DD219363A5 - Neues verfahren zur herstellung von chromen-derivate - Google Patents

Neues verfahren zur herstellung von chromen-derivate Download PDF

Info

Publication number: DD219363A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; given above; meanings given; meanings; item
Prior art date: 1983-02-15

Application number

DD84260074A

Other languages

German (de)

English (en)

Inventor

Tibor Timar

Kalman Zsupan

Janos Repasi

Iren Borsos

Istvan Kiss

Andras Fodor

Peter Maroy

Original Assignee

Alkaloida Vegyeszeti Gyar

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-02-15

Filing date

1984-02-14

Publication date

1985-03-06

1984-02-14 Application filed by Alkaloida Vegyeszeti Gyar filed Critical Alkaloida Vegyeszeti Gyar

1985-03-06 Publication of DD219363A5 publication Critical patent/DD219363A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 36
150000001875 compounds Chemical class 0.000 claims abstract description 26
-1 mercapto, amino Chemical group 0.000 claims abstract description 25
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
230000008569 process Effects 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000002252 acyl group Chemical group 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
150000002989 phenols Chemical class 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 claims description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
230000002829 reductive effect Effects 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 5
235000001671 coumarin Nutrition 0.000 claims description 5
150000004775 coumarins Chemical class 0.000 claims description 5
JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical class CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
239000000010 aprotic solvent Substances 0.000 claims description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
150000001728 carbonyl compounds Chemical class 0.000 claims description 4
150000004795 grignard reagents Chemical class 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
MGSHXMOLUWTMGP-UHFFFAOYSA-N 3'-carboxy-alpha-chromanol Chemical class C1=CC=C2C(O)CCOC2=C1 MGSHXMOLUWTMGP-UHFFFAOYSA-N 0.000 claims description 3
KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
150000001993 dienes Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
239000011230 binding agent Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
238000009835 boiling Methods 0.000 claims 4
150000002170 ethers Chemical class 0.000 claims 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
150000001298 alcohols Chemical class 0.000 claims 3
125000001931 aliphatic group Chemical group 0.000 claims 3
239000007800 oxidant agent Substances 0.000 claims 3
230000003647 oxidation Effects 0.000 claims 3
238000007254 oxidation reaction Methods 0.000 claims 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
239000003849 aromatic solvent Substances 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
125000005595 acetylacetonate group Chemical group 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
229910001508 alkali metal halide Inorganic materials 0.000 claims 1
150000008045 alkali metal halides Chemical class 0.000 claims 1
150000001350 alkyl halides Chemical class 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
238000010411 cooking Methods 0.000 claims 1
230000018044 dehydration Effects 0.000 claims 1
238000006297 dehydration reaction Methods 0.000 claims 1
PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
229910001385 heavy metal Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
238000006263 metalation reaction Methods 0.000 claims 1
238000001465 metallisation Methods 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims 1
239000012454 non-polar solvent Substances 0.000 claims 1
239000002798 polar solvent Substances 0.000 claims 1
229920000151 polyglycol Polymers 0.000 claims 1
239000010695 polyglycol Substances 0.000 claims 1
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 claims 1
150000003608 titanium Chemical class 0.000 claims 1
150000000463 2H-chromenes Chemical class 0.000 abstract description 11
241000607479 Yersinia pestis Species 0.000 abstract description 4
239000003921 oil Substances 0.000 description 44
230000000694 effects Effects 0.000 description 17
239000000243 solution Substances 0.000 description 14
239000013543 active substance Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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239000004480 active ingredient Substances 0.000 description 8
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101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 6
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239000000047 product Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
230000004071 biological effect Effects 0.000 description 5
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241000258916 Leptinotarsa decemlineata Species 0.000 description 4
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238000001035 drying Methods 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000008371 chromenes Chemical class 0.000 description 3
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238000011835 investigation Methods 0.000 description 3
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239000002609 medium Substances 0.000 description 3
241000894007 species Species 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
241000244203 Caenorhabditis elegans Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241001127120 Dysdercus fasciatus Species 0.000 description 2
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RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
241000255969 Pieris brassicae Species 0.000 description 2
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239000008272 agar Substances 0.000 description 2
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VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 2
150000004777 chromones Chemical class 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
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229940079593 drug Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
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ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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SAXKWTPDZMBKSQ-UHFFFAOYSA-N 2,2-dimethylchromene Chemical compound C1=CC=C2C=CC(C)(C)OC2=C1 SAXKWTPDZMBKSQ-UHFFFAOYSA-N 0.000 description 1
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DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
RFJPSAYWKBGVAW-UHFFFAOYSA-N precocene III Chemical compound O1C(C)(C)C=CC2=C1C=C(OCC)C(OC)=C2 RFJPSAYWKBGVAW-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000015099 wheat brans Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- 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
- A01N43/14—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 six-membered rings
- A01N43/16—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 six-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
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
- 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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Photoreceptors In Electrophotography (AREA)
Saccharide Compounds (AREA)
Amplifiers (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Oscillators With Electromechanical Resonators (AREA)
Measurement And Recording Of Electrical Phenomena And Electrical Characteristics Of The Living Body (AREA)
Developing Agents For Electrophotography (AREA)

DD84260074A 1983-02-15 1984-02-14 Neues verfahren zur herstellung von chromen-derivate DD219363A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU83504A HU194214B (en)	1983-02-15	1983-02-15	Process for producing 7-alkoxy-2h-chromene derivatives and insecticide and nematocide compositions containing them as active components

Publications (1)

Publication Number	Publication Date
DD219363A5 true DD219363A5 (de)	1985-03-06

Family

ID=10949885

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84260074A DD219363A5 (de)	1983-02-15	1984-02-14	Neues verfahren zur herstellung von chromen-derivate

Country Status (16)

Country	Link
US (1)	US4716238A (cs)
EP (2)	EP0208147A3 (cs)
JP (1)	JPS59210077A (cs)
AT (1)	ATE32461T1 (cs)
AU (1)	AU580729B2 (cs)
CS (1)	CS261865B2 (cs)
DD (1)	DD219363A5 (cs)
DE (1)	DE3469299D1 (cs)
DK (1)	DK70284A (cs)
ES (2)	ES8700855A1 (cs)
FI (1)	FI840585A7 (cs)
HU (1)	HU194214B (cs)
IL (1)	IL70926A (cs)
PL (1)	PL246226A1 (cs)
PT (1)	PT78110B (cs)
SU (1)	SU1468418A3 (cs)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU194855B (en) *	1983-02-16	1988-03-28	Alkaloida Vegyeszeti Gyar	Process for producing chromene derivatives, insecticide and nematocide compositions containing chromene derivatives as active components
JPS6051189A (ja) *	1983-08-30	1985-03-22	Sankyo Co Ltd	チアゾリジン誘導体およびその製造法
GB8323293D0 (en) *	1983-08-31	1983-10-05	Zyma Sa	Substituted flavene and thioflavene derivatives
JP2514945B2 (ja) *	1987-02-05	1996-07-10	三井石油化学工業株式会社	芳香族アミン誘導体
HU207861B (en) *	1989-07-21	1993-06-28	Alkaloida Vegyeszeti Gyar	Process for producing benzopirane derivative of blood pressure lowering activity
US5223629A (en) *	1989-07-21	1993-06-29	Alkaloida Vegyeszeti Gyar	Process for the preparation of anti-hypertensive benzopyran
FR2760748A1 (fr) *	1997-03-14	1998-09-18	Rhodia Chimie Sa	Procede de preparation de 2h-1-benzopyranes
FR2766820B1 (fr) *	1997-07-31	1999-10-22	Rhodia Chimie Sa	Procede de preparation de 2h-1-benzopyranes et intermediaires de synthese utiles dans la mise en oeuvre du procede
ITTO20030140U1 (it) *	2003-09-16	2005-03-17	Interfila Srl	Matita cosmetica
WO2005033093A1 (en)	2003-09-19	2005-04-14	Galileo Pharmaceuticals, Inc.	7,8-bicycloalkyl-chroman derivatives
WO2014137811A1 (en)	2013-03-05	2014-09-12	The United States Of America, As Represented By The Secretary Of Agriculture	Compositions and methods for repelling blood-sucking and biting insects, ticks and mites
CN106749147B (zh) *	2016-12-01	2018-12-07	南昌大学	降血糖化合物及其制备方法、用途
KR102692932B1 (ko) *	2019-07-30	2024-08-07	주식회사 글라세움	2-((6-(히드록시메틸)크로멘-5-일)옥시)-1-페닐에타논 유도체의 합성 방법
KR102505284B1 (ko)	2020-07-20	2023-03-03	항저우 두이 테크놀로지 컴퍼니 리미티드	치환된 크로마논 유도체의 제조방법
CN113024500B (zh) *	2021-03-11	2023-02-03	西华大学	6,8-二溴苯并吡喃衍生物及其在农药中的应用
CN113004240B (zh) *	2021-03-11	2023-02-03	西华大学	苯并吡喃类化合物及其在农药中的用途
CN112939919B (zh) *	2021-03-11	2023-02-03	西华大学	2-氨基苯并吡喃类化合物及其在农药中的应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH213149A (de) *	1939-07-28	1941-01-15	Hoffmann La Roche	Verfahren zur Darstellung von d,l-a-Tocopherol.
US2354492A (en) *	1941-11-26	1944-07-25	Adams Roger	Marihuana active compound
BR7606195A (pt) *	1975-09-17	1977-06-14	Cornell Res Foundation Inc	Processo para tratar insetos para inibir a atividade hormonal juvenil,e processo para produzir um composto de cromeno
US4542150A (en) *	1975-09-17	1985-09-17	Cornell Research Foundation, Inc.	Anti-juvenile hormones
NL7513616A (en) *	1975-11-21	1977-05-24	Beecham Group Ltd	(Thio)chroman and tetralin basic ethers - with anorexigenic and antidepressant activity
JPS5424895A (en) *	1977-07-28	1979-02-24	Eisai Co Ltd	Pyranochromone derivatives and remedies for allergic disorder
JPS5540637A (en) *	1978-09-19	1980-03-22	Mitsui Petrochem Ind Ltd	Preparation of chromene
US4162326A (en) *	1978-09-27	1979-07-24	Stauffer Chemical Company	Insect control agents
JPS565475A (en) *	1979-06-27	1981-01-20	Mitsui Petrochem Ind Ltd	Polyalkyl-7-hydroxy-4h-chromene and its preparation
JPS57109779A (en) *	1980-12-27	1982-07-08	Kumiai Chem Ind Co Ltd	Polyalkyl-5-hydroxy-2h-chromene and its preparation

1983
- 1983-02-15 HU HU83504A patent/HU194214B/hu not_active IP Right Cessation
1984
- 1984-01-13 CS CS841011A patent/CS261865B2/cs unknown
- 1984-02-10 IL IL70926A patent/IL70926A/xx unknown
- 1984-02-14 DD DD84260074A patent/DD219363A5/de not_active IP Right Cessation
- 1984-02-14 US US06/580,097 patent/US4716238A/en not_active Expired - Fee Related
- 1984-02-14 FI FI840585A patent/FI840585A7/fi not_active Application Discontinuation
- 1984-02-14 SU SU843703452A patent/SU1468418A3/ru active
- 1984-02-15 PT PT78110A patent/PT78110B/pt not_active IP Right Cessation
- 1984-02-15 JP JP59026912A patent/JPS59210077A/ja active Pending
- 1984-02-15 EP EP86107710A patent/EP0208147A3/de not_active Ceased
- 1984-02-15 DK DK70284A patent/DK70284A/da not_active Application Discontinuation
- 1984-02-15 ES ES529746A patent/ES8700855A1/es not_active Expired
- 1984-02-15 AT AT84101540T patent/ATE32461T1/de not_active IP Right Cessation
- 1984-02-15 DE DE8484101540T patent/DE3469299D1/de not_active Expired
- 1984-02-15 PL PL24622684A patent/PL246226A1/xx unknown
- 1984-02-15 AU AU24601/84A patent/AU580729B2/en not_active Ceased
- 1984-02-15 EP EP84101540A patent/EP0118794B1/de not_active Expired
1986
- 1986-01-31 ES ES551816A patent/ES8708112A1/es not_active Expired

Also Published As

Publication number	Publication date
IL70926A (en)	1989-08-15
FI840585A0 (fi)	1984-02-14
ATE32461T1 (de)	1988-02-15
CS261865B2 (en)	1989-02-10
JPS59210077A (ja)	1984-11-28
EP0118794B1 (de)	1988-02-10
PT78110B (en)	1986-04-30
IL70926A0 (en)	1984-05-31
PT78110A (en)	1984-03-01
FI840585A7 (fi)	1984-08-16
SU1468418A3 (ru)	1989-03-23
DE3469299D1 (de)	1988-03-17
HU194214B (en)	1988-01-28
EP0118794A1 (de)	1984-09-19
ES551816A0 (es)	1987-10-16
CS101184A2 (en)	1988-07-15
DK70284A (da)	1984-08-16
ES8708112A1 (es)	1987-10-16
AU2460184A (en)	1984-08-23
EP0208147A2 (de)	1987-01-14
ES8700855A1 (es)	1986-11-16
DK70284D0 (da)	1984-02-15
AU580729B2 (en)	1989-02-02
EP0208147A3 (de)	1987-11-04
US4716238A (en)	1987-12-29
ES529746A0 (es)	1986-11-16
PL246226A1 (en)	1985-07-30

Legal Events

Date	Code	Title	Description
1996-06-20	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD219363A5 (de)	1985-03-06	Neues verfahren zur herstellung von chromen-derivate
EP0060617A1 (en)	1982-09-22	Fluorobenzyl cyclopropane carboxylates, their preparation, compositions and use as insecticides
DE2760220C2 (cs)	1987-08-20
DE2032919A1 (de)	1971-01-14	Verfahren zur Herstellung von Polyen verbindungen
DE2418343A1 (de)	1974-11-07	Phenyl-aralkyl-aether, -thioaether und -amine, verfahren zu ihrer herstellung und ihre verwendung
DE2516331A1 (de)	1975-11-06	Phenylaralkyl-aether und -thioaether
DE2524577A1 (de)	1975-12-11	Oxacyclohexanderivate, verfahren zu ihrer herstellung und ihre verwendung als wirkstoffe in herbiziden
DE2639671A1 (de)	1977-04-14	Chromenverbindungen, verfahren zu deren herstellung sowie dieselben enthaltende, als antijuvenilhormon wirkende insektizide
DE69210639T2 (de)	1996-10-24	3-(3,3,3-Trifluor-2-Chlorpropenyl)-2,2-Dimethylcyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestitzide
DE1643608C3 (cs)	1974-04-25
DE2526982A1 (de)	1976-01-08	2-phenoxymethylen-1,4-benzodioxan- derivate
DE2327736A1 (de)	1974-01-03	Polyenverbindungen
EP0129636A1 (de)	1985-01-02	Neues Verfahren zur Herstellung von Chromen-Derivaten
EP0097854B1 (de)	1987-01-21	Thiolphosphorsäureester, ihre Herstellung und Verwendung
DE2162821A1 (de)	1972-08-03	Polyen verbindungen
EP0053756A1 (de)	1982-06-16	2,6-Diethyl-3,5-dimethyl-2,3-dihydro-4H-pyran, Verfahren zu seiner Herstellung und seine Verwendung zur Früherkennung, Lokalisierung und Bekämpfung von Lasioderma serricorne F
DE2510569A1 (de)	1975-09-18	Phenylderivate
US3567833A (en)	1971-03-02	Polycyclic polyhalogenated pesticides
DE2528345A1 (de)	1976-01-08	Phenylalkinylaether, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
DE2313505C3 (de)	1977-09-08	2,3-Dihydrobenzofuranderivate, Verfahren zu ihrer Herstellung und Schädlingsbekämpfungsmittel mit einem Gehalt dieser Verbindungen
DE2347242A1 (de)	1974-03-28	Neue ketone
DE1011416B (de)	1957-07-04	Verfahren zur Herstellung von 0, 0-Dialkyl-thiol- und -thiol-thiono-phosphorsaeuretriestern
DE1543603C (de)	1973-03-22	8-Chromanylcarbamate und Verfahren zu deren Herstellung sowie deren Verwendung als Pestizide
AT365566B (de)	1982-01-25	Verfahren zur herstellung von neuen substituierten 2-(1-alkoxy- oder -alkenyloxyaminoalkyliden)-cyclohexan-1,3-dionen und deren metall- und ammoniumsalzen
DE3205456A1 (de)	1983-08-25	Halogenierte 1-hydroxipyrazole und verfahren zu ihrer herstellung