CN103641732B - Glycine betaine type plant growth regulator containing naphthalene acetamide groups - Google Patents
Glycine betaine type plant growth regulator containing naphthalene acetamide groups Download PDFInfo
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- CN103641732B CN103641732B CN201310730592.8A CN201310730592A CN103641732B CN 103641732 B CN103641732 B CN 103641732B CN 201310730592 A CN201310730592 A CN 201310730592A CN 103641732 B CN103641732 B CN 103641732B
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- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 37
- RFRMFTYHFLNORD-UHFFFAOYSA-N acetamide;naphthalene Chemical group CC(N)=O.C1=CC=CC2=CC=CC=C21 RFRMFTYHFLNORD-UHFFFAOYSA-N 0.000 title claims abstract description 8
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title abstract description 10
- 229960003237 betaine Drugs 0.000 title abstract description 6
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 19
- 235000016068 Berberis vulgaris Nutrition 0.000 claims description 6
- 241000335053 Beta vulgaris Species 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 230000035784 germination Effects 0.000 abstract description 10
- 230000001737 promoting effect Effects 0.000 abstract 1
- 230000004083 survival effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 241000209140 Triticum Species 0.000 description 14
- 235000021307 Triticum Nutrition 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 235000013399 edible fruits Nutrition 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 0 C[Mn](c1cccc2ccccc12)([N+](*)[O-])=C Chemical compound C[Mn](c1cccc2ccccc12)([N+](*)[O-])=C 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MRKGZSUOHWCQNB-UHFFFAOYSA-N 4-(1h-indol-2-yl)butanoic acid;sodium Chemical compound [Na].C1=CC=C2NC(CCCC(=O)O)=CC2=C1 MRKGZSUOHWCQNB-UHFFFAOYSA-N 0.000 description 2
- KPMNIDFNWOSWOJ-UHFFFAOYSA-N CC(Cl)=O.c1ccc2ccccc2c1 Chemical compound CC(Cl)=O.c1ccc2ccccc2c1 KPMNIDFNWOSWOJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- JTEDVYBZBROSJT-UHFFFAOYSA-N indole-3-butyric acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CNC2=C1 JTEDVYBZBROSJT-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000001161 mammalian embryo Anatomy 0.000 description 2
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 230000007226 seed germination Effects 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CCBICDLNWJRFPO-UHFFFAOYSA-N 2,6-dichloroindophenol Chemical compound C1=CC(O)=CC=C1N=C1C=C(Cl)C(=O)C(Cl)=C1 CCBICDLNWJRFPO-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- IXVMHGVQKLDRKH-VRESXRICSA-N Brassinolide Natural products O=C1OC[C@@H]2[C@@H]3[C@@](C)([C@H]([C@@H]([C@@H](O)[C@H](O)[C@H](C(C)C)C)C)CC3)CC[C@@H]2[C@]2(C)[C@@H]1C[C@H](O)[C@H](O)C2 IXVMHGVQKLDRKH-VRESXRICSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XAPZTDQEQZUXOM-UHFFFAOYSA-N CC1C=CC=C2C=CC=C(CC(Cl)=O)C12 Chemical compound CC1C=CC=C2C=CC=C(CC(Cl)=O)C12 XAPZTDQEQZUXOM-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- QUDLOWBMTFLAQM-UHFFFAOYSA-N Cc1ccc(cccc2CC(O)=O)c2c1 Chemical compound Cc1ccc(cccc2CC(O)=O)c2c1 QUDLOWBMTFLAQM-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005985 Paclobutrazol Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- IXVMHGVQKLDRKH-KNBKMWSGSA-N brassinolide Chemical compound C1OC(=O)[C@H]2C[C@H](O)[C@H](O)C[C@]2(C)[C@H]2CC[C@]3(C)[C@@H]([C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C)CC[C@H]3[C@@H]21 IXVMHGVQKLDRKH-KNBKMWSGSA-N 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- -1 compound sodium salt Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000014284 seed dormancy process Effects 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a glycine betaine type plant growth regulator containing naphthalene acetamide groups. The structure of the glycine betaine type plant growth regulator is described as a general formula I, wherein X is selected from Cl and Br, and M is selected from K, Na and NH4. The glycine betaine type plant growth regulator with the general formula I has useful functions of promoting germination, rooting and increasing the yield and improving the quality, and can be widely applied to the yield increase or survival rate increase of agriculture and forestry.
Description
Technical field the invention belongs to pesticide plant growth regulator field, relates to a kind of Beet alkaline plant growth regulator containing naphthalene acetamide group.
Background technology
Plant-growth regulator is in control seed germination and dormancy, and hestening rooting, promotes cell elongation and division, control lateral bud or tiller, controlling plant type, control to bloom, induction s.m.p fruit, flower and fruit thinning, controls shedding, controls fruit shape or ripening stage, strengthen resistance (disease-resistant, drought resisting, anti-salinity, freeze proof), strengthen and absorb fertilizer ability, increase sugar or change acidity, improve the aspect such as fragrance and color and luster and serve positive effect.Guo Qifang (Guo Qifang, Ma Qianquan, Sun Can etc., exogenous betaine improves the research of wheat seedling salt resistance, northwest Botany Gazette, 2004, 24 (9): 1680-1686), Li Xinmei (Li Xinmei, Sun Bingyao, Tan Jianzhong, the progress of trimethyl-glycine and plant stress-resistance sexual intercourse, research of agricultural science, 2006, 27 (3): 66-70), Meng Feng (Meng Feng, Yu Songlin, Zheng Qiangqing etc., the progress of trimethyl-glycine and plant stress-resistance sexual intercourse, China's agronomy circular, 2008, 24 (4): 225-228) etc. betaine type quaternary ammonium salt is reported respectively such as formula the purposes of II compound as plant-growth regulator, for agricultural produce, improve quality and improve resistance.In the prior art, a kind of Beet alkaline plant growth regulator containing naphthalene acetamide group and activity thereof have no open at home and abroad as described in the present invention.
Summary of the invention the object of this invention is to provide the plant-growth regulator of the low and use safety of a kind of hestening rooting, volume increase, precocity, raising quality, cost, is to provide a kind of Beet alkaline plant growth regulator containing naphthalene acetamide group specifically.It can be used in agriculture significantly volume increase or surviving rate raising.
Technical scheme of the present invention is as follows:
Containing a Beet alkaline plant growth regulator for naphthalene acetamide group, structure is as shown in general formula I:
In formula, X is selected from Cl or Br;
M is selected from K, Na or NH
4.
The preparation feedback formula of formula I is as follows:
Compound of formula III in suitable solvent with equimolar alkaline solution in 20-40 DEG C of saponification reaction 2h, revolve and steam solvent and water obtains general formula compound I, the preparation of compound of formula III is shown in that the present invention synthesizes example.
Suitable solvent selected from methanol, ethanol, Virahol, DMF, dimethyl sulfoxide (DMSO) etc.; Alkaline solution is selected from NaOH, KOH or the ammonia soln of 20 ~ 30%.
The present invention also comprises the plant growth regulator composition of formula I as active ingredient, in said composition, active ingredient refers to formula I or formula I and other active ingredients a kind of, two or more composition formed as plant-growth regulator such as Nafusaku, sodium nitrophenolate, indolebutyric acid sodium, and also comprises acceptable carrier in agricultural or forestry in this plant growth regulator composition.
The formulation of composition of the present invention can be aqua, wettable powder, water dispersible granules etc., in order to improve the utilization ratio of active principle, usually adds appropriate tensio-active agent when formulated.
The method of plant growth regulator composition coordinate plant growth of the present invention: the present composition is imposed on by the concentration of active ingredient 0.1 ~ 1000 μ g/mL and needs on the medium of growth regulation, preferred working concentration scope is 10 ~ 100 μ g/mL, for some application, can as required in plant growth regulator composition of the present invention, add one or more other sterilant, sterilant, middle amount or trace element fertilizer etc., additional good effect can be produced thus.
Advantage of the present invention and positively effect:
Current commercial plant-growth regulator is mainly divided into water-soluble, solubility in acid, caustic solubility and insoluble four classes with solvability classification.Water-soluble plant growth regulator as choline dichloride, help strong element, it is long to be mainly used in dwarfing plants control; Solubility in acid plant-growth regulator is as DA-6(diethylamino ethanol caproate Citrate trianion) owing to easily separating out Sum decomposition in the basic conditions, therefore can only dissolve in acidic aqueous solution and use; Caustic solubility plant-growth regulator such as sodium nitrophenolate, Nafusaku etc. are easily separated out or indissoluble in acidic aqueous solution, dissolve and use in alkaline aqueous solution; Insoluble plant growth regulator such as paclobutrazol, brassinolide etc. not easily make aqua product because being insoluble in water; Optimal plant-growth regulator formulation is aqua formulation.
Formula I plant-growth regulator of the present invention has amino acid pattern amide structure, it has water-soluble, solubility in acid and alkali-soluble feature simultaneously, therefore can add in various neutrality, acidity or alkaline fertilizer, this is not available for current most efficient plant growth regulator.And plant-growth regulator of the present invention is compared with existing plant-growth regulator and is also had superior over-all properties, as being better than DA-6, naphthylacetic acid etc. in growth-promoting root, field experiment shows, this plant-growth regulator can make wheat increase yield reach more than 10 ~ 19%, can apple with ripe color be accelerated and obviously improve mouthfeel, also show for crops such as great Jiang, capsicum, tomatoes that stem stalk is sturdy, leaf look dark green, volume increase reaches more than 20%.Plant-growth regulator of the present invention has cost advantage low, safe and convenient to use, has very high using value and commercialization potentiality.
It is clearly understood that, in claim limited range of the present invention, can various conversion and change be carried out.
Embodiment
Following synthesis example, formulation examples and raw experimental result of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthesis example
Example 1, formula I
athe synthesis of compound:
(1) preparation of naphthalene Acetyl Chloride 98Min.:
Get 104g (0.5mol) Nafusaku and, in 500mL four-hole bottle, add suitable quantity of water, heating makes it dissolve, and while hot with concentrated hydrochloric acid (36%) acidifying, adjusts pH to 2 ~ 3, and cooling suction filtration obtains naphthylacetic acid white solid, dries, obtains white solid 87.4g, yield 94%.
55.8g(0.3mol is added successively in 500mL there-necked flask) naphthylacetic acid, 71.4g(0.6mol) sulfur oxychloride and 150mL toluene, 0.3mLN is dripped under stirring, dinethylformamide, temperature rising reflux 2h, revolve and steam toluene and excessive sulfur oxychloride, obtain pale yellowish oil liquid 58.1g, yield 95%.
(2) preparation of naphthalene acetyl-N, N-dimethyl-1,3-propylene diamine:
10.2g(0.1mol is added successively in 250mL there-necked flask) N, N-dimethyl-1,3-propylene diamine and 100mL ethyl acetate, ice bath temperature control 0 ~ 20 DEG C, drips the mixed solution by 20.4g naphthalene Acetyl Chloride 98Min. and 30mL ethyl acetate, drips and finishes, stirring at room temperature 2h; Room temperature drips 20.0g20%NaOH solution, and separatory gets organic phase, uses appropriate anhydrous sodium sulfate drying, and filter, filtrate revolving steams solvent, obtains pale yellowish oil liquid 26.2g, yield 97%.
(3) preparation of naphthalene acetyl-N, N-dimethyl-1,3-propylene diamine quaternary ammonium salt:
13.5g (0.05mol) naphthalene acetyl-N is added successively, N-dimethyl-1,3-propylene diamine and 100mL toluene in 250mL there-necked flask; stir lower dropping 5.4g methyl chloroacetate, drip and finish, temperature rising reflux reaction 4h; revolve and steam toluene, obtain white waxy solid 18.1g, yield 96%.
(4) formula I
athe preparation of compound:
The above-mentioned obtained naphthalene acetyl-N of 18.9g (0.05mol) is added successively, N-dimethyl-1,3-propylene diamine quaternary ammonium salt and 100mL methyl alcohol in 250mL there-necked flask; stirring and dissolving, room temperature drips 10.0g20%NaOH solution, drips and finishes; temperature control 20-40 DEG C of reaction 2h; be cooled to room temperature, revolve and steam solvent and water, add 20mL Virahol; separate out a large amount of white powdery solid; suction filtration, dries to obtain white solid 17.4g, yield 90%.
Formula I
athe proton magnetic data of compound sodium salt is as follows:
1HNMR（500MHzDMSO-d6)δ(ppm)：8.212-8.230(1H,N-H),7.415-8.084(m,7H,Ar-H),4.19(s,2H,CH2),3.877(s,2H,CH2),3.056-3.094(q,2H,CH2),2.124-2.153(t,2H,CH2),3.331(s,6H,CH3),1.470-1.526(m,2H,CH2)，m.p.:146-150℃。
According to the method for example 1, methyl chloroacetate is changed into the bromide that methyl bromoacetate can obtain formula I, by formula I 30 ~ 40% potassium hydroxide solutions or ammoniacal liquor saponification, sylvite or the ammonium salt of formula I can be obtained.
Test through preliminary raw test, X is Br, M when being K or NH4, and survey active substantially without impact on raw, therefore following life survey is with I
a(M is Na, X is Cl) carries out Formulation and raw survey is tested.
Example of formulations
Example 2,5% formula I
athe preparation of compound aqua:
In 250mL there-necked flask, add 5g formula I respectively
acompound and 90mL water, stirring and dissolving, adds 5g tween-80, stirs, and obtains 5% formula I
athe aqua of compound.
Example 3,10% formula I
athe preparation of Compound D A-6 composition aqua:
In 250mL there-necked flask, add 6g formula I respectively
acompound, 4gDA-6 and 85mL water, stirring and dissolving, adds 5g tween-80, stirs, and obtains the composition aqua of 100g clear.
Example 4,20% formula I
athe preparation of compound indolebutyric acid composition of sodium aqua:
In 250mL there-necked flask, add 15g formula I respectively
acompound, 5g indolebutyric acid sodium and 75mL water, stirring and dissolving, adds 5g tween 20, stirs to clarify transparent, obtains 100g formula I
acompound and indolebutyric acid composition of sodium aqua.
Raw survey embodiment
Example 5, wheat seed germinating are tested: respectively by formula I
acompound and DA-6(Henan Zheng Shi Chemical Co., Ltd. produce) be mixed with 5% formula I
acompound aqua and 5%DA-6 aqua, be diluted with distilled water into the plant-growth regulator solution that concentration is 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL respectively.The above-mentioned diluent of wheat seed is cultivated 8h, often process 100 seeds, repeat, after process, seed is placed in the culture dish of double-layer filter paper for each 3 times, 25 DEG C of insulation vernalization, and keep every day filter paper moistening, in vernalization, every day observes the germination of each process, radicel length about with seed long 1/2 for standard, wheat germination rate in each ware is added up after 24h, compare with the DA-6 of same concentrations and clear water (Ck), calculate each diluent germination promotion rate, result is as following table 1 simultaneously simultaneously.
Table 1 wheat germination testing data
As can be seen from Table 1, the percentage of germination that compound of the present invention respectively processes is better than contrast agents DA-6 on the whole, is significantly better than the situation of clear water process (Ck).
Example 6, the experiment of seed soaking growth-promoting root: respectively by formula I
acompound and DA-6(Henan Zheng Shi Chemical Co., Ltd. produce) be mixed with 5% formula I
acompound aqua and 5%DA-6 aqua, be diluted with distilled water into the plant-growth regulator solution that concentration is 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL respectively.Select the wheat seed that Seed size is even, full, after sterilization being carried out to seed with hypochlorite solution, put it in gauze, 10h is soaked with above-mentioned diluent in beaker, then by wheat seed uniform discharge on moistening paper bed, when to put bed, embryo portion is upwards and towards the same side of germination box, certain distance to be had between seed, to ensure that seed fully absorbs moisture, 20 wheats are put in each process, put it into after being well placed seed in complete intelligent weather vegetation box and carry out germination treatment 24h, period regularly will add distilled water makes paper bed keep moistening.Treat that wheat main root exposes about 2mm, by its kind in the solid medium solidified, multiple 3 times of each process counterpoise, then puts into complete intelligent weather vegetation box and cultivates.Use kind of calliper main root, stem high after 40h, and make detailed record.Compare with the DA-6 of same concentrations and clear water (Ck), result is as following table 2 simultaneously.
Table 2 is soaked seed Rooting data
Experiment of taking root executed by example 7, base: respectively by formula I
acompound and DA-6(Henan Zheng Shi Chemical Co., Ltd. produce) be mixed with 5% formula I
acompound aqua and 5%DA-6 aqua, be diluted with distilled water into the plant-growth regulator solution that concentration is 2.5 μ g/mL, 5 μ g/mL, 10 μ g/mL, 50 μ g/mL, 100 μ g/mL respectively.Select the wheat seed that Seed size is even, full, after sterilization being carried out to seed with hypochlorite solution, put it in gauze, with the water soaking 10h of flowing in beaker, then by wheat seed uniform discharge on moistening paper bed, when to put bed, embryo portion is upwards and towards the same side of germination box.Certain distance to be had between seed, to ensure that seed fully absorbs moisture, 20 wheats are put in each process, multiple 3 times of each process counterpoise, put it into after being well placed seed in complete intelligent weather vegetation box and carry out germination treatment 24h, period regularly will add distilled water makes paper bed keep moistening.Treat that wheat main root exposes about 2mm, its kind is added with in the solid medium of above-mentioned diluent what solidified, then put into complete intelligent weather vegetation box and cultivate.Use kind of calliper main root, stem high after 48h, and make detailed record, compare with the DA-6 of same concentrations and clear water (Ck), result is as following table 3 simultaneously.
Rooting data executed by table 3 base
Example 8, field experiment: 3 process are established altogether to apple experiment, the bough that the new Gala apple of each processing selecting sets upper 3 growth potentials suitable carries out, and test gets strain at random, tree-plot, repeats, respectively sprays once respectively at red fuji apple young fruit period and fruit expanding period for 3 times, foliage-spray clear water in contrast, after results, measure the quality parameter of apple respectively, wherein, VC content adopts 2,6-Dichlorophenol indophenol method measures, and soluble sugar content adopts anthrone colorimetry to measure, and result is as following table 4.
Table 4 apple quality index Test data
To sum up data can find out formula I of the present invention
acompound seed germination, take root in there is unusual effect, have a clear superiority in than contrast agents (DA-6); After foliage-spray is carried out to apple, while improving apple production, the outward appearance of apple and many-sided quality are also significantly improved, can find out that the compounds of this invention is a kind of plant-growth regulator of excellence.
Claims (2)
1. containing a Beet alkaline plant growth regulator for naphthalene acetamide group, as shown in general formula I:
In formula, X is selected from Cl or Br; M is selected from K, Na or NH
4.
2. a plant growth regulator composition, containing formula I according to claim 1 as acceptable carrier in Activities of Plant Growth Regulators component and agricultural or forestry.
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