DK164667B - N-substitueret 2,6-transdimethylmorpholinderivat og fungicid indeholdende et saadant derivat - Google Patents
N-substitueret 2,6-transdimethylmorpholinderivat og fungicid indeholdende et saadant derivat Download PDFInfo
- Publication number
- DK164667B DK164667B DK293484A DK293484A DK164667B DK 164667 B DK164667 B DK 164667B DK 293484 A DK293484 A DK 293484A DK 293484 A DK293484 A DK 293484A DK 164667 B DK164667 B DK 164667B
- Authority
- DK
- Denmark
- Prior art keywords
- trans
- dimethylmorpholine
- derivative
- parts
- substituted
- Prior art date
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- 239000000417 fungicide Substances 0.000 title claims abstract description 18
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 14
- -1 N-SUBSTITUTED 2,6-TRANSDIMETHYLMORPHOLINE Chemical class 0.000 title description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052751 metal Chemical class 0.000 claims abstract description 5
- 239000002184 metal Chemical class 0.000 claims abstract description 5
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 4
- HNVIQLPOGUDBSU-PHDIDXHHSA-N (2r,6r)-2,6-dimethylmorpholine Chemical class C[C@@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-PHDIDXHHSA-N 0.000 claims abstract 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 21
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
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- BABJTMNVJXLAEX-UHFFFAOYSA-N Triamiphos Chemical compound N1=C(N)N(P(=O)(N(C)C)N(C)C)N=C1C1=CC=CC=C1 BABJTMNVJXLAEX-UHFFFAOYSA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- LJOZMWRYMKECFF-UHFFFAOYSA-N benodanil Chemical compound IC1=CC=CC=C1C(=O)NC1=CC=CC=C1 LJOZMWRYMKECFF-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- CSNJTIWCTNEOSW-UHFFFAOYSA-N carbamothioylsulfanyl carbamodithioate Chemical compound NC(=S)SSC(N)=S CSNJTIWCTNEOSW-UHFFFAOYSA-N 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- WHDGWKAJBYRJJL-UHFFFAOYSA-K ferbam Chemical compound [Fe+3].CN(C)C([S-])=S.CN(C)C([S-])=S.CN(C)C([S-])=S WHDGWKAJBYRJJL-UHFFFAOYSA-K 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- UYJUZNLFJAWNEZ-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2NC3=CC=CC=C3N=2)=C1 UYJUZNLFJAWNEZ-UHFFFAOYSA-N 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OYRIKLVYHTWHCZ-UHFFFAOYSA-N n-cyclohexyl-2,5-dimethylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC2CCCCC2)=C1C OYRIKLVYHTWHCZ-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon 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
- A01N43/72—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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (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)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
i
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Opfindelsen angår hidtil ukendte N-substituerede 2,6-di-methylmorpholinderivater og fungicider, der indeholder sådanne.
5 Det er kendt at anvende N-substituerede 2,6-dimethylmor-pholiner, især tridecyl-2,6-dimethylmorpholin (Tride-morph) som fungicider, hvilket er omtalt i DE fremlæggelsesskrift nr. 1164152. Andre N-substituerede 2,6-dime-thylmorpholiner kendes fra DE fremlæggelsesskrifterne nr.
10 1198125, 1173722 og 1214471.
Disse kendte 2,6-dimethylmorpholinderivater består af blandinger af 2,6-cis- og 2,6-trans-isomere og har en ganske god fungicid effekt. Planteforligeligheden af dis-15 se stoffer er dog ringe og anvendelse af disse stoffer giver ofte anledning til betydelige bladskader på den behandlede plante.
Et andet fungicid som er solgt under handelsnavnet Fen-20 propiomorph er omtalt i DE offentliggørelsesskrift nr. 2656747. I dette fungicid er det et cis-2,6-dimethylmor-pholinderivat der finder anvendelse, nemlig forbindelsen 4-[3-[4-(1,1-dimethyl)phenyl]-2-methyl]-propyl-2,6(cis)-dimethylmorpholin. Dette foretrækkes altså i forhold til 25 trans-derivatet. Man måtte derfor antage, at det også for andre derivater måtte gælde, at cis-derivatet i hvert tilfælde ville være det mere værdifulde af de to isomere.
Det har nu overraskende vist sig, at N-substituerede 2,6-30 dimethylmorpholinderivater, som er trans-isomere, udviser en langt bedre planteforligelighed end de tilsvarende cis-isomere og blandinger af trans/cis-isomere. Den fungicide effekt er i det væsentligste uafhængig af om forbindelsen er trans- eller cis-isomere eller en blanding 35 af disse.
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2
Forbindelserne ifølge opfindelsen, som er af den i krav l's indledende del angivne art, er ejendommelig ved det i krav 1's kendetegnende del angivne.
5 R betyder f.eks. n-nonyl, n-decyl, n-tridecyl, n-dodecyl, n-C^I^g, n-Ci5H3l' n-C20H41' 1,5,9-trimethyldecyl, 3,7,11-trimethyldodecyl, 3-ethyl-l,3,7-trimethyl-octyl, 2-methyl-tridecyl, 3,5,5-trimethyl-hexyl, 4-ethyl-l- methyloctyl, 1,4-diethyl-octyl, 2-hexyl-hexyl, 1-methyl-10 dodecyl, 2-methyldodecyl, 2-ethyl-5~cyclohexyl-pentyl, cyclododecylmethyl, 4-ethyl-1-i sobuty1-octyl, cyclooctyl, cyclononyl, cyclododecyl, N-oxider er f.eks. N-n-tri-decyl-2,6-trans-dimethylmorpholin-N-oxid, N-cyclododecyl- 2,6-trans-dimethylmorpholin-N-oxid, en blanding bestående 15 af N-alkyl-2,6-trans-dimethylmorpholin-N-oxider, hvorved alkylgruppen indeholder 11 til 14 carbonatomer.
Syreadditionssalte er f.eks. salte med saltsyre, HBr, H2SO4, H^PO^, eddikesyre, propionsyre, oxalsyre, n-dode-20 cylsulfonsyre, n-dodecylphenylsulfonsyre.
Metalkomplexer er f.eks. komplexerne med kobber, magnesium, zink.
25 De alifatiske eller cycloalifatiske grupper R kan indeholde asymmetriske carbonatomer. De aktive stoffer med formel I kan således foreligge i form af forskellige en-antiomere eller diastereomere. De rene enantiomere og diastereomere samt blandinger deraf omfattes af denne op-30 findelse.
Fremstillingen af trans-forbindelserne kan gennemføres på følgende måde: 35 1. Separation af cis-/trans-blandingerne ved tyndtlags- kromatografi (n-hexan/acetone 9:1 - silicagel).
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3 2. Destillative separation af cis/trans-blandingerne.
3. Omsætning af 2,6-trans-dimethylmorpholin med en forbindelse med formel RX, hvori R har de i krav 1 angiv- 5 ne betydninger, og X er et halogenatom (fortrinsvis chlor eller brom).
4. Separation af 2,6-cis-dimethylmorpholin og 2,6-trans-dimethylmorpholin ved destillation og påfølgende om- 10 sætning af 2,6-trans-dimethylmorpholin med en forbin delse med formel RX eller omsætning med ROH eller de tilsvarende ketoner eller aldehyder og reduktion.
Forskrift 1 15
Fremstilling af iso-tridecylchlorid (A)
Til 322 g SOC^ tildryppedes 450 g iso-tridecanol (iso-tridecanol betegner her en kommerciel blanding af for-20 skellige homologe C^-C^-alkoholer, der indeholder 60- 70% tridecylalkohol). Man rørte natten over, opvarmede 2 h til 140 °C, destillerede råproduktet og opnåede 433 g farveløs olie kp. 84 til 86 °C/0,3 bar.
25 EKSEMPEL 1
Fremstilling af N-iso-tridecyl-2,6-trans-dimethylmorpholin (aktivt stof nr. 1) 30 30 g A og 48 g 2,6-trans-dimethylmorpholin opvarmedes i 8 h til 150 °C. Råproduktet opløstes i CI^C^ og det vaskedes med fortyndet vandigt NaOH og derpå flere gange med vand. Man tørrede over Na2S04, koncentrerede, destillerede og opnåede 16 g farveløs olie, kp. 122 °C/0,2 mbar.
35
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4 EKSEMPEL 2
Fremstilling af N-cyclododecyl-2,6-trans-dimethylmorpho-lin (aktivt stof nr. 23) 5 130 g cyclododecanon, 138 g 2,6-trans-dimethylmorpholin og 1 g p-toluen-sulfonsyre opvarmedes i 15 timer til tilbagesvaling ved vandudskilleren. Det således fremkomne råprodukt vaskedes efter afkøling med vand, tørredes over 10 MgSO^, koncentreredes og destilleredes. Efter ikke omsatte forprodukter destillerede 64 g (140 til 145 °C/0,3 mbar) gullig olie = N-cyclododecenyl-2,6-trans-dimethyl-morpholin (5).
15 Den fremkomne enamin (B) opløstes i eddikeester og hydre-redes efter tilsætning af 5 g Pd/C-kontakt (10 vægt-% Pd) ved 60 til 70 °C/100 bar. Derpå koncentrerede man og destillerede. Man opnåede 45 g farveløs olie, kp. 136 til 138 °C/0,2 mbar.
20 På tilsvarende måde fremstillede man de følgende forbindelser, der er kendetegnet ved fysiske data: CH,
A
r * CH3 30 35
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5
Eksempel nr._R_kp. °C/mbar 1 isotridecyl 122°/0,2 2 n-nonyl 5 3 n-decyl 4 n-tridecyl 132-133 °C/0,3 5 n-dodecyl 6 n-C15H31 7 N-C20H41 10 8 1,5,3-trimethyldecyl 9 3,7-11-trimethyldodecyl 10 3-ethyl-l,3,7-trimethyloctyl 11 2-methyltridecyl 12 3,5,5-trimethylhexyl 15 13 4-ethyl-l-methyl-octyl 14 1,4-diethyl-octyl 15 2-hexyl-hexyl 16 1 -methyldodecyl 17 2-methyldodecyl 20 18 2-ethyl-5-cyclohexyl-pentyl 19 cyclododecyl-methyl 20 4-ethyl-l-isobutyl-octyl 21 cyclooctyl 22 cyclononyl 25 23 cyclododecyl 136-138 °/0,2
De nye forbindelser og deres salte, metalkomplexforbin-delser og oxider udmærker sig ved en fremragende aktivitet mod et bredt spektrum af plantepatogene svampe, især 30 fra den klasse, der omfatter ascomyceter og basidiomyce-ter. De er delvist systemisk aktive og kan anvendes som blad- og jordfungicider. Desuden kan de anvendes til mater ialebeskyttel se.
35 Særligt interessant er de fungicide forbindelser til bekæmpelse af mange forskellige svampe på forskellige kulturplanter eller disses frø, især hvede, rug, byg, havre,
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6 ris, majs, bomuld, soja, kaffe, bananer, sukkerrør, frugt og prydplanter i haven, samt grøntsager, såsom agurker, bønner og græskar.
5 De nye forbindelser er især velegnet til bekæmpelse af følgende plantesygdomme:
Erysiphe graminis (ægte meldug) i korn,
Erysiphe cichoriacearum (ægte meldug) ved græskar, 10 Podosphaera leucotricha ved æbler,
Unicinula necator ved vin,
Erysiphe polygoni ved bønner,
Spaerotheca pannosa ved roser,
Puccinia-Arten ved korn, 15 Mycosphaerella musicola ved bananer,
Corticium salmonicolor ved Hevea,
Ganoderma pseudoferreum ved Hevea og Exobasidium vexans ved te.
20 Forbindelserne anvendes på den måde, at man besprøjter eller bestøver planterne eller behandler frøene af planterne med de aktive stoffer. Anvendelsen foregår før eller efter infektionen af planterne eller frøene med svampene .
25
De nye stoffer kan overføres til de sædvanlige formuleringer, såsom opløsninger, emulsioner, suspensioner, puddere, pulvere, pastaer og granulater. Anvendelsesformerne retter sig helt efter anvendelsesformålene? de skal i 30 hvert tilfælde sikre en fin og regelmæssig fordeling af det aktive stof. Formuleringerne fremstilles på kendt måde, f.eks. ved strækning af det aktive stof med opløsningsmidler og/eller bærestoffer, eventuelt under anvendelse af emulgeringsmidler og dispergeringsmidler, hvor-35 ved man i tilfælde af anvendelsen af vand som fortyndingsmiddel også kan anvende andre organiske opløsningsmidler som hjælpeopløsningsmiddel. Som hjælpestoffer kom-
DK 164667B
7 mer til dette formål i det væsentlige følgende materialer i betragtning: opløsningsmidler, såsom aromater (f.eks. xylen, benzen), chlorerede aromater (f.eks. chlorbenze-ner), paraffiner (f.eks. jordoliefraktioner), alkoholer, 5 (f.eks. methanol, butanol), aminer (f.eks. ethanolamin, dimethylformamid) og vand; bærestoffer som naturlige stenmel, f.eks. kaoliner, ler, talkum, kridt og syntetiske stenmel (f.eks. højdispers kiselsyre, silikater); emulgeringsmidler, såsom ikke ionogene og anioniske emul-10 gatorer (f.eks. polyoxyethylen-fedtalkohol-ethere, alkyl-sulfonater og arylsulfonater) og dispergeringsmidler, såsom lignin, sulfit-affaldslud og methylcellulose.
De fungicide midler indeholder i almindelighed mellem 0,1 15 og 95 vægt-% aktivt stof, fortrinsvis mellem 0,5 og 90 vægt-% aktivt stof.
De anvendte mængder ligger i afhængighed af arten af den ønskede virkning mellem 0,1 og 3 kg aktivt stof eller 20 derover per ha. De nye forbindelser kan også anvendes til materialebeskyttelse, blandt andet til bekæmpelse af træ-ødelæggende svampe, såsom coniophora puteana og polystictus versicolor. De aktive stoffer egner sig også til behandling af frugter mod skimmelsvampeangreb. Des-25 uden kan de anvendes til sårbehandlinger mod svampeinfektioner i forbindelse med formstofdispersioner. De nye aktive stoffer kan også anvendes som fungicidt aktive bestanddele i olieagtige træbeskyttelsesmidler til beskyttelse af træ mod træmisfarvende svampe. Anvendelsen fore-30 går på den måde, at man behandler træet med disse midler, f.eks. ved imprægnering eller påstrygning.
Midlerne eller de på basis af disse fremstillede brugsfærdige præparater, såsom opløsninger, emulsioner, sus-35 pensioner, pulvere, puddere, pastaer eller granulater, anvendes på kendt måde, f.eks. ved udsprøjtning, tågedan-nelse, forstøvning, udstrøning, bejdsning eller udhæld-
DK 164667B
8 ning.
Eksempler på sådanne præparater er: 5 I. Man blander 90 vægtdele af forbindelsen fra eksempel 1 med 10 vægtdele N-methyl-alpha-pyrrolidon og opnår en opløsning, der er velegnet til anvendelse i form af meget små dråber.
10 II. 20 vægtdele af forbindelsen fra eksempel 2 opløses i en blanding, der består af 80 vægtdele xylen, 10 vægtdele af tillej ringsproduktet af 8 til 10 mol ethylenoxid til 1 mol oliesyre-N-monoethanolamid, 5 vægtdele calciumsalt af dodecylbenzensulfonsyre og 5 15 vægtdele af tillej ringsproduktet af 40 mol ethylen oxid til 1 mol ricinusolie. Ved udhældning og fin fordeling af opløsningen i vand opnår man en vandig dispersion.
20 III. 20 vægtdele af forbindelsen 4 opløses i en blanding, der består af 40 vægtdele cyclohexanon, 30 vægtdele isobutanol, 20 vægtdele af tillejringsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie. Ved udhældning og fin fordeling af opløsningen i vand op-25 når man en vandig dispersion.
IV. 20 vægtdele af forbindelsen fra eksempel 1 opløses i en blanding, der består af 25 vægtdele cyclohexanol, 65 vægtdele af en mineraloliefraktion med kogepunkt 30 210 til 280 °C og 10 vægtdele af tillej ringsproduk tet af 40 mol ethylenoxid til 1 mol ricinusolie. Ved udhældning og fin fordeling af opløsningen i vand opnår man en vandig dispersion.
35 V. 20 vægtdele af forbindelsen fra eksempel 2 blandes godt med 3 vægtdele af natriumsaltet af diisobutyl-naphthalen-alfa-sulfonsyre, 17 vægtdele af natrium-
DK 164667 B
9 saltet af en ligningsulfonsyre fra en sulfitaffaldslud og 60 vægtdele pulverformig kiselsyregel og formales i en hammermølle. Ved fin fordeling af blandingen i vand opnår man en sprøjtevæske.
5 VI. 3 vægtdele af forbindelsen 4 blandes grundigt med 97 vægtdele findelt kaolin. Man opnår på denne måde et pudringsmiddel, der indeholder 3 vægt-% af det aktive stof.
10 VII. 30 vægtdele af forbindelsen fra eksempel 2 blandes grundigt med en blanding af 92 vægtdele pulverformig kiselsyregel og 8 vægtdele paraffinolie, der blev sprøjtet på overfladen af denne kiselsyregel. Man 15 opnår på denne måde et præparat af det aktive stof med god adhæsionsevne.
VIII 40 vægtdele af forbindelsen fra eksempel 1 blandes grundigt med 10 dele natriumsalt af et phenolsulfon-20 syre-urinstof-formaldehyd-kondensat, 2 dele kiselgel og 48 dele vand. Man opnår en stabil vandig dispersion. Ved fortynding med vand opnår man en fortyndet, vandig dispersion.
25 IX- 20 dele af forbindelsen fra eksempel 4 blandes grundigt med 2 dele calciumsalt af dodecylbenzensulfonsyre, 8 dele fedtalkohol-polyglycolether. 2 dele natriumsalt af et phenolsulfonsyre-urinstof-formalde-hyd-kondensat og 68 dele af en paraffinisk mineral-30 olie. Man opnår en stabil olieagtig dispersion.
De nye midler kan også i disse anvendelsesformer foreligge sammen med andre aktive stoffer, såsom f.eks. herbicider, insekticider, vækstregulatorer og fungicider, eller 35 de kan blandes med gødningsmidler og udbringes. Ved blanding med fungicider opnår man derved i mange tilfælde en udfladning af det fungicide virkningsspektrum.
DK 164667 B
10
Den følgende liste af fungicider, med hvilke forbindelserne ifølge opfindelsen kan kombineres, skal forklare, men ikke begrænse kombinationsmulighederne.
5 Fungicider, med hvilke de nye forbindelser kan kombineres, er f.eks.: svovl, dithiocarbamater og disses derivater, såsom ferridime-10 thyldithiocarbamat, zinkdimethyldithiocarbamat, mangan- ethylen-bi s-dithiocarbamat, mangan-z ink-ethylendiamin- bis-dithiocarbamat eller zinkethylen-bis-dithiocarbamat, tetramethy1thiuramdisulfider, ammoniak-kompleks af zink-(N,N-ethylen-bis-dithiocarba-15 mat) og N,N*-polyethylen-bis(thiocarbamoyl)-disulfid, zink-(N,N’-propylen-bis-dithiocarbamat), ammoniak-komplex af zink-(N,Ν'-propylen-bis-dithiocarba-mat) og N,Ν’-propylen-bis(thiocarbamoyl)-disulfid; nitroderivater, såsom 20 dinitro-(1-methylheptyl)-phenylcrotonat, 2-sek.-butyl-4,6-dinitrophenyl-3,3-dimethylacrylat, 2-sek.-butyl-4,6-dinitrophenyl-isopropylcarbonat; heterocycliske stoffer, såsom N-trichlormethylthio-tetrahydrophthalimid, 25 N-(1,1,2,2-tetrachlorethylthio)-tetrahydrophthalimid, N-trichlormethylthio-phthalimid, 2-heptadecy1-2-imidazolin-acetat, 2,4-dichlor-6-(o-chloranilino)-s-triazin, 0,O-diethyl-phthalimidophosphonothioat, 30 5-amino-l-(bis(dimethylamino)-phosphinyl)-3-phenyl-l,2,4- triazol, 5-ethoxy-3-trichlormethyl-l,2,4-thiadiazol, 2,3-dicyano-l,4-dithioanthraquinon, 2-thio-l,3-dithio-(4,5-b)-quinoxalin, 35 1-(butylcarbamoyl)-2-benzimidazol-carbaminsyremethyl- ester, 2-methoxycarbonylamino-benzimidazol,
DK 164667 B
11 2-thodanmethylthio-benzthiazol, 4 - (2-chlorphenylhydrazono)-3-methyl-5-i soxazolon, pyridin-2-thiol-1-oxid, 8-hydroxyquinolin eller dettes kobbersalt, 5 2,3-dihydro-5-carboxanilodo-6-methyl-l,4-oxathiin-4,4- dioxid, 2,3-dihydro-5-carboxanilido-6-methyl-l,4-oxathiin, 2-(furyl)-benzimidazol, piperazin-1,4-diyl-bis-(1-(2,2,2-trichlor-ethyl)-10 formamid), 2- (thiazolyl-(4))-benzimidazol, 5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin, bis-(p-chlorphenyl)-pyridinmethanol, 1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzen, 15 1,2-bis-(3-methoxycarbonyl-2-thioureido)-benzen og andre stoffer, såsom dodecylguanidinacetat, 3- (3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl)glu- 20 taramid, hexachlorbenzen, N-dichlorfluormethylthio-N',n'-dimethyl-N-phenyl-svovl-syrediamid, 2,5-dimethyl-furan-3-carboxylsyreanilid, 25 2,5-dimethyl-furan-3-carboxylsyre-cyclohexylamid, 2-cyan-N-(ethylaminocarbonyl)-2-(methoxyimino)-acetamid, 2-methyl-benzoesyre-anilid, 2-iod-benzoesyre-anilid, l-(3,4-dichloranilino)-l-formylamino-2,2,2-trichlorethan, 30 DL-methyl-N-2,6-dimethyl-phenyl)-N-furoyl(2)-alaniat, DL-N-(2,6-dimethyl-phenyl)-N-(2'-methoxyacetyl)-alanin-methylester, 5-nitro-isophthalsyre-di-isopropylester, 35 1—(1^2^41 -trizolyl-1' )-4 ' -chlorphenoxy)-3,3-dimethyl- butan-2-on, 1-(1',2',4'-triazolyl-1')-l-(4'-chlorphenoxy)-3,3-di-
DK 164667 B
12 methylbutan-2-ol, N-(2,6-dimethylphenyl)-N-chloracetyl-D, L-2-aminobutyrolacton, N-(n-propyl)-N-(2,4,6-trichlorphenoxyethyl)-N'-5 imidazolylurinstof.
Det følgende forsøg viser den biologiske aktivitet mod ægte meldug (erysiphe graminis var. hordei) og især planteforligeligheden af de nye N-substituerede 2,6-10 trans-dimethylmorpholiner.
Forsøg
Bygkimplanter (Hauters Pfålzer sommerbyg) besprøjtedes i 15 etbladstadiet med en vandig opløsning af aktivt stof i forskellige koncentrationer. 24 timer efter behandlingen gennemførte man den kunstige podning med sporer af bygmeldug (Erysiphe graminis var. hordei). Forsøgsbedømmelsen gennemførtes 10 dage efter infektionen.
20
Som testforbindelser (fungicider) anvendtes N-isotridecyl 2,6-dimethylmorpholin dels som ren trans-isomer ifølge opfindelsen og dels som henholdsvis ren cis-isomer og som en cis/trans-isomerblanding (tridemorph). Forbindelserne 25 blev anvendt i fire forskellige koncentrationer og 24 timer efter behandlingen med fungiciderne blev virkningen på planterne visuelt bedømt. Skadevirkningen på planterne blev bedømt efter en skala fra 1-5, hvor 1 svarede til ingen skadevirkning og 5 svarede til total bladdød. I ne-30 denstående skema ses bedømmelsen. Det ses tydeligt at den trans-isomere form har en meget større planteforligelig-hed end henholdsvis den cis-isomere form og den cis/trans-blandings-isomere form. Den fungicide effekt var i alle tilfælde tilfredsstillende. Der var ingen 35 synlig forskel på den fungicide effekt af de tre testfungicider.
13
DK 164667 B
Behandlings koncentration
Forbindelse (%) Bladskade (1-5)
Tridecyl-2,6- 0,02 3 dimethyl-morpholin 0,01 2 5 Cis/trans-isomer- 0,005 1 form (Tridemorph kendt 0,0025 1 fra DE 1164152) N-isotridecyl-2,6- 0,02 3 dimethyl-morpholin 0,01 2
Cis-isomer 0,005 1 10 form 0,0025 1 N-isotridecyl-2,6- 0,02 1 dimethyl-morpholin 0,01 1
Trans-isomer 0,005 1 form (Ifølge opfindel- 0,0025 1 15 sen) 20 25 30 35
Claims (5)
1. N-substitueret 2,6-trans-dimethylraorpholinderivat med 5 formlen Λ-Γ3 R-N P I , N—4 CH, 10 j hvori R betyder en cycloalkyl-, cycloalkylalkyl- eller alkylgruppe, der kan være substitueret med en eller flere C^-C^-alkylgrupper, og hvor antallet af carbonatomer i 15 substituenten R ialt andrager mellem 7 og 20, samt dettes N-oxider og planteforligelige syreadditionssalte og me-talkomplexer, kendetegnet ved, at derivatet er en trans-isomer. 20 2.
2,6-trans-dimethylmorpholinderivat ifølge krav 1, kendetegnet ved, at det er N-n-tridecyl-2,6-trans-dimethylmorpholin, N-cyclododecyl-2,6-trans-dime-thylmorpholin eller en blanding bestående af N-alkyl-2,6-trans-dimethylmorpholiner, hvorved alkylgruppen eventuelt 25 er forgrenet og indeholder 11 til 14 carbonatomer.
3. Fungicid, kendetegnet ved, at det indeholder en forbindelse med formlen I ifølge krav 1.
4. Fungicid ifølge krav 3, kendetegnet ved, at det indeholder et fast eller flydende bærestof.
5. Fungicid ifølge krav 3 eller 4, kendetegnet ved, at 2,6-trans-dimethylmorpholinderivatet er N-n-tri-35 decyl-2,6-trans-dimethylmorpholin, N-cyclododecyl-2,6-trans-dimethylmorpholin eller en blanding bestående af N-alkyl-2,6-trans-dimethylmorpholinen, hvor alkylgruppen DK 164667 B eventuelt er forgrenet og indeholder 11 til 14 carbonato-mer. 5 10 20 25 30 35
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3321712A DE3321712A1 (de) | 1983-06-16 | 1983-06-16 | 2,6-trans-dimethylmorpholinderivate und diese enthaltende fungizide und verfahren zur bekaempfung von pilzen |
| DE3321712 | 1983-06-16 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK293484D0 DK293484D0 (da) | 1984-06-15 |
| DK293484A DK293484A (da) | 1984-12-17 |
| DK164667B true DK164667B (da) | 1992-07-27 |
| DK164667C DK164667C (da) | 1992-12-21 |
Family
ID=6201614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK293484A DK164667C (da) | 1983-06-16 | 1984-06-15 | N-substitueret 2,6-transdimethylmorpholinderivat og fungicid indeholdende et saadant derivat |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0129211B1 (da) |
| AT (1) | ATE25379T1 (da) |
| CS (1) | CS249138B2 (da) |
| DD (1) | DD215931A5 (da) |
| DE (2) | DE3321712A1 (da) |
| DK (1) | DK164667C (da) |
| MY (1) | MY101892A (da) |
| PH (1) | PH20933A (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3506117A1 (de) * | 1985-02-22 | 1986-08-28 | Basf Ag, 6700 Ludwigshafen | Amine, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE3507420A1 (de) * | 1985-03-02 | 1986-09-04 | Basf Ag, 6700 Ludwigshafen | Holzschutzmittel |
| DD256072A1 (de) * | 1985-03-04 | 1988-04-27 | Adl Der Ddr Inst Fuer Pflanzen | Fungizide und pflanzenwachstumsregulierende mittel |
| DE3539412A1 (de) * | 1985-11-07 | 1987-05-14 | Basf Ag | Holzschutzmittel |
| GB2192881A (en) * | 1986-07-16 | 1988-01-27 | Ici Plc | Tertiary amine compounds |
| FI874121A7 (fi) * | 1986-09-24 | 1988-03-25 | Sumitomo Chemical Co | Heterocykliska foereningar, och deras framstaellning och anvaendning. |
| DE3643009A1 (de) * | 1986-12-17 | 1988-06-30 | Basf Ag | Fungizide cyclohexylamine |
| DE3839640A1 (de) * | 1988-11-24 | 1990-05-31 | Wolman Gmbh Dr | Holzschutzmittel |
| CZ304041B6 (cs) * | 2001-03-16 | 2013-09-04 | Basf Aktiengesellschaft | Zpusob prípravy N-substituovaných 2,6-dialkylmorfolinu |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL275086A (da) * | 1961-02-22 | |||
| DE1214471B (de) * | 1965-01-16 | 1966-04-14 | Basf Ag | Fungizid fuer den Pflanzenschutz |
| DE2461513A1 (de) * | 1974-12-27 | 1976-07-08 | Basf Ag | Morpholinderivate |
| AT354187B (de) * | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | Fungizides mittel |
| DE2656747C2 (de) * | 1976-12-15 | 1984-07-05 | Basf Ag, 6700 Ludwigshafen | Morpholinderivate |
| DE2700680A1 (de) * | 1977-01-08 | 1978-07-20 | Basf Ag | Verfahren zur herstellung von n-substituierten morpholiniumsalzen |
| DE2921221A1 (de) * | 1979-05-25 | 1980-12-11 | Basf Ag | Trans-3-(4'-tert.-butyl-cyclohexyl-1')- 2-methyl-1-(3'-methylpiperidino, 3', 5'- dimethylpiperidino und 2', 6'-dimethylmorpholino)-propan, verfahren zu ihrer reinherstellung und diese enthaltende antimykotische mittel |
-
1983
- 1983-06-16 DE DE3321712A patent/DE3321712A1/de not_active Withdrawn
-
1984
- 1984-06-14 EP EP84106796A patent/EP0129211B1/de not_active Expired
- 1984-06-14 DE DE8484106796T patent/DE3462332D1/de not_active Expired
- 1984-06-14 AT AT84106796T patent/ATE25379T1/de active
- 1984-06-15 PH PH30829A patent/PH20933A/en unknown
- 1984-06-15 DK DK293484A patent/DK164667C/da not_active IP Right Cessation
- 1984-06-15 DD DD84264195A patent/DD215931A5/de not_active IP Right Cessation
- 1984-06-18 CS CS844633A patent/CS249138B2/cs unknown
-
1987
- 1987-06-20 MY MYPI87000856A patent/MY101892A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3462332D1 (en) | 1987-03-12 |
| DD215931A5 (de) | 1984-11-28 |
| DK293484A (da) | 1984-12-17 |
| MY101892A (en) | 1992-02-15 |
| DK293484D0 (da) | 1984-06-15 |
| EP0129211B1 (de) | 1987-02-04 |
| ATE25379T1 (de) | 1987-02-15 |
| PH20933A (en) | 1987-06-05 |
| DE3321712A1 (de) | 1984-12-20 |
| DK164667C (da) | 1992-12-21 |
| CS249138B2 (en) | 1987-03-12 |
| EP0129211A1 (de) | 1984-12-27 |
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Legal Events
| Date | Code | Title | Description |
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| PBP | Patent lapsed |