CN103636602A - Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators - Google Patents
Application of naphthaleneacetamide type compounds and salts thereof as plant growth regulators Download PDFInfo
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- CN103636602A CN103636602A CN201310730571.6A CN201310730571A CN103636602A CN 103636602 A CN103636602 A CN 103636602A CN 201310730571 A CN201310730571 A CN 201310730571A CN 103636602 A CN103636602 A CN 103636602A
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- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 23
- 150000003839 salts Chemical class 0.000 title claims abstract description 19
- XFNJVKMNNVCYEK-UHFFFAOYSA-N 1-naphthaleneacetamide Chemical class C1=CC=C2C(CC(=O)N)=CC=CC2=C1 XFNJVKMNNVCYEK-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 230000008635 plant growth Effects 0.000 claims abstract 2
- -1 inorganic acid salt Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000012545 processing Methods 0.000 claims description 9
- 239000007921 spray Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 7
- RFRMFTYHFLNORD-UHFFFAOYSA-N acetamide;naphthalene Chemical class CC(N)=O.C1=CC=CC2=CC=CC=C21 RFRMFTYHFLNORD-UHFFFAOYSA-N 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 235000013399 edible fruits Nutrition 0.000 abstract description 5
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract description 2
- 230000033228 biological regulation Effects 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 238000005728 strengthening Methods 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 241000209140 Triticum Species 0.000 description 14
- 235000021307 Triticum Nutrition 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- AEIJVYPRKAWFPN-UHFFFAOYSA-N 2-(diethylamino)ethyl hexanoate Chemical compound CCCCCC(=O)OCCN(CC)CC AEIJVYPRKAWFPN-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 230000035784 germination Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 5
- 230000018109 developmental process Effects 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- YGGXZTQSGNFKPJ-UHFFFAOYSA-N methyl 2-naphthalen-1-ylacetate Chemical compound C1=CC=C2C(CC(=O)OC)=CC=CC2=C1 YGGXZTQSGNFKPJ-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002791 soaking Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 3
- PUFFIFSUMICMHS-UHFFFAOYSA-N ClCC(=O)Cl.C1=CC=CC2=CC=CC=C12 Chemical compound ClCC(=O)Cl.C1=CC=CC2=CC=CC=C12 PUFFIFSUMICMHS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 239000001630 malic acid Substances 0.000 description 3
- 235000011090 malic acid Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229930191978 Gibberellin Natural products 0.000 description 2
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000002872 contrast media Substances 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000003203 everyday effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 2
- 239000003448 gibberellin Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000001161 mammalian embryo Anatomy 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-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
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 0 C*(NCCc1c(cccc2)c2ccc1)N(C)C Chemical compound C*(NCCc1c(cccc2)c2ccc1)N(C)C 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000035126 Facies Diseases 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000021393 food security Nutrition 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
- 238000000338 in vitro Methods 0.000 description 1
- JTEDVYBZBROSJT-UHFFFAOYSA-N indole-3-butyric acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CNC2=C1 JTEDVYBZBROSJT-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- ZRGKYCBSAYCCTD-UAIGNFCESA-M sodium;(z)-but-2-enedioic acid;prop-2-enoate Chemical compound [Na+].[O-]C(=O)C=C.OC(=O)\C=C/C(O)=O ZRGKYCBSAYCCTD-UAIGNFCESA-M 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses an application of naphthaleneacetamide type compounds as shown in the structural formula I and salts thereof as plant growth regulators. The compounds as shown in the formula I and the salts thereof have excellent plant growth regulation functions of promoting rooting, increasing yield and improving quality, can be widely used for rooting, strengthening seedlings, increasing yield and improving quality of grains, cotton, fruits, vegetables and other crops or plants through root or seed treatment, stem and leaf spraying and other ways, and have the characteristics of safety in use, low cost and significant effects.
Description
Technical field the invention belongs to plant growth regulator field in agricultural chemicals, relates to a kind of naphthalene acetamide compounds and salt thereof as the purposes of plant growth regulator.
Background technology plant growth regulator, as the large classification of one in agricultural chemicals, has been brought into play important effect at aspects such as agricultural production and income, raising qualities.Along with arable area reduces increasingly, the taking place frequently of the growing and natural calamity of population, plant growth regulator more and more receives publicity at aspects such as Ensuring Food Safety, food securities.
The plant growth regulator of Chinese commodity is mainly imitated kind at present, as gibberellin, ethrel, methyl α-naphthyl acetate, heteroauxin, 6-benzyl aminopurine and DA-6 (diethylamino ethanol caproate citrate) etc., the plant growth regulator kind that belongs to China's independent intellectual property right is very few for counting, and above-mentioned kind mostly exists that effect is not ideal enough, safety in utilization is poor or the high deficiency of use cost, is difficult to meet the agriculture of China's fast development, the needs of production of forestry.Therefore Development and Production use cost is low, effect remarkable, use safe new plant growth regulator to play effect energetically to promoting China's pesticide industry integral level.Domestic have Introduction of Literatures about 1-naphthalene acetamide compounds the application (Wang Lin in agricultural, Liu Shanshan, Yan Jiawei, synthetic and the bioactivity research of N-naphthalene acetyl group N-aromatic acylamido thiocarbamide, Nanyang Normal College's journal, 2007,6(3): 5:35-36), its structure is different from compound structure of the present invention; By Von Staekr, W.G. wait and studied feasibility (the By Von Staekr of formula I compound on animal tumor cell, W.G., Karzel, K., Influence of auxins and auxin derivatives on viability and reproducibility of animal tumor cells in vitro, Chimica Therapeutica, 1966, (7): 444-51), in the prior art, the compounds of this invention and salt thereof have no open at home and abroad as plant growth regulator.
Summary of the invention the object of this invention is to provide a kind ofly promote plant establishment, effect of increasing production is good, use cost is low and use safe plant growth regulator, specifically be to provide a kind of naphthalene acetamide compounds and salt thereof as the purposes of plant growth regulator, volume increase or survival rate that it can be used for agricultural or forestry improve.
Technical scheme of the present invention is as follows:
Naphthalene acetamide compounds and salt thereof are as a plant growth regulator, and structure is as shown in general formula I:
Formula I compound can be prepared by the following method:
Naphthalene chloroacetic chloride and N, N-dimethyl-1,3-propane diamine is in ethyl acetate solution, and 10～20 ℃ of ice bath temperature controls reaction 2h, drip 20%NaOH solution, adjust pH to 9～10, washing, with anhydrous sodium sulfate drying, suction filtration filtrate is revolved and is steamed solvent and obtain formula I compound.
The inorganic acid salt of formula I compound is by corresponding inorganic acid and this compound direct salify and obtaining in water, methyl alcohol or ethanol; Its organic acid salt is made by this compound and corresponding organic acid direct salify in water, methyl alcohol, ethanol equal solvent.Described inorganic acid is hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid; Described organic acid is selected from citric acid, malic acid, succinic acid, oxalic acid, tartaric acid.In order to improve the dissolubility of this compound and to be beneficial to plant, absorb, during this compound salify, inorganic acid or organic acid and this compound all according to etc. mole proportioning.
Formula I compound of the present invention and salt thereof are as the application of plant growth regulator: formula I compound has water-insoluble, during application, must be processed into emulsion, suspending agent, wetting powder etc., and in preparation, working substance content is 1～80%; The salt of formula I compound is soluble in water, therefore can be made into the aqua of working substance 1～20%, during use, can according to actual needs above-mentioned preparation be watered to suspension or the aqueous solution that is diluted to 0.1～1000 μ g/mL concentration, soak root, dip in root, seed soaking, seed dressing, seed pelleting or spray cauline leaf.
Formula I compound of the present invention and salt thereof can be used separately, also can be used in combination with other active components, and as formed composition with methyl α-naphthyl acetate, indolebutyric acid, 6-benzyl aminopurine, gibberellin etc., composition also comprises acceptable carrier in agricultural or forestry.
Advantage of the present invention and good effect:
By a large amount of indoor and field trials, formula I compound and salt thereof have significant growth-promoting root and increasing yield and improving quality effect, and as taken root for wheat, root is long, radical all improves more than 45%; At wheat growth stage, according to 50～100 μ g/mL concentration, spray three times, rate of growth can reach 15～22%; In the apple development phase, according to 100 μ g/mL concentration, spray secondary, one-level fruit rate improves 20%, and painted good, and mouthfeel is sweet, and single fruit increases weight more than 15%; For cotton in Xinjiang, spray the solution of 50 μ g/mL concentration seedling stage, show as that well developed root system, the strong stem of seedling are thick, sprout term disease significantly alleviates, great Jiang, capsicum and tomato etc. are had to similar effect.
Formula I compound of the present invention and salt thereof, have produce and use cost low, consumption is little, working concentration wide ranges is safe and convenient to use, can be widely used in the short root of various crops or plant, volume increase, degeneration-resistant and upgrading etc.
Formula I compound of the present invention and salt thereof, as novel plant growth regulator, are promoting to have good market potential and commercialized development value aspect China's green agriculture development and Ensuring Food Safety.
Should be clear and definite, in claim limited range of the present invention, can carry out various conversion and change.
Embodiment
Following synthetic example, formulation examples and the raw experimental result of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthetic example
Synthesizing of example 1, formula I compound
(1) preparation of naphthalene chloroacetic chloride:
Get 104g (0.5mol) Nafusaku and, in 500mL four-hole bottle, add suitable quantity of water, heating is dissolved it, while hot with concentrated hydrochloric acid (36%) acidifying, adjusts pH to 2～3, and cooling suction filtration obtains methyl α-naphthyl acetate white solid, dries, and obtains white solid 87.4g, yield 94%.
In 500mL there-necked flask, add successively 55.8g(0.3mol) methyl α-naphthyl acetate, 71.4g(0.6mol) thionyl chloride and 150mL toluene, stir the lower 0.3mLN of dropping, N,-dimethyl formamide, temperature rising reflux 2h, revolves and steams toluene and excessive thionyl chloride, obtain light yellow oily liquid 59.9g, yield 98%.
(2) naphthalene acetyl group-N, N-dimethyl-1, the preparation of 3-propane diamine:
In 250mL there-necked flask, add successively 10.2g (0.1mol) N, N-dimethyl-1,3-propane diamine and 100mL ethyl acetate, 0～20 ℃ of ice bath temperature control, drips the mixed liquor by 20.4g naphthalene chloroacetic chloride and 30mL ethyl acetate, drips and finishes, stirring at room 2h; Room temperature drips 20.0g20%NaOH solution, and separatory is got organic facies, uses appropriate anhydrous sodium sulfate drying, filters, and filtrate revolving steams solvent, with isopropyl alcohol recrystallization, obtains light yellow oily liquid 26.2g, yield 97%.
The proton magnetic data of formula I compound sodium salt is as follows:
1h NMR(500MHz DMSO-d6) δ (ppm): 8.212-8.230 (1H, N-H), 7.415-8.084 (m, 7H, Ar-H), 3.877 (s, 2H, CH
2), 3.056-3.094 (q, 2H, CH
2), 2.124-2.153 (t, 2H, CH
2), 2.031 (s, 6H, CH
3), 1.470-1.526 (m, 2H, CH
2), fusing point: 76-78 ℃.
The preparation of example 2, formula I compound hydrochloride
Take 5.4g(0.02mol) formula I compound (example 1 makes), join in the there-necked flask of 100mL, add water 30mL, stir the lower 1.7mL(0.02mol of dropping) solution of concentrated hydrochloric acid (11.7mol/L) and 8mL water composition, drip and finish, continue to stir 0.5h, obtain clear solution, revolve and steam water, obtain white solid, dry, obtain powdery white solid 6.13g, yield 100%.
With similarity method, can make sulphate, nitrate and the phosphate of formula I compound.
The preparation of example 3, formula I compound citrate
In 250mL there-necked flask, add respectively 5g citric acid and 60mL methyl alcohol, stirring and dissolving, stirs lower gradation and adds 5g formula I compound (example 1 makes), and stirring at room 2h revolves and steams methyl alcohol and obtain white solid, and 60 ℃ of following oven dry, obtain 9.8g white powdery solid.
The preparation of example 4, formula I compound oxalate
According to example 3 methods, change citric acid into oxalic acid, change methyl alcohol into ethanol, make 9.7g formula I compound oxalate.
The preparation of example 5, formula I compound malate
In 250mL there-necked flask, add respectively 5g malic acid and 50mL water, stirring and dissolving, gradation adds 5g formula I compound, and stirring at room is to reaction system clear, and decompression steams water, dries (60 ℃ are following) and obtains 9.8g white solid.
The preparation of example 6, formula I compound succinate
Method according to example 4, changes malic acid into succinic acid, makes the succinate of 9.9g formula I compound.
FORMULATION EXAMPLE
The preparation of example 7,10% naphthalene acetamide suspending agent:
Take respectively 15g formula I compound, 2g sodium lignin sulfonate, 3g polycarboxylate salt dispersant SokalanCP5(maleic acid-acrylic acid sodium salt), 1g organosilicon breast defoamer (THIX-108 water-based silicon emulsification defoamer), 2g aluminium-magnesium silicate and 5g ethylene glycol are in 250mL beaker, add 77g water, stir, with sand mill, grind 2h, rotating speed is 3000 revs/min, detect granularity 3-5 μ m, obtain white mobility suspending agent.
The preparation of example 8,5% formula I compound hydrochloride aqua:
Take 5g formula I compound hydrochloride (example 2 makes), add water 90g, stirring and dissolving, adds 5g Tween-80, continues to stir to clarify transparent, obtains 5% formula I compound hydrochloride aqua.
The preparation of example 9,10% formula I compound citrate aqua:
Take 10g formula I compound citrate in 200mL beaker, add 85mL water, stirring and dissolving, adds 5g Tween-20 surfactant, stirs to clarify transparently, obtains 10% formula I compound citrate aqua.
The preparation of example 10,20% formula I compound oxalate aqua:
Take 20g formula I compound oxalate in 250mL beaker, add 75mL water, stirring and dissolving, then adds 5g Tween-80 surfactant, stirs and obtains 20% formula I compound oxalate aqua.
The preparation of example 11,10% formula I compound citrate-methyl α-naphthyl acetate composition aqua:
Take 2g methyl α-naphthyl acetate, add 12mL methyl alcohol, agitating solution, adds 5g agriculture breast 602# emulsifier, stirs; Take 8g formula I compound citrate, by the water-soluble solution of 75mL, under stirring with the above-mentioned naphthalene acid solution making, mix, obtain citrate-methyl α-naphthyl acetate composition aqua of 10% formula I compound.
The raw embodiment that surveys
Example 12, wheat seed germinating experiment: respectively formula I compound citrate and DA-6(Henan Zheng Shi Chemical Co., Ltd. are produced) be mixed with 5% formula I compound aqua and 5%DA-6 aqua, being diluted with distilled water into respectively concentration is the plant growth regulator solution of 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL.Wheat seed is cultivated to 8h with above-mentioned dilution, 100 seeds of every processing, repeat, after processing, seed are placed in the culture dish of double-deck filter paper for each 3 times, 25 ℃ of insulation vernalization, and every day keep filter paper moistening, in vernalization, observe each germination of processing every day, radicel length approximately take seed long 1/2 be standard, after 24h, add up wheat germination rate in each ware, DA-6 and clear water (Ck) with same concentrations compares simultaneously, calculates each dilution germination promotion rate simultaneously, and result is as following table 1.
Table 1 wheat germination test data
As can be seen from Table 1, each germination rate of processing of compound of the present invention is better than contrast agents DA-6 on the whole, is significantly better than the situation that clear water is processed (Ck).
Example 13, the experiment of seed soaking growth-promoting root: respectively formula I compound citrate and DA-6(Henan Zheng Shi Chemical Co., Ltd. are produced) be mixed with 5% formula I compound aqua and 5%DA-6 aqua, being diluted with distilled water into respectively concentration is the plant growth regulator solution of 10 μ g/mL, 20 μ g/mL, 30 μ g/mL, 60 μ g/mL and 120 μ g/mL.Select even, the full wheat seed of Seed size, with hypochlorous acid solution, seed is carried out after sterilization, put it in gauze, in beaker, with above-mentioned dilution, soak 10h, then wheat seed is evenly emitted on moistening paper bed, while putting bed, embryo portion is upwards and towards the same side of germination box, between seed, to there is certain distance, to guarantee that seed fully absorbs moisture, 20 wheats are put in each processing, be well placed after seed and put it in complete intelligent weather vegetation box and carry out germination treatment 24h, during to regularly add distilled water to make paper bed keep moistening.Treat that wheat main root exposes 2mm left and right, by its kind, in the solid culture medium having solidified, each processes counterpoise multiple 3 times, then puts into complete intelligent weather vegetation box and cultivates.High with kind of calliper main root, stem after 40h, and make detailed record.DA-6 and clear water (Ck) with same concentrations compares simultaneously, and result is as following table 2.
Table 2 seed soaking Rooting data
Example 14, base are executed the experiment of taking root: respectively formula I compound citrate and DA-6(Henan Zheng Shi Chemical Co., Ltd. are produced) be mixed with 5% formula I compound aqua and 5%DA-6 aqua, being diluted with distilled water into respectively concentration is the plant growth regulator solution of 2.5 μ g/mL, 5 μ g/mL, 10 μ g/mL, 50 μ g/mL, 100 μ g/mL.Select even, the full wheat seed of Seed size, with hypochlorous acid solution, seed is carried out, after sterilization, putting it in gauze, in beaker with mobile water soaking 10h, then wheat seed is evenly emitted on moistening paper bed, while putting bed, embryo portion is upwards and towards the same side of germination box.Between seed, to there is certain distance, to guarantee that seed fully absorbs moisture, 20 wheats are put in each processing, and each processes counterpoise multiple 3 times, be well placed after seed and put it in complete intelligent weather vegetation box and carry out germination treatment 24h, during to regularly add distilled water to make paper bed keep moistening.Treat that wheat main root exposes 2mm left and right, in the solid culture medium that is added with above-mentioned dilution having solidified, then puts into its kind complete intelligent weather vegetation box and cultivates.High with kind of calliper main root, stem after 48h, and make detailed record, DA-6 and the clear water (Ck) with same concentrations compares simultaneously, and result is as following table 3.
Table 3 base is executed Rooting data
Example 15, field experiment: to apple, 3 processing are established in experiment altogether, and the new Gala apple of each processing selecting is set 3 suitable boughs of growth potential and carried out, and strain is got in test at random, individual plant community, 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 respectively the index of quality of apple, wherein, VC content adopts 2,6-dichloropheno-lindophenol method is measured, and soluble sugar content adopts anthrone colorimetric method for determining, and result is as following table 4.
Table 4 apple quality index Test data
Data to sum up, can find out that formula I compound of the present invention has remarkable result seed sprouting, seedling aspect taking root, and is better than contrast agents (DA-6); After apple foliage-spray, the output of apple is improved more than 15%, improved outward appearance and the interior quality of apple simultaneously, can find out that this compound is a kind of plant growth regulator of excellent combination property.
Claims (4)
1. a structure is used as the plant growth regulator of crops and each Plants suc as formula the naphthalene acetamide compounds shown in I and salt thereof.
2. one kind refers to inorganic acid salt or organic acid salt according to formula I compound salt claimed in claim 1; Its mineral salt refer to the salt being formed by formula I compound and inorganic acid, comprise hydrochloride, phosphate, sulphate, nitrate; Organic acid salt refers to the salt being formed by formula I compound and organic acid, comprises citrate, malate, succinate, oxalate.
3. the using method as the plant growth regulator of crops and each Plants according to compound described in claim 1 and claim 2: according to crop or plant growth needs, adopt foliar spray, seed (or root) processing, agent, soil treatment method to implement, working concentration is 0.1～1000 μ g/mL effective dose.
4. a plant growth regulator composition, contains described in claim 1 and claim 2 compound as active component and the upper acceptable carrier of agricultural.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105777618A (en) * | 2016-01-26 | 2016-07-20 | 青岛科技大学 | Naphthylacetic acid pyridine ethyl ester compounds and use thereof |
| CN106831494A (en) * | 2017-03-14 | 2017-06-13 | 青岛科技大学 | A kind of mebenil base hexichol carbamide compounds and application thereof |
| CN114982757A (en) * | 2022-05-09 | 2022-09-02 | 郑州尼采生物科技有限公司 | Method for preparing ester or tertiary amine plant growth regulator aqueous solution |
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| 赵书华: "用植物生长调节剂解决果树生产中的难题 ", 《西南园艺》 * |
| 赵书华: "用植物生长调节剂解决果树生产中的难题", 《西南园艺》, no. 01, 15 January 2005 (2005-01-15), pages 37 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105777618A (en) * | 2016-01-26 | 2016-07-20 | 青岛科技大学 | Naphthylacetic acid pyridine ethyl ester compounds and use thereof |
| CN105777618B (en) * | 2016-01-26 | 2018-04-20 | 青岛科技大学 | A kind of methyl α-naphthyl acetate pyridine ethyl ester type compound and purposes |
| CN106831494A (en) * | 2017-03-14 | 2017-06-13 | 青岛科技大学 | A kind of mebenil base hexichol carbamide compounds and application thereof |
| CN106831494B (en) * | 2017-03-14 | 2018-04-17 | 青岛科技大学 | A kind of mebenil base hexichol carbamide compounds and application thereof |
| CN114982757A (en) * | 2022-05-09 | 2022-09-02 | 郑州尼采生物科技有限公司 | Method for preparing ester or tertiary amine plant growth regulator aqueous solution |
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