CN103636602B - 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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- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 title claims abstract description 22
- 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
- 238000000034 method Methods 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 239000007921 spray Substances 0.000 claims description 8
- -1 inorganic acid salt Chemical class 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 6
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 230000012010 growth Effects 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-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 3
- 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
- 239000003795 chemical substances by application Substances 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
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 2
- 239000002689 soil Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 7
- 235000013399 edible fruits Nutrition 0.000 abstract description 5
- 229920000742 Cotton Polymers 0.000 abstract description 2
- 230000033228 biological regulation Effects 0.000 abstract 1
- 230000008635 plant growth Effects 0.000 abstract 1
- 230000001737 promoting effect 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
- 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
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution 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
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003786 synthesis reaction 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
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000001630 malic acid Substances 0.000 description 3
- 235000011090 malic acid Nutrition 0.000 description 3
- 238000002791 soaking 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 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
- 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
- 239000003921 oil Substances 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
- 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
- 0 *[N+](Nc(c(cccc1)c1cc1)c1-c1cc(c(N[N+]([O-])OC=I)c(Cc(ccc2ccc3)cc2c3N[N+]([N-])[O-])cc2)c2cc1)[O-] Chemical compound *[N+](Nc(c(cccc1)c1cc1)c1-c1cc(c(N[N+]([O-])OC=I)c(Cc(ccc2ccc3)cc2c3N[N+]([N-])[O-])cc2)c2cc1)[O-] 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
- 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 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
- 239000002518 antifoaming agent Substances 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
- 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
- 239000013530 defoamer Substances 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
- 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
- 238000002386 leaching 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
- 238000012545 processing Methods 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
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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 shown in the structural formula I and salts thereof as plant growth regulators. The compounds of 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 the purposes as plant growth regulator.
Background technology plant growth regulator, as the large classification of one in agricultural chemicals, has played important effect in agricultural production and income, raising quality etc.Along with arable area reduces increasingly, taking place frequently of the growing and natural calamity of population, plant growth regulator more and more receives publicity in Ensuring Food Safety, food security etc.
The plant growth regulator mainly imitated kind of current Chinese commodity, as gibberellin, ethrel, methyl α-naphthyl acetate, heteroauxin, 6-benzyl aminopurine and DA-6 (diethylamino ethanol caproate citrate) etc., the plant growth regulator kind belonging 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, be difficult to meet the agriculture of China's fast development, the needs of production of forestry.Therefore low, Be very effective, use safety the new plant growth regulator of Development and Production use cost plays lifting China pesticide industry integral level and acts on energetically.Domestic have document introduction about 1-naphthalene acetamide compounds at application (Wang Lin agriculturally, Liu Shanshan, Yan Jiawei, the synthesis of N-naphthalene acetyl N-aromatic acylamido thiocarbamide and bioactivity research, 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, etc. W.G. have studied the feasibility of formula I on animal tumor cell (By Von Staekr, W.G., Karzel, K., Influence of auxins and auxin derivatives on viabilityand 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 the plant growth regulator of use safety, specifically be to provide a kind of naphthalene acetamide compounds and salt thereof the purposes as plant growth regulator, it can be used for the volume increase of agricultural or forestry or survival rate improves.
Technical scheme of the present invention is as follows:
A kind of naphthalene acetamide compounds and salt thereof are used as plant growth regulator, and structure is as shown in general formula I:
Formula I can be prepared by the following method:
Naphthalene chloroacetic chloride and N, N-dimethyl-1,3-propane diamine are in ethyl acetate solution, and ice bath temperature control 10 ~ 20 DEG C reaction 2h, drips 20%NaOH solution, adjust pH to 9 ~ 10, washing, and with anhydrous sodium sulfate drying, suction filtration filtrate is revolved and steamed solvent and obtain formula I.
The inorganic acid salt of formula I is by corresponding inorganic acid and this compound direct salify and obtaining in water, methyl alcohol or ethanol; By this compound and corresponding organic acid, direct salify in water, methyl alcohol, ethanol equal solvent obtains its organic acid salt.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 be beneficial to plant absorption, during this compound salify, inorganic acid or organic acid and this compound all according to etc. mol ratio.
Formula I and salt thereof are as the application of plant growth regulator: formula I has water-insoluble, and must be processed into emulsion, suspending agent, wetting powder etc. during application, in preparation, working substance content is 1 ~ 80%; The salt of formula I is soluble in water, therefore can be made into the aqua of working substance 1 ~ 20%, according to actual needs above-mentioned preparation can be watered the suspension or the aqueous solution that are diluted to 0.1 ~ 1000 μ g/mL concentration during use, carry out leaching root, dip in root, seed soaking, seed dressing, seed pelleting or spray cauline leaf.
Formula I and salt thereof can be used alone, and also can use with other active ingredient combinations, 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 trial, formula I 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%; Spray three times at wheat growth stage according to 50 ~ 100 μ g/mL concentration, rate of growth can reach 15 ~ 22%; Spray secondary in the apple development phase according to 100 μ g/mL concentration, one-level fruit rate improves 20%, and painted good, and mouthfeel is sweet, single fruit weightening finish more than 15%; For cotton in Xinjiang, spray the solution of 50 μ g/mL concentration seedling stage, show as well developed root system, seedling strengthens that stem is thick, sprout term disease significantly alleviates, to great Jiang, capsicum and tomato etc., there is similar effect.
Formula I and salt thereof, there is production and use cost low, consumption is little, working concentration wide ranges, safe and convenient to use, can be widely used in various crop or plant and urge root, volume increase, degeneration-resistant and upgrading etc.
Formula I and salt thereof, as novel plant growth regulator, have good market potential and commercialized development value in the green agriculture development of promotion China and Ensuring Food Safety.
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
The synthesis of example 1, formula I
(1) preparation of naphthalene chloroacetic chloride:
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 methyl α-naphthyl acetate white solid, dries, obtains white solid 87.4g, yield 94%.
55.8g(0.3mol is added successively in 500mL there-necked flask) methyl α-naphthyl acetate, 71.4g(0.6mol) thionyl chloride and 150mL toluene, 0.3mLN is dripped under stirring, N,-dimethyl formamide, temperature rising reflux 2h, revolves and steams toluene and excessive thionyl chloride, obtain pale yellowish oil liquid 59.9g, yield 98%.
(2) preparation of naphthalene acetyl-N, N-dimethyl-1,3-propane diamine:
In 250mL there-necked flask, add 10.2g (0.1mol) N, N-dimethyl-1,3-propane diamine and 100mL ethyl acetate successively, ice bath temperature control 0 ~ 20 DEG C, drip the mixed liquor by 20.4g naphthalene chloroacetic chloride and 30mL ethyl acetate, drip and finish, stirring at room temperature 2h; Room temperature drips 20.0g20%NaOH solution, and separatory gets organic facies, uses appropriate anhydrous sodium sulfate drying, and filter, filtrate revolving steams solvent, with recrystallisation from isopropanol, obtains pale yellowish oil liquid 26.2g, yield 97%.
The proton magnetic data of type 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 DEG C.
The preparation of example 2, formula I hydrochloride
Take 5.4g(0.02mol) formula I (example 1 obtains), join in the there-necked flask of 100mL, add water 30mL, drips 1.7mL(0.02mol under stirring) concentrated hydrochloric acid (11.7mol/L) and 8mL water composition solution, drip and finish, continue to stir 0.5h, obtain clear transparent solutions, revolve and steam water, obtain white solid, dry, obtain powdery white solid 6.13g, yield 100%.
The sulphate of formula I, nitrate and phosphate can be obtained with similarity method.
The preparation of example 3, formula I citrate
In 250mL there-necked flask, add 5g citric acid and 60mL methyl alcohol respectively, stirring and dissolving, stir lower gradation and add 5g formula I (example 1 obtains), stirring at room temperature 2h, revolve and steam methyl alcohol and obtain white solid, less than 60 DEG C oven dry, obtain 9.8g white powdery solid.
The preparation of example 4, formula I oxalate
According to example 3 method, change citric acid into oxalic acid, change methyl alcohol into ethanol, obtained 9.7g formula I oxalate.
The preparation of example 5, formula I malate
In 250mL there-necked flask, add 5g malic acid and 50mL water respectively, stirring and dissolving, gradation adds 5g formula I, and stirring at room temperature is to reaction system clear, and decompression steams water, dries (less than 60 DEG C) and obtains 9.8g white solid.
The preparation of example 6, formula I succinate
According to the method for example 4, change malic acid into succinic acid, the succinate of obtained 9.9g formula I.
Example of formulations
The preparation of example 7,10% naphthalene acetamide suspending agent:
Take 15g formula I respectively, 2g sodium lignin sulfonate, 3g polycarboxylate salt dispersant SokalanCP5(maleic-acrylic acid sodium salt), 1g organosilicon breast defoamer (THIX-108 water-based silicon emulsified antifoam agent), 2g aluminium-magnesium silicate and 5g ethylene glycol are in 250mL beaker, add 77g water, stir, grind 2h with sand mill, rotating speed is 3000 revs/min, detect granularity 3-5 μm, obtain white mobility suspending agent.
The preparation of example 8,5% formula I hydrochloride aqua:
Take 5g formula I hydrochloride (example 2 obtain), add water 90g, stirring and dissolving, adds 5g Tween-80, continues to stir to clarify transparent, obtain 5% formula I hydrochloride aqua.
The preparation of example 9,10% formula I citrate aqua:
Take 10g formula I citrate in 200mL beaker, add 85mL water, stirring and dissolving, add 5g Tween-20 surfactant, stir to clarify transparent, obtain 10% formula I citrate aqua.
The preparation of example 10,20% formula I oxalate aqua:
Take 20g formula I oxalate in 250mL beaker, add 75mL water, stirring and dissolving, then add 5g Tween-80 surfactant, stir and obtain 20% formula I oxalate aqua.
The preparation of example 11,10% formula I citrate-methyl α-naphthyl acetate composition aqua:
Take 2g methyl α-naphthyl acetate, add 12mL methyl alcohol, agitating solution, add 5g agriculture breast 602# emulsifier, stir; Take 8g formula I citrate, by the water-soluble solution of 75mL, mix under stirring with above-mentioned obtained naphthalene acid solution, obtain the citrate-methyl α-naphthyl acetate composition aqua of 10% formula I.
Raw survey embodiment
Example 12, wheat seed germinating are tested: formula I citrate and DA-6(Henan Zheng Shi Chemical Co., Ltd. are produced respectively) be mixed with 5% formula I 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 dilution 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 dilution germination promotion rate, result is as following table 1 simultaneously simultaneously.
Table 1 wheat germination test data
As can be seen from Table 1, the germination rate 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 13, the experiment of seed soaking growth-promoting root: respectively formula I citrate and DA-6(Henan Zheng Shi Chemical Co., Ltd. are produced) be mixed with 5% formula I 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 dilution 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 culture 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 14, base: formula I citrate and DA-6(Henan Zheng Shi Chemical Co., Ltd. are produced respectively) be mixed with 5% formula I 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 culture medium of above-mentioned dilution 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 15, 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 index of quality of apple respectively, wherein, VC content adopts 2,6-dichloropheno-lindophenol 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 that formula I of the present invention has remarkable result in seed sprouting, seedling take root, be better than contrast agents (DA-6); After apple foliage-spray, make the output increased more than 15% of apple, improve 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. structure is used as a plant growth regulator for crops such as formula the naphthalene acetamide compounds shown in I and salt thereof,
2. a kind of structure as claimed in claim 1 is used as the plant growth regulator of crops such as formula the naphthalene acetamide compounds shown in I and salt thereof, it is characterized in that: the salt of described formula I refers to inorganic acid salt or organic acid salt; Its inorganic acid salt refers to the salt formed by formula I and inorganic acid, is specially hydrochloride, phosphate, sulphate or nitrate; Organic acid salt refers to the salt formed by formula I and organic acid, is specially citrate, malate, succinate or oxalate.
3. if formula I according to claim 1 or claim 2 and salt thereof are as the using method of the plant growth regulator of crops: according to crop growth needs, adopt foliar spray, seed or root process or agent, soil treatment method to implement, working concentration is 0.1 ~ 1000 μ g/mL effective dose.
4. a plant growth regulator composition, containing formula I according to claim 1 or claim 2 or its salt as active component and agriculturally acceptable carrier.
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