NO134604B - - Google Patents
Download PDFInfo
- Publication number
- NO134604B NO134604B NO2640/71A NO264071A NO134604B NO 134604 B NO134604 B NO 134604B NO 2640/71 A NO2640/71 A NO 2640/71A NO 264071 A NO264071 A NO 264071A NO 134604 B NO134604 B NO 134604B
- Authority
- NO
- Norway
- Prior art keywords
- acetoxy
- solution
- methyl
- pregnen
- dione
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 5
- 229910052793 cadmium Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 23
- -1 16-pregnene-20-one compound Chemical class 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 238000005893 bromination reaction Methods 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 230000031709 bromination Effects 0.000 description 12
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000009518 sodium iodide Nutrition 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- 150000003431 steroids Chemical class 0.000 description 8
- 239000002026 chloroform extract Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
- SNAYLCYCEXREJX-WWSDEZETSA-N [(3r,8s,9s,10s,13s,14s)-17-acetyl-10,13,16-trimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1C(=O)[C@@H]2[C@@]3(C)CC[C@@H](OC(=O)C)CC3CC[C@H]2[C@@H]2CC(C)=C(C(C)=O)[C@]21C SNAYLCYCEXREJX-WWSDEZETSA-N 0.000 description 6
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960003280 cupric chloride Drugs 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- AURFZBICLPNKBZ-YZRLXODZSA-N 3alpha-hydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-YZRLXODZSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XNZVWYTZHNXHGV-NYXFBQOWSA-N [(3r,8s,9s,10s,13s,14s,16r,17s)-17-acetyl-10,13,16-trimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1CC2C[C@H](OC(C)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(C)=O)[C@@]1(C)CC2=O XNZVWYTZHNXHGV-NYXFBQOWSA-N 0.000 description 2
- SVAAKGCTWRXDHY-UHFFFAOYSA-N [Cd]C Chemical class [Cd]C SVAAKGCTWRXDHY-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VAXHCDMMDVEMNC-PSQDVFTCSA-N (3R,8S,9S,10S,13S,14S,17R)-17-bromo-17-(2-bromoacetyl)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one Chemical compound Br[C@]1(C(CBr)=O)CC[C@H]2[C@@H]3CCC4C[C@@H](CC[C@]4(C)[C@H]3C(C[C@]12C)=O)O VAXHCDMMDVEMNC-PSQDVFTCSA-N 0.000 description 1
- PQGMAKFMGGZKBA-SRJGTTDWSA-N 1-[(8r,9s,10s,13s,14s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 PQGMAKFMGGZKBA-SRJGTTDWSA-N 0.000 description 1
- RSRDWHPVTMQUGZ-OZIWPBGVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RSRDWHPVTMQUGZ-OZIWPBGVSA-N 0.000 description 1
- GWGBNENHEGYJSN-UHFFFAOYSA-N 2,4-dinitrobenzenesulfonic acid;hydrate Chemical compound O.OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O GWGBNENHEGYJSN-UHFFFAOYSA-N 0.000 description 1
- DRSZTATWOSZRAK-UHFFFAOYSA-N 3,4-dibromobutan-2-one Chemical compound CC(=O)C(Br)CBr DRSZTATWOSZRAK-UHFFFAOYSA-N 0.000 description 1
- JWSNVFJCKKXKRE-UHFFFAOYSA-N 3,5-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 JWSNVFJCKKXKRE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FYLIIYMKGIPDGK-LCDJSOJUSA-N [(3R,8S,9S,10S,13S,14S,16R,17R)-17-bromo-17-(2-bromoacetyl)-10,13,16-trimethyl-11-oxo-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C(C)(=O)O[C@H]1CC2CC[C@H]3[C@@H]4C[C@H]([C@](C(CBr)=O)([C@]4(CC([C@@H]3[C@]2(CC1)C)=O)C)Br)C FYLIIYMKGIPDGK-LCDJSOJUSA-N 0.000 description 1
- JAZBMNIJZWDVQJ-UKQOWTAJSA-N [(3r,8s,9s,10s,13s,14s)-17-acetyl-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C1C(=O)[C@@H]2[C@@]3(C)CC[C@@H](OC(=O)C)CC3CC[C@H]2[C@@H]2CC=C(C(C)=O)[C@]21C JAZBMNIJZWDVQJ-UKQOWTAJSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- VQNPSCRXHSIJTH-UHFFFAOYSA-N cadmium(2+);carbanide Chemical compound [CH3-].[CH3-].[Cd+2] VQNPSCRXHSIJTH-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2034540A DE2034540C3 (de) | 1970-07-11 | 1970-07-11 | Mikrobizide Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134604B true NO134604B (de) | 1976-08-09 |
| NO134604C NO134604C (de) | 1976-11-17 |
Family
ID=5776530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2640/71A NO134604C (de) | 1970-07-11 | 1971-07-09 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3801576A (de) |
| AT (1) | AT307151B (de) |
| BE (1) | BE769814A (de) |
| CA (1) | CA979896A (de) |
| CH (1) | CH552340A (de) |
| DE (1) | DE2034540C3 (de) |
| FI (1) | FI51548C (de) |
| FR (1) | FR2098346B1 (de) |
| GB (1) | GB1355677A (de) |
| IT (1) | IT1001468B (de) |
| NL (1) | NL167081C (de) |
| NO (1) | NO134604C (de) |
| SE (1) | SE401077B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3928607A (en) * | 1973-10-05 | 1975-12-23 | Cosan Chem Corp | Antibacterial composition and method employing a certain hexamethylenetetramine adduct |
| FR2415641A1 (fr) * | 1978-01-27 | 1979-08-24 | Nativelle Sa Ets | Amino-3-cardenolides, procede pour leur preparation, et medicaments les contenant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH471541A (de) * | 1965-01-29 | 1969-04-30 | Agripat Sa | Wachstumsförderndes Beifuttermittel |
-
1970
- 1970-07-11 DE DE2034540A patent/DE2034540C3/de not_active Expired
-
1971
- 1971-07-07 US US00160568A patent/US3801576A/en not_active Expired - Lifetime
- 1971-07-07 GB GB3183071A patent/GB1355677A/en not_active Expired
- 1971-07-08 CA CA117,723A patent/CA979896A/en not_active Expired
- 1971-07-08 FI FI711932A patent/FI51548C/fi active
- 1971-07-09 SE SE7108948A patent/SE401077B/xx unknown
- 1971-07-09 CH CH1015671A patent/CH552340A/de not_active IP Right Cessation
- 1971-07-09 FR FR7125346A patent/FR2098346B1/fr not_active Expired
- 1971-07-09 NL NL7109542.A patent/NL167081C/xx not_active IP Right Cessation
- 1971-07-09 AT AT598271A patent/AT307151B/de not_active IP Right Cessation
- 1971-07-09 NO NO2640/71A patent/NO134604C/no unknown
- 1971-07-09 IT IT26793/71A patent/IT1001468B/it active
- 1971-07-09 BE BE769814A patent/BE769814A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH552340A (de) | 1974-08-15 |
| FI51548C (fi) | 1977-02-10 |
| AT307151B (de) | 1973-05-10 |
| NL7109542A (de) | 1972-01-13 |
| DE2034540A1 (de) | 1972-01-20 |
| FR2098346A1 (de) | 1972-03-10 |
| NL167081C (nl) | 1981-11-16 |
| FI51548B (de) | 1976-11-01 |
| NO134604C (de) | 1976-11-17 |
| GB1355677A (en) | 1974-06-05 |
| SE401077B (sv) | 1978-04-24 |
| US3801576A (en) | 1974-04-02 |
| IT1001468B (it) | 1976-04-20 |
| FR2098346B1 (de) | 1975-09-26 |
| DE2034540C3 (de) | 1975-11-20 |
| BE769814A (fr) | 1972-01-10 |
| NL167081B (nl) | 1981-06-16 |
| CA979896A (en) | 1975-12-16 |
| DE2034540B2 (de) | 1975-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO148662B (no) | Haarkondisjoneringssjampo. | |
| NO129797B (de) | ||
| NO140069B (no) | Pulverformet, lagringsbestandig vaskemiddelblanding | |
| NO128152B (de) | ||
| NO143159B (no) | Fremgangsmaate for fremstilling av metylmetakrylat-alkylakrylatkopolymerer. | |
| NO134604B (de) | ||
| EHRENSTEIN | INVESTIGATIONS ON STEROIDS I. 6-OXOPROGESTERONE AND THE STEREOCHEMICAL CONFIGURATION OF SEVERAL 3, 5, 6-TRIOLS | |
| US2777843A (en) | Preparation of 4-pregnen-17alpha-ol-3, 20-dione | |
| Fried et al. | Neogermitrine, a New Ester Alkaloid from Veratrum Viride1 | |
| Irvine et al. | CX.—The alkylation of galactose | |
| US2334695A (en) | 17-hydroxy-3-keto-compounds of the cyclopentano polyhydropkenanthrene series and a method for producing the same | |
| NO149353B (no) | Fremgangsmaate ved fremstilling av 6-klor-alfa-metylkarbazol-2-eddiksyre | |
| US2387706A (en) | Compounds of the cyclopentanopolyhydrophenanthrene series and process of making same | |
| US2984677A (en) | Ethers of 1, 3, 5, 16-estratetraen-3-ol | |
| NO154276B (no) | Innretning for ¨ skumme av stoffer som flyter p¨ vann. | |
| NO312593B1 (no) | Fremgangsmåte til fremstilling av et deoksyuridinderivat | |
| US3005835A (en) | D-homo-18-norestra-1, 3, 5(10)-trien-17alpha-ones and intermediates thereto | |
| US3032563A (en) | 16-ethynylated steroid compounds and process for their production | |
| US3124570A (en) | F hypohalites to | |
| US2989522A (en) | Process for the preparation of 11, 18-oxido steroids and novel compounds obtained fro this process | |
| NO129905B (de) | ||
| US3639394A (en) | Process for the manufacture of 14beta-hydroxy-3-oxo-5alpha-card-20(22)-enolides | |
| US3398147A (en) | Morpholinoacetohydrazide alkyl halides and process for their preparation | |
| US2593248A (en) | Androstatrienes and method of preparing the same | |
| US3933791A (en) | Obtention of digitoxigenin from neriifolin and 2'-acetylneriifolin |