CN1166670C - ANtioxidizing pseudo-enzyme compound and its preparing process and application - Google Patents

ANtioxidizing pseudo-enzyme compound and its preparing process and application Download PDF

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CN1166670C
CN1166670C CNB021155224A CN02115522A CN1166670C CN 1166670 C CN1166670 C CN 1166670C CN B021155224 A CNB021155224 A CN B021155224A CN 02115522 A CN02115522 A CN 02115522A CN 1166670 C CN1166670 C CN 1166670C
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compound
enzyme compound
antioxidizing
sodium
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CN1369495A (en
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廖展如
向道风
梅伏生
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Huazhong Normal University
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Abstract

The present invention relates to an antioxidizing pseudo-enzyme compound, a preparing method thereof and an application thereof. The pseudo-enzyme compound has the activity of natural superoxide dimutase (SOD) and catalase (CAT), 1 to 100 ppm of antioxidizing pseudo-enzyme compound can simultaneously remove O2 <-> and H2O2, can activate self defense mechanisms of plants, and can enhance the resistance capability of the plants to adversity stress of cold, dryness, diseases, etc., so the yields of farm crops and vegetable crops are increased by 5.1 to 49.42%. The present invention has the advantages of simple production technique, low energy consumption, good environment compatibility and the combined functions of pesticide and trace fertilizer.

Description

Antioxidizing pseudo-enzyme compound and preparation thereof and application
Technical field
The present invention relates to a class and have superoxide dismutase (superoxide dismutase, SOD) and catalase (Catalase, CAT) active anti-oxidant pseudo-enzyme compound and preparation and as the application of plant-growth regulator, sterilant and trace element fertilizer.
Background technology
Superoxide-dismutase (SOD) and catalase (CAT) are the oxidation resistant important meals enzymes of plant.Plant is when environment stress such as high temperature, cold, arid, water stain, salt marsh or pathogenic micro-organism invasion, and the plant defense system can produce a large amount of active oxygens (as O 2 -, H 2O 2And OH) resist coercing of biological and abiotic environment, but the active oxygen accumulation can damage lipid film and nucleic acid, protein and other.Antioxidase SOD and CAT can remove O 2 -, H 2O 2, protective membrane tissue and biomacromolecule escape injury.Therefore, improve the antioxidase level and just can strengthen the resistance of crop, improve output and the quality of crop.
Naturally occurring SOD enzyme has five kinds: Cu-ZnSOD, MnSOD, FeSOD, NiSOD, Fe-ZnSOD; And bacterium catalase activity position contains dinuclear manganese (II).Although these antioxidase central metals and coordination are not quite similar for how much, all contain Histidine (His) imidazoles nitrogen and the coordination of polynary amino acid carboxylic oxygen; Physiological function is disproportionation O 2 -Be O 2And H 2O 2, prevent that them from reacting to be converted into by Fenton reaction and Haber-Weiss and have more destructive hydroxy radical qiao (OH).Present commercially available SOD extracts from humans and animals blood, intestinal bacteria (E.Coli), plant, separation and purification formality complexity; Molecular weight is big, is difficult for striding film; Survival time is short, and only Japan in 1993 is used for blood reperfusion.Owing to cost an arm and a leg, may on crop, not use.
Summary of the invention
The objective of the invention is activity part structure, antioxidizing pseudo-enzyme compound and preparation thereof and application are provided according to natural SOD and CAT.Such pseudo-enzyme compound has SOD and CAT activity, can remove O simultaneously 2 -And H 2O 2The protection biomacromolecule avoids the active oxygen injury; reduce the electrolyte leakage rate; improve chlorophyll content and photosynthetic efficiency; regulate pore closure and vapour lock; strengthen the ability of plant cold resistance, drought resisting, anti-stain, disease-resistant, premature senescence resistance, make crop yield, have the effect of intending enzyme type plant-growth regulator, antiseptic-germicide and trace element fertilizer concurrently.
The antioxidizing pseudo-enzyme compound that reaches the object of the invention has the activity of superoxide dismutase (SOD) and catalase (CAT), has the chemical formula of general formula (I) expression:
M 1M 2L 1L 2Xn·pH 2O·qEtOH (I)
In the formula: M 1M 2=Cu (II) Zn (II), Fe (III) Zn (II), Fe (II) Zn (II), Mn (II) Mn (II), Fe (II) Fe (II), Zn (II) Zn (II), Cu (II) Mn (II), Cu (II) Mg (II), Ni (II) Zn (II), Co (II) Zn (II), Ni (II) Ni (II), Co (II) Co (II), Mn (III) Mn (III);
X＝Cl -、NO 3 -、ClO 4 -、Ac -；
n＝2、3、4、5；p＝0、2、2.5、3、4、5、6、7、8、10；q＝0、1、2；
L 1=TBIED i.e. four (benzimidazolyl-2 radicals methyl) quadrol, (tetrakis (benzimidazoly1-2methyl) ethylene diamine, chemical formula C 34H 32N 10);
L 2=benzoate anion PhCO 2 -, salicylate Sal -, nicotinic acid root PyCO 2 -, Yi Yansuan root reason i-PyCO 2 -, succinic BD 2-, glutarate pD 2-, terephthaldehyde's acid group o-PhD 2-
The described part TBIED that contains benzoglyoxaline is that the low temperature liquid phase reaction makes, promptly be to be solvent with a kind of in ethylene glycol or dimethylbenzene, oil of mirbane, polyphosphoric acid, the dimethyl formamide, ratio by polynary ammonia carboxylic acid and O-Phenylene Diamine amount is 1: 4～5, be total to thermal condensation 2～6 hours in 140～200 ℃, adopt gac or molecular sieve decolouring purifying, recrystallization, purification refine form in the ethanol (EtOH).
The preparation method's of described general formula (I) compound step is: part TBIED low-grade fever is dissolved in ethanol, adds equimolar M 1, M 2Soluble chloride or nitrate, perchlorate, acetate, perhaps add equimolar sodium salicylate or naotin, Yi Yansuan sodium, Soduxin, Sodium glutarate, para-phthalic sodium again, the stirring at room reaction, the throw out of generation, filtration, washing, the dry product that gets.
Compound of the present invention can be used as plant-growth regulator, sterilant and trace element fertilizer, and its consumption concentration is 1～100ppm, makes crop yield 5.1～49.42%.
With etc. the ligand L of mol ratio 1And L 2Reaction obtains dinuclear complex under 60～90 ℃ or the room temperature being heated to respective metal salt, is the anti-oxidant pseudo-enzyme compound of combination of pesticide and fertilizer.(190～400nm), particularly (going into＜300nm) distinguishing has multiple absorption peak to extreme ultraviolet, can strengthen absorption and the utilization of plant to luminous energy, improves photosynthetic efficiency, and avoids the injury of uv-radiation at ultraviolet region for this compounds and composition thereof.These pseudo-enzyme compounds have cold resistance, drought-resistant, anti-waterlogging, premature senescence resistance effect owing to itself is anti-oxidant, and can produce phytoalexin (phytoalexins by inducing plant, PA), the activated plant host defence mechanism has preventive and therapeutic effect to cotton wilt, rice sheath blight disease, ring rot of apple, asparagus splash disease, cucumber downy mildew, wheat hypochnus, Powdery Mildew etc.
Embodiment
Embodiment 1 CuZn (TBIED) Cl 42.5H 2Synthetic, the character of O and application
Part TBIED low-grade fever is dissolved in ethanol, adds to wait mole CuCl 22H 2O and ZnCl 2, stirring at room is separated out the bright green precipitation.Filtration, washing precipitation, infrared drying obtains light green powder, i.e. CuZnC 34H 37N 10Cl 4O 2.5The character of this compound is as follows:
Ultimate analysis % calculated value (Cacld.) C:45.55, N:15.62, H:4.13
Experimental value (Exp.) C:45.88, N:15.47, H:4.12
Molar conductance Λ m=87 S-cm 2Mol -1
UV, visible light (UV-Vis) spectrum, λ max/nm (ε m/ cm -1M -1): 278 (16830), 282 (16920), 720 (126).
Infrared (IR) spectrum/cm -1Except that the part eigen vibration, also have 282 (w), υ M-N324 (m), υ M-Cl
Electron paramagnetic resonance (EPR) spectrum; g ∏=2.28, g ⊥=2.10, A ∏=12.gmT.
Cyclic voltammetric (CV); Ec=-385mV (I c=87 μ A), E a=623mV (Ia=75.5 μ A).
Obtain catalysis O with nitroblue tetrazolium (NBT) (NBT) photoreduction method 2 -Disproportionation constant k=7.0 * 10 6M -1s -1
Use: this compound 10-20ppm aqueous solution sprays in important vegetative period or when meeting natural disaster by chance, but drought resisting, cold-resistant, anti-stain, premature senescence resistance make vegetable crop volume increase 6.7-15%.The 50-100ppm aqueous solution has the inhibiting rate of 47-64% to Rhizoctonia solani Kuhn, cotton-wilt fusarium, ring rot of apple bacterium, asparagus splash germ.
Embodiment 2 [FeZn (the TBIED) (Cl of μ-O) 2] Cl10H 2Synthetic, the character of O and application
Part TBIED is slightly soluble in ethanol, adds to wait mole FeCl 36H 2O and ZnCl 2, obtain salmon precipitation.Filter, washing, it is FeZnC that infrared drying obtains the reddish-brown powder 34H 52N 10O 11Cl 3The character of this compound is as follows:
Ultimate analysis % Cacld.C:40.65, N:13.95, H:5.18
Exp.C：40.63，N：13.90，H：4.97
Λm＝89?S·cm 2·mol -1
UV-Vis.λmax/nm(εm/cm -1M -1)：272(13500)，283(14950)，491(722)。IR/cm -1；279(m)，υ M-N；374(m)，υ M-Cl；434(m)，υ M-O。
EPR：gi＝4.3。
CV：Ec＝57mV(Ic＝3.4μA)，Ea＝498mV(Ia＝4.6μA)。
k＝3.69×10 6M -1s -1。
Use: this compound 5-15ppm aqueous solution is tillered at gramineous crop, blooming stage or meet natural disaster by chance and spray, and can increase production 5-21%.
Embodiment 3 FeZn (TBIED) are (NO (OH) 3) 44H 2Synthetic, the character of OEtOH and application
Part TBIED low-grade fever is dissolved in ethanol, adds to wait mole Fe (NO 3) 39H 2O, and Zn (NO 3) 26H 2O obtains red-brown precipitation.Filter, washing, infrared drying, obtaining the reddish-brown powder is FeZnC 36H 47N 14O 18The character of this compound is as follows:
Ultimate analysis (%) Cacld.C:39.85, N:18.08, H:4.34.
Exp.C：39.77，N：17.93，H：4.10。
Λ m＝176?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：283(17040)。
IR/cm -1：286(m)，υ M-N；434(m)υ M-O。
EPR：gi＝4.3。
CV：Ec＝298mV(Ic＝0.45μA)；Ea＝551mV(Ia＝0.69μA)。
k＝3.58×10 6M -1s -1。
Use: this compound 5-20ppm aqueous solution is tillered at gramineae crop, blooming stage or meet natural disaster by chance and spray, and can increase production 8.7-20.9%.
Embodiment 4 Fe 2(TBIED) (O) Cl 46H 2Synthetic, the character of O and application
Part TBIED low-grade fever is dissolved in ethanol, adds the FeCl that doubles the ligand substance amount 36H 2O stirs, and has red-brown precipitation to produce.Filter, washing, it is Fe that infrared drying obtains orange red powder 2C 34H 44N 10Cl 4O 7The character of this compound is as follows:
Ultimate analysis % Cacld.C:42.60, N:14.62, H:4.59
Exp.C：42.98，N：14.75，H：4.93
Λ m＝137?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：272(25500)，280(26200)，319(23060)，514(1630)。
IR/cm -1：297(m)，υ N-Fe；368(m)，υ Fe-Cl；430(m)，υ Fe-O。
EPR：g i＝4.3。
CV：Ec＝140mV(I c＝37.7μA)，Ea＝217mV(Ia＝5.8μA)；
E c′＝292mV(I o′＝5.8μA)，E a′＝396mV(I a′＝5.9μA)。
k＝4.64×10 7M -1s -1。
Use: Rhizoctonia solani Kuhn, cotton-wilt fusarium, wheat rust bacterium, ring rot of apple bacterium, asparagus splash bacterium are resisted this compound 50-100ppm aqueous solution but rate is 60-76%.
Embodiment 5 Zn 2(TBIED) Cl 43H 2Synthetic, the character of O2EtOH and application
Part TBIED low-grade fever is dissolved in ethanol, adds the ZnCl that doubles part 2, produce a large amount of white precipitates.Filter, washing, it is Zn that infrared drying obtains white precipitate 2C 38H 50N 10O 5Cl 4The character of this compound is as follows:
Ultimate analysis % Cacld.C:45.66, N:14.02, H:5.01
Exp.C：45.75，N：13.98，H：4.64
Λ m＝147?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：276(16500)，282(18600)。
IR/cm -1：292(m)，ν Zn-N；346(m)，ν Zn-Cl。
k＝1.87×10 6M -1s -1。
Use: this compound 12-20ppm aqueous solution is in important vegetative period of gramineous crop or meet natural disaster by chance and spray, and can increase production 10-25%.
Embodiment 6 CuMn (TBIED) (NO 3) 43H 2O is synthetic, character and application
Part TBIED low-grade fever is dissolved in ethanol, adds to wait mole Cu (NO 3) 23H 2O and 50% Mn (NO 3) 2Solution produces blue precipitation.Filter, washing, it is CuMnC that infrared drying obtains light blue powder 34H 38N 14O 15The character of this compound is as follows:
Ultimate analysis % Cacld.C:40.78, N:19.59, H:3.80
Exp.C：40.34，N：19.97，H：3.84
Λm＝89?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：275(18700)，283(17000)，704(274)。
IR/cm -1：286(m)，υ M-N，434(m)，υ M-O。
EPR：g ∏＝2.267，g ⊥＝2.106，A ∏＝12.0mT；
g 3＝2.0848，g 4＝1.975，A i＝9.0mT。
CV：Ec＝-161mV(ic＝14μA)，Ea＝-30mV(Ia＝16μA)；
E a′＝595(I a′＝3.0μA)。
k＝1.70×10 7M -1s -1。
Use: this compound 5-50ppm can strengthen the resistance of farm crop and vegetable crop, volume increase 7.5-24%.The 50-100ppm aqueous solution is 40-60% to Rhizoctonia solani Kuhn, cotton-wilt fusarium, ring rot of apple bacterium and asparagus splash germ inhibiting rate.
Embodiment 7 CuMg (TBIED) Cl 4EtOH is synthetic, character and application
Part TBIED low-grade fever is dissolved in ethanol, adds to wait mole CuCl 22H 2O and MgCl 26H 2O, the bright green precipitation appears in stirring.Filter, washing, it is CuMgC that infrared drying obtains the light green powder 36H 38N 10Cl 4O.The character of this compound is as follows:
Ultimate analysis % Cacld.C:50.48, N:16.36, H:4.44
Exp.C：50.60，N：16.60，H：4.87
Λ m＝156?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：275(27000)，281(31100)，720(127)。
IR/cm -1：286(m)，υ M-N，347(m)，υ M-Cl。
EPR：g ∏＝2.27，g ⊥＝2.11，A ∏＝13.6mT。
CV：Ec＝50mV(Ic＝5.87μA)，Ea＝188mV(Ia＝8.57μA)。
k＝1.56×10 6M -1s -1。
Use: this compound 10-30ppm aqueous solution can strengthen farm crop and vegetable crop photosynthesis and resistance,
Volume increase 5.0-49.42%.
Embodiment 8 [FeZn (TBIED) (Sal -) (OH)] Cl 36H 2Synthetic, the character of O and application
Part TBIED low-grade fever is dissolved in ethanol, adds to wait mole FeCl 36H 2Cl 2And ZnCl 2And sodium salicylate NaSal, obtain the intense violet color precipitation.Filter, wash, it is FeZnC that infrared drying obtains black purple powder 41H 50N 10O 10Cl 3
The character of this compound is as follows:
Ultimate analysis % Cacld.C:52.73, N:15.02, H:5.36
Exp.C：52.51，N：15.32，H：5.54
Λm＝96?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：275(28000)，280(32000)，305(3200)，490(1500)。
IR/cm -1；275(m)、297(m)，υ M-N；430(m)，υ M-O。
EPR：g i＝4.30。
CV：Ec＝351mV(Ic＝3.16μA)，Ea＝489mV(Ia＝2.47μA)。
k＝1.37×10 6M -1s -1。
Use: this compound 10-20ppm aqueous solution energy inducing paddy rice, wheat, lettuce produce phytoalexin (PA).
Embodiment 9 NiZn (TBIED) (PyCO 2 -) Cl 34H 2Synthetic, the character of O and application
Part TBIED low-grade fever is dissolved in ethanol, adds to wait mole NiCl 26H 2O and ZnCl 2And naotin PyCOONa or PyCOOH+NaOH, obtain the red-purple precipitation.Filter, wash, infrared drying, obtaining the red-purple powder is NiZnC 40H 44N 11O 6Cl 3The character of this compound is as follows:
Ultimate analysis % Cacld.C:47.78, N; 15.33, H:4.38
Exp.C：47.53，N：15.16，H：4.34
Λm＝142?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：268(25000)，275(26000)，282(29000)，343(1690)，369(1650)，572(400)，880(280)。
IR/cm -1；285(m)，297(m)，υ M-N；360(m)，υ M-Cl，430(m)，υ M-O。
CV：Ec＝840mV(Ic＝5.0μA)，Ea＝1130mV(Ia＝25μA)。
EPR: no signal.
k＝3.6×10 5M -1s -1。
Use: this compound 5-25ppm aqueous solution sprays, and can strengthen crop anti-adversity, volume increase 5.1-15%.
Embodiment 10 [Ni 2(TBIED) (BD 2-)] Cl 22H 2Synthetic, the character of O and application
Part TBIED heating is dissolved in ethanol, adds the NiCl that doubles the ligand substance amount 26H 2O produces a large amount of red-purple precipitations, adds to wait mole Soduxin BDNa again 2Or Succinic Acid H 2BD+2NaOH, stirring at room 2 hours.Filter, wash, it is Ni that infrared drying obtains the red-purple powder 2C 38H 40N 10O 6Cl 2The character of this compound is as follows:
Ultimate analysis % Cacld.C:49.54, N:15.22, H:4.35
Exp.C：49.87，N：15.39，H：4.44
Λm＝135?S·cm 2·mol -1
UV-Vis，λmax/nm(εm/cm -1M -1)：268(17800)，276(16500)，282(19800)，339(1300)，369(1400)，890(140)。
IR/cm -1；274(m)，285(m)，υ Ni-N；430(m)，υ Ni-O。
CV：Ec＝850mV(Ic＝4.50μA)，Ea＝1120mV(Ia＝25μA)。
EPR: no signal
k＝1.50×10 6M -1s -1。
Use: this compound 4-20ppm aqueous solution sprays, and can strengthen crop anti-adversity; And can improve the utilization ratio of nitrogenous fertilizer in the soil, volume increase 7.51-14.0%.
Embodiment 11 [Mn 2(TBIED) (PD 2-)] (ClO 4) 48H 2Synthetic and the character of O
Part TBIED low-grade fever is dissolved in ethanol, adds the Mn (ClO that is twice in part 4) 36H 2O produces white precipitate, and what be incorporated in that the ligand substance amount equates defends diacid sodium Na again 2PD or H 2PD+2NaOH, stirring at room 2 hours is filtered, is washed, and it is Mn that infrared drying obtains the light yellow crystal powder 2C 39H 54N 10O 12Cl 4The character of this compound is as follows:
Ultimate analysis % Cacld.C:34.36, N:10.28, H:3.96
Exp.C：34.21，N：10.56，H：4.14
Λm＝256?S·cm 2·mol -1
UV-Vis，λmax/nm(ε m/cm -1M -1)：274(12400)，280(13400)，340(sh)。
IR/cm -1；275(m)，υ Mn-N；380，433(m)，υ Mn-O。
CV：Ec＝720mV，-350mV；Ea＝1260mV。
EPR：g i＝2.0030。
k＝1.18×10 7M -1s -1。
Embodiment 12 Fe 2(TBIED) 2(o-PhD 2-) (NO 3) 45H 2Synthetic and the character of O
Deng mole part TBIED and Fe (NO 3) 39H 2The O heating was reacted 2 hours in ethanolic soln, added a phthalic acid sodium Na again 2(o-PhD) or o-PhDH 2+ 2NaOH, stirring at room 2～3 hours obtains reddish brown precipitation.Filter, wash, it is Fe that infrared drying obtains the red-brown powder 2C 76H 78N 24O 21The character of this compound is as follows:
Ultimate analysis % Cacld.C:51.42, N:18.94, H:4.40
Exp.C：51.82，N：18.80，H：4.62
Λm＝146?S·cm 2·mol -1
UV-Vis，λmax/nm(ε m/cm -1M -1)：275(25000)，280(26000)，305(3200)，490(1500)。
IR/cm -1；278(m)，297(m)，υ Fe-N；430(m)，υ Fe-O。
EPR：g i＝4.30。
CV：Ec＝351mV(Ic＝3.16μA)，Ea＝489mV(Ia＝2.47μA)。
k＝2.6×10 7M -1s -1。
Also can synthesize listed compound in the table 1 according to similar method among the embodiment, their character and application see Table 1.
Embodiment 13
Mix with moles such as example I title complex and example VI title complexs, the aqueous solution of this composition 5～20ppm has production-increasing function better than with the corresponding simplification compound of concentration to cotton, corn, increases production 2～5% more.
When compound of the present invention uses as sterilant, can be with carrier or the mixing diluents that allows in compound of the present invention and other plant protection, whereby it is modulated into normally used various formulation, wait as mixture, granule, aqueous emulsion and to use, also can mix and use or simultaneously and use with other agricultural chemicals such as sterilant, Insecticides (tech) ﹠ Herbicides (tech), plant-growth regulator etc.
Table 1 TBIED other anti-oxidant plan enzymatic property and application

Claims (4)

1, antioxidizing pseudo-enzyme compound has superoxide dismutase and catalatic activity, it is characterized in that having general formula (I) expression chemical formula:
M 1M 2L 1L 2Xn·pH 2O·qEtOH (I)
In the formula: M 1M 2=Cu (II) Zn (II), Fe (III) Zn (II), Fe (II) Zn (II), Mn (II) Mn (II), Fe (II) Fe (II), Zn (II) Zn (II), Cu (II) Mn (II), Cu (II) Mg (II), Ni (II) Zn (II), Co (II) Zn (II), Ni (II) Ni (II), Co (II) Co (II), Mn (III) Mn (III);
X＝Cl -、NO 3 -、ClO 4 -、Ac -；
n＝2、3、4、5；
p＝0、2、2.5、3、4、5、6、7、8、10；
q＝0、1、2?；
L 1=four (benzimidazolyl-2 radicals methyl) quadrol;
L 2＝PhCO 2 -、Sal -、PyCO 2 -、i-PyCO 2 -、BD 2-、pD 2-、o-PhD 2-。
2, the described pseudo-enzyme compound of claim 1, it is characterized in that part is four (benzimidazolyl-2 radicals methyl) quadrol, be so that any is a solvent by the ratio 1: 4～5 of polynary ammonia carboxylic acid and O-Phenylene Diamine amount in 140～200 ℃ of thermal condensations 2～6 hours altogether in ethylene glycol, dimethylbenzene, oil of mirbane, polyphosphoric acid, the dimethyl formamide, the decolouring purifying, refining forming.
3, the preparation method of the described pseudo-enzyme compound of claim 1, its characterization step is: part four (benzimidazolyl-2 radicals methyl) quadrol low-grade fever is dissolved in ethanol, adds equimolar M 1, M 2Soluble chloride or nitrate, perchlorate, acetate, perhaps add equimolar sodium salicylate or naotin, Yi Yansuan sodium, Soduxin, Sodium glutarate, para-phthalic sodium again, the stirring at room reaction, the throw out of generation, filtration, washing, the dry product that gets.
4, the application of the described pseudo-enzyme compound of claim 1 is characterized in that as plant-growth regulator, antiseptic-germicide and trace element fertilizer its consumption concentration is 1～100ppm.
CNB021155224A 2002-02-04 2002-02-04 ANtioxidizing pseudo-enzyme compound and its preparing process and application Expired - Fee Related CN1166670C (en)

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