CN115232101B - 一种1-酰氧基芝麻酚类衍生物及其制备方法和应用 - Google Patents
一种1-酰氧基芝麻酚类衍生物及其制备方法和应用 Download PDFInfo
- Publication number
- CN115232101B CN115232101B CN202210755877.6A CN202210755877A CN115232101B CN 115232101 B CN115232101 B CN 115232101B CN 202210755877 A CN202210755877 A CN 202210755877A CN 115232101 B CN115232101 B CN 115232101B
- Authority
- CN
- China
- Prior art keywords
- compound
- sesamol
- acyloxy
- derivative
- plant pathogenic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 241000233654 Oomycetes Species 0.000 claims abstract description 21
- 244000000004 fungal plant pathogen Species 0.000 claims abstract description 18
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 3
- 241000196324 Embryophyta Species 0.000 claims description 8
- 241000233616 Phytophthora capsici Species 0.000 claims description 4
- 244000061456 Solanum tuberosum Species 0.000 claims description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 2
- 244000241235 Citrullus lanatus Species 0.000 claims description 2
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 claims description 2
- 241000223218 Fusarium Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 206010039509 Scab Diseases 0.000 claims 1
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 53
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 13
- 239000005794 Hymexazol Substances 0.000 abstract description 9
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003899 bactericide agent Substances 0.000 abstract description 5
- 238000011160 research Methods 0.000 abstract description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
- 238000012512 characterization method Methods 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000001735 carboxylic acids Chemical class 0.000 description 7
- 239000001963 growth medium Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 4
- 102000012440 Acetylcholinesterase Human genes 0.000 description 3
- 108010022752 Acetylcholinesterase Proteins 0.000 description 3
- 150000001262 acyl bromides Chemical class 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- 241000223195 Fusarium graminearum Species 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- 102100024295 Maltase-glucoamylase Human genes 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 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
- 229940022698 acetylcholinesterase Drugs 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 108010028144 alpha-Glucosidases Proteins 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 244000000005 bacterial plant pathogen Species 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012153 distilled water 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
- 244000053095 fungal pathogen Species 0.000 description 2
- 238000010413 gardening Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- -1 sesamol sulfonate derivatives Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 description 2
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 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
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241001270517 Cytospora mali Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241001477928 Mythimna Species 0.000 description 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
- 241001674251 Serpula lacrymans Species 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000021060 food property Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000011835 investigation Methods 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
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000006959 non-competitive inhibition Effects 0.000 description 1
- 229960002296 paroxetine Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003175 pesticide synergist Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- 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
- A01N43/24—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 two or more hetero atoms
- A01N43/26—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 two or more hetero atoms five-membered rings
- A01N43/28—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—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 two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
- Microbiology (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
本发明公开了一种1‑酰氧基芝麻酚类衍生物及其制备方法和应用,该衍生物的结构通式如式(Ⅰ)所示:式(Ⅰ)中:取代基R选自Ph、(o‑Me)Ph、(m‑Me)Ph、(p‑Me)Ph、(p‑OMe)Ph、(p‑tert‑butyl)Ph、(o‑Cl)Ph、(p‑Cl)Ph、(o‑Br)Ph、(p‑Br)Ph、(p‑NO2)Ph、3‑Pyridyl、4‑Pyridyl、1‑Naphthylmethylene。经研究证明,本发明公开的1‑酰氧基芝麻酚类衍生物对植物病原真菌/卵菌具有显著的抑菌活性,其中部分化合物抑菌活性超过现已上市的抗菌剂恶霉灵,可用于制备植物源杀菌剂。
Description
技术领域
本发明属于植物源农药技术领域,涉及一种1-酰氧基芝麻酚类衍生物及其制备方法以及该1-酰氧基芝麻酚类衍生物在制备新型高效植物病原真菌/卵菌抗菌剂中的应用。
背景技术
芝麻酚,即3,4-亚甲二氧基苯酚,为一种天然的酚类化合物。芝麻酚活性广谱,具有良好的抑菌和抗氧化活性,为多种药品合成的重要原料。例如,芝麻酚为农药增效剂胡椒基丁醚的合成原料;亦可用于合成抗肿瘤药物VP-16与VM-26、抗心血管病药物ACEI和抗忧郁症药物帕罗西汀(Paroxetine)等。
芝麻酚对α-糖苷酶和乙酰胆碱酯酶的抑制作用研究已有文献报道,如TopalMeryem评估了芝麻酚对乙酰胆碱酯酶和α-糖苷酶的抑制作用,表明芝麻酚对这两种代谢酶都表现出非竞争性抑制(TopalMeryem,The inhibition profile of sesamolagainst alpha-glycosidase and acetylcholinesterase enzymes,InternationalJournal of Food Properties,2019,22(1):1527-1535)。芝麻酚磺酸酯类衍生物杀粘虫(Mythimna separate Walker)活性方面的研究已有文献报道,如CheZhiping等报道了芝麻酚磺酸酯类衍生物的合成及其杀粘虫活性方面的研究(Che Zhiping,Yang Jinming,ShanXijie,Tian Yuee,Liu Shengming,Lin Xiaomin,Jiang Jia,Hu Mei,Chen Genqiang,Synthesis and insecticidal activity of sulfonatederivatives of sesamolagainst Mythimna separatain vivo,Journal of Asian Natural ProductsResearch,2020,22(7):678-688)。
芝麻酚活性广谱,如抑菌活性、抗氧化活性、抗肿瘤活性等,然而1-酰氧基芝麻酚类衍生物的合成及其在抗植物病原真菌/卵菌活性方面的研究还未见报道。
发明内容
本发明的目的在于提供一种1-酰氧基芝麻酚类衍生物及其制备方法和应用。本发明研究表明,1-酰氧基芝麻酚类衍生物具有显著的抗植物病原真菌/卵菌活性,能够用于制备植物病原真菌/卵菌抗菌剂。
为实现上述任务,本发明是通过下列技术措施得以实现:
1-酰氧基芝麻酚类衍生物,该衍生物的结构通式如式(Ⅰ)所示:
式(Ⅰ)中:取代基R选自Ph、(o-Me)Ph、(m-Me)Ph、(p-Me)Ph、(p-OMe)Ph、(p-tert-butyl)Ph、(o-Cl)Ph、(p-Cl)Ph、(o-Br)Ph、(p-Br)Ph、(p-NO2)Ph、3-Pyridyl、4-Pyridyl、1-Naphthylmethylene。
在结构通式(Ⅰ)中按表1对应取代基R,得到1-酰氧基芝麻酚类衍生物1~14。
表1:本发明制备的1-酰氧基芝麻酚类衍生物1~14对应取代基R
上述1-酰氧基芝麻酚类衍生物的制备方法,首先将不同羧酸酰溴化合成对应的酰溴,不需纯化,酰溴进一步与芝麻酚的羟基发生酯化反应得到。
作为一种优选技术方案,不同羧酸与芝麻酚的摩尔比为1.0~1.5:1.0。
作为一种优选技术方案,将不同羧酸酰溴化合成对应的酰溴的方法为:将不同羧酸与三苯基膦(PPh3)和三溴甲基苯砜(Br3CSO2Ph)在溶剂中反应至结束合成对应的酰溴。进一步优选的,所述不同羧酸、三苯基膦(PPh3)和三溴甲基苯砜(Br3CSO2Ph)的摩尔比为1.0:1.2:1.0。
进一步优选的,所述的不同羧酸选自:苯甲酸、2-甲基苯甲酸、3-甲基苯甲酸、4-甲基苯甲酸、4-甲氧基苯甲酸、4-叔丁基苯甲酸、2-氯苯甲酸、4-氯苯甲酸、2-溴苯甲酸、4-溴苯甲酸、4-硝基苯甲酸、烟酸、异烟酸和萘乙酸。
进一步优选的,所述的溶剂为纯二氯甲烷;最优选的,整个反应体系中二氯甲烷的浓度为1M。
作为一种优选技术方案,所合成的酰溴不需纯化,直接向酰溴反应液中加入芝麻酚和三乙胺(Et3N)继续反应至结束得到1-酰氧基芝麻酚类衍生物。进一步优选的,所述芝麻酚与三乙胺(Et3N)的摩尔比为1.0:1.5。
上述的1-酰氧基芝麻酚类衍生物在防治植物病原真菌或/和卵菌方面的应用。
上述的1-酰氧基芝麻酚类衍生物在制备植物病原真菌或/和卵菌抗菌剂中的应用。
上述的1-酰氧基芝麻酚类衍生物在制备植物源杀菌剂中的应用。
进一步优选的,上述1-酰氧基芝麻酚类衍生物制备方法详细过程为:
首先,将一定量的不同羧酸溶于纯二氯甲烷中(整个反应体系中二氯甲烷的浓度为1M),再加入一定量的PPh3和Br3CSO2Ph,在室温下反应一定时间,TLC跟踪监测至反应结束。反应结束后,生成的酰溴不需纯化,进一步在反应液中加入一定量的芝麻酚和三乙胺(Et3N),室温继续反应一定时间,以TLC检测为准,二氯甲烷萃取,无水硫酸钠干燥,分离的目标产物(Ⅰ)。
本发明所述的室温为25±10℃。
本发明的有益效果:
经实验证明,1-酰氧基芝麻酚类衍生物具有显著的抗植物病原真菌或/和卵菌活性,可在制备新型高效植物病原真菌或/和卵菌抗菌剂中应用。
附图说明
图1为化合物1的氢谱;
图2为化合物2的氢谱;
具体实施方式
以下结合附图和实施例对本发明做进一步详细阐述。
鉴于1-酰氧基芝麻酚类衍生物具有较强的理论和应用价值,申请人制备了1-酰氧基芝麻酚类衍生物,并进行体外抗植物病原真菌/卵菌活性研究;结果表明,该1-酰氧基芝麻酚类衍生物具有显著的抗植物病原真菌/卵菌活性,能够用于制备植物病原真菌/卵菌抗菌剂。根据申请人所进行的资料检索,目前还未见文献报道。
以下是发明人给出的具体实施例。
实施例1:1-酰氧基芝麻酚类衍生物1~14
在结构通式中按表1对应取代基R,可以得到1-酰氧基芝麻酚类衍生物1~14。
一、产品:1-酰氧基芝麻酚类衍生物1~14(各化合物理化性质详见以下内容)。
二、制备方法:
首先,在100mL烧瓶中加入不同取代的羧酸(1.0equiv)溶于纯二氯甲烷中(整个反应体系中二氯甲烷的浓度为1M),后加入PPh3(1.2equiv)和Br3CSO2Ph(1.0equiv),在室温下反应2-6h;TLC跟踪监测至反应结束后,生成的酰溴不需纯化,进一步加入芝麻酚(1.0equiv)和Et3N(1.5equiv),室温继续反应6-10h。以TLC检测为准,反应结束后,加入10mL的水(萃取时要求有机溶剂的体积是水体积的三倍;因此,水如果加太多会浪费有机溶剂,不利于节约成本),并用二氯甲烷萃取,合并有机相,后用饱和食盐水洗,最后用无水硫酸钠干燥。浓缩蒸干溶剂后经硅胶柱层析法分离得到目标产物1~14,产率为63~90%。
反应通式如下:
化合物1:
该化合物的理化性质如下:
1)、白色固体,熔点80~83℃,产率为69%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.16-8.19(m,2H),7.61-7.65(m,1H),7.48-7.52(m,2H),6.83(d,J=8.4Hz,1H),6.73(d,J=2.4Hz,1H),6.66(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C14H11O4([M+H]+),243.0652;found,243.0655。
4)、反应式为:
化合物2:
该化合物的理化性质如下:
1)、浅黄色油状液体,产率为87%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.11-8.14(m,1H),7.45-7.49(m,1H),7.29-7.33(m,2H),6.83(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.65(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H),2.66(s,3H)。
3)、该化合物的HRMS(ESI):Calcd for C15H13O4([M+H]+),257.0808;found,257.0812。
4)、反应式为:
化合物3:
该化合物的理化性质如下:
1)、无色油状液体,产率为78%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:7.96-7.99(m,2H),7.36-7.45(m,2H),6.82(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.58(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H),2.43(s,3H)。
3)该化合物的HRMS(ESI):Calcd for C15H13O4([M+H]+),257.0808;found,257.0808。
4)、反应式为:
化合物4:
该化合物的理化性质如下:
1)、浅黄色固体,熔点89~90℃,产率为73%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.07(d,J=8.4Hz,2H),7.30(d,J=8.0Hz,2H),6.82(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.65(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H),2.44(s,3H)。
3)、该化合物的HRMS(ESI):Calcd for C15H13O4([M+H]+),257.0808;found,257.0809。
4)、反应式为:
化合物5:
该化合物的理化性质如下:
1)、浅黄色固体,熔点145~146℃,产率为66%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.11-8.14(m,2H),6.95-6.99(m,2H),6.82(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.50(dd,J=8.4Hz,2.4Hz,1H),5.99(s,2H),3.89(s,3H)。
3)、该化合物的HRMS(ESI):Calcd for C15H13O5([M+H]+),273.0757;found,273.0759。
4)、反应式为:
化合物6:
该化合物的理化性质如下:
1)、白色固体,熔点108~110℃,产率为75%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.08-8.12(m,2H),7.50-7.53(m,2H),6.82(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.65(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H),1.36(s,9H)。
3)、该化合物的HRMS(ESI):Calcd for C18H19O4([M+H]+),299.1278;found,299.1281。
4)、反应式为:
化合物7:
该化合物的理化性质如下:
1)、白固体,熔点61~62℃,产率为83%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:7.98-8.01(m,1H),7.46-7.53(m,2H),7.36-7.40(m,1H),6.83(d,J=8.4Hz,1H),6.77(d,J=2.4Hz,1H),6.70(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C14H10ClO4([M+H]+),277.0262;found,277.0263。
4)、反应式为:
化合物8:
该化合物的理化性质如下:
1)、白色固体,熔点89~90℃,产率为79%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.09-8.12(m,2H),7.46-7.49(m,2H),6.83(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.65(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C14H10ClO4([M+H]+),277.0262;found,277.0265。
4)、反应式为:
化合物9:
该化合物的理化性质如下:
1)、白固体,熔点64~65℃,产率为90%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:7.95-7.98(m,1H),7.71-7.73(m,1H),7.37-7.45(m,2H),6.83(d,J=8.4Hz,1H),6.78(d,J=2.4Hz,1H),6.71(dd,J=8.4Hz,2.4Hz,1H),6.01(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C14H10BrO4([M+H]+),320.9757;found,320.9759。
4)、反应式为:
化合物10:
该化合物的理化性质如下:
1)、白色固体,熔点108~109℃,产率为64%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.01-8.05(m,2H),7.63-7.66(m,2H),6.82(d,J=8.4Hz,1H),6.72(d,J=2.4Hz,1H),6.65(dd,J=8.4Hz,2.4Hz,1H),6.00(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C14H10BrO4([M+H]+),320.9757;found,320.9758。
4)、反应式为:
化合物11:
该化合物的理化性质如下:
1)、黄色固体,熔点149~150℃,产率为71%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.36(s,4H),6.85(d,J=8.4Hz,1H),6.74(d,J=2.4Hz,1H),6.68(dd,J=8.4Hz,2.4Hz,1H),6.03(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C14H10NO6([M+H]+),288.0503;found,288.0505。
4)、反应式为:
化合物12:
该化合物的理化性质如下:
1)、黄色固体,熔点83~85℃,产率为71%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:9.37(dd,J=2.4Hz,1.2Hz,1H),8.85(dd,J=4.8Hz,1.6Hz,1H),8.41-8.44(m,1H),7.44-7.47(m,1H),6.83(d,J=8.4Hz,1H),6.74(d,J=2.4Hz,1H),6.68(dd,J=8.4Hz,2.4Hz,1H),6.01(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C13H10NO4([M+H]+),244.0604;found,244.0601。
4)、反应式为:
化合物13:
该化合物的理化性质如下:
1)、白色固体,熔点143~145℃,产率为81%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.85(dd,J=4.4Hz,1.6Hz,2H),7.98(dd,J=4.4Hz,1.6Hz,2H),6.83(d,J=8.4Hz,1H),6.74(d,J=2.4Hz,1H),6.67(dd,J=8.4Hz,2.4Hz,1H),6.01(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C13H10NO4([M+H]+),244.0604;found,244.0603。
4)、反应式为:
化合物14:
该化合物的理化性质如下:
1)、浅黄色固体,熔点93~95℃,产率为63%。
2)、该化合物的核磁共振图谱(1H NMR,400MHz)特征:
以氘代CDCl3为溶剂,TMS为内标物,其中各峰归属为:δ:8.06-8.09(m,1H),7.87-7.90(m,1H),7.81-7.84(m,1H),7.44-7.59(m,4H),6.71(d,J=8.4Hz,1H),6.51(d,J=2.4Hz,1H),6.45(dd,J=8.4Hz,2.4Hz,1H),5.93(s,2H),4.26(s,2H)。
3)、该化合物的HRMS(ESI):Calcd for C19H15O4([M+H]+),307.0965;found,307.0966。
4)、反应式为:
实施例2:抑制植物病原真菌/卵菌活性实验
1、供试植物病原菌
(1)植物病原真菌共5种,分别是小麦赤霉病菌(Fusariumgraminearum)、水稻稻瘟病菌(Pyricularia oryzae)、西瓜枯萎病菌(Fusariumoxysporum)、马铃薯干腐病菌(Fusariumsulphureum)和苹果腐烂病菌(Valsamali),均由河南科技大学园艺与植物保护学院植物保护系实验室提供。
(2)植物病原卵菌共1种,即辣椒疫霉病菌(Phytophthoracapsici),由河南科技大学园艺与植物保护学院植物保护系实验室提供。
2、供试样品及试剂
已商品化杀菌剂恶霉灵(Hymexazol)为阳性对照,实施例1制备的1-酰氧基芝麻酚类衍生物1~14,丙酮(分析纯)。
3、生测方法
采用菌丝生长速率法。
培养基:PDA培养基(其配比为:去皮马铃薯200g、葡萄糖20g、琼脂20g、蒸馏水定容至1000mL)和V8培养基(其配比为:V-8蔬菜汁160mL、琼脂15g、蒸馏水1 500mL)。
采用菌丝生长速率法分别测定了芝麻酚、1-酰氧基芝麻酚类衍生物1~14对6种常见植物病原真菌/卵菌的室内毒力,以商品化杀菌剂恶霉灵作为阳性对照。将化合物1~14和恶霉灵用丙酮溶解,待灭菌后的培养基冷却至50-55℃时分别与化合物1~14和恶霉灵混合,充分混匀后制成含有100mg/L带药培养基,以不加药剂的为空白对照(CK),每个处理设三个重复。待培养基充分冷却后,接种生长活力一致,直径7mm的供试病原真菌/卵菌菌片,于28±1℃恒温培养,待不同菌CK组菌落长到超过7.5cm时调查。调查时,用十字交叉法测量菌落直径,并用下述公式计算出各个样品对所测病原菌的生长抑制率。
4、杀菌活性测定结果见表2
表2:1-酰氧基芝麻酚类衍生物1~14对供试菌株的抑菌效果
5、结论
结果表明,本发明公开的1-酰氧基芝麻酚类衍生物1~14对所测6种植物病原真菌/卵菌均表现出较好的抑菌活性;特别是化合物1、3、4和13,其对所测6种供试菌株的抑菌活性均高于已商品化的抗菌剂恶霉灵(Hymexazol);另外,所有化合物1~14对马铃薯干腐病菌(真菌)和辣椒疫霉病菌(卵菌)两种植物病原菌的抑菌活性均超过已商品化的广谱抗菌剂恶霉灵。鉴于此,本发明公开的一种1-酰氧基芝麻酚类衍生物抑制植物病原真菌/卵菌活性显著,今后有望用于制备新型高效植物源杀菌剂。
Claims (1)
1.结构通式如式(Ⅰ)所示的1-酰氧基芝麻酚类衍生物在制备植物病原真菌或/和卵菌抗菌剂中的应用;
所述的植物病原真菌为小麦赤霉病菌、水稻稻瘟病菌、西瓜枯萎病菌、马铃薯干腐病菌和苹果腐烂病菌中的至少一种;所述的植物病原卵菌为辣椒疫霉病菌;
式(Ⅰ)中:取代基R选自Ph、(o-Me)Ph、(m-Me)Ph、(p-Me)Ph、(p-OMe)Ph、(p-tert-butyl)Ph、(o-Cl)Ph、(p-Cl)Ph、(o-Br)Ph、(p-Br)Ph、(p-NO2)Ph、3-Pyridyl、4-Pyridyl、1-Naphthylmethylene。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210755877.6A CN115232101B (zh) | 2022-06-30 | 2022-06-30 | 一种1-酰氧基芝麻酚类衍生物及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210755877.6A CN115232101B (zh) | 2022-06-30 | 2022-06-30 | 一种1-酰氧基芝麻酚类衍生物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115232101A CN115232101A (zh) | 2022-10-25 |
CN115232101B true CN115232101B (zh) | 2024-02-27 |
Family
ID=83671314
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210755877.6A Active CN115232101B (zh) | 2022-06-30 | 2022-06-30 | 一种1-酰氧基芝麻酚类衍生物及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115232101B (zh) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2654348A1 (de) * | 1976-12-01 | 1978-06-08 | Bayer Ag | Insektizide und akarizide mittel |
JP2000154109A (ja) * | 1998-03-12 | 2000-06-06 | Oji Paper Co Ltd | 天然物由来殺菌剤 |
CN111511211A (zh) * | 2017-12-21 | 2020-08-07 | 国立比利时根特大学 | 用于控制植物病原体的化合物 |
EP3818828A1 (en) * | 2019-11-11 | 2021-05-12 | Institute of Plant Protection, Gansu Academy of Agricultural Sciences | Use of cinnamamide derivatives in the control of fungal diseases of crops |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011507910A (ja) * | 2007-12-21 | 2011-03-10 | ユニバーシティー オブ ロチェスター | 真核生物の寿命を変更するための方法 |
-
2022
- 2022-06-30 CN CN202210755877.6A patent/CN115232101B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2654348A1 (de) * | 1976-12-01 | 1978-06-08 | Bayer Ag | Insektizide und akarizide mittel |
JP2000154109A (ja) * | 1998-03-12 | 2000-06-06 | Oji Paper Co Ltd | 天然物由来殺菌剤 |
CN111511211A (zh) * | 2017-12-21 | 2020-08-07 | 国立比利时根特大学 | 用于控制植物病原体的化合物 |
EP3818828A1 (en) * | 2019-11-11 | 2021-05-12 | Institute of Plant Protection, Gansu Academy of Agricultural Sciences | Use of cinnamamide derivatives in the control of fungal diseases of crops |
Non-Patent Citations (6)
Title |
---|
"STN检索报告";Columbus, Ohio, US Registry[Online];《STN Registry》;第1-7页 * |
-1-甲基-3-二氟甲基吡唑酰胺类化合物的合成及抑菌活性;张琨 等;《农药学学报》;第13卷(第6期);第576-580页 * |
Sesamol-based terpenoids as promising bio-sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici;Audrey Damiens,et al.;《Pest Manag Sci》;第77卷;第2403-2414页 * |
Synthesis of thymyl esters and their insecticidal activity against Spodoptera litura (Lepidoptera: Noctuidae);Sorachat Tharamak,et al.;《Pest Manag Sci》;第1-8页 * |
Zhiping Che,et al..Synthesis, anti-oomycete activity of 1-sulfonyloxy/acyloxysesamol derivatives.《Journal of Molecular Structure》.2023,第1283卷135260. * |
张琨 等.-1-甲基-3-二氟甲基吡唑酰胺类化合物的合成及抑菌活性.《农药学学报》.2011,第13卷(第6期),第576-580页. * |
Also Published As
Publication number | Publication date |
---|---|
CN115232101A (zh) | 2022-10-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104016886B (zh) | 一种n-1,2-二取代乙基缬氨酰胺氨基甲酸酯衍生物及应用 | |
Prashanth et al. | Synthesis of some new glutamine linked 2, 3-disubstituted quinazolinone derivatives as potent antimicrobial and antioxidant agents | |
CN109810062B (zh) | 一种苯基咪唑衍生物及其合成方法和在农药中的应用 | |
Tan et al. | Activity of lycorine analogues against the fish bacterial pathogen Flavobacterium columnare | |
Guo et al. | Synthesis of osthol-based botanical fungicides and their antifungal application in crop protection | |
CN112062759B (zh) | 含乙砜基吡啶联1,2,4-噁二唑取代苯甲酰胺类化合物及其制备方法和应用 | |
CN114230519B (zh) | 一类具有抗耐药菌活性的截短侧耳素肉桂酸酯类化合物及其合成方法和应用 | |
Al-Bogami | Mechanochemical synthesis of cyclohexenones and indazoles as potential antimicrobial agents | |
KR20240067949A (ko) | 디페닐 에테르 에스테르 화합물 및 그 응용과 농약살균제 | |
Feng et al. | Synthesis and biological evaluation of curcuminoid derivatives | |
CN111642504A (zh) | 一种喹啉4-位羟基吡啶甲酸酯类化合物及其防治水稻稻瘟病菌的用途 | |
CN113429398B (zh) | 一类苯乙酮肟酯咪唑衍生物及其制备方法和应用 | |
CN115232101B (zh) | 一种1-酰氧基芝麻酚类衍生物及其制备方法和应用 | |
CN108314679B (zh) | 一种含1,3,4-噁二唑环二苯乙烯酰胺杀菌剂及其制备方法和应用 | |
CN108558850B (zh) | 一种含噻吩环二苯乙烯酰胺杀菌剂及其制备方法和应用 | |
Chang et al. | The discovery of new scaffold of plant activators: from salicylic acid to benzotriazole | |
Khan et al. | Eco-friendly synthesis and in vitro antibacterial activities of some novel chalcones | |
CN107721956B (zh) | 苯并丁内酯类衍生物、合成方法及其制备杀菌剂的应用 | |
CN113698378B (zh) | 一类萘醌类化合物及其制备与杀螨、杀菌用途 | |
CN114716487B (zh) | 一种呋喃双酯类化合物及其制备方法和应用 | |
CN109678827A (zh) | 一种3-磺酰基麦芽酚衍生物及制备方法和应用,植物源杀菌剂 | |
CN105503712A (zh) | 一种吡乙苯醚肟酯化合物及其制备方法与应用 | |
CN104003924B (zh) | N-取代-3-[3-(取代苯基)-2-烯-1-酮]-4-羟基吡咯啉-2-酮类化合物及制备方法和应用 | |
CN103664844A (zh) | N-(2-苯氧基苯)呋喃甲酰胺类化合物及其制备方法和杀菌活性 | |
CN102795953A (zh) | 以咖啡酸与磺胺类药物为原料合成咖啡酸酰胺衍生物的方法及用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |