CN114874165A - Phenethyl ester vinyl ether lactone compound with strigolactone activity as well as preparation and application thereof - Google Patents
Phenethyl ester vinyl ether lactone compound with strigolactone activity as well as preparation and application thereof Download PDFInfo
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- CN114874165A CN114874165A CN202210696963.4A CN202210696963A CN114874165A CN 114874165 A CN114874165 A CN 114874165A CN 202210696963 A CN202210696963 A CN 202210696963A CN 114874165 A CN114874165 A CN 114874165A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 Phenethyl ester vinyl ether lactone compound Chemical class 0.000 title claims abstract description 13
- 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 23
- 230000000694 effects Effects 0.000 title abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 241000336315 Cistanche salsa Species 0.000 claims abstract description 17
- 235000007164 Oryza sativa Nutrition 0.000 claims abstract description 11
- 235000009566 rice Nutrition 0.000 claims abstract description 11
- 235000003222 Helianthus annuus Nutrition 0.000 claims abstract description 6
- 244000020551 Helianthus annuus Species 0.000 claims abstract 2
- 240000007594 Oryza sativa Species 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 230000035784 germination Effects 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 15
- 230000001737 promoting effect Effects 0.000 claims description 13
- 239000005648 plant growth regulator Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 230000003071 parasitic effect Effects 0.000 claims description 6
- 238000006266 etherification reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 241000219194 Arabidopsis Species 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 230000018109 developmental process Effects 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 241000209140 Triticum Species 0.000 claims description 2
- 235000021307 Triticum Nutrition 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 240000001705 Striga asiatica Species 0.000 claims 1
- 241000219195 Arabidopsis thaliana Species 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 238000012360 testing method Methods 0.000 abstract description 6
- 230000004071 biological effect Effects 0.000 abstract description 3
- 230000007226 seed germination Effects 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
- 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 10
- 239000003208 petroleum Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000003960 organic solvent Substances 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
- 238000004440 column chromatography Methods 0.000 description 5
- 241000208818 Helianthus Species 0.000 description 4
- 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
- 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
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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
- 239000012153 distilled water Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 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
- LNSXRXFBSDRILE-UHFFFAOYSA-N Cucurbitacin Natural products CC(=O)OC(C)(C)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(C)(C)C(O)C(O)CC4(C)C3(C)C(=O)CC12C LNSXRXFBSDRILE-UHFFFAOYSA-N 0.000 description 2
- CVKKIVYBGGDJCR-SXDZHWHFSA-N Cucurbitacin B Natural products CC(=O)OC(C)(C)C=CC(=O)[C@@](C)(O)[C@@H]1[C@@H](O)C[C@]2(C)C3=CC[C@@H]4C(C)(C)C(=O)[C@H](O)C[C@@]4(C)[C@@H]3CC(=O)[C@@]12C CVKKIVYBGGDJCR-SXDZHWHFSA-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
- 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
- 150000001904 cucurbitacins Chemical class 0.000 description 2
- PIGAXYFCLPQWOD-UHFFFAOYSA-N dihydrocucurbitacin I Natural products CC12C(=O)CC3(C)C(C(C)(O)C(=O)CCC(C)(O)C)C(O)CC3(C)C1CC=C1C2C=C(O)C(=O)C1(C)C PIGAXYFCLPQWOD-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000013641 positive control Substances 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
- 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
- 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
- 229920000742 Cotton Polymers 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 241001508464 Orobanche Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 229930006000 Sucrose Natural products 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
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000002585 base Substances 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
- 229940125773 compound 10 Drugs 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000012258 culturing 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
- 238000013461 design Methods 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- QAUASTLEZAPQTB-UHFFFAOYSA-N ethyl 3-bromobenzoate Chemical compound CCOC(=O)C1=CC=CC(Br)=C1 QAUASTLEZAPQTB-UHFFFAOYSA-N 0.000 description 1
- XZIAFENWXIQIKR-UHFFFAOYSA-N ethyl 4-bromobenzoate Chemical compound CCOC(=O)C1=CC=C(Br)C=C1 XZIAFENWXIQIKR-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000003803 hair density Effects 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 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 1
- 150000002596 lactones Chemical group 0.000 description 1
- 230000014634 leaf senescence Effects 0.000 description 1
- 239000000463 material Substances 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000034655 secondary growth Effects 0.000 description 1
- 210000000582 semen Anatomy 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
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 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
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Images
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
Abstract
The invention discloses a phenethyl ester vinyl ether lactone compound with strigolactone activity and preparation and application thereof. The structural formula is shown as formula I. The invention provides a phenethyl ester vinyl ether lactone compound with simple structure, convenient synthesis and high biological activity, and simultaneously performs sunflower broomrape and broomrape seed germination, arabidopsis thaliana hypocotyl elongation and rice tillering tests on the compound.
Description
Technical Field
The invention belongs to the field of plant growth regulators, and particularly 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, increasing yield, improving quality, enhancing stress resistance of crops and the like. Strigolactones (SLs), a novel class of endogenous plant hormones of interest in recent years, are present in many plants, particularly in root exudates. The first SLs are carotenoid terpene lactone small molecules separated from root exudates of cotton in 1966. Strigolactones that have been found in different plant species are largely divided into two classes, typical and atypical, typical SL S From the butenolide ring (D ring) via an enol ether bridge to a tricyclic lactone ring (ABC ring), atypical SL S Wherein the ABC ring is replaced by an irregular ring structure.
Strigolactone molecules of different structures may exhibit different biological activities as a class of naturally occurring plant signal molecules. SL (Long-side) S Regulating and controlling the coordinated development of roots and overground parts such as branch/tillering and secondary growth of branches, and determining the formation of primary roots, lateral roots, tree crowns, adventitious roots and root hair density. Further, SL S Also regulates and controls leaf senescence and root nodulation, and participates in pathogenic bacteria defense and abiotic stress reaction. SL (Long-side) S As a rhizosphere signal molecule to induce seed germination in parasitic plants by thornsThe hypha branches of the arbuscular mycorrhizal fungi are excited to establish a beneficial symbiotic relationship with the arbuscular mycorrhizal fungi.
Natural SL S The SLs analogue with high activity and simple structure is designed and synthesized as the content in the plant is extremely low, the structure is complex, the artificial synthesis cost is high, and the large-scale preparation cannot be realized. At present, the most widely used and effective analogue is GR24, but the production cost is high due to the complicated synthesis steps and low yield, so that the large-scale popularization and application of the analogue in agricultural production are limited. Therefore, the monolaurate functional analogue which is simple in design, low in cost and reasonable in efficiency is very important.
Disclosure of Invention
The invention aims to provide a phenethyl ester vinyl 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 the formula I:
in the formula I, the compound is shown in the specification,
R 1 at least one selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy and halogenated C1-C4 alkyl; r 2 At least one selected from hydrogen and C1-C4 alkyl.
In the compounds of 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 2 Preferably a methyl group, more preferably at least one of a 3-methyl group and a 4-methyl group.
The compound represented by the formula I may specifically 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 an alkaline condition to obtain a compound shown in a formula I;
in the formula II R 1 And R in the formula III 2 Are respectively connected with R in the formula I 1 And R 2 The same is true.
In the above-mentioned production process, 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-mentioned preparation method, the alkaline condition may be provided by an alkali,
the base can be at least one of potassium carbonate and potassium tert-butoxide;
in the preparation method, the temperature of the etherification reaction can be-10-25 ℃, the room temperature is preferred, and the reaction time can be 1-24 h;
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 specifically can be 1: 1.2-10.
In the present invention, the compound represented by the formula II is prepared according to the following route:
r in the formula (1) 1 And R in the formula II 1 The same;
the preparation method comprises the following steps:
a substituent-containing group R represented by the formula (1) 1 Reacting ethyl phenylacetate with ethyl formate shown in a formula (2) in the presence of sodium hydride to obtain a compound shown in a formula II;
wherein the molar ratio of the ethyl phenylacetate shown in the formula (1) to the ethyl formate can be 1: 1-3, specifically 1:1,
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 present invention, the compounds of formula II I are prepared as follows:
r in the formula (3) 2 And R in the 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, and the organic solvent can be dichloromethane.
The temperature of the bromination reaction can be 20-25 ℃, and the time can be 1.5-3.5 h. The application of the compound shown in the formula I as a plant growth regulator in the following aspects also belongs to the protection scope of the invention:
1) promoting germination of parasitic weed seeds;
2) inhibiting the elongation of hypocotyls of the plant seedlings;
3) promoting the growth of root hair of the plant;
4) inhibiting lateral root production in a plant;
5) inhibiting the development of branches in plants;
6) promoting the aging of plant leaves;
7) promoting the growth of mycorrhizal fungi hyphae from branches.
The plant can be specifically arabidopsis, rice and wheat.
The parasitic weed can be herba Helianthi, herba Orobanches, and herba strigae Asiaticae.
The invention also provides a plant growth regulator.
The plant growth regulator contains the phenethyl ester vinyl ether lactone compound shown in the formula I.
The invention provides a phenethyl ester vinyl ether lactone compound with simple structure, convenient synthesis and high biological activity, and simultaneously performs sunflower broomrape and broomrape seed germination, arabidopsis thaliana hypocotyl elongation and rice tillering tests on the compound.
Drawings
FIG. 1 is a scheme showing the synthesis scheme of compound C-03 in example 1 of the present invention.
FIG. 2 is a synthesis scheme of compound D-07 in example 2 of the present invention.
Detailed Description
The present invention is described in further detail below with reference to specific embodiments, which are given for the purpose of illustration only and are not intended to limit the scope of the invention. The examples provided below serve as a guide for further modifications by a person skilled in the art and do not constitute a limitation of the invention in any way.
The experimental procedures in the following examples, unless otherwise indicated, are conventional and are carried out according to the techniques or conditions described in the literature in the field or according to the instructions of the products. Materials, reagents and the like used in the following examples 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:
5-hydroxy-3-methyl-2- (5H) -furanone 1.14g (10.00mmol) was dissolved in dry dichloromethane 15mL, carbon tetrabromide 4.00g (12.08mmol) and triphenylphosphine 3.20g (12.21mmol) were added slowly in that order at 0 deg.C, and the reaction system was returned to room temperature after the addition. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate): 2: 1], after 2H, the reaction was terminated, concentrated under reduced pressure, and purified by column chromatography [ V (petroleum ether): V (ethyl acetate): 1] to give 5-bromo-3-methyl-2- (5H) -furanone) as a brown liquid 1(0.8g, 45.19%).
Ethyl 4-bromobenzoate (1.00g,4.11mmol) and ethyl formate (15mL) were added to a 5mL tetrahydrofuran solution, and sodium hydride (0.15g,6.25mmol) was added in portions to the reaction system at 0 ℃. After 5min, the reaction was cooled to room temperature and monitored by thin layer chromatography [ TLC, 4: 1 ratio of V (petroleum ether) to V (ethyl acetate) ] and was complete after 12 h. The pH was adjusted to 6 to 7 by the addition of 10% dilute hydrochloric acid at 0 ℃, 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 obtain yellow liquid 2(0.96g, 86.16%).
The yellow liquid 2(0.40g, 1.48mmol) obtained above was dissolved in 10mL of dry N, N-dimethylformamide, potassium tert-butoxide (0.19g, 1.55mmol) was added at-10 ℃ for reaction for 15min, and 5-bromo-3-methyl-2- (5H) -furanone (0.4g,2.26mmol) was added dropwise and the mixture was allowed to warm to room temperature for reaction. The reaction was monitored by thin layer chromatography [ TLC, with the ratio of V (petroleum ether) to V (ethyl acetate) being 3: 1], and the reaction was complete after 2 h. Extracting the reaction system with ethyl acetate, washing the organic phase with saturated saline solution, drying with anhydrous sodium sulfate, concentrating under reduced pressure, purifying by column chromatography [ V (petroleum ether): (V (ethyl acetate) ═ 3: 1], separating and purifying by column chromatography to obtain yellow oily liquid C-03(0.26g, 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 (96.49mmol) of 4-methyl-5-hydroxyfuran-2-one was dissolved in 150mL of dry methylene chloride, 38.33g (115.80mmol) of carbon tetrabromide and 30.33g (115.78mmol) of triphenylphosphine were added slowly in this order at 0 ℃ and the reaction system was returned to room temperature after completion of the addition. 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 a brown liquid 1(7.28g, 42.62%).
Ethyl 3-bromobenzoate (2.00g,8.22mmol) and ethyl formate (20mL) were added to 10mL of tetrahydrofuran solution, and sodium hydride (0.30g, 12.50mmol) was added in portions to the reaction system at 0 ℃. After 5min, the reaction was cooled to room temperature and monitored by thin layer chromatography [ TLC, 4: 1 ratio of V (petroleum ether) to V (ethyl acetate) ] and was complete after 12 h. The pH was adjusted to 6 to 7 by the addition of 10% dilute hydrochloric acid at 0 ℃, 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(1.74g, 74.22%).
The brown liquid 2(1.00g, 3.69mmol) obtained above was dissolved in 15mL of dry N, N-dimethylformamide, potassium tert-butoxide (0.49g, 4.38mmol) was added at-10 ℃ for reaction for 15min, and 5-bromo-4-methyl-2- (5H) -furanone (0.70g,4.07mmol) was added dropwise and the mixture was allowed to warm to room temperature for reaction. The reaction was monitored by thin layer chromatography [ TLC, 3: 1 ratio of V (petroleum ether) to V (ethyl acetate), and was complete after 2.5 h. 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, purified by column chromatography [ V (petroleum ether): V (ethyl acetate) ═ 3: 1] to give D-07(0.56g, 41.34%) as a yellow oily liquid.
Compounds C-01 to C-07 and D-01 to D-08 were synthesized according to the above two routes, and the physical and chemical data of the compounds are shown in Table 1, and the NMR data of typical compounds are shown in Table 2.
TABLE 1 appearance and yield of partial compounds of formula I
| Compound (I) | R 1 | R 2 | Yield of | Status of state |
| 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 NMR data for partial compounds of formula I
Example 3, compounds of formula I were tested for germination activity in broomrape sunflower and broomrape seeds as follows:
soaking semen Helianthi in 75% ethanol for 2min for surface sterilization, and washing with sterile distilled water. A plastic culture dish with the diameter of 9cm is taken, two pieces of filter paper are laid on the bottom layer and are wetted by sterile distilled water, and then a glass fiber filter paper sheet with the diameter of 10mm is fully laid. The seeds were sprinkled evenly onto a wet glass fiber filter paper sheet, with a seed number of about 30-80. The petri dish was sealed with a sealing compound and the seeds were pre-incubated in the dark at 25 ℃ for 3-7 days. Placing the glass fiber filter paper of the pre-cultured seeds in a plastic culture dish, adding 50 mu L of solution of the compound to be detected, and sealing the culture dish by using sealing glue. Culturing the seeds in a constant-temperature incubator at 25 ℃ for 7 days, observing and counting the germination rate of the broomrape seeds by using a binocular microscope, regarding the broomrape seeds as sprouting when radicles appear, and taking commercial GR24 as a positive control and sterile distilled water as a negative control. Compounds at each concentration were tested in triplicate and the mean and standard deviation calculated for each of the five compound concentrations, and dose-response analysis was performed using GraphPad Prism 8.0 software, with results given as EC 50 (half maximal effect concentration) means that the EC of the compound is calculated 50 The value is obtained. The germination activity test method of the seed of the broomrape is the same, and the germination activity data of the compound of the formula I on the broomrape sunflower and the germination activity data of part of the compound on the broomrape seed are shown in tables 3 and 4.
TABLE 3 Compound 10 of formula I -7 Induced germination rate of broomrape seeds under M concentration
| Compound (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 compounds of formula I10 -7 Induced germination rate of seed of Orobanchus cucurbitaceous under M concentration
| Compound (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 the broomrape is significantly higher than that of the D series compounds, wherein the C series compounds have a significant germination promoting activity on the broomrape seeds compared with the control GR 24. Wherein EC of Compound C-02 50 The value was 2.25X 10 -9 M ratio GR24 (1.82X 10) -7 M) is two orders of magnitude higher, and shows excellent germination-promoting activity. Then, the germination activity test of the seed of the cucurbitacin is carried out on the C series compound, and the table 4 shows that the C series compound has better germination promoting activity on the seed of the cucurbitacin, wherein the EC of C-02 and C-07 50 The values are respectively 9.07X 10 -10 M、1.29×10 -9 M, germination promoting activity is obviously better than GR24 (1.59X 10) -9 M),C-03(1.71×10 -9 M) and C-05 (5.64X 10) -9 M) has the germination-promoting activity on the seed of the seed. In general, the C series compounds have good germination promoting activity on sunflower broomrape seeds and cucurbita pepo seeds, and have great potential in application of the parasitic weed seed germinator.
Example 4 Columbia wild-type Arabidopsis thaliana hypocotyl elongation Activity assay
Wild type Arabidopsis seeds (Columbia-0, Col-0) were sown in 1/2MS (0.8% agar, 1% sucrose and compounds at the indicated concentrations) with 1% sodium hypochlorite for 15min, washed clean with sterile water; vernalization was performed in a refrigerator at 4 ℃ for 3 days, followed by transfer to an artificial climate chamber in the dark, culture was performed at 22 ℃ for 7 days, and after the whole plant was photographed, the length of hypocotyl was measured by ImageJ software. By the formula: elongation inhibition of hypocotyl (hypocotyl length of blank group one drug group)/hypocotyl length of blank group × 100%, elongation inhibition of each compound and control drug GR24 on the hypocotyl of arabidopsis thaliana at a concentration of 25 μ M was calculated, and the test results of all compounds are shown in table 5.
TABLE 5 inhibition of hypocotyl elongation of Arabidopsis thaliana cultured for 7 days at a compound of formula I concentration of 25. mu.M
| Compound (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 ester ether lactone compound of the present invention has similar functions as strigolactone and has higher activity. Inhibitory Effect of multiple Compounds on Arabidopsis thaliana hypocotyls at 25. mu.MThe fruit exceeds GR24, and especially the compound C-03 has the inhibition rate of 72.2 percent on the lower embryonic axis of Arabidopsis thaliana which is obviously higher than GR24(48.8 percent). In addition, by calculating its IC 50 Compounds whose best inhibitory effect can be found are C-03, C-05, C-07, IC for Arabidopsis thaliana hypocotyls 50 The values are respectively 7.52 mu M, 9.39 mu M and 11.12 mu M, the inhibition activity is obviously better than that of GR24(19.64 mu M), and the hypocotyl elongation inhibition activity of partial compounds such as D-03 and D-07 is equivalent to that of GR 24. The result shows that the compound has the activity related to strigolactone, and meanwhile, the designed compound has low cost and high utilization value under the same condition.
Example 5 inhibitory Effect of Compounds on Rice tillering
Rice seeds (nipponlily) were surface-sterilized by washing with 1.5% sodium hypochlorite for 30 minutes, then thoroughly rinsed with sterile deionized water, and cultured in water at 30 ℃ for 2 days in the dark. The pre-germinated seeds were transferred to filter paper in 90mm petri dishes and incubated in fluorescent white light (130- 2 s -1 ) The cells were incubated at 30 ℃ for 1 week under 16h light and 8h dark. 7-day-old seedlings were transferred to nutrient solution and grown in a climatic chamber. Rice plants were 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 weekly for a total of six times. The number of tillers per plant was measured at final harvest and all compound test results are shown in table 6.
TABLE 6 inhibitory Activity of partial Compounds of formula I on Rice tillering
As can be seen from Table 6, the C series compounds all have different degrees of inhibitory effects on rice tillering. Under the test of 2 mu M, the inhibiting activity of the compounds C-01, C-02, C-03 and C-04 on rice tillering is superior to that of GR24, especially the compound C-02 has strong inhibiting effect on the growth of rice tillering buds, the inhibiting effect is more prominent than that of GR24, the inhibiting activity of the compounds C-05, C-06 and C-07 on rice tillering is equivalent to that of GR24, and the compound C-01, C-02 and C-04 have potential application value in agricultural production.
The present invention has been described in detail above. It will be apparent to those skilled in the art that the 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 reference to specific embodiments, it will be appreciated that the invention can 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 (8)
1. Phenethyl ester vinyl ether lactone compounds shown in formula I:
in the formula I, the compound is shown in the specification,
R 1 at least one selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy and halogenated C1-C4 alkyl;
R 2 at least one selected from hydrogen and C1-C4 alkyl.
2. A compound of formula I according to claim 1, characterized in that: in the compounds of formula I, R 1 Is fluorine, chlorine, bromine, methyl, methoxy or H; r 2 Is methyl.
3. A compound of formula I according to claim 1 or 2, characterized in that: the compound shown in the formula I is any one of the following compounds:
4. a process for the preparation of a compound according to any one of claims 1 to 3, 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 a compound shown in a formula I;
in the formula II R 1 And R in the formula III 2 Are independently related to R in formula I of claim 1 1 And R 2 The same is true.
5. The method of claim 4, wherein: the alkaline conditions are provided by a base,
the base can be at least one of potassium carbonate and potassium tert-butoxide;
the temperature of the etherification reaction is-10 to 25 ℃, and the reaction time is 1 to 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.
6. The use of a compound of formula I as defined in any one of claims 1 to 3 as a plant growth regulator in:
1) promoting germination of parasitic weed seeds;
2) inhibiting the elongation of hypocotyls of the plant seedlings;
3) promoting the growth of root hair of the plant;
4) inhibiting lateral root production in a plant;
5) inhibiting the development of branches in plants;
6) promoting the aging of plant leaves;
7) promoting the growth of mycorrhizal fungi hyphae from branches.
7. Use according to claim 6, characterized in that: the plants are arabidopsis, rice and wheat;
the parasitic weeds are broomrape sunflower, broomrape cucurbitaceous, striga asiatica.
8. A plant growth regulator comprising the phenethyl ester alkenyl ether lactone compound represented by the formula I according to any one of claims 1 to 3.
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