KR890005029A - (7-(헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체 - Google Patents
(7-(헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체 Download PDFInfo
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- KR890005029A KR890005029A KR1019880012173A KR880012173A KR890005029A KR 890005029 A KR890005029 A KR 890005029A KR 1019880012173 A KR1019880012173 A KR 1019880012173A KR 880012173 A KR880012173 A KR 880012173A KR 890005029 A KR890005029 A KR 890005029A
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- Prior art keywords
- alkyl
- halogen
- group
- hydrogen
- optionally
- Prior art date
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- 239000002253 acid Substances 0.000 title claims 13
- 125000005842 heteroatom Chemical group 0.000 title claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 28
- -1 cyanoamino Chemical group 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 239000000460 chlorine Substances 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 239000003085 diluting agent Substances 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 150000001340 alkali metals Chemical class 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims 3
- 125000006323 alkenyl amino group Chemical group 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229950011260 betanaphthol Drugs 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000005879 dioxolanyl group Chemical group 0.000 claims 3
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 3
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 3
- WEDKTMOIKOKBSH-UHFFFAOYSA-N 4,5-dihydrothiadiazole Chemical compound C1CN=NS1 WEDKTMOIKOKBSH-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 239000004009 herbicide Substances 0.000 claims 2
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000005353 silylalkyl group Chemical group 0.000 claims 2
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
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- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
- C07C255/13—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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Abstract
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Description
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Claims (10)
- 다음 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체.상기식에서, R1은 할로겐, 시아노 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X는 질소 또는 그룹 C-R5(여기에서, R5는 수소 또는 할로겐이다)이고, 단 R1이 염소 또는 시아노이고, 동시에 R3은 트리플루오로메틸이며 X는 CH인 경우, 치환체 R2또는 R4중의 하나 이상은 수소가 아니며, X가 질소인 경우, R3은 트리플루오로메틸이 아니고, A는 임의 의 촉쇄 알칸디일이며, Z는 시아노 또는 그룹 -CO-Y[여기에서, Y는 할로겐, 하이드록실, 아미노, 알킬아미노, 알케닐아미노, 알키닐아미노, 아릴아미노, 아르알킬아미노, 알콕시카보닐알킬아미노, 시아노아미노, 디알킬아미노, 디알케닐아미노, N-알킬아릴아미노, 알킬설포닐아미노, 아릴설포닐아미노, 하이드록시아미노, 알콕시아미노, 하이드라지노, 알킬설포닐하이드라지노, 아릴설포닐하이드라지노, 알킬티오, 아릴티노, 아르알킬티오, 알콕시카보닐알킬티오 또는 그룹 -O-R6(여기에서, R6은 알킬, 알케닐, 알키닐, 알콕시알킬, 알킬티오알킬, 알킬설피닐알킬, 알킬설포닐알킬, 아릴옥시알킬, 아르알콕시알킬, 트리알킬실릴알킬, 아릴티오알킬, 아르알킬티오알킬, 알목시카보닐알킬, 알킬아미노카보닐알킬, 아릴아미노카보닐알킬, N-알킬-N-아릴아미노카보닐알킬, 아르알킬, 아졸릴알킬 및 알킬리덴아미노중에서 선택된 임의로 할로겐-치환된 라디칼이거나, 등가의 암모늄, 등가의 알킬암모늄, 등가의 알칼리금속 또는 등가의 알칼리 토금속이거나, 그룹(여기에서, R7은 수소, 알킬, 아릴, 푸릴, 티에닐 또는 피리딜이고, R8은 알킬 또는 알콕시이며, R9는 알콕시이고, Q는 산소 또는 황이다)이거나, 그룹 -(CH2)n-R10(여기에서, R10은 푸릴, 테트라히이드로푸릴, 옥소테트라하이드로푸릴, 티에닐, 테트라하이드로티에닐, 퍼하이드로피라닐, 옥사졸릴, 티아졸린, 티아디아졸린, 디옥솔라닐, 퍼하이드로피롤릴, 옥소퍼하이드로피롤릴, 피리디닐 및 피리미디닐중에서 선택된 임의로 할로겐-치환되고/되거나 임의로 알킬-치환된 헤테로사이클릭 라디칼이고, n은 0,1 또는 2이다)이다)이다]이다.
- 제1항에 있어서, R1은 불소, 염소, 브롬, 시아노 또는 트리플루오로메틸이고, R2는 수소, 불소 또는 염소이며, R3은 불소, 염소, 브롬, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소, 불소 또는 염소이며, X는 질소 또는 그룹 C-R5(여기에서, R5는 수소, 불소, 염소 또는 브롬이다)이고, 단 R1이 염소 또는 시아노이고, 동시에 R3은 트리플루오로메틸이며 X는 CH인 경우, 치환체 R2또는 R4중의 하나 이상은 수소가 아니며, X가 질소인 경우, R3은 트리플루오로메틸이 아니고, A는 임의의 측쇄 C1-4알칸디일이며, Z는 시아노 또는 그룹 -CO-Y[여기에서, Y는 염소, 하이드록실, 아미노, C1-6알킬아미노, C3-4알케닐아미노, C3-4알키닐아미노, 페닐아미노, 벤질아미노, C1-4알콕시카보닐-C1-2알킬아미노, 시아노마이노, 디-(C1-4알킬) 아미노, 디-(C3-4알케닐)아미노, N-(C1-4알킬)페닐아미노, C1-4알킬설포닐아미노, 페닐설포닐아미노, 톨릴설포닐아미노, 하이드록시아미노, C1-6알콕시아미노, 하이드라지노, C1-4알킬설포닐하이드라지노, 페닐설포닐하이드라지노, 톨릴설포닐하이드라지노, C1-4알킬티오, 페닐티오, 벤질티오, C1-4알콕시카보닐-C1-2알킬티오 또는 그룹-O-R6(여기에서,R6은 C1-6알킬, C3-4알케닐, C3-4알키닐, C1-4알콕시-C1-4알킬, C1-4알킬티오-C1-4알킬, C14알킬설피닐-C1-4알킬, C1-4알킬설포닐-C1-4알킬, 페녹시-C1-3알킬, 트리-(C1-2알킬)실릴-C1-2알킬, 페닐티오-C1-3알킬, 벤질옥시-C1-3-알킬, 벤질티오-C1-3알킬, C1-4알콕시카보닐-C1-2알킬, C1-4알칼아미노카보닐-C1-2알킬, 페닐아미노카보닐-C1-4알킬, N-(C1-4알킬)-N-페닐아미노카보닐-C1-4알킬, 벤질, 피라졸릴-C1-4알킬 및 C2-4알킬덴아미노중에서 선택된 임의 로 불소-치환되고/되거나 임의 로 염소-치화뇐 라디칼이거나, 등가의 암모늄, 등가의 C1-4알킬암모늄, 등가의 나트륨, 등가의 칼륨 또는 등가의 칼슘이거나, 그룹(R7은 수소, C1-4알킬, 페닐, 푸릴, 티에닐 또는 피리딜이고, R8은 C1-4알콕시이며, R9는 C1-4알콕시이고, Q는 산소 또는 황이다)이거나, 그룹 -(CH2)n-R10(여기에서, n은 0,1 또는 2이고, R10은 불소, 염소 브롬 및/또는 C1-4알킬에 의해 임의 로 치환되며, 푸릴, 테트라히이드로푸릴, 옥소테트라하이드로푸릴, 티에닐, 테트라하이드로티에닐, 퍼하이드로피라닐, 옥사졸린, 티아졸린, 티아디아졸린, 디옥솔라닐, 퍼하이드로피롤릴, 옥소퍼하이드로피롤릴, 피리디닐 또는 피리미디닐중에서 선택된 헤테로사이클릭 라디칼이다)이다)이다)인 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸 카복실산 유도체.
- (a) 다음 일반식(II)의 7-(헤테로)아릴옥시-2-나프톨을, 경우에 따라 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(III)의 카복실산 유도체와 반응시키거나, (b) 다음 일반식(IV)의 할로게노-(헤테로)아릴화합물을, 경우에 따라 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(V)의 (7-하이드록시나프탈렌-2-일-옥시)알칸-카복실산 유도체와 반응시키거나, (c) 일반식(I)에서 Z가 그룹 -CO-Y(여기에서, Y는 하이드록실이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 경우, Z가 시아노 또는 그룹 -CO-Y(여기에서, Y는 메톡시 또는 에톡시이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을 유기용매의 존재하에 알칼리 금속수산화물과 반응시키고, 반응 혼합물을 농축시킨 다음, 경우에 따라, 무기산으로 산성화시키거나, (d) 일반식(I)에서 Z가 그룹 -CO-Y(여기에서, Y는 할로겐이다)이고, A, R1, R2, R3, R4 및 X는 상기에서 정의한 바와 같은 경우, Z가 그룹 -CO-Y(여기에서, Y는 하이드록실이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을, 경우에 따라 희석제의 존재하에 할로겐화제와 반응시키거나, (e) 일반식 (I)에서 Z가 그룹 -CO-Y(여기에서, Y는 할로겐을 제외한 상기에서 정의한 바와 같다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 경우, Z가 시아노 또는 그룹 -CO-Y(여기에서, Y는 할로겐이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을, 경우에 다라 산 또는 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(VI)(여기에서, Y는 할로겐을 제외한 상기에서 정의한 바와 같다)의 화합물과 반응시키거나, (f) 일반식(I)에서 Z가 그룹 -CO-Y (여기에서, Y는 그룹 -O-R6(여기에서, R6은 암모늄, 알킬암모늄, 알칼리금속 및 알칼리토금속을 제외한 상기에서 정의한 바와 같다)이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 경우, Z가 그룹 -CO-Y(여기에서 Y는 하이드록실이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을, 경우에 따라 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(VII)의 화합물과 반응시킴을 특징으로 하여, 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 제조하는 방법.상기식에서, R1은 할로겐, 시아노 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X는 질소 또는 그룹 C-R5(여기에서, R5는 수소 또는 할로겐이다)이고, 단 R1이 염소 또는 시아노이고, 동시에 R3은 트리플루오로메틸이며 X는 CH인 경우, 치환체 R2또는 R4중의 하나 이상은 수소가 아니며, X가 질소인 경우, R3은 트리플루오로메틸이 아니고, A는 임의 의 촉쇄 알칸디일이며, Z는 시아노 또는 그룹 -CO-Y[여기에서, Y는 할로겐, 하이드록실, 아미노, 알킬아미노, 알케닐아미노, 알키닐아미노, 아릴아미노, 아르알킬아미노, 알콕시카보닐알킬아미노, 시아노아미노, 디알킬아미노, 디알케닐아미노, N-알킬아릴아미노, 알킬설포닐아미노, 아릴설포닐아미노, 하이드록시아미노, 알콕시아미노, 하이드라지노, 알킬설포닐하이드라지노, 아릴설포닐하이드라지노, 알킬티오, 아릴티노, 아르알킬티오, 알콕시카보닐알킬티오 또는 그룹 -O-R6(여기에서, R6은 알킬, 알케닐, 알키닐, 알콕시알킬, 알킬티오알킬, 알킬설피닐알킬, 알킬설포닐알킬, 아릴옥시알킬, 아르알콕시알킬, 트리알킬실릴알킬, 아릴티오알킬, 아르알킬티오알킬, 알목시카보닐알킬, 알킬아미노카보닐알킬, 아릴아미노카보닐알킬, N-알킬-N-아릴아미노카보닐알킬, 아르알킬, 아졸릴알킬 및 알킬리덴아미노중에서 선택된 임의로 할로겐-치환된 라디칼이거나, 등가의 암모늄, 등가의 알킬암모늄, 등가의 알칼리금속 또는 등가의 알칼리 토금속이거나, 그룹(여기에서, R7은 수소, 알킬, 아릴, 푸릴, 티에닐 또는 피리딜이고, R8은 알킬 또는 알콕시이며, R9는 알콕시이고, Q는 산소 또는 황이다)이거나, 그룹 -(CH2)n-R10(여기에서, R10은 푸릴, 테트라히이드로푸릴, 옥소테트라하이드로푸릴, 티에닐, 테트라하이드로티에닐, 퍼하이드로피라닐, 옥사졸릴, 티아졸린, 티아디아졸린, 디옥솔라닐, 퍼하이드로피롤릴, 옥소퍼하이드로피롤릴, 피리디닐 및 피리미디닐중에서 선택된 임의로 할로겐-치환되고/되거나 임의로 알킬-치환된 헤테로사이클릭 라디칼이고, n은 0,1 또는 2이다)이다)이다)이다. Z1은 친핵성 이탈기이며, Z2는 할로겐이고, R6-1은 암모늄, 알킬암모늄, 알칼리금속 및 알칼리토금속을 제외한 상기에서 R6엘 대하여 정의한 바와 같으며, Z3은 할로겐이다.
- 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 하나 이상 함유함을 특징으로 하는 제초제.
- 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 잡초 및/또는 이의 서식처에 작용시킴을 특징으로 하여, 잡초를 방제하는 방법.
- 잡초를 방제하기 위한, 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체의 용도.
- 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 중량제 및/또는 계면활성제와 혼합시킴을 특징으로 하여, 제초제를 제조하는 방법.
- 다음 일반식의 화합물.
- 다음 일반식(IIa)의 7-(헤테로)아릴옥시-2-나프톨.상기식에서, R1-1은 할로겐 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸 또는 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X1는 질소 또는 그룹 C-R5-1(여기에서, R5-1은 할로겐이다)이다.
- 다음 일반식(IVa)의 할로게노(헤테로(아릴 화합물을 산 수용체의 존재하 및 희석제의 존재하에 2,7-디하이드록시나프탈렌과 반응시킴을 특징으로하여, 다음 일반식(IIa)의 7-(헤테로)아릴옥시-2-나프톨을 제조하는 방법.상기 식에서, R1은 할로겐 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X1는 질소 또는 그룹 C-R5-1(여기에서5-1은 할로겐이다)이고, Z2는 할로겐이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19873731801 DE3731801A1 (de) | 1987-09-22 | 1987-09-22 | (7-(hetero)aryloxy-naphthalin-2-yl-oxy) -alkancarbonsaeure-derivate |
DEP3731801.2 | 1987-09-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
KR890005029A true KR890005029A (ko) | 1989-05-11 |
Family
ID=6336547
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019880012173A KR890005029A (ko) | 1987-09-22 | 1988-09-21 | (7-(헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체 |
Country Status (10)
Country | Link |
---|---|
US (1) | US5041609A (ko) |
EP (1) | EP0308755B1 (ko) |
JP (1) | JPH01113334A (ko) |
KR (1) | KR890005029A (ko) |
AR (1) | AR245696A1 (ko) |
AU (1) | AU624338B2 (ko) |
DE (2) | DE3731801A1 (ko) |
DK (1) | DK527188A (ko) |
HU (1) | HU200585B (ko) |
ZA (1) | ZA887045B (ko) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3737179A1 (de) * | 1987-11-03 | 1989-05-18 | Bayer Ag | (6-(hetero)aryloxy-naphthalin-2-yl-oxy)-alkancarbonsaeure-derivate |
DE4012711A1 (de) * | 1990-04-21 | 1991-10-24 | Bayer Ag | Fluor-substituierte (alpha)-(5-aryloxy-naphthalin-l-yl-oxy)-propionsaeure-derivate |
DE4111619A1 (de) * | 1991-04-10 | 1992-10-15 | Bayer Ag | (alpha)-(5-aryloxy-naphthalin-1-yl-oxy)-carbonsaeure-derivate |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3434447A1 (de) * | 1984-09-17 | 1986-03-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 7-(aryloxy)-2-naphthyloxy-alkancarbonsaeurederivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider wirkung |
AU570341B2 (en) * | 1984-09-17 | 1988-03-10 | Schering Aktiengesellschaft | 7-(aryloxy)-2-naphthoxy alkanecarboxylic acid |
EP0179015B1 (en) * | 1984-09-17 | 1988-04-13 | Schering Aktiengesellschaft | 7-(aryloxy)-2-naphthoxyalkanecarboxylic acid derivatives, processes for the preparation of these compounds, as well as agents having herbicidal activity containing these compounds |
JPS61165346A (ja) * | 1985-01-16 | 1986-07-26 | Mitsubishi Petrochem Co Ltd | フエノキシナフトキシ酢酸誘導体及びこれを含有する除草剤 |
JPS6210041A (ja) * | 1985-07-08 | 1987-01-19 | Sumitomo Chem Co Ltd | ナフトキシプロピオン酸誘導体、その製造法およびそれを有効成分とする除草剤 |
DE3737179A1 (de) * | 1987-11-03 | 1989-05-18 | Bayer Ag | (6-(hetero)aryloxy-naphthalin-2-yl-oxy)-alkancarbonsaeure-derivate |
DE3821389A1 (de) * | 1988-06-24 | 1989-12-28 | Bayer Ag | 1,7-dioxy-naphthalin-derivate |
-
1987
- 1987-09-22 DE DE19873731801 patent/DE3731801A1/de not_active Withdrawn
-
1988
- 1988-09-10 DE DE8888114847T patent/DE3875572D1/de not_active Expired - Lifetime
- 1988-09-10 EP EP88114847A patent/EP0308755B1/de not_active Expired - Lifetime
- 1988-09-14 AU AU22181/88A patent/AU624338B2/en not_active Ceased
- 1988-09-16 US US07/246,119 patent/US5041609A/en not_active Expired - Fee Related
- 1988-09-16 JP JP63230216A patent/JPH01113334A/ja active Pending
- 1988-09-21 KR KR1019880012173A patent/KR890005029A/ko not_active Application Discontinuation
- 1988-09-21 ZA ZA887045A patent/ZA887045B/xx unknown
- 1988-09-21 HU HU884951A patent/HU200585B/hu not_active IP Right Cessation
- 1988-09-22 AR AR88312009A patent/AR245696A1/es active
- 1988-09-22 DK DK527188A patent/DK527188A/da not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
AU624338B2 (en) | 1992-06-11 |
HU200585B (en) | 1990-07-28 |
DK527188A (da) | 1989-03-23 |
US5041609A (en) | 1991-08-20 |
JPH01113334A (ja) | 1989-05-02 |
DE3731801A1 (de) | 1989-03-30 |
AR245696A1 (es) | 1994-02-28 |
EP0308755A3 (en) | 1989-07-26 |
EP0308755B1 (de) | 1992-10-28 |
DE3875572D1 (de) | 1992-12-03 |
ZA887045B (en) | 1989-06-28 |
HUT47526A (en) | 1989-03-28 |
DK527188D0 (da) | 1988-09-22 |
AU2218188A (en) | 1989-03-23 |
EP0308755A2 (de) | 1989-03-29 |
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