CN114874165B - Phenethyl ester vinyl ether lactone compound with strigolactone activity and preparation and application thereof - Google Patents
Phenethyl ester vinyl ether lactone compound with strigolactone activity and preparation and application thereof Download PDFInfo
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- CN114874165B CN114874165B CN202210696963.4A CN202210696963A CN114874165B CN 114874165 B CN114874165 B CN 114874165B CN 202210696963 A CN202210696963 A CN 202210696963A CN 114874165 B CN114874165 B CN 114874165B
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- -1 Phenethyl ester vinyl ether lactone compound Chemical class 0.000 title claims abstract description 15
- 230000000694 effects Effects 0.000 title abstract description 28
- XHSDUVBUZOUAOQ-WJQMYRPNSA-N (3e,3ar,8bs)-3-[[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxymethylidene]-4,8b-dihydro-3ah-indeno[1,2-b]furan-2-one Chemical compound O1C(=O)C(C)=C[C@@H]1O\C=C/1C(=O)O[C@@H]2C3=CC=CC=C3C[C@@H]2\1 XHSDUVBUZOUAOQ-WJQMYRPNSA-N 0.000 title abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 241000336315 Cistanche salsa Species 0.000 claims abstract description 18
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 14
- 235000009566 rice Nutrition 0.000 claims abstract description 14
- 235000003222 Helianthus annuus Nutrition 0.000 claims abstract description 10
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 244000241257 Cucumis melo Species 0.000 claims abstract description 5
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims abstract description 5
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims abstract description 5
- 240000007594 Oryza sativa Species 0.000 claims abstract 3
- 244000020551 Helianthus annuus Species 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims description 22
- 230000035784 germination Effects 0.000 claims description 18
- 230000001737 promoting effect Effects 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 241000219195 Arabidopsis thaliana Species 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 6
- 230000003071 parasitic effect Effects 0.000 claims description 6
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 3
- 230000018109 developmental process Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 241000209140 Triticum Species 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 230000003779 hair growth Effects 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000009758 senescence Effects 0.000 claims description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract description 16
- 238000012360 testing method Methods 0.000 abstract description 7
- 241000219194 Arabidopsis Species 0.000 abstract description 6
- 230000007226 seed germination Effects 0.000 abstract description 6
- 230000004071 biological effect Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000007788 liquid Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- 241000209094 Oryza Species 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 10
- 241000208818 Helianthus Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 240000003444 Paullinia cupana Species 0.000 description 6
- 235000000556 Paullinia cupana Nutrition 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 238000012271 agricultural production Methods 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 2
- WYKYMYXAZMGUPM-UHFFFAOYSA-N 2-bromo-3-methyl-2h-furan-5-one Chemical compound CC1=CC(=O)OC1Br WYKYMYXAZMGUPM-UHFFFAOYSA-N 0.000 description 2
- FKOULKPQMBAJDG-UHFFFAOYSA-N 2-bromo-4-methyl-2h-furan-5-one Chemical compound CC1=CC(Br)OC1=O FKOULKPQMBAJDG-UHFFFAOYSA-N 0.000 description 2
- HQIZYPQNJWENRT-UHFFFAOYSA-N 2-hydroxy-4-methyl-2h-furan-5-one Chemical compound CC1=CC(O)OC1=O HQIZYPQNJWENRT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical group C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- KWAHADSKPFGJQF-UHFFFAOYSA-N 2-iodoprop-1-ene Chemical compound CC(I)=C KWAHADSKPFGJQF-UHFFFAOYSA-N 0.000 description 1
- VUTGXYAFVUUFCK-UHFFFAOYSA-N 5-hydroxy-4-methyl-3h-furan-2-one Chemical compound CC1=C(O)OC(=O)C1 VUTGXYAFVUUFCK-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 101100375585 Arabidopsis thaliana YAB1 gene Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001508464 Orobanche Species 0.000 description 1
- 241000353135 Psenopsis anomala Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000036579 abiotic stress Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- CAERSDJFKGMKLY-UHFFFAOYSA-N ethyl 2-(3-bromophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(Br)=C1 CAERSDJFKGMKLY-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000014634 leaf senescence Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000024121 nodulation Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000034655 secondary growth Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Botany (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a phenethyl ester vinyl ether lactone compound with strigolactone activity, and preparation and application thereof. The structural formula is shown in formula I. The invention provides the phenethyl ester vinyl ether lactone compound which has simple structure, convenient synthesis and high biological activity, and simultaneously, the compound is subjected to sunflower broomrape and melon broomrape seed germination, arabidopsis hypocotyl elongation and rice tillering test, and the result shows that the compound has better promotion activity on broomrape seed germination, has better inhibition activity on arabidopsis hypocotyl elongation and rice tillering, and is a plant growth regulator with wide application prospect.
Description
Technical Field
The invention belongs to the field of plant growth regulators, and in particular relates to a phenethyl ester vinyl ether lactone compound with strigolactone activity, and preparation and application thereof.
Background
The plant growth regulator is widely used in agricultural production, can effectively regulate the growth process of crops, and achieves the purposes of stabilizing yield and increasing yield, improving quality, enhancing stress resistance of crops and the like. Strigolactones (SLs) are a new class of endogenous plant hormones of interest in recent years, and SLs are present in many plants, particularly in root secretions. The first SLs was a class of carotenoid terpene lactone small molecules isolated from cotton root secretions in 1966. Strigolactone, which has been found in different plant species, is largely divided into two classes of compounds, typical and atypical, typical SL S By the bridge of butenolide ring (D ring) to tricyclic lactone (ABC ring) via enol ether, atypical SL S The ABC ring in (a) is replaced by an irregular ring structure.
As a class of naturally occurring plant signal molecules, strigolactone molecules of different structures may exhibit different biological activities. SL (SL) device S Regulating the coordinated development of root and overground part, such as branch branching/tillering and secondary growth of branch, and determining the density formation of primary root, lateral root, crown and adventitious root and root hair. Furthermore, SL S Also regulates leaf senescence and root nodulation, and is involved in pathogenic bacteria defense and abiotic stress response. SL (SL) device S As a rhizosphere signal molecule, the seed germination of the parasitic plant is induced, and a beneficial symbiotic relationship is established with the arbuscular mycorrhizal fungi by stimulating hyphal branching of the arbuscular mycorrhizal fungi.
Natural SL S The SLs analogue with high activity and simple structure is designed and synthesized as the current research hot spot. At present, the most widely used and effective analogue is GR24, but the complicated synthesis steps and low yield lead to high production cost, so that the large-scale popularization and use of the analogue in agricultural production are limited. Therefore, the strigolactone functional analogue with simple, cheap and reasonable design is particularly important.
Disclosure of Invention
The invention aims to provide a phenethyl ether lactone compound with strigolactone activity, and preparation and application thereof.
The structural formula of the phenethyl ester vinyl ether lactone compound provided by the invention is shown as formula I:
in the formula I, the compound (I),
R 1 at least one selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy and halogenated C1-C4 alkyl; r is R 2 At least one selected from hydrogen and C1-C4 alkyl.
In the compound shown in the formula I, R 1 Preferably fluorine, chlorine, bromine, methyl, methoxy or H, more preferably at least one of 4-fluorine, 4-chlorine, 4-bromine, 4-methyl, 4-methoxy, 3-bromine, 2-chlorine, H; r is R 2 Preferably methyl, more preferably at least one of 3-methyl and 4-methyl.
The compound shown in the formula I can be any one of the following compounds:
the compound shown in the formula I is prepared by a method comprising the following steps:
carrying out etherification reaction on a compound shown in a formula II and a compound shown in a formula III under alkaline conditions to obtain a compound shown in a formula I;
r in formula II 1 And R in formula III 2 Respectively with R in formula I 1 And R is 2 The same applies.
In the above-mentioned production method, the etherification reaction may be carried out in an organic solvent,
the organic solvent can be at least one selected from dichloromethane, tetrahydrofuran and N, N-dimethylformamide;
in the above preparation method, the alkaline condition may be provided by a base,
the alkali can be at least one of potassium carbonate and potassium tert-butoxide;
in the preparation method, the temperature of the etherification reaction can be between-10 and 25 ℃, room temperature is preferred, and the reaction time can be between 1 and 24 hours;
the molar ratio of the compound shown in the formula II to the compound shown in the formula III can be 1:1-10, and can be 1:1.2-10.
In the invention, the compound shown in the formula II is prepared according to the following route:
r in formula (1) 1 And R in formula II 1 The same;
the preparation method comprises the following steps:
r in formula (1) containing substituent 1 Reacting ethyl phenylacetate shown in formula (2) with ethyl formate in the presence of sodium hydride to obtain a compound shown in formula II;
wherein, the mol ratio of the ethyl phenylacetate to the ethyl formate shown in the formula (1) can be 1:1-3, and can be 1:1 in particular,
the temperature of the reaction may be 25 ℃;
the reaction is carried out in an organic solvent,
the organic solvent is any one of tetrahydrofuran and N, N-dimethylformamide;
in the invention, the compound shown in the formula II I is prepared according to the following route:
r in formula (3) 2 And R in formula III 2 The same;
the preparation method comprises the following steps:
and (3) carrying out bromination reaction on the compound shown in the formula (3) and carbon tetrabromide in the presence of triphenylphosphine to obtain the compound shown in the formula III.
The bromination reaction is carried out in an organic solvent, which may be specifically dichloromethane.
The bromination reaction can be carried out at a temperature of 20-25 ℃ for 1.5-3.5 hours. The use of the compounds of the formula I described above as plant growth regulators is also within the scope of the invention:
1) Promoting germination of parasitic weed seeds;
2) Inhibiting the elongation of hypocotyl of plant seedling;
3) Promoting root hair growth of plants;
4) Inhibiting lateral root formation of plants;
5) Inhibiting branch development of the plant;
6) Promoting senescence of plant leaves;
7) Promote the growth of mycorrhizal fungi hyphae from mycorrhizal fungi.
The plant can be Arabidopsis thaliana, rice, wheat.
The parasitic weeds can be sunflower broomrape, melon broomrape and strigola.
The invention also provides a plant growth regulator.
The plant growth regulator contains phenethyl ester vinyl ether lactone compounds shown in the formula I.
The invention provides the phenethyl ester vinyl ether lactone compound which has simple structure, convenient synthesis and high biological activity, and simultaneously, the compound is subjected to sunflower broomrape and melon broomrape seed germination, arabidopsis hypocotyl elongation and rice tillering test, and the result shows that the compound has better promotion activity on broomrape seed germination, has better inhibition activity on arabidopsis hypocotyl elongation and rice tillering, and is a plant growth regulator with wide application prospect.
Drawings
FIG. 1 is a synthetic scheme for compound C-03 of example 1 of the present invention.
FIG. 2 is a synthetic scheme for compound D-07 in example 2 of the present invention.
Detailed Description
The following detailed description of the invention is provided in connection with the accompanying drawings that are presented to illustrate the invention and not to limit the scope thereof. The examples provided below are intended as guidelines for further modifications by one of ordinary skill in the art and are not to be construed as limiting the invention in any way.
The experimental methods in the following examples, unless otherwise specified, are conventional methods, and are carried out according to techniques or conditions described in the literature in the field or according to the product specifications. Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Example 1 preparation of Compound C-03
Preparation of Compound C-03 according to the synthetic scheme shown in FIG. 1
The specific reaction steps are as follows:
1.14g (10.00 mmol) of 5-hydroxy-3-methyl-2- (5H) -furanone was dissolved in 15mL of dry dichloromethane, 4.00g (12.08 mmol) of carbon tetrabromide and 3.20g (12.21 mmol) of triphenylphosphine were slowly added in this order at 0℃and the reaction system was returned to room temperature after the dropwise addition. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =2:1 ], after 2H the reaction was completed, concentrated under reduced pressure, and purified by column chromatography [ V (petroleum ether): V (ethyl acetate) =1:1 ] to give 5-bromo-3-methyl-2- (5H) -furanone) as brown liquid 1 (0.8 g, 45.19%).
Ethyl 4-bromophenylacetate (1.00 g,4.11 mmol) and ethyl formate (15 mL) were added to a 5mL tetrahydrofuran solution, and sodium hydride (0.15 g,6.25 mmol) was added in portions to the reaction system at 0 ℃. After 5min the reaction was allowed to warm to room temperature, monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =4:1 ] and after 12h the reaction was completed. 10% diluted hydrochloric acid was added at 0℃to adjust pH to 6-7, dichloromethane extraction was performed, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give yellow liquid 2 (0.96 g, 86.16%).
The yellow liquid 2 (0.40 g,1.48 mmol) obtained above was dissolved in 10mL of dry N, N-dimethylformamide, and potassium tert-butoxide (0.19 g,1.55 mmol) was added at-10℃and reacted for 15min, and 5-bromo-3-methyl-2- (5H) -furanone (0.4 g,2.26 mmol) was added dropwise thereto and the reaction was allowed to proceed to room temperature. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =3:1 ] and after 2h the reaction was completed. The reaction system was extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography [ V (petroleum ether): V (ethyl acetate) =3:1 ] to give yellow oily liquid C-03 (0.26 g, 47.87%)
EXAMPLE 2 preparation of Compound D-07
Preparation of Compound D-07 according to the synthetic scheme shown in FIG. 2
The specific reaction steps are as follows:
11.00g (96.49 mmol) of 4-methyl-5-hydroxyfuran-2-one was dissolved in 150mL of dry dichloromethane, 38.33g (115.80 mmol) of carbon tetrabromide and 30.33g (115.78 mmol) of triphenylphosphine were slowly added in this order at 0℃and the reaction system was returned to room temperature after the addition was completed. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =4:1 ], after 2H the reaction was complete, concentrated under reduced pressure, and purified by column chromatography [ V (petroleum ether): V (ethyl acetate) =3:1 ] to give 5-bromo-4-methyl-2- (5H) -furanone as brown liquid 1 (7.28 g, 42.62%).
Ethyl 3-bromophenylacetate (2.00 g,8.22 mmol) and ethyl formate (20 mL) were added to a 10mL tetrahydrofuran solution, and sodium hydride (0.30 g,12.50 mmol) was added in portions to the reaction system at 0 ℃. After 5min the reaction was allowed to warm to room temperature, monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =4:1 ] and after 12h the reaction was completed. 10% diluted hydrochloric acid was added at 0℃to adjust pH to 6-7, dichloromethane extraction was performed, and the organic phase was washed successively with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give brown liquid 2 (1.74 g, 74.22%).
The brown liquid 2 (1.00 g,3.69 mmol) obtained above was dissolved in 15mL of dry N, N-dimethylformamide, potassium tert-butoxide (0.49 g,4.38 mmol) was added at-10℃and reacted for 15min, and 5-bromo-4-methyl-2- (5H) -furanone (0.70 g,4.07 mmol) was added dropwise and the reaction was brought to room temperature. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =3:1 ] and after 2.5h the reaction was complete. The reaction system was extracted with ethyl acetate, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography [ V (petroleum ether): V (ethyl acetate) =3:1 ] to give yellow oily liquid D-07 (0.56 g, 41.34%).
Compounds C-01 to C-07 and D-01 to D-08 were synthesized according to the two routes described above, the data for the physical chemistry of the compounds are shown in Table 1, and the NMR data for typical compounds are shown in Table 2.
TABLE 1 appearance and yield of partial Compounds of formula I
| Compounds of formula (I) | R 1 | R 2 | Yield is good | Status of |
| C-01 | 4-CH 3 | 3-CH 3 | 51.23％ | Yellow oily liquid |
| C-02 | 4-OCH 3 | 3-CH 3 | 46.62％ | Yellow oily liquid |
| C-03 | 4-Br | 3-CH 3 | 47.87％ | Yellow oily liquid |
| C-04 | 4-F | 3-CH 3 | 43.15％ | Yellow oily liquid |
| C-05 | 4-Cl | 3-CH 3 | 45.69％ | Yellow oily liquid |
| C-06 | 2-Cl | 3-CH 3 | 42.36％ | Yellow oily liquid |
| C-07 | 3-Br | 3-CH 3 | 41.08％ | Yellow oily liquid |
| D-01 | 4-CH 3 | 4-CH 3 | 46.52％ | Yellow oily liquid |
| D-02 | 4-OCH 3 | 4-CH 3 | 43.29％ | Yellow oily liquid |
| D-03 | 4-Br | 4-CH 3 | 45.75％ | White solid |
| D-04 | 4-F | 4-CH 3 | 47.82％ | White solid |
| D-05 | 4-Cl | 4-CH 3 | 42.09％ | Yellow oily liquid |
| D-06 | 2-Cl | 4-CH 3 | 43.59％ | Yellow oily liquid |
| D-07 | 3-Br | 4-CH 3 | 41.34％ | Yellow oily liquid |
| D-08 | H | 4-CH 3 | 47.96％ | Yellow oily liquid |
TABLE 2 partial Compound Nuclear magnetic resonance data of formula I
Example 3 compounds of formula I were tested for germination activity in sunflower and melon seeds as follows:
soaking seed of Orobanches Helianthi in 75% ethanol for 2min for surface sterilization, and washing with sterile distilled water. A plastic petri dish with a diameter of 9cm was taken, two filter papers were laid on the bottom layer and wetted with sterile distilled water, and then a glass fiber filter paper sheet with a diameter of 10mm was laid on the bottom layer. The seeds were uniformly sprinkled on a wet glass fiber filter paper sheet, the number of seeds being about 30-80. The dishes were sealed with sealer and the seeds were pre-incubated in the dark at 25℃for 3-7 days. The glass fiber filter paper sheets of the precultured seeds are placed in a plastic culture dish, 50 mu L of the compound solution to be tested is added, and the culture dish is sealed by sealing glue. The seeds are placed into a constant temperature incubator at 25 ℃ for 7 days to be cultivated, a binocular microscope is adopted to observe and count the germination rate of the broomrape seeds, when radicle appears, the broomrape seeds are regarded as sprouting, commercial GR24 is used as a positive control, and sterile distilled water is used as a negative control. Each concentration compound was tested in triplicate, each concentration compound was tested five times per set of experiments and mean and standard deviation calculated, dose-response analysis was performed using GraphPad Prism 8.0 software, results were expressed as EC 50 (half maximal effect concentration) means that the EC of the compound is calculated 50 Values. The germination activity test method of the Guarana seeds is the same as that of the test method, and the germination activity data of the compound of the formula I on the sunflower broomrape seeds and the germination activity data of partial compounds on the Guarana seeds are shown in the table 3 and the table 4.
TABLE 3 Compound 10 of formula I -7 Induction of germination Rate of sunflower broomrape seed at M concentration
| Compounds of formula (I) | Germination rate (%) | EC 50 (M) |
| C-01 | 48.7 | 4.64×10 -9 |
| C-02 | 50.9 | 2.25×10 -9 |
| C-03 | 46.5 | 3.49×10 -8 |
| C-04 | 37.6 | 6.53×10 -7 |
| C-05 | 42.6 | 2.82×10 -8 |
| C-06 | 42.2 | 2.09×10 -5 |
| C-07 | 40.7 | 6.99×10 -6 |
| D-01 | 12.4 | / |
| D-02 | 2.6 | / |
| D-03 | 7.4 | / |
| D-04 | 45.9 | / |
| D-05 | 23.8 | / |
| D-06 | 14.7 | / |
| D-07 | 16.7 | / |
| D-08 | 6.6 | / |
| GR24 | 53.1 | 1.82×10 -7 |
TABLE 4 partial Compound 10 of formula I -7 Induction germination Rate of Guarana seeds at M concentration
| Compounds of formula (I) | Germination rate (%) | EC 50 (M) |
| C-01 | 96.2 | 1.61×10 -8 |
| C-02 | 95.2 | 9.07×10 -10 |
| C-03 | 76.6 | 1.71×10 -9 |
| C-04 | 42.9 | 2.96×10 -7 |
| C-05 | 95.5 | 5.64×10 -9 |
| C-06 | 90.9 | 2.06×10 -8 |
| C-07 | 95.6 | 1.29×10 -9 |
| GR24 | 98.3 | 1.59×10 -9 |
From table 3 it can be seen that the germination promoting activity of the C-series compounds on sunflower broomrape is significantly higher than that of the D-series compounds, wherein both C-series compounds have a significant germination promoting activity on sunflower broomrape seeds compared to the control GR 24. EC of Compound C-02 50 The value was 2.25X10 -9 M ratio GR24 (1.82×10) -7 M) two orders of magnitude higher, exhibiting excellent germination promoting activity. Then, the C series compound is subjected to germination activity test of the Guarana seeds, and the table 4 shows that the C series compound has better germination promoting activity on the Guarana seeds, wherein the EC of C-02 and C-07 50 The values were 9.07X 10, respectively -10 M、1.29×10 -9 M, germination-promoting Activity was significantly better than GR24 (1.59X10) -9 M),C-03(1.71×10 -9 M) and C-05 (5.64×10) -9 M) germination promoting activity on Guarana seeds was comparable to GR 24. In general, C series compounds have good germination promoting activity on sunflower broomrape and melon broomrape seeds, and have great potential in the application of parasitic weed seed germination agents.
Example 4 Columbia wild type Arabidopsis thaliana hypocotyl elongation Activity test
Wild type Arabidopsis seeds (Columbia-0, col-0) were sown in 1/2MS (0.8% agar, 1% sucrose and specified concentrations of compounds) with 1% sodium hypochlorite for 15min, washed with sterile water; the whole plant was subjected to vernalization at 4℃for 3 days in a refrigerator, then transferred to a climatic chamber in the dark, cultured at 22℃for 7 days, and after photographing, the hypocotyl length was measured by imageJ software. The formula is: hypocotyl elongation inhibition = (blank hypocotyl length-drug group hypocotyl length)/blank hypocotyl length x 100%, and the elongation inhibition of each compound and the control drug GR24 on the arabidopsis hypocotyl at a concentration of 25 μm was calculated, and the test results of all the compounds are shown in table 5.
TABLE 5 inhibition of the elongation of the hypocotyl of Arabidopsis thaliana cultivated for 7 days at a concentration of 25. Mu.M of the compound of formula I
| Compounds of formula (I) | Inhibition ratio (%) | IC 50 (μM) |
| C-01 | 43.0 | 29.6 |
| C-02 | 38.2 | 56.82 |
| C-03 | 72.2 | 7.52 |
| C-04 | 33.0 | 92.23 |
| C-05 | 66.2 | 9.39 |
| C-06 | 28.6 | 102.1 |
| C-07 | 61.2 | 11.12 |
| D-01 | 49.1 | 38.2 |
| D-02 | 24.0 | 201.3 |
| D-03 | 54.5 | 19.72 |
| D-04 | 32.0 | 131.2 |
| D-05 | 44.3 | 27.52 |
| D-06 | 31.6 | / |
| D-07 | 44.2 | 22.17 |
| D-08 | 24.0 | 171.8 |
| GR24 | 48.8 | 19.64 |
As can be seen from Table 5, the phenethyl vinyl ether lactone compounds of the present invention have similar functions to strigolactone and are highly active. The inhibition effect of a plurality of compounds on the hypocotyl of Arabidopsis thaliana at 25 mu M exceeds GR24, and the inhibition rate of the compound C-03 on the hypocotyl of Arabidopsis thaliana is 72.2%Significantly higher than GR24 (48.8%). Furthermore, by calculating its IC 50 The compounds with optimal inhibition effect are C-03, C-05 and C-07, and IC for hypocotyl of Arabidopsis thaliana 50 The values were 7.52. Mu.M, 9.39. Mu.M, 11.12. Mu.M, respectively, and the inhibitory activity was significantly better than GR24 (19.64. Mu.M), and the inhibitory hypocotyl elongation activity of some compounds such as D-03 and D-07 was comparable to GR 24. The result shows that the compound has the related activity of strigolactone, and the design compound has low cost and high utilization value under the same condition.
Example 5 inhibition of tillering in Rice by Compounds
Rice seeds (Nippon-Qing) were surface sterilized by washing with 1.5% sodium hypochlorite for 30 minutes, then thoroughly rinsing the seeds with sterile deionized water, and culturing in water at 30℃for 2 days in the dark. The pre-germinated seeds were transferred to filter paper in a 90mm dish and incubated with fluorescent white light (130-180 μm 2 s -1 ) Culturing at 30deg.C for 1 week, and 16 hr with light for 8 hr darkness. Seedlings of 7 days old were transferred to nutrient solution and grown in a climatic chamber. Rice was treated with the C series of compounds of formula I at a concentration of 2. Mu.M using GR24 as a positive control. These compounds were administered twice a week for six total administrations. Tillering per strain was measured at the final harvest and the test results for all compounds are shown in table 6.
TABLE 6 inhibition Activity of partial Compounds of formula I on tillering in Rice
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As can be seen from Table 6, the C-series compounds have different degrees of inhibition effect on rice tillering. Under the test of 2 mu M, the inhibition activity of the compounds C-01, C-02, C-03 and C-04 on rice tillering is superior to GR24, especially the compound C-02 has a strong inhibition effect on the growth of rice tillering buds, the inhibition effect is more prominent than the expression of GR24, and the inhibition activity of the compounds C-05, C-06 and C-07 on rice tillering is equivalent to GR24, thus the compound has potential application value in agricultural production.
The present invention is described in detail above. It will be apparent to those skilled in the art that the present invention can be practiced in a wide range of equivalent parameters, concentrations, and conditions without departing from the spirit and scope of the invention and without undue experimentation. While the invention has been described with respect to specific embodiments, it will be appreciated that the invention may be further modified. In general, this application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the invention and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains.
Claims (6)
1. The phenethyl ester vinyl ether lactone compound is any one of the following compounds:
2. a process for preparing the compound of claim 1, comprising the steps of: carrying out etherification reaction on a compound shown in a formula II and a compound shown in a formula III under an alkaline condition to obtain the phenethyl ester vinyl ether lactone compound;
in formula II, R 1 4-chloro, 4-bromo, 4-methyl, 4-methoxy or 3-bromo;
in formula III, R 2 Is 3-methyl.
3. The method according to claim 2, characterized in that: the alkaline conditions are provided by a base;
the alkali is at least one of potassium carbonate and potassium tert-butoxide;
the temperature of the etherification reaction is between-10 and 25 ℃ and the reaction time is between 1 and 24 hours;
the molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1:1-10.
4. Use of the phenethyl ester vinyl ether lactones of claim 1 as plant growth regulators in the following aspects:
1) Promoting germination of parasitic weed seeds;
2) Inhibiting the elongation of hypocotyl of plant seedling;
3) Promoting root hair growth of plants;
4) Inhibiting lateral root formation of plants;
5) Inhibiting branch development of the plant;
6) Promoting senescence of plant leaves;
7) Promote the growth of mycorrhizal fungi hyphae from mycorrhizal fungi.
5. The use according to claim 4, characterized in that: the plant is Arabidopsis thaliana, rice and wheat;
the parasitic weeds are sunflower broomrape, melon broomrape and strigola.
6. A plant growth regulator comprising the phenethyl ester vinyl ether lactone compound according to claim 1.
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