CN115557855A - 多取代2-羟基二苯甲酮类化合物及其制备方法与应用 - Google Patents
多取代2-羟基二苯甲酮类化合物及其制备方法与应用 Download PDFInfo
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- CN115557855A CN115557855A CN202210368887.4A CN202210368887A CN115557855A CN 115557855 A CN115557855 A CN 115557855A CN 202210368887 A CN202210368887 A CN 202210368887A CN 115557855 A CN115557855 A CN 115557855A
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- Prior art keywords
- alkyl
- group
- polysubstituted
- ring
- alkoxy
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- -1 Polysubstituted 2-hydroxybenzophenone compound Chemical class 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title abstract description 19
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- MGKPCLNUSDGXGT-UHFFFAOYSA-N 1-benzofuran-3-one Chemical class C1=CC=C2C(=O)COC2=C1 MGKPCLNUSDGXGT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000007960 acetonitrile Chemical class 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 238000004440 column chromatography Methods 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims 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 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005577 anthracene group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 239000003814 drug Substances 0.000 abstract description 12
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 6
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 3
- 241000238631 Hexapoda Species 0.000 abstract description 2
- 239000002250 absorbent Substances 0.000 abstract description 2
- 230000002745 absorbent Effects 0.000 abstract description 2
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 235000013601 eggs Nutrition 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 17
- 240000008067 Cucumis sativus Species 0.000 description 15
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 15
- 241000221785 Erysiphales Species 0.000 description 13
- 239000003513 alkali Substances 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 9
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 241000233679 Peronosporaceae Species 0.000 description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005580 one pot reaction Methods 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000005730 Azoxystrobin Substances 0.000 description 3
- 239000005754 Cyazofamid Substances 0.000 description 3
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 3
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- QUTHCURCAWPHIN-UHFFFAOYSA-N 4-[2-(1-methyl-5-nitroimidazol-2-yl)ethynyl]pyrimidin-2-amine Chemical compound C1=C([N+]([O-])=O)N(C)C(C#CC=2N=C(N)N=CC=2)=N1 QUTHCURCAWPHIN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- DWBOSISZPCOPFS-UHFFFAOYSA-N 2-nitroacetonitrile Chemical compound [O-][N+](=O)CC#N DWBOSISZPCOPFS-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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Abstract
本发明公开了一种多取代2‑羟基二苯甲酮类化合物及其制备方法与应用，该衍生物具有如下的结构：
Description
技术领域
本发明属于有机合成技术领域，涉及一种多取代2-羟基二苯甲酮衍生物及其制备方法以及作为农用杀虫、杀菌剂和紫外线吸收剂的应用。
背景技术
多取代2-羟基二苯甲酮化合物在自然界广泛存在，尤其是在医药、农药等方面应用广泛，同时，由于其特殊结构使得该类化合物在材料领域也被广泛应用，如：从甘遂中分离得到的具有抗白血病及抗病毒等药物活性的天然产物Cynandione A，具有抗癌活性的熏草菌素A、等。基于多取代2-羟基二苯甲酮化合物在医药、农药以及材料领域中的重要性，目前化学家们开发了多种方法用于构建该类化合物，但是文献报道的多取代苯酚化合物的制备方法主要集中与二取代、三取代及少量四取代的2-羟基二苯甲酮，然而得到的这些多取代苯酚化合物种类及取代基的种类有限，在苯酚中引入一些功能性的基团便于对其进行衍生，以改变化合物的理化性质和光电性能；同时，对于五取代的2-羟基二苯甲酮化合物的合成方法目前文献少有报道，对于全取代的苯酚化合物，由于其特殊的结构，使得其在医药及材料领域具有很好的应用前景。因此，采取多组分串联反应，高效构建制备具有多个官能团取代的全取代苯酚衍生物，来开发种类多样、结构新颖的全取代苯酚衍生物对药物化学及材料领域的发展具有重要的意义。
“一锅煮”反应具有反应连续、操作简单、中间体不需分离等优势，与传统的化学反应相比，“一锅煮”反应在一个容器内进行反应，可以显著节省时间，提高产率，可以将较简单的原料经过一锅煮多组分反应方便地转化成复杂的分子，实现专有结构的合成。尤其是在结构复杂的分子及天然产物的合成中，一锅煮反应往往可以起到非常关键的作用，因此，近年来，该类反应的开发及应用引起了越来越多的关注。
发明内容
针对现有技术中存在的问题，本发明提供一种多取代2-羟基二苯甲酮衍生物及其制备方法与应用，该方法具有高效、便捷、成本低等优势，所述化合物在农业和动物相关领域中显示出较好的杀菌、杀虫活性。
为解决上述技术问题，本发明采用以下技术方案：
一种多取代2-羟基二苯甲酮类化合物，所述多取代2-羟基二苯甲酮化合物具有如下的结构
其中R1、R2的结构式分别独立选自氢、羟基、卤素、腈基、硝基、酰胺基、C1-C12烷基、卤代C1-C12烷基、C3-C8环烷基、C1-C12烷氧基、卤代C1-C12烷氧基、C2-C12链烯基、卤代C2-C12链烯基、C2-C12链炔基、卤代C2-C12链炔基、C2-C12链烯基氧基、卤代C2-C12链烯基氧基、C2-C12链炔基氧基、卤代C2-C12链炔基氧基、C1-C12烷基羰基、C1-C12烷氧基、C1-C12烷基、卤代C1-C12烷氧基、C1-C12烷基、C1-C12烷基氨基、C1-C12烷硫基、C1-C12烷基磺酰基、芳基、杂芳基中的一种。
其中R3的结构式选自下述结构式中的一种：
进一步，所述R1’、R2’分别独立选自氢、卤素、烷基、卤代烷基、羟基、环烷基、烷氧基、硝基、酯基、胺基、酰胺基、卤代烷氧基、烷基氨基、烷酰氧基、烷硫基、氰基、烷基磺酰基、芳基、杂芳基、烯基、卤代苄氧基、卤代苄胺基或卤代苯氧基中的一种。
进一步，所述烷基为C1-C18的直链或支链烷基，碳环或杂环(含有1-3个氧、硫或氮)，取代或不取代的烷基，其中取代基为卤素、羟基、羧基、硝基、氰基、取代的氨基、酰胺基、羧基、酯基、烷氧基、烷氨基烷酰氧基、芳基。
进一步，所述芳基以及芳烷基、芳氧基和芳氧基烷基中的芳基为取代或不取代的芳环，或取代或不取代的芳杂环。
进一步，所述芳环为苯环、萘环、蒽环、菲环、喹啉环、异喹啉环、吡咯环、吡啶环、嘧啶环、呋喃环、噻吩环；取代基为卤素、甲基、三氟甲基、羟基、硝基、氨基、取代的氨基、羧基、酯基、烷氧基、烷酰氧基或氰基。
进一步，所述杂芳基为含1个或多个N、O、S杂原子的5元环或6元环。例如吡啶、呋喃、吡嗪、哒嗪、喹啉或苯并呋喃。
进一步，所述卤素为氟、氯、溴或碘。
进一步，所述卤代烷基为直链或支链烷基，在这些烷基上的氢原子可以部分或全部被卤素所取代，例如，卤代烷基诸如氯甲基，二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯二氟甲基等。
进一步，所述烷氧基为直链或直链烷基，经氧原子键连接到结构上。
进一步，所述卤代烷氧基为直链或支链烷氧基，在这些烷氧基上的氢原子可部分或全部被卤素所取代。例如，卤代烷氧基诸如氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基。
进一步，所述链烯基为直链或支链并可在任何位置上存在双键，例如乙烯基、烯丙基。取代链烯基包括任意取代的芳基链烯基。
进一步，所述炔基为直链或支链并可在任何位置上存在三键，例如乙炔基、炔丙基。取代炔基包括任意取代的芳炔基。
进一步，所述烷硫基为直链或支链烷基，经硫原子键连接到结构上。
进一步，所述卤代烷硫基为直链或支链烷硫基，在这些烷硫基上的氢原子可部分或全部被卤素所取代。例如，卤代烷硫基诸如氯甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、三氟乙硫基。
进一步，其中R4的结构式选自：CN，NO2、酯基、酰胺、醛基、酮基；
进一步，其中R5的结构式选自：CN，NO2、酯基、酰胺、醛基、酮基、卤素或OH。
部分列表化合物见表1。
表1
本发明所述的多取代2-羟基二苯甲酮类化合物的制备方法，可以通过下述反应式所示的反应步骤来制备，R1、R2、R3、R4、R5的定义如上，
通式(I)化合物可以这样来制备：将醛、乙腈衍生物及3-苯并呋喃酮类化合物在适宜的碱性物质为催化剂、在适当的有机溶剂中，在适当的温度下反应一定时间后分离纯化处理得多取代2-羟基二苯甲酮类化合物。
进一步，适当的有机溶剂可选自如四氢呋喃、1,4-二氧六环、二氯甲烷、氯仿、乙腈、二氯乙烷、甲苯、DMF、DMSO、丙酮、环己烷、四氯甲烷、甲基叔丁基醚、乙醇、甲醇等。
进一步，适宜的碱性物质选自乙酸钠、碳酸钾、碳酸铯、碳酸钠、碳酸氢钠、氟化铯、氢氧化钠、氢氧化钾、三乙胺、二异丙基乙基胺、三丙基胺、吡啶、哌啶、四甲基胍、吡咯、N-甲基吗啉、吗啉、1,5,7-三氮杂二环[4.4.0]癸-5-烯(TBD)、N-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯(MTBD)、三乙醇胺、1,5-二氮双环[5,4,0]十一烯-5(DBU)、1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)、4-二甲氨基吡啶(DMAP)、三苯基膦、三丁基膦、N,N-二甲苯胺、喹啉、四丁基氢氧化铵、甲醇钠、乙醇钠、叔丁醇钾、胆碱、三(对甲苯基)膦。
进一步，上述方法中醛、乙腈衍生物及3-苯并呋喃酮类化合物的物质的量之比为1:1:1～5:5:1。
进一步，反应温度可在零度至溶剂沸点温度之间，通常为0-100℃。
进一步，反应时间为1小时至120小时，通常为1-12小时。
进一步，所述的分离纯化为：将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，以石油醚：乙酸乙酯50：1～3:1为洗脱剂，经柱层析纯化得目标产物。
本发明的另一目的涉及式(I)化合物在农业或其他领域中用作杀虫剂和/或杀菌剂的应用。尤其是，式(I)化合物对下列的重要品种有活性：有很好的杀菌活性，可用于防治水稻纹枯病、水稻稻瘟病、番茄晚疫病、黄瓜霜霉病、黄瓜灰霉病、黄瓜白粉病、小麦白粉病、小麦灰霉病、炭疽病、赤霉病、大豆锈病等。同时，本发明的部分化合物具有很好的杀虫活性，可以用于防治各种作物上的害虫。例如可以用于防治粘虫、小菜蛾、桃蚜朱砂叶螨、二斑叶螨等。
本发明的多取代2-羟基二苯甲酮化合物作为紫外线吸收剂的应用。
本发明的有益效果：本发明提供了一种简单、高效、便捷的多取代2-羟基二苯甲酮化合物制备方法，以碱为催化剂、有机溶剂为溶剂制备多取代2-羟基二苯甲酮化合物，具有高效、便捷、成本低等优点，应用前景好。本发明所述的多取代2-羟基二苯甲酮化合物在制备抗肿瘤、抗菌药物，同时还表现出较好的杀菌活性，该类化合物对农业、民用和动物领域中有害的昆虫的成虫、幼虫和卵都显示出一定的杀虫活性；还具有吸收紫外线的作用，可以作为紫外线吸收剂。
具体实施方式
下面结合具体实施例，对本发明做进一步说明。应理解，以下实施例仅用于说明本发明而非用于限制本发明的范围，该领域的技术熟练人员可以根据上述发明的内容作出一些非本质的改进和调整。
实施例1
本实施例的全取代苯酚化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol 4-氟苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,Chloroform-d)δ11.28(s,1H),7.69–6.77(m,10H),6.70–6.38(m,2H),5.20(d,J＝8.8Hz,1H),4.87(s,2H)ppm.
实施例2
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 6-甲基-3-苯并呋喃酮、0.3mmol苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,DMSO-d6)δ10.64(t,J＝2.1Hz,1H),9.32(s,1H),8.11(dd,J＝8.2,2.3Hz,1H),8.06(dt,J＝8.5,1.7Hz,2H),7.98(p,J＝2.1Hz,1H),7.70(d,J＝7.6Hz,1H),7.62–7.43(m,4H),7.23–7.07(m,2H),6.60(dt,J＝7.4,3.2Hz,2H),6.30(s,2H),3.37(d,J＝2.3Hz,3H)ppm.
实施例3
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 6-氟-3-苯并呋喃酮、0.3mmol苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应3h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,DMSO-d6)δ11.11(s,1H),7.20–6.60(m,11H),6.60–6.13(m,2H),4.97(s,1H),4.70(s,2H)ppm.
实施例4
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol乙醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应4h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,DMSO-d6)δ11.25(s,1H),7.57–7.23(m,2H),7.23–7.02(m,2H),6.02(s,2H),5.27(s,1H),2.30(s,6H)ppm.
实施例5
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(400MHz,Chloroform-d)δ11.38(s,1H),7.33-7.10(m,3H),7.05(d,J＝7.6Hz,2H),6.94(d,J＝7.8Hz,2H),6.66–6.41(m,2H),5.40–5.14(m,1H),4.82(s,2H)ppm.
实施例6
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol苯甲醛、0.3mmol硝基乙腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,DMSO-d6)δ11.21(s,1H),7.57–7.23(m,2H),7.23–7.02(m,2H),6.95–6.51(m,8H),6.02(s,2H)ppm.
实施例7
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol4-甲基苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,DMSO-d6)δ11.21(s,1H),7.57–7.23(m,2H),7.23–7.02(m,2H),6.95–6.51(m,8H),6.02(s,2H),3.40(s,6H)ppm.
实施例8
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol2-三氟甲基苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,Chloroform-d)δ11.28(s,1H),7.53–6.91(m,10H),6.83–6.33(m,2H),5.22(s,1H),4.90(s,2H)ppm.
实施例9
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol 2-硝基基苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,Chloroform-d)δ11.29(s,1H),7.63–6.81(m,10H),6.80–6.33(m,2H),5.23(s,1H),4.80(s,2H)ppm.
实施例10
本实施例的2-羟基二苯甲酮化合物的结构式如下：
本实施例的2-羟基二苯甲酮化合物的制备方法为：将0.20mmol 3-苯并呋喃酮、0.3mmol 3-氰基苯甲醛、0.3mmol丙二腈、10％eq碱、有机溶剂(1mL)加入到反应试管内，40℃的条件下搅拌反应2h，反应结束后，将反应液倒入饱和食盐水中，调PH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，用柱层析分离得到目标产物(洗脱剂为：石油醚和乙酸乙酯体积比为15:1到1:1)。1H NMR(500MHz,Chloroform-d)δ11.28(s,1H),7.67–6.80(m,10H),6.80–6.42(m,2H),5.24(d,J＝25.4Hz,1H),4.90(s,2H)ppm.
下面通过活性实验说明多取代2-羟基二苯甲酮化合物对黄瓜霜霉病、小麦白粉病、黄瓜锈病的抑制作用。
本实验中以小麦白粉病、玉米锈病、黄瓜霜霉病、黄瓜白粉病为靶标，对20个多取代2-羟基二苯甲酮化合物进行了活性测定。对照药剂分别为95％乙密酚原药，95％氰霜唑原药，96％嘧菌酯原药。实验浓度为防治小麦白粉病、黄瓜白粉病、玉米锈病、黄瓜霜霉病药剂的处理浓度分别为400mg/L。对照药剂氰霜唑、嘧菌酯、乙密酚的处理浓度分别为100mg/L。另设不喷药的空白对照。
药液的配制：准确称取样品，溶于丙酮(含量为药液量的5％)中，加入含0.1％吐温80的水，配制成药液，用于活体苗杀菌活性研究。防治小麦白粉病、黄瓜白粉病、玉米锈病、黄瓜霜霉病药剂的处理浓度分别为400mg/L。对照药剂氰霜唑、嘧菌酯、乙密酚的处理浓度分别为100mg/L。
结果调查参照美国植病学会编写的《A Manual of Assessment Keys for PlantDiseases》，根据对照的发病程度，采用目测方法，调查试验样品的杀菌活性，用100-0来表示，以“100”级代表无病和“0”级代表最严重的发病程度。
表2.F-1等20个化合物对小麦白粉病等5个靶标盆栽幼苗实验结果
表2的生测结果显示，本发明所设计的大部分化合物对所测的黄瓜霜霉病、及玉米锈病均表现出良好的抑制作用，部分化合物对黄瓜白粉病及小麦白粉病表现出良好的抑制作用。其中化合物F-2，F-4，F-20在400mg/L时对黄瓜霜霉病的抑制率均为100％；化合物F-7，F-20在400mg/L时对黄瓜白粉病的抑制率均为90％；化合物F-2，F-6，F-11，F-13，F-15，F-18在400mg/L时对玉米锈病的抑制率均为90％以上；化合物F-12，F-13，F-19在400mg/L时对小麦白粉病的抑制率均为80％以上。
以上显示和描述了本发明的基本原理和主要特征以及本发明的优点。本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明精神和范围的前提下，本发明还会有各种变化和改进，这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。
Claims (10)
1.一种多取代2-羟基二苯甲酮类化合物，其特征在于具有如下的结构：
其中R1、R2分别独立选自氢、羟基、卤素、腈基、硝基、酰胺基、C1-C12烷基、卤代C1-C12烷基、C3-C8环烷基、C1-C12烷氧基、卤代C1-C12烷氧基、C2-C12链烯基、卤代C2-C12链烯基、C2-C12链炔基、卤代C2-C12链炔基、C2-C12链烯基氧基、卤代C2-C12链烯基氧基、C2-C12链炔基氧基、卤代C2-C12链炔基氧基、C1-C12烷基羰基、C1-C12烷氧基、C1-C12烷基、卤代C1-C12烷氧基、C1-C12烷基、C1-C12烷基氨基、C1-C12烷硫基、C1-C12烷基磺酰基、芳基、杂芳基中的一种；
其中R3选自下述结构式中的一种：
所述R1’、R2’分别独立选自氢、卤素、烷基、卤代烷基、羟基、环烷基、烷氧基、硝基、酯基、胺基、酰胺基、卤代烷氧基、烷基氨基、烷酰氧基、烷硫基、氰基、烷基磺酰基、芳基、杂芳基、烯基、卤代苄氧基、卤代苄胺基或卤代苯氧基中的一种；
其中R4选自：CN，NO2、酯基、酰胺、醛基或酮基；
其中R5选自：CN，NO2、酯基、酰胺、醛基、酮基、卤素或OH。
2.根据权利要求1所述的多取代2-羟基二苯甲酮类化合物，其特征在于：
所述烷基为C1-C18的直链或支链烷基，碳环或杂环，取代或不取代的烷基，其中取代基为卤素、羟基、羧基、硝基、氰基、取代的氨基、酰胺基、羧基、酯基、烷氧基、烷氨基烷酰氧基、芳基；
所述芳基以及芳烷基、芳氧基和芳氧基烷基中的芳基为取代或不取代的芳环，或取代或不取代的芳杂环；
所述芳环为苯环、萘环、蒽环、菲环、喹啉环、异喹啉环、吡咯环、吡啶环、嘧啶环、呋喃环、噻吩环；取代基为卤素、甲基、三氟甲基、羟基、硝基、氨基、取代的氨基、羧基、酯基、烷氧基、烷酰氧基或氰基；
所述杂芳基为含1个或多个N、O、S杂原子的5元环或6元环；
所述卤素为氟、氯、溴或碘；
所述卤代烷基为直链或支链烷基，在这些烷基上的氢原子可以部分或全部被卤素所取代；
所述烷氧基为直链或直链烷基，经氧原子键连接到结构上；
所述卤代烷氧基为直链或支链烷氧基，在这些烷氧基上的氢原子可部分或全部被卤素所取代；
所述链烯基为直链或支链并可在任何位置上存在双键，取代链烯基包括任意取代的芳基链烯基；
所述炔基为直链或支链并可在任何位置上存在三键，所述炔基包括乙炔基、炔丙基，取代炔基包括任意取代的芳炔基；
所述烷硫基为直链或支链烷基，经硫原子键连接到结构上；
所述卤代烷硫基为直链或支链烷硫基，在这些烷硫基上的氢原子可部分或全部被卤素所取代。
3.一种如权利要求1或2所述的多取代2-羟基二苯甲酮类化合物的制备方法，其特征在于按照以下方法制备：将醛、乙腈衍生物及3-苯并呋喃酮类化合物溶于有机溶剂中，以碱性物质为催化剂进行反应，反应结束后分离纯化得多取代2-羟基二苯甲酮类化合物。
4.根据权利要求3所述的多取代2-羟基二苯甲酮类化合物的制备方法，其特征在于：所述有机溶剂采用四氢呋喃、1,4-二氧六环、二氯甲烷、氯仿、乙腈、二氯乙烷、甲苯、DMF、DMSO、丙酮、环己烷、四氯甲烷、甲基叔丁基醚、乙醇或甲醇中的任意一种。
5.根据权利要求3所述的多取代2-羟基二苯甲酮类化合物的制备方法，其特征在于：所述碱性物质采用乙酸钠、碳酸钾、碳酸铯、碳酸钠、碳酸氢钠、氟化铯、氢氧化钠、氢氧化钾、三乙胺、二异丙基乙基胺、三丙基胺、吡啶、哌啶、四甲基胍、吡咯、N-甲基吗啉、吗啉、1,5,7-三氮杂二环[4.4.0]癸-5-烯(TBD)、N-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯(MTBD)、三乙醇胺、1,5-二氮双环[5,4,0]十一烯-5(DBU)、1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)、4-二甲氨基吡啶(DMAP)、三苯基膦、三丁基膦、N,N-二甲苯胺、喹啉、四丁基氢氧化铵、甲醇钠、乙醇钠、叔丁醇钾、胆碱或三(对甲苯基)膦中的任意一种。
6.根据权利要求3所述的多取代2-羟基二苯甲酮类化合物的制备方法，其特征在于：所述醛、乙腈衍生物及3-苯并呋喃酮类化合物的物质的量之比为1:1:1～5:5:1。
7.根据权利要求3所述的多取代2-羟基二苯甲酮类化合物的制备方法，其特征在于：反应温度在零度至溶剂沸点温度之间，反应时间为1小时至120小时。
8.根据权利要求3所述的多取代2-羟基二苯甲酮类化合物的制备方法，其特征在于：所述的分离纯化是将反应液倒入饱和食盐水中，调pH值后，过滤分离，然后用乙酸乙酯萃取数次，干燥，脱溶后，以石油醚:乙酸乙酯(v:v)＝50:1～3:1为洗脱剂，经柱层析纯化得目标产物。
9.根据权利要求1或2所述的多取代2-羟基二苯甲酮类化合物在农业领域中用作杀虫剂和/或杀菌剂和/或紫外线吸收剂的应用。
10.根据权利要求1或2所述的多取代2-羟基二苯甲酮类化合物作为紫外线吸收剂的应用。
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