CN107417673A - The heterocyclic radical propylene hydrazide derivative of 2 cyano group of N (2 pyridine radicals) methylene 3 and its application - Google Patents
The heterocyclic radical propylene hydrazide derivative of 2 cyano group of N (2 pyridine radicals) methylene 3 and its application Download PDFInfo
- Publication number
- CN107417673A CN107417673A CN201710486194.4A CN201710486194A CN107417673A CN 107417673 A CN107417673 A CN 107417673A CN 201710486194 A CN201710486194 A CN 201710486194A CN 107417673 A CN107417673 A CN 107417673A
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- Prior art keywords
- compound
- application
- heterocyclic
- antioxidant
- methylene
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 title abstract description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 16
- 241000144210 Culex pipiens pallens Species 0.000 claims description 7
- 241000346285 Ostrinia furnacalis 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
- 241000607479 Yersinia pestis 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
- -1 heterocyclic Schiff base Chemical class 0.000 abstract description 7
- 239000002917 insecticide Substances 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 239000002262 Schiff base Substances 0.000 abstract description 4
- 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 21
- 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
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000523 sample Substances 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
- 230000003026 anti-oxygenic effect Effects 0.000 description 6
- 239000007788 liquid 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
- 239000003905 agrochemical Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 239000012153 distilled water Substances 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000005909 ethyl alcohol group Chemical group 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
- 241000238631 Hexapoda Species 0.000 description 3
- 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
- 150000003254 radicals Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- 238000000034 method Methods 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
- 239000000126 substance Substances 0.000 description 2
- 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
- 0 C*(C)c1ccc(C)[o]1 Chemical compound C*(C)c1ccc(C)[o]1 0.000 description 1
- KBLXTGMUYMHUGO-RIMRSHBZSA-N C/C=C/CC1=CC=C[U]1 Chemical compound C/C=C/CC1=CC=C[U]1 KBLXTGMUYMHUGO-RIMRSHBZSA-N 0.000 description 1
- GWQOOADXMVQEFT-UHFFFAOYSA-N Cc1ccc(C)[s]1 Chemical compound Cc1ccc(C)[s]1 GWQOOADXMVQEFT-UHFFFAOYSA-N 0.000 description 1
- VQKFNUFAXTZWDK-UHFFFAOYSA-N Cc1ccc[o]1 Chemical compound Cc1ccc[o]1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 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
- 238000005842 biochemical reaction Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 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
- 239000003814 drug Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 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
- 239000000575 pesticide Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 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
- 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
- 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
-
- 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 present invention relates to heterocyclic Schiff base class compound and application thereof, the heterocyclic radical propylene hydrazide derivative of 2 cyano group of more particularly to N (2 pyridine radicals) methylene 3 and its application.Present invention solves the technical problem that being to provide a kind of heterocyclic Schiff base class compound used as antioxidant and agricultural insecticide, its structural formula is as shown in formula I.The present invention is using bio-active group splicing principle, heterocyclic compound is introduced into Schiff class compound, some novel structures, the reactive compound of superior activity or active lead compound are found that, so as to establish preferable basis for the initiative of novel antioxidant and insecticide.
Description
Technical field
The present invention relates to heterocyclic Schiff base class compound and application thereof, more particularly to N- (2- pyridine radicals) methylene -2-
Cyano group -3- heterocyclic radical propylene hydrazide derivatives and its application.
Background technology
Antioxidant effectively can delay or suppress many materials, particularly big point of the biology such as sugar, fat, protein, nucleic acid
The oxidation deterioration of son, quite varied application is suffered from many fields：(1) in terms of food processing, antioxidant can suppress
Oxidation of Fat and Oils, prevent it from becoming sour, frequently as food oxydating resistance additive；(2) in life science and medical domain, antioxidant energy
Interior free yl is removed, slows down the formation of peroxidation state, prevents and treats various diseases caused by free radical, improves machine
Body immunocompetence, so as to protect health；(3) add in chemical industrial field, antioxidant as the stability of chemical products
Add agent, improve the antioxygenic property of product, so as to extend its service life.Because antioxidant is in industrial and agricultural production and daily life
Irreplaceable effect 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 agricultural chemicals particularly insecticide not only pollutes environment, destroys the ecological balance,
It also results 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 paid close attention to, and how to efficiently solve these problems is the one long-term and arduous of facing mankind
Task.So, huge challenge is faced with agricultural chemicals, and in the case that the mankind be unable to do without agricultural chemicals, 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 agricultural chemicals " or " environment friendly agricultural " the focus into pesticide research and forward position.
Schiff refers to occur condensation reaction and containing for generating by primary amine and aldehydes or ketones>One kind of C=N- structures 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 medical science, catalysis, analytical chemistry, corrosion and the field 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 research and develop to it shows great interest, special
It is not even more of great interest in the field such as biology, medicine, agricultural chemicals, and constantly has structure novelty, excellent performance, work
Come out with unique, the environment-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 as research main body.Wherein, the compound such as furans, thiophene, pyridine, pyrimidine, pyrazoles, imidazoles, thiazole, triazole, because not
It is disconnected to emerge novel agents that some have an epoch-marking significance and attract people's attention, also ground as bioactive compound
The focus studied carefully and forward position.
Up to the present, it yet there are no what heterocyclic Schiff base class compound used as antioxidant and agricultural insecticide
Report.
The content of the invention
Present invention solves the technical problem that it is to provide a kind of heterocycle used as antioxidant and agricultural insecticide
Schiff class compound.
N- (2- pyridine radicals) methylene -2- cyano group -3- heterocyclic radical propylene hydrazide derivatives of the present invention, its 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, R1For
Preferred R1For
The present invention also provides application of the compounds of this invention in antioxidant is prepared.
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 agricultural pests are prevented and treated.
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.
Heterocyclic compound is introduced into Schiff class compound, sent out using bio-active group splicing principle by the present invention
Some novel structures, the reactive compound of superior activity or active lead compound are showed, so as to be novel antioxidant and kill
Preferable basis has been established in the initiative of worm agent.
Embodiment
The present invention provides compound of the structural formula 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, R1For
Preferred R1For
It is currently preferred structural formula below.
The compound of the present invention, conventional preparation method can be used to obtain.
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.
The embodiment of the present invention is further described with reference to embodiment, therefore not limited the present invention
System is among described scope of embodiments.
The synthesis of the compound 1~4 of embodiment 1
Composition principle：
1st, the synthesis of compound 1
(1) synthesis of intermediate
0.01mol cyano acethydrazide is placed in three-necked bottle, 15mL dichloromethane is added and makees solvent, 3mL acetic acid is urged
Agent, stir under normal temperature.Take 0.01mol pyridine-2-formaldehyde to be added in 5mL dichloromethane, fully after dissolving, use constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, and terminal is detected with thin layer silica gel plate (TLC).Place 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
Taking intermediate 0.01mol to be placed in three-necked bottle, add 15mL absolute ethyl alcohols and make solvent, 3mL triethylamines make catalyst,
Stirred under conditions of 50 DEG C.Take 0.01mol furfural to be added in 5mL dichloromethane, fully after dissolving, use constant pressure funnel
It is added dropwise in three-necked bottle, reacts 1h, terminal is detected with thin layer silica gel plate (TLC).After reaction completely, reaction solution is poured into
In 500mL beakers, 300mL petroleum ether and stirring are added, there is solid matter precipitation.After being filtered and being dried, acetonitrile is used：Nothing
Water-ethanol=1：10 mixed solution recrystallizes to 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.
2nd, the synthesis of compound 2
(1) synthesis of intermediate
0.01mol cyano acethydrazide is placed in three-necked bottle, 15mL dichloromethane is added and makees solvent, 3mL acetic acid is urged
Agent, stir under normal temperature.Take 0.01mol pyridine-2-formaldehyde to be added in 5mL dichloromethane, fully after dissolving, use constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, and terminal is detected with thin layer silica gel plate (TLC).Place 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
Taking intermediate 0.01mol to be placed in three-necked bottle, add 15mL absolute ethyl alcohols and make solvent, 3mL triethylamines make catalyst,
Stirred under conditions of 50 DEG C.Take 0.01mol 5 methyl furfural to be added in 5mL dichloromethane, fully after dissolving, dripped with constant pressure
Liquid funnel is added dropwise in three-necked bottle, reacts 1h, and terminal is detected with thin layer silica gel plate (TLC).After reaction completely, reaction solution is fallen
Enter in 500mL beakers, add 300mL petroleum ether and stirring, there is solid matter precipitation.After being filtered and being dried, acetonitrile is used：
Absolute ethyl alcohol=1：10 mixed solution recrystallizes to 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.
3rd, the synthesis of compound 3
(1) synthesis of intermediate
0.01mol cyano acethydrazide is placed in three-necked bottle, 15mL dichloromethane is added and makees solvent, 3mL acetic acid is urged
Agent, stir under normal temperature.Take 0.01mol pyridine-2-formaldehyde to be added in 5mL dichloromethane, fully after dissolving, use constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, and terminal is detected with thin layer silica gel plate (TLC).Place 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
Taking intermediate 0.01mol to be placed in three-necked bottle, add 15mL absolute ethyl alcohols and make solvent, 3mL triethylamines make catalyst,
Stirred under conditions of 50 DEG C.Take 0.01mol thiophene -2-formaldehyde to be added in 5mL dichloromethane, fully after dissolving, use constant pressure
Dropping funel is added dropwise in three-necked bottle, reacts 1h, and terminal is detected with thin layer silica gel plate (TLC).After reaction completely, by reaction solution
Pour into 500mL beakers, add 300mL petroleum ether and stirring, there is solid matter precipitation.After being filtered and being dried, second is used
Nitrile：Absolute ethyl alcohol=1：10 mixed solution recrystallizes to crude product, obtains target product.
Kermesinus 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.
4th, the synthesis of compound 4
(1) synthesis of intermediate
0.01mol cyano acethydrazide is placed in three-necked bottle, 15mL dichloromethane is added and makees solvent, 3mL acetic acid is urged
Agent, stir under normal temperature.Take 0.01mol pyridine-2-formaldehyde to be added in 5mL dichloromethane, fully after dissolving, use constant pressure addition
Funnel is added dropwise in three-necked bottle, reacts 5h, and terminal is detected with thin layer silica gel plate (TLC).Place 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
Taking intermediate 0.01mol to be placed in three-necked bottle, add 15mL absolute ethyl alcohols and make solvent, 3mL triethylamines make catalyst,
Stirred under conditions of 50 DEG C.0.01mol 2- furylacroleins are taken to be added in 5mL dichloromethane, fully after dissolving, with perseverance
Pressure dropping funel is added dropwise in three-necked bottle, reacts 1h, and terminal is detected with thin layer silica gel plate (TLC).After reaction completely, it will react
Liquid is poured into 500mL beakers, adds 300mL petroleum ether and stirring, there is solid matter precipitation.After being filtered and being dried, use
Acetonitrile：Absolute ethyl alcohol=1：10 mixed solution recrystallizes to 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 measure of the compounds of this invention insecticidal activity of test example 1
1. for examination insect
The instar larvae of mythimna separata 3, the instar larvae of corn borer 3, Tetranychus cinnabarinus is into mite, and the instar larvae of Culex pipiens pallens 3, they are indoor normal
The sensitive strain that year for many generations raises.
2. the assay method of mythimna separata
Testing sample is dissolved in dimethyl sulfoxide and is diluted to certain concentration with the 0.1% Tween-80 aqueous solution, to be not added with
The corresponding solution of testing sample is negative control.Maize leaf is cut into 2 × 4cm segment, taken after soaking 5s in solution to be measured
Open, bottom is put into after draining and is covered with the culture dish (6cm) of filter paper, access 15 first 3 instar larvaes, then place it in temperature as 22
~24 DEG C, relative humidity 60%, light application time 14:Continue to raise in 10h laboratory, death condition is recorded after 24h, often
One experiment is repeated 3 times, and calculates corrected mortality with following equation：
3. the assay method of corn borer
Testing sample is dissolved in dimethyl sulfoxide and is diluted to certain concentration with the 0.1% Tween-80 aqueous solution, to be not added with
The corresponding solution of testing sample is negative control.The tender fringe of corn and tender bract are cut into segment, taken after soaking 10s in solution to be measured
Open, be put into a diameter of 6cm after draining, in high 9cm glass culture dish, access that 15 sizes are neat, the age of corn borer 3 of health children
Worm, then it is 22~24 DEG C to place it in temperature, relative humidity 60%, light application time 14:Continue to raise in 10h laboratory
Support, death condition is recorded after 24h, each experiment is repeated 3 times, and calculates corrected mortality with following equation：
4. the assay method of Tetranychus cinnabarinus
Testing sample is dissolved in dimethyl sulfoxide and is diluted to certain concentration with the 0.1% Tween-80 aqueous solution, to be not added with
The corresponding solution of testing sample is negative control.Gather the big Kidney bean leaf of insect density, carefully choose make health into mite (30~
50) stay on blade face, taken away after the Kidney bean leaf with worm is immersed into solution 5s to be measured, the training that bottom is covered with filter paper is put into after draining
Support in ware (6cm), it is 22~24 DEG C to be placed on temperature, relative humidity 60%, light application time 14:10h laboratory relaying
It is continuous to raise, death condition is recorded after 24h, each experiment is repeated 3 times, and calculates corrected mortality with following equation：
5. the assay method of Culex pipiens pallens
Using the method for world health organisation recommendations, testing sample is dissolved in dimethyl sulfoxide and with 0.1% Tween-80 water
Solution is diluted to certain concentration, to be not added with the corresponding solution of testing sample as negative control.Every kind of solution 1mL is taken, is added respectively
Enter into the 118mL wax dixie cups equipped with 99mL distilled water and 20 instar larvaes of Culex pipiens pallens 3, these dixie cups are placed on temperature
For 22~24 DEG C, relative humidity 60%, light application time 14:Continue to raise in 10h laboratory, dead feelings are recorded after 24h
Condition, each experiment are repeated 3 times, and calculate corrected mortality with following equation：
6. result of the test
The desinsection of the compounds of this invention the results are shown in Table 1.
Table 1
a：The average value repeated three times.
Understand that the compounds of this invention has preferable cytotoxicity to these insects from upper table 1.
The measure of the antioxygenic property of the compounds of this invention of test example 2
1. instrument and reagent
721B type spectrophotometers, 1,1- diphenyl -2- picryls hydrazine (DPPH), 95% ethanol.
2. determination step
(1) preparation of DPPH and sample solution
0.0130 gram of DPPH is accurately weighed with assay balance, is settled to 95% ethanol in 500mL volumetric flasks, obtains concentration
For 26mg/L solution；0.0100g testing samples accurately are weighed, is settled to 95% ethanol in 100mL volumetric flasks, obtains concentration
For 100mg/L sample solution.
(2) 4mL DPPH solution and 1mL95% ethanol solutions is sequentially added in 10mL conical flasks, mixes stable reaction
Afterwards, using 95% ethanol as reference solution, its absorbance is determined at λ max=518nm, is designated as A0。
(3) 4mL DPPH solution and 1mL solution to be measured is sequentially added in 10mL conical flasks, shakes up, reacts at room temperature
After 40min is stable, using 95% ethanol as reference solution, its absorbance is determined at wavelength X max=518nm, is designated as AS.Often
One is tested 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 radicals
| Compound | Clearance ratea(%) |
| Compound 1 | 93.2 |
| Compound 2 | 88.3 |
| Compound 3 | 92.9 |
| Compound 4 | 91.0 |
a：The average value repeated three times.
It was found from upper table 2, the compounds of this invention to the clearance rate of DPPH free radicals all more than 88%, i.e., they have compared with
Good antioxygenic property.
Claims (6)
1. compound of the structural formula as shown in formula I：
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, it is characterised in that R1For
4. application of the compound described in any one of claims 1 to 3 in antioxidant is prepared.
5. application of the compound in agricultural pests are prevented and treated described in any one of claims 1 to 3.
6. application of the compound according to claim 5 in agricultural pests are prevented and treated, it is characterised in that：The agricultural pests
For mythimna separata, corn borer, Tetranychus cinnabarinus or Culex pipiens pallens.
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| CN87104648A (en) * | 1986-07-08 | 1988-04-13 | 合成实验室公司 | Nitrofuran derivatives and preparation method thereof and the application in treatment |
| EP0286746A1 (en) * | 1987-04-15 | 1988-10-19 | Rohm And Haas Company | Insecticidal N-(optionally substituted) - N'-substituted-N,N'-disubstituted- hydrazines |
| CN1040191A (en) * | 1988-06-15 | 1990-03-07 | 罗姆和哈斯公司 | Parasiticidal N '-replacement-N-alkyl-carbonyl-N '-acylhydrazine and N '-replacement-N-acyl group-N '-alkyl-carbonyl hydrazine |
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| FR2580281B1 (en) * | 1985-04-11 | 1987-09-18 | Synthelabo | NITROFURAN DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| US6350771B1 (en) * | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
| JP2000297086A (en) * | 1999-02-08 | 2000-10-24 | Sankyo Co Ltd | Heteroarylhydrazone compound |
| UY32940A (en) * | 2009-10-27 | 2011-05-31 | Bayer Cropscience Ag | AMIDAS REPLACED WITH HALOGENO RENT AS INSECTICIDES AND ACARICIDES |
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| US3549767A (en) * | 1966-12-16 | 1970-12-22 | Geigy Chem Corp | Method of controlling insects and acarinae,employing certain acylated hydrazones and hydrazines |
| CN87104648A (en) * | 1986-07-08 | 1988-04-13 | 合成实验室公司 | Nitrofuran derivatives and preparation method thereof and the application in treatment |
| EP0286746A1 (en) * | 1987-04-15 | 1988-10-19 | Rohm And Haas Company | Insecticidal N-(optionally substituted) - N'-substituted-N,N'-disubstituted- hydrazines |
| CN1040191A (en) * | 1988-06-15 | 1990-03-07 | 罗姆和哈斯公司 | Parasiticidal N '-replacement-N-alkyl-carbonyl-N '-acylhydrazine and N '-replacement-N-acyl group-N '-alkyl-carbonyl hydrazine |
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