CN103694129B - Beet alkaline plant growth regulator containing cinnamamide groups - Google Patents
Beet alkaline plant growth regulator containing cinnamamide groups Download PDFInfo
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- CN103694129B CN103694129B CN201310732463.2A CN201310732463A CN103694129B CN 103694129 B CN103694129 B CN 103694129B CN 201310732463 A CN201310732463 A CN 201310732463A CN 103694129 B CN103694129 B CN 103694129B
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- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 33
- 235000016068 Berberis vulgaris Nutrition 0.000 title claims abstract description 8
- 241000335053 Beta vulgaris Species 0.000 title claims abstract description 8
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical group NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 19
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical group NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 230000004083 survival effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 241000209140 Triticum Species 0.000 description 14
- 235000021307 Triticum Nutrition 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- 230000035784 germination Effects 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 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
- 235000013399 edible fruits Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 230000007226 seed germination Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 description 2
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- NQBWNECTZUOWID-QSYVVUFSSA-N cinnamyl cinnamate Chemical compound C=1C=CC=CC=1\C=C/C(=O)OC\C=C\C1=CC=CC=C1 NQBWNECTZUOWID-QSYVVUFSSA-N 0.000 description 2
- 239000002872 contrast media Substances 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
- 230000000704 physical effect Effects 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
- 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
- 238000003786 synthesis reaction 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
- KJRRTHHNKJBVBO-AATRIKPKSA-N (e)-3-(2-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1Cl KJRRTHHNKJBVBO-AATRIKPKSA-N 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
- IWZNLKUVIIFUOG-UHFFFAOYSA-N 2-chloro-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(Cl)=CC1=CC=CC=C1 IWZNLKUVIIFUOG-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- MEBWABJHRAYGFW-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(Cl)C=C1Cl MEBWABJHRAYGFW-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
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 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
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000539 amino acid group Chemical group 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
- 150000008430 aromatic amides Chemical group 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
- 235000009508 confectionery Nutrition 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
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 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
- 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
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012074 organic phase 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
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000014284 seed dormancy process Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 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)
Abstract
The invention discloses a beet alkaline plant growth regulator containing cinnamamide groups. The structure is shown as a general formula I. In the formula, X is selected from C1 or Br; Y is selected from H or C1; Z is selected from H or C1; M is selected from Na, K or NH4. The compound with the general formula I has excellent functions of promoting sprouting and rooting, increasing yield and improving quality, and can be widely applied to the yield increase or the survival rate increase of agriculture or forestry.
Description
Technical field
The invention belongs to plant-growth regulator field in agricultural chemicals, be specifically related to a kind of Beet alkaline plant growth regulator containing cinnamide 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 cinnamide group and activity thereof have no open as described in the present invention.
Summary of the invention
The object of the present invention is to provide a kind of plant-growth regulator promoting the low and use safety of seed germination, growth-promoting root, volume increase, precocity, raising quality, use cost, be to provide a kind of Beet alkaline plant growth regulator containing cinnamide group specifically, it can be used for agricultural, the significantly volume increase of forestry or surviving rate and improves.
Technical scheme of the present invention is as follows:
The invention provides a kind of Beet alkaline plant growth regulator containing cinnamide group, its structure is as shown in general formula I:
In formula: X is selected from Cl or Br;
Y is selected from H or Cl;
Z is selected from H or Cl;
M is selected from Na, K or NH
4.
Compound of Formula I can be obtained by following reaction:
In formula, each group definition is the same.
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%.
Table 1 lists structure and the physical properties of partial Formula I.
The structure of table 1 segment bounds I and physical properties
| Compound | X | Y | Z | M | Outward appearance | Fusing point/DEG C |
| Ia | Cl | H | H | Na | Light yellow solid | 182-185 |
| Ib | Cl | Cl | H | Na | Light yellow solid | 194-196 |
| Ic | Cl | H | Cl | Na | Light yellow solid | 205-207 |
| Id | Cl | Cl | Cl | Na | Light yellow solid | 264-267 |
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, a large amount of or trace element fertilizer etc., additional excellent results can be produced thus.
Advantage of the present invention and positively effect:
Current commercial plant-growth regulator is mainly divided into water-soluble, acid-soluble, 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; Acid-soluble 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 of the present invention has unique chemical structure, containing amino acid group and aromatic amides group, it has water-soluble, acid-soluble, alkali-soluble feature simultaneously, therefore can add in various neutrality, acidity or alkaline fertilizer, this point is not available for current most efficient plant growth regulator.Moreover, plant-growth regulator of the present invention is compared with existing plant-growth regulator has 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 15 ~ 20%; Accelerate apple with ripe color, improve soluble sugar and VC content in apple, make mouthfeel more sweet, improve one-level fruit rate; Show for great Jiang, capsicum, tomato etc. 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, Compound I
a, I
b, I
cpreparation
(1) preparation of cinnamyl chloride
74g(0.5mol is added successively in 500mL there-necked flask) styracin, 119g(1.0mol) sulfur oxychloride and 150mL toluene, drip 0.2mLN under stirring, N ,-dimethyl formamide, temperature rising reflux 2h, revolve and steam toluene and excessive sulfur oxychloride, obtain pale yellowish oil liquid 80.5g, yield 97%.
(2) preparation of cinnamoyl-N, N-dimethyl-1,3-propylene diamine
In 250mL there-necked flask, add 10.2g (0.1mol) N, N-dimethyl-1,3-propylene diamine and 100mL ethyl acetate successively, ice bath temperature control 0 ~ 20 DEG C, drip the mixed solution by 16.6g cinnamyl chloride and 30mL ethyl acetate, drip and finish, 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 22.0g, yield 96%.
(3) preparation of cinnamoyl-N, N-dimethyl-1,3-propylene diamine quaternary ammonium salt
11.6g (0.05mol) cinnamoyl-N is added successively, N-dimethyl-1,3-propylene diamine and 100mL toluene in 250mL there-necked flask; stir lower dropping 6.1g ethyl chloroacetate, drip and finish, temperature rising reflux reaction 4h; revolve and steam toluene, obtain white waxy solid 17.2g, yield 98%.
(4) I
athe preparation of compound
The above-mentioned obtained cinnamoyl-N of 17.6g (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 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 15.0g, yield 86%.
According to the method for example 1, change 20%NaOH solution into equimolar 20%KOH solution and 20% ammonia soln respectively, can I be obtained
athe sylvite of compound and ammonium salt.
Same method, changes styracin into o-chlorocinnamic acid respectively, to chloro-cinnamic acid and 2,4-dichloro-cinnamic acid, can obtain Compound I by aforesaid operations step
b, I
cand I
d.
I
a, I
b, I
cand I
dthe proton magnetic data of compound sodium salt is as follows:
I
acompound:
1hNMR (500MHz, DMSO-d6), δ (ppm): 8.244-8.246 (t, 1H, NH), 7.315-7.548 (m, 5H, Ar-H), 6.634-6.655 (2H, CH=CH), 4.20 (s, 2H, CH
2), 3.875 (s, 2H, CH
2), 3.058-3.096 (q, 2H, CH
2), 2.126-2.156 (t, 2H, CH
2), 2.035 (s, 6H, CH
3), 1.474-1.530 (m, 2H, CH
2);
I
bcompound:
1hNMR (500MHz, DMSO-d6), δ (ppm): 8.250-8.252 (t, 1H, NH), 7.326-7.568 (m, 4H, Ar-H), 6.644-6.664 (2H, CH=CH), 4.20 (s, 2H, CH
2), 3.885 (s, 2H, CH
2), 3.068-3.119 (q, 2H, CH
2), 2.128-2.159 (t, 2H, CH
2), 2.045 (s, 6H, CH
3), 1.478-1.535 (m, 2H, CH
2);
I
ccompound: HNMR (500MHz, DMSO-d6), δ (ppm): 8.251-8.253 (t, 1H, NH), 7.325-7.567 (m, 4H, Ar-H), 6.645-6.665 (2H, CH=CH), 4.21 (s, 2H, CH
2), 3.887 (s, 2H, CH
2), 3.068-3.118 (q, 2H, CH
2), 2.126-2.157 (t, 2H, CH
2), 2.046 (s, 6H, CH
3), 1.478-1.536 (m, 2H, CH
2);
I
dcompound: HNMR (500MHz, DMSO-d6), δ (ppm): 8.255-8.258 (t, 1H, NH), 7.330-7.573 (m, 3H, Ar-H), 6.650-6.670 (2H, CH=CH), 4.222 (s, 2H, CH
2), 3.888 (s, 2H, CH
2), 3.068-3.118 (q, 2H, CH
2), 2.128-2.159 (t, 2H, CH
2), 2.045 (s, 6H, CH
3), 1.476-1.536 (m, 2H, CH
2).
Test through preliminary raw test, X is Br, M is K or NH
4time, survey activity substantially without impact to raw, therefore example of formulations of the present invention and raw embodiment of surveying are with I
a(M is Na, X is Cl) tests.
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 90g 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 85g 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 75g 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 Compound I
a, I
b, I
c, I
dwith DA-6(Henan Zheng Shi Chemical Co., Ltd. produce) be mixed with 5% Compound I
a, I
b, I
cand I
daqua 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 filter paper moistening, observe the germination of each process in vernalization, 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 2 simultaneously simultaneously.
Table 2 wheat germination testing data
As can be seen from Table 2, 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 short Rooting of seed soaking: respectively by Compound I
a, I
b, I
c, I
dwith DA-6(Henan Zheng Shi Chemical Co., Ltd. produce) be mixed with 5% Compound I
a, I
b, I
c, I
daqua 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 3 simultaneously.
Table 3 is soaked seed Rooting data
Experiment of taking root executed by example 7, base: respectively by Compound I
a, I
b, I
c, I
dwith DA-6(Henan Zheng Shi Chemical Co., Ltd. produce) be mixed with 5% Compound I
a, I
b, I
c, I
daqua 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 4 simultaneously.
Rooting data executed by table 4 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 5.
Table 5 apple quality index Test data
To sum up data, can find out formula I of the present invention seed germination, take root in comparatively contrast agents (DA-6) have a clear superiority in; After apple foliage-spray, while raising output, outward appearance and interior quality are also significantly improved, and are a kind of plant-growth regulator of excellent combination property.
Claims (2)
1., containing a Beet alkaline plant growth regulator for cinnamide group, structure is as shown in general formula I:
In formula: X is selected from Cl or Br;
Y is selected from H or Cl;
Z is selected from H or Cl;
M is selected from Na, K or NH
4.
2. a plant growth regulator composition, containing compound of Formula I according to claim 1 as active ingredient and acceptable carrier agriculturally or in forestry.
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| CN1091123A (en) * | 1993-02-18 | 1994-08-24 | 武汉大学 | Plant-growth regulator N, N dimethylamine base ethyl-4-chloro-α-isopropyl benzyl carboxylate hydrochloride synthetic |
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| CN103130663A (en) * | 2013-01-25 | 2013-06-05 | 青岛科技大学 | Cinnamylate ester compound and application thereof |
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| JPH02104568A (en) * | 1988-06-22 | 1990-04-17 | Yoshitomi Pharmaceut Ind Ltd | Acting agent of production promotion of nerve growth factor |
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| CN1091123A (en) * | 1993-02-18 | 1994-08-24 | 武汉大学 | Plant-growth regulator N, N dimethylamine base ethyl-4-chloro-α-isopropyl benzyl carboxylate hydrochloride synthetic |
| WO1997035471A2 (en) * | 1996-03-25 | 1997-10-02 | Proguard, Inc. | Use of aromatic aldehydes as pesticides |
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