the early needle-setting of the peanuts can be promoted, thereby providing a foundation for early results, multiple results and increased yield in the later period.
(4) Effect of each treatment on nitrogen, phosphorus, potassium, boron and molybdenum element content of peanut leaf
As shown in the data of the table, compared with the single application of fertilizer, the compound of the invention 2, namely the diethylaminoethanol caprylate malate, has a certain promotion effect on the content of nitrogen and phosphorus elements in peanut leaves in the growing period when being treated as a fertilizer synergist, and has a remarkable promotion effect on the content of potassium, boron and molybdenum elements. The absorption and synergism of the fertilizer synergist on the fertilizer are related to the fertilizer requirement characteristics of crops in different periods, and the increase of the content of potassium, boron and molybdenum elements is beneficial to promoting early needle setting and more needle setting and is beneficial to the later yield increase.
(5) Effects of treatments on peanut yield and quality
The quality protein and fat content of the peanut are measured by using GB/T14489.2 and GB/T14488.1 methods respectively. As can be seen from the data in the table, compared with the single application of fertilizer, the compound diethyl aminoethyl octanoate malate prepared in the embodiment 2 of the invention has a certain promotion effect on the yield and quality of peanuts by being treated as a fertilizer synergist, and the yield increase is mainly based on the comprehensive factors of early needle setting, increasing the number of needles and increasing the plumpness of seeds by combining the data of the number of full fruits of a single plant.
Test example 3 influence of the Compound prepared according to the invention on the absorption and utilization of cucumber Fertilizer (hydroponics)
Test crop: cucumber
Test site: biological testing laboratory, center of research on physical and chemical control engineering technology in Henan province
Test treatment: the compound prepared in example 3 was used with different concentrations added using standard Hoagland nutrient solution as culture medium. The seedlings are cultivated on a seedling raising tray, two true leaves are grown, and then the seedlings are transplanted into a water planting box. 800g of nutrient solution was added to each cassette and 8 cassettes were repeated for each treatment. The compound prepared in example 2 was cultured for 2 days, and then replaced with pure Hoagland nutrient solution for culturing. The nutrient solution is replaced every two days, and the culture period is 8 days. And after the cultivation is finished, taking stem and leaf parts of seedlings, drying, crushing and grinding the dried samples, and then performing digestion and determination of nitrogen and phosphorus content. Specific detection methods are performed with reference to NY/T2017-2011.
Test agent test design:
the detection results are as follows:
from the data in the table, the cucumber seedlings are subjected to water culture by using different dosages of diethylaminoethanol caprylate malate and Hoagland nutrient solution, so that the absorption of nitrogen and phosphorus in the nutrient solution by the cucumber seedlings can be effectively promoted; with the increase of the dosage, the absorption promotion rate of the total nitrogen and the total phosphorus both show a trend of increasing and then decreasing; the highest nitrogen absorption promoting rate reaches 27.18%, and the highest phosphorus absorption promoting rate reaches 10.52%. The optimal dosage is comprehensively evaluated to be 2.5-5 mg/L.
Test example 4 influence of the Compound prepared according to the invention on the absorption and utilization of corn fertilizer (bottom application)
Test crop: corn
Test site: biological testing laboratory, center of research on physical and chemical control engineering technology in Henan province
Test treatment: urea was mixed with the compound prepared in example 4 in different amounts, and then mixed with a matrix, and then the test was carried out using a potting method. Wherein the test substrate was turf (imported from the netherlands), 6 pots were treated each, 6 seedlings of corn/pot. And (3) investigating chlorophyll content of each treated leaf when the seedling grows to 5-6 leaves, then cutting fresh samples of overground parts, and detecting total nitrogen content of plants after treatment.
Test agent test design:
the effect of different treatments on nitrogen fertilizer utilization of maize seedlings is shown in the following table:
as can be seen from the data in the table, compared with the single application of the fertilizer, the compound of the invention, namely the diethylaminoethanol caprylate malate, prepared in the embodiment 4 of the invention is used as a fertilizer synergist to treat corn seedlings, so that the absorption and utilization rate of the nitrogen fertilizer can be effectively improved, and the promotion rate shows a gentle trend along with the improvement of the dosage of the fertilizer; the highest nitrogen absorption promotion rate reaches 44.09%, and the nitrogen absorption promotion rate reaches 34.50% under the highest concentration treatment. And comprehensively evaluating the optimal dosage to be 40-60 g/mu.
Test example 5 regulating action of the Compounds prepared according to the invention on metabolism of Soybean fertilizers (drip irrigation)
Test crop: soybean
Test treatment: 5kg humic acid macroelement (humic acid is more than or equal to 40g/L, N+P) 2 O 5 +K 2 O is more than or equal to 200 g/L) is used as a base fertilizer, and the compound prepared in the example 5 with different concentrations is matched for drip irrigation treatment in the seedling stage. Function She Xiaosuan reductase activity and amino acid content were measured at the early flowering phase, full flowering phase, initial grain phase, and grain filling phase, respectively, and soybean yield and quality were measured at the harvest phase.
Test agent test design:
the test results are as follows:
(1) Influence of each treatment on the activity of nitric acid reductase and the amino acid content of soybean functional leaves
Nitrate nitrogen is reduced to ammonia under the catalysis of Nitrate Reductase (NR) and then participates in the metabolic cycle of nitrogen. The NR activity of the compound of the invention, namely the diethylaminoethanol caprylate malate, prepared in the embodiment 5 of the invention, which is used as a fertilizer synergist is higher than that of CK, so that the nitrogen conversion can be accelerated, and the accumulation of nitrogen in seeds is facilitated. From the amino acid content variation, the variation of each treatment was consistent with the growth cycle from the early flowering phase to the grain filling phase. In the grain filling period, the content of amino acid accumulated and manufactured by the leaves is 14.7-33.2% higher than that of a control, so that nutrition is transferred to the grains, the grain filling is promoted, and the yield is increased.
(2) Effect on soy yield composition
As can be seen from the data in the table, compared with the single application of humic acid macroelement drip irrigation fertilizer, the compound of the invention, namely the diethylaminoethanol caprylate malate, prepared in the embodiment 5 of the invention is treated as a fertilizer synergist, so that the soybean yield, the total nitrogen content of seeds and the protein content are improved to different degrees, and the compound has important promotion effects on improving the soybean yield and the soybean quality.
In summary, test examples 1 to 5 respectively adopt a plurality of comprehensive test methods of flushing, foliar spraying, water planting, bottom spraying and drip irrigation to study the effect of the compound prepared by the invention on the absorption and utilization of fertilizer, and test results show that the compound (diethylaminoethanol octoate malate) prepared by the invention is used as a fertilizer synergist, and the absorption and utilization of nitrogen fertilizer, phosphate fertilizer and zinc fertilizer by corn can be promoted by flushing treatment at the bottom of the seedling stage or the large bell mouth stage of corn; the foliar spraying treatment in the early flowering stage of the peanuts can effectively promote the absorption and utilization of potassium fertilizer, boron fertilizer and molybdenum fertilizer by the peanuts; the water planting treatment in the cucumber seedling stage can effectively promote the seedlings to absorb nitrogenous fertilizer and phosphate fertilizer; the drip irrigation treatment in the soybean seedling stage can effectively promote the absorption and utilization of nitrogen by the functional leaves, and improve the yield and protein content of seeds.
Claims (3)
1. The compound for improving the absorption and utilization efficiency of the fertilizer is characterized by having the chemical name of diethylaminoethanol octanoate malate and the structural formula:
the compound is used as a fertilizer synergist and applied to fertilizer synergism;
the application mode of the compound is bottom application, drip irrigation, flushing, foliar spraying or water planting;
the effective dosage of the compound is 10-200 g/mu;
the effective amount of the compound for drip irrigation is 2-40 g/mu;
the effective dosage of the compound for flushing is 10-100 g/mu;
the effective dosage of the compound foliar spray is 5-100 mg/L;
the effective dosage of the compound for water culture is 1-20 mg/L.
2. A method for preparing the compound for improving the absorption and utilization efficiency of fertilizer according to claim 1, comprising the steps of:
(1) Reflux-separating octanoic acid and N, N-diethylaminoethanol with the molar ratio of 1:1-2 at the temperature of 110-145 ℃ in the presence of an organic solvent and an esterification catalyst for reaction for 3-10 hours until the mole number of separated water is equal to the mole number of the octanoic acid put into the reaction kettle, filtering the solid esterification catalyst, distilling the organic solvent and the excessive N, N-diethylaminoethanol under reduced pressure, sleeving the reaction kettle substrate on the next batch for use, and continuously distilling the reaction kettle substrate under reduced pressure by using a vacuum pump to obtain yellowish liquid diethylaminoethanol octanoate;
(2) And (3) placing the diethylaminoethanol octoate and the malic acid in a molar ratio of 1:1 into a reactor, heating to 50-80 ℃ under stirring, and gradually crystallizing to obtain white solid powder, thus obtaining the diethylaminoethanol octoate malate.
3. The method for preparing a compound for improving the absorption and utilization efficiency of a fertilizer according to claim 2, wherein in the step (1), the organic solvent is toluene or xylene, and the mass ratio of the organic solvent to the octanoic acid is 1-2:1; the esterification catalyst is concentrated sulfuric acid, sulfamic acid, phosphotungstic acid or strong acid ion resin, and the dosage of the esterification catalyst is 1.0-4.2% of the mass of octanoic acid.
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| JPH0995548A (en) * | 1995-09-29 | 1997-04-08 | Nippon Paint Co Ltd | Method for improving conductivity of molded resin and production of coated material made of resin |
| CN111362817A (en) * | 2020-03-06 | 2020-07-03 | 河南福联生物科技有限公司 | Preparation and application of plant growth regulator caprylic-N, N-diethylaminoethyl ester salt |
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| JPH01290606A (en) * | 1988-05-17 | 1989-11-22 | Nitto Baion Kk | Plant growth promoter and production thereof |
| JPH0995548A (en) * | 1995-09-29 | 1997-04-08 | Nippon Paint Co Ltd | Method for improving conductivity of molded resin and production of coated material made of resin |
| CN111362817A (en) * | 2020-03-06 | 2020-07-03 | 河南福联生物科技有限公司 | Preparation and application of plant growth regulator caprylic-N, N-diethylaminoethyl ester salt |
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