CN107417673B - N- (2-pyridyl) methylene-2-cyano-3-heterocyclic acrylhydrazide derivative and application thereof - Google Patents
N- (2-pyridyl) methylene-2-cyano-3-heterocyclic acrylhydrazide derivative and application thereof Download PDFInfo
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- CN107417673B CN107417673B CN201710486194.4A CN201710486194A CN107417673B CN 107417673 B CN107417673 B CN 107417673B CN 201710486194 A CN201710486194 A CN 201710486194A CN 107417673 B CN107417673 B CN 107417673B
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 15
- 241000144210 Culex pipiens pallens Species 0.000 claims description 7
- 241000346285 Ostrinia furnacalis Species 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 241000409991 Mythimna separata Species 0.000 claims description 6
- 241000344246 Tetranychus cinnabarinus Species 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 abstract description 7
- 239000002262 Schiff base Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- -1 heterocyclic Schiff base compound Chemical class 0.000 abstract description 5
- 230000000975 bioactive effect Effects 0.000 abstract description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 3
- 150000002611 lead compounds Chemical class 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229960000935 dehydrated alcohol Drugs 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000003026 anti-oxygenic effect Effects 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HPHBOJANXDKUQD-UHFFFAOYSA-N 2-cyanoacetohydrazide Chemical compound NNC(=O)CC#N HPHBOJANXDKUQD-UHFFFAOYSA-N 0.000 description 4
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000013642 negative control Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012088 reference solution Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- WCBPJVKVIMMEQC-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 WCBPJVKVIMMEQC-UHFFFAOYSA-N 0.000 description 1
- VZIRCHXYMBFNFD-HNQUOIGGSA-N 3-(2-Furanyl)-2-propenal Chemical compound O=C\C=C\C1=CC=CO1 VZIRCHXYMBFNFD-HNQUOIGGSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 208000031320 Teratogenesis Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000005842 biochemical reaction Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07D307/38—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- A01N43/10—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 sulfur as the ring hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/22—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing an amide or imide moiety
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a heterocyclic Schiff base compound and application thereof, in particular to an N- (2-pyridyl) methylene-2-cyano-3-heterocyclic acrylhydrazide derivative and application thereof. The technical problem to be solved by the invention is to provide a heterocyclic Schiff base compound which can be used as an antioxidant and an agricultural insecticide and has a structural formula shown in a formula I. The invention adopts the splicing principle of bioactive groups,heterocyclic compounds are introduced into Schiff base compounds, and active compounds or active lead compounds with novel structures and excellent activity are found, so that a good foundation is laid for the creation of novel antioxidants and insecticides.
Description
Technical field
The present invention relates to heterocyclic Schiff base class compound and application thereof, in particular to N- (2- pyridyl group) methylene -2-
Cyano -3- heterocycle propylene hydrazide derivative and its application.
Background technique
Antioxidant effectively can delay or inhibit many substances, especially big point of the biology such as sugar, rouge, protein, nucleic acid
The oxidation deterioration of son, very extensive application is suffered from many fields: (1) in terms of food processing, antioxidant can inhibit
Oxidation of Fat and Oils prevents its rancid, frequently as food oxydating resistance additive；(2) in life science and medical domain, antioxidant energy
Interior free yl is removed, the formation of peroxidation state is slowed down, prevents and treats various diseases caused by free radical, improves machine
Body immunocompetence, to protect human health；(3) in chemical industrial field, antioxidant adds as the stability of chemical products
Add agent, improve the antioxygenic property of product, to prolong its service life.Since antioxidant is in industrial and agricultural production and daily life
Irreplaceable role is all played in work, therefore, the research and development of efficient, economic, low toxicity antioxidant have very
Important meaning.
On the other hand, long-term a large amount of use of pesticide especially insecticide not only polluted environment, destroy the ecological balance,
Also result in serious " 3R " (residual, resistance and pest resurgence) and " three cause " (carcinogenic, teratogenesis shape and mutagenesis) problem.This
A little problems cause the mankind and widely pay close attention to, and how to efficiently solve these problems is the one long-term and arduous of facing mankind
Task.In this way, being faced with huge challenge in the case where the too busy to get away pesticide of the mankind in pesticide, find to harmful organism height
Effect, to non-target organism safety, degradable in the environment and catabolite to human health and ecological environment security " environment and
Humorous pesticide " or " environment friendly agricultural " the hot spot at pesticide research and forward position.
Schiff refer to condensation reaction occurs by primary amine and aldehydes or ketones and generate contain > one kind of C=N- structure has
Machine compound, both can be isolated from natural products, can also be obtained by artificial synthesized method.Numerous studies table
Bright, Schiff class compound suffers from extremely important in medicine, catalysis, analytical chemistry, corrosion and the fields such as photochromic
Effect.Meanwhile Schiff class compound also has good bioactivity, for example, desinsection, antimycotic, antibacterium, anti-
Cancer, anti parasitic, weeding etc..Therefore, in recent decades, people, which research and develop it, shows great interest, special
Not being is even more to have received widespread attention, and constantly have structure novel, have excellent performance, make in the fields such as biology, medicine, pesticide
It is come out with unique, the environmental-friendly kind of mode.
In recent years, during the research and development of bioactive compound, heterocyclic compound shows more and more important
Effect.Due to its selective good, active height, dosage is few, toxicity is low and special in harmful organism biochemical reactions
Property and become research main body.Wherein, the compounds such as furans, thiophene, pyridine, pyrimidine, pyrazoles, imidazoles, thiazole, triazole, because not
It is disconnected to emerge some novel agents having an epoch-marking significance and attract people's attention, it also has become bioactive compound and grinds
The hot spot studied carefully and forward position.
Up to the present, it yet there are no what heterocyclic Schiff base class compound was used as antioxidant and agricultural insecticide
Report.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of heterocycles that can be used as antioxidant and agricultural insecticide and use
Schiff class compound.
N- (2- pyridyl group) methylene -2- cyano -3- heterocycle propylene hydrazide derivative of the invention, structural formula is such as
Shown in formula I:
Wherein, R1ForR2For hydrogen,
C1-C4 alkyl or halogen；R3For hydrogen, C1-C4 alkyl or halogen；X is O or S.
Preferably, R1ForPreferred R1For
The present invention also provides the compounds of this invention to prepare the application in antioxidant.
The compound of the present invention has excellent antioxygenic property, can be used as antioxidant.
The present invention also provides application of the compounds of this invention in prevention and treatment agricultural pests.
The compound of the present invention, it is also possible to make insecticide, to the agricultural evil such as mythimna separata, corn borer, Tetranychus cinnabarinus, Culex pipiens pallens
Worm has preferable cytotoxicity.It is therefore preferable that the agricultural pests are mythimna separata, corn borer, Tetranychus cinnabarinus or Culex pipiens pallens.
The present invention splices principle using bio-active group, and heterocyclic compound is introduced into Schiff class compound, sends out
The reactive compound or active lead compound of some structure novels, superior activity are showed, to be novel antioxidant and kill
Preferable basis has been established in the initiative of worm agent.
Specific embodiment
The present invention provides structural formula such as I compound represented of formula:
Wherein, R1ForR2For hydrogen,
C1-C4 alkyl or halogen；R3For hydrogen, C1-C4 alkyl or halogen；X is O or S.
Preferably, R1ForPreferred R1For
It is currently preferred structural formula below.
The compound of the present invention can be obtained using conventional preparation method.
The compound of the present invention has excellent antioxygenic property, can be used as antioxidant.
The compound of the present invention, it is also possible to make insecticide, to the agricultural evil such as mythimna separata, corn borer, Tetranychus cinnabarinus, Culex pipiens pallens
Worm has preferable cytotoxicity.
A specific embodiment of the invention is further described below with reference to embodiment, is not therefore limited the present invention
System is among the embodiment described range.
The synthesis of 1 compound 1~4 of embodiment
Composition principle:
1, the synthesis of compound 1
(1) synthesis of intermediate
The cyano acethydrazide of 0.01mol is placed in three-necked bottle, 15mL methylene chloride is added and makees solvent, 3mL acetic acid is urged
Agent stirs under room temperature.It takes the pyridine-2-formaldehyde of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, uses constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, detects terminal with thin layer silica gel plate (TLC).It places reaction liquid into beaker, with steaming
Distilled water is washed till neutrality repeatedly.Liquid separation is simultaneously evaporated under reduced pressure, and is dried after suction filtration, is obtained intermediate.
(2) synthesis of target compound
It taking intermediate 0.01mol to be placed in three-necked bottle, 15mL dehydrated alcohol is added and makees solvent, 3mL triethylamine makees catalyst,
It is stirred under conditions of 50 DEG C.It takes the furfural of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, uses constant pressure funnel
It is added dropwise in three-necked bottle, reacts 1h, terminal is detected with thin layer silica gel plate (TLC).After fully reacting, reaction solution is poured into
In 500mL beaker, the petroleum ether of 300mL and stirring is added, there is solid matter precipitation.After being filtered and being dried, with acetonitrile: nothing
Water-ethanol=1:10 mixed solution recrystallizes crude product, obtains target product.
Yellow powder；IR(KBr)νmax(cm-1):3439,2207,1683,1604,1530,939；1H NMR(400MHz,
DMSO-d6) δ (ppm): 11.99 (1H, s), 8.71 (1H, d, J=4.4Hz), 8.24 (2H, s), 8.17-8.13 (1H, m),
7.86 (1H, d, J=8.0Hz), 7.81 (1H, s), 7.64-7.61 (1H, m), 7.52 (1H, d, J=3.6Hz), 6.89 (1H,
dd,J1=1.6Hz, J2=1.6Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):151.99(1C),150.08(1C),
149.23(1C),148.38(1C),140.76(1C),139.37(1C),138.05(1C),127.05(1C),125.75(1C),
124.48(1C),124.46(1C),116.57(1C),114.69(1C),98.73(1C)；HRMS(ESI)m/z:Calcd for
C14H11N4O2[M+H]+:267.0877,Found:267.0867.
2, the synthesis of compound 2
(1) synthesis of intermediate
The cyano acethydrazide of 0.01mol is placed in three-necked bottle, 15mL methylene chloride is added and makees solvent, 3mL acetic acid is urged
Agent stirs under room temperature.It takes the pyridine-2-formaldehyde of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, uses constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, detects terminal with thin layer silica gel plate (TLC).It places reaction liquid into beaker, with steaming
Distilled water is washed till neutrality repeatedly.Liquid separation is simultaneously evaporated under reduced pressure, and is dried after suction filtration, is obtained intermediate.
(2) synthesis of target compound
It taking intermediate 0.01mol to be placed in three-necked bottle, 15mL dehydrated alcohol is added and makees solvent, 3mL triethylamine makees catalyst,
It is stirred under conditions of 50 DEG C.It takes the 5 methyl furfural of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, is dripped with constant pressure
Liquid funnel is added dropwise in three-necked bottle, reacts 1h, detects terminal with thin layer silica gel plate (TLC).After fully reacting, reaction solution is fallen
Enter in 500mL beaker, the petroleum ether of 300mL and stirring is added, there is solid matter precipitation.After being filtered and being dried, with acetonitrile:
Dehydrated alcohol=1:10 mixed solution recrystallizes crude product, obtains target product.
Orange crystal；IR(KBr)νmax(cm-1):3439,2205,1682,1607,1557,951；1H NMR(400MHz,
DMSO-d6) δ (ppm): 15.92 (1H, s), 8.71 (1H, d, J=4.4Hz), 8.15-8.11 (2H, m), 7.84 (1H, d, J=
7.6Hz),7.77(1H,s),7.62(1H,dd,J1=4.8Hz, J2=4.8Hz), 7.44 (1H, d, J=3.6Hz), 6.56 (1H,
D, J=3.2Hz), 2.46 (3H, s)；13C NMR(100MHz,DMSO-d6)δ(ppm):160.55(1C),158.97(1C),
152.04(1C),148.34(1C),148.11(1C),140.46(1C),139.32(1C),137.47(1C),126.97(1C),
126.54(1C),125.67(1C),116.82(1C),111.86(1C),96.50(1C),14.45(1C)；HRMS(ESI)m/z:
Calcd forC15H13N4O2[M+H]+:281.1033,Found:281.1020.
3, the synthesis of compound 3
(1) synthesis of intermediate
The cyano acethydrazide of 0.01mol is placed in three-necked bottle, 15mL methylene chloride is added and makees solvent, 3mL acetic acid is urged
Agent stirs under room temperature.It takes the pyridine-2-formaldehyde of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, uses constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, detects terminal with thin layer silica gel plate (TLC).It places reaction liquid into beaker, with steaming
Distilled water is washed till neutrality repeatedly.Liquid separation is simultaneously evaporated under reduced pressure, and is dried after suction filtration, is obtained intermediate.
(2) synthesis of target compound
It taking intermediate 0.01mol to be placed in three-necked bottle, 15mL dehydrated alcohol is added and makees solvent, 3mL triethylamine makees catalyst,
It is stirred under conditions of 50 DEG C.It takes the thiophene -2-formaldehyde of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, uses constant pressure
Dropping funel is added dropwise in three-necked bottle, reacts 1h, detects terminal with thin layer silica gel plate (TLC).After fully reacting, by reaction solution
It pours into 500mL beaker, the petroleum ether of 300mL and stirring is added, there is solid matter precipitation.After being filtered and being dried, second is used
Nitrile: dehydrated alcohol=1:10 mixed solution recrystallizes crude product, obtains target product.
Dark red crystal；IR(KBr)νmax(cm-1):3439,2196,1684,1578,1523,917；1H NMR
(400MHz,DMSO-d6) δ (ppm): 15.96 (1H, s), 8.72 (1H, d, J=4.0Hz), 8.69 (1H, s), 8.20 (1H, d, J
=5.2Hz), 8.17-8.12 (1H, m), 8.07 (1H, d, J=3.2Hz), 7.85 (1H, d, J=8.0Hz), 7.80 (1H, s),
7.64-7.61(1H,m),7.37(1H,dd,J1=4.0Hz, J2=3.6Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):
158.50(1C),152.02(1C),148.40(1C),146.43(1C),140.73(1C),140.19(1C),139.36(1C),
136.75(1C),136.55(1C),129.27(1C),127.07(1C),125.75(1C),116.92(1C),99.65(1C)；
HRMS(ESI)m/z:Calcd forC14H11N4OS[M+H]+:283.0648,Found:283.0638.
4, the synthesis of compound 4
(1) synthesis of intermediate
The cyano acethydrazide of 0.01mol is placed in three-necked bottle, 15mL methylene chloride is added and makees solvent, 3mL acetic acid is urged
Agent stirs under room temperature.It takes the pyridine-2-formaldehyde of 0.01mol to be added in 5mL methylene chloride, after completely dissolution, uses constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, detects terminal with thin layer silica gel plate (TLC).It places reaction liquid into beaker, with steaming
Distilled water is washed till neutrality repeatedly.Liquid separation is simultaneously evaporated under reduced pressure, and is dried after suction filtration, is obtained intermediate.
(2) synthesis of target compound
It taking intermediate 0.01mol to be placed in three-necked bottle, 15mL dehydrated alcohol is added and makees solvent, 3mL triethylamine makees catalyst,
It is stirred under conditions of 50 DEG C.The 2- furylacrolein of 0.01mol is taken to be added in 5mL methylene chloride, after completely dissolution, with perseverance
Pressure dropping funel is added dropwise in three-necked bottle, reacts 1h, detects terminal with thin layer silica gel plate (TLC).After fully reacting, it will react
Liquid pours into 500mL beaker, and the petroleum ether of 300mL and stirring is added, and has solid matter precipitation.After being filtered and being dried, use
Acetonitrile: dehydrated alcohol=1:10 mixed solution recrystallizes crude product, obtains target product.
Yellow powder；IR(KBr)νmax(cm-1):3441,2200,1689,1674,1581,988；1H NMR(400MHz,
DMSO-d6) δ (ppm): 15.87 (1H, s), 8.71 (1H, d, J=4.0Hz), 8.24 (1H, d, J=12.0Hz), 8.13 (1H,
D, J=7.6Hz), 7.97 (1H, s), 7.83 (1H, d, J=8.0Hz), 7.76 (1H, s), 7.62-7.54 (2H, m), 7.05-
6.98 (2H, m), 6.72 (1H, t, J=1.6Hz)；13C NMR(100MHz,DMSO-d6)δ(ppm):158.29(1C),153.85
(1C),152.03(1C),151.59(1C),148.38(1C),147.62(1C),140.52(1C),139.27(1C),134.87
(1C),127.02(1C),125.62(1C),120.70(1C),117.93(1C),115.84(1C),114.02(1C),104.32
(1C)；HRMS(ESI)m/z:Calcd for C16H13N4O2[M+H]+:293.1033,Found:293.1028.
The measurement of 1 the compounds of this invention insecticidal activity of test example
1. test pest
3 instar larvae of mythimna separata, 3 instar larvae of corn borer, Tetranychus cinnabarinus adult mite, 3 instar larvae of Culex pipiens pallens, they are indoor normal
The sensitive strain that year for many generations raises.
2. the measuring method of mythimna separata
Sample to be tested is dissolved in dimethyl sulfoxide and is diluted to certain concentration with 0.1% Tween-80 aqueous solution, to be not added
The corresponding solution of sample to be tested is negative control.Maize leaf is cut into the segment of 2 × 4cm, is taken after soaking 5s in solution to be measured
It opens, bottom is put into after draining and is covered in the culture dish (6cm) of filter paper, access 15 3 instar larvaes, then placing it in temperature is 22
~24 DEG C, relative humidity 60%, light application time records death condition, often to continue to raise in the laboratory of 14:10h afterwards for 24 hours
One experiment is repeated 3 times, and calculates corrected mortality with following equation:
3. the measuring method of corn borer
Sample to be tested is dissolved in dimethyl sulfoxide and is diluted to certain concentration with 0.1% Tween-80 aqueous solution, to be not added
The corresponding solution of sample to be tested is negative control.The tender fringe of corn and tender bract are cut into segment, taken after soaking 10s in solution to be measured
It opens, diameter is put into after draining as 6cm, in the glass culture dish of high 9cm, accesses 3 age of the corn borer children that 15 sizes are neat, healthy
Worm, then placing it in temperature is 22~24 DEG C, relative humidity 60%, continues to raise in the laboratory that light application time is 14:10h
It supports, records death condition afterwards for 24 hours, each experiment is repeated 3 times, and calculates corrected mortality with following equation:
4. the measuring method of Tetranychus cinnabarinus
Sample to be tested is dissolved in dimethyl sulfoxide and is diluted to certain concentration with 0.1% Tween-80 aqueous solution, to be not added
The corresponding solution of sample to be tested is negative control.Acquire the big Kidney bean leaf of insect density, carefully choose make health adult mite (30~
50) it stays on blade face, it is taken away after the Kidney bean leaf with worm is immersed solution 5s to be measured, the training that bottom is covered with filter paper is put into after draining
It supports in ware (6cm), being placed on temperature is 22~24 DEG C, relative humidity 60%, and the laboratory that light application time is 14:10h relays
Continuous raising, records death condition afterwards for 24 hours, and each experiment is repeated 3 times, and calculates corrected mortality with following equation:
5. the measuring method of Culex pipiens pallens
Using the method for world health organisation recommendations, sample to be tested is dissolved in dimethyl sulfoxide and with 0.1% Tween-80 water
Solution is diluted to certain concentration, the corresponding solution of sample to be tested is not added as negative control.Take every kind of solution 1mL, respectively plus
Enter into the 118mL wax dixie cup equipped with 99mL distilled water and 20 3 instar larvaes of Culex pipiens pallens, these dixie cups are placed on temperature
It is 22~24 DEG C, relative humidity 60%, light application time records dead feelings to continue to raise in the laboratory of 14:10h afterwards for 24 hours
Condition, each experiment are repeated 3 times, and calculate corrected mortality with following equation:
6. test result
The desinsection of the compounds of this invention the results are shown in Table 1.
Table 1
a: duplicate average value three times.
There is preferable cytotoxicity to these pests from the compounds of this invention known to upper table 1.
The measurement of the antioxygenic property of 2 the compounds of this invention of test example
1. instrument and reagent
721B type spectrophotometer, 1,1- diphenyl -2- picryl hydrazine (DPPH), 95% ethyl alcohol.
2. determination step
(1) preparation of DPPH and sample solution
0.0130 gram of DPPH is accurately weighed with assay balance, is settled in 500mL volumetric flask with 95% ethyl alcohol, obtains concentration
For the solution of 26mg/L；0.0100g sample to be tested is accurately weighed, is settled in 100mL volumetric flask with 95% ethyl alcohol, obtains concentration
For the sample solution of 100mg/L.
(2) the DPPH solution and 1mL95% ethanol solution of 4mL are sequentially added in 10mL conical flask, mix stable reaction
Afterwards, using 95% ethyl alcohol as reference solution, its absorbance value is measured at λ max=518nm, is denoted as A0。
(3) the DPPH solution and 1mL solution to be measured that 4mL is sequentially added in 10mL conical flask, shake up, react at room temperature
After 40min stablizes, using 95% ethyl alcohol as reference solution, its absorbance value is measured at wavelength X max=518nm, is denoted as AS.Often
One tests in triplicate, and the free radical scavenging activity Y (%) of antioxidant is calculated with following equation:
3. the measurement result of antioxygenic property
Table 2 is when concentration is 100mg/L, clearance rate of the compound to DPPH free radical
| Compound | Clearance ratea(%) |
| Compound 1 | 93.2 |
| Compound 2 | 88.3 |
| Compound 3 | 92.9 |
| Compound 4 | 91.0 |
a: duplicate average value three times.
From upper table 2 it is found that the compounds of this invention to the clearance rate of DPPH free radical all 88% or more, i.e., they have compared with
Good antioxygenic property.
Claims (5)
1. structural formula such as I compound represented of formula:
Wherein, R1For
R2For hydrogen, C1-C4 alkyl or halogen；R3For hydrogen, C1-C4 alkyl or halogen；X is O or S.
2. compound according to claim 1, it is characterised in that: R1For
3. compound according to claim 2, which is characterized in that R1For
4. the described in any item compounds of claims 1 to 3 are preparing the application in antioxidant.
5. application of the described in any item compounds of claims 1 to 3 in prevention and treatment agricultural pests, it is characterised in that: the agriculture
Industry pest is mythimna separata, corn borer, Tetranychus cinnabarinus or Culex pipiens pallens.
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