CS273340B2 - Herbicide and method of its active substances production - Google Patents
Herbicide and method of its active substances production Download PDFInfo
- Publication number
- CS273340B2 CS273340B2 CS83988A CS83988A CS273340B2 CS 273340 B2 CS273340 B2 CS 273340B2 CS 83988 A CS83988 A CS 83988A CS 83988 A CS83988 A CS 83988A CS 273340 B2 CS273340 B2 CS 273340B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- align
- dione
- nitrobenzoyl
- methyl
- chloro
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 17
- 239000004009 herbicide Substances 0.000 title abstract description 7
- 239000013543 active substance Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 hydroxy, carboxy Chemical group 0.000 claims abstract description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- FYKJJDMEILLSHC-UHFFFAOYSA-N 3-benzoylpiperidine-2,4-dione Chemical class C=1C=CC=CC=1C(=O)C1C(=O)CCNC1=O FYKJJDMEILLSHC-UHFFFAOYSA-N 0.000 claims description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- MYQNZVJCSRCWOC-UHFFFAOYSA-N 3-(4-chloro-2-nitrobenzoyl)-1-methylpiperidine-2,4-dione Chemical compound O=C1N(C)CCC(=O)C1C(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O MYQNZVJCSRCWOC-UHFFFAOYSA-N 0.000 claims description 3
- FMLAGBRCXAXMRB-UHFFFAOYSA-N 3-(4-chloro-2-nitrobenzoyl)-5-methylpiperidine-2,4-dione Chemical compound O=C1C(C)CNC(=O)C1C(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O FMLAGBRCXAXMRB-UHFFFAOYSA-N 0.000 claims description 3
- CMKHMGBMWXDXPO-UHFFFAOYSA-N 3-(4-chloro-2-nitrobenzoyl)piperidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C(=O)C1C(=O)NCCC1=O CMKHMGBMWXDXPO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 241000196324 Embryophyta Species 0.000 description 61
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 38
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- 125000001309 chloro group Chemical group Cl* 0.000 description 29
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 230000012010 growth Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
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- RDNZDMDLRIQQAX-UHFFFAOYSA-N piperidine-2,4-dione Chemical compound O=C1CCNC(=O)C1 RDNZDMDLRIQQAX-UHFFFAOYSA-N 0.000 description 11
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- 239000000969 carrier Substances 0.000 description 10
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- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- NTBYHAZMHVUNFA-UHFFFAOYSA-N methyl 1-methyl-2,4-dioxo-6-phenylpiperidine-3-carboxylate Chemical compound CN1C(=O)C(C(=O)OC)C(=O)CC1C1=CC=CC=C1 NTBYHAZMHVUNFA-UHFFFAOYSA-N 0.000 description 1
- JOTOUSGKSPPFQF-UHFFFAOYSA-N methyl 3-amino-3-methylbutanoate Chemical compound COC(=O)CC(C)(C)N JOTOUSGKSPPFQF-UHFFFAOYSA-N 0.000 description 1
- HUJBVSPHSJJTGK-UHFFFAOYSA-N methyl 3-amino-3-methylbutanoate;hydrochloride Chemical compound Cl.COC(=O)CC(C)(C)N HUJBVSPHSJJTGK-UHFFFAOYSA-N 0.000 description 1
- FCXDIYVVOCFIMV-UHFFFAOYSA-N methyl 6,6-dimethyl-2,4-dioxopiperidine-3-carboxylate Chemical compound COC(=O)C1C(=O)CC(C)(C)NC1=O FCXDIYVVOCFIMV-UHFFFAOYSA-N 0.000 description 1
- GPPAYVNPJRZZEM-UHFFFAOYSA-N methyl 6-methyl-2,4-dioxo-6-(trifluoromethyl)piperidine-3-carboxylate Chemical compound COC(=O)C1C(=O)CC(C)(C(F)(F)F)NC1=O GPPAYVNPJRZZEM-UHFFFAOYSA-N 0.000 description 1
- QWGRLQNQEFPRTN-UHFFFAOYSA-N methyl 6-methyl-2,4-dioxo-6-phenylpiperidine-3-carboxylate Chemical compound N1C(=O)C(C(=O)OC)C(=O)CC1(C)C1=CC=CC=C1 QWGRLQNQEFPRTN-UHFFFAOYSA-N 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- CNMOHEDUVVUVPP-UHFFFAOYSA-N piperidine-2,3-dione Chemical compound O=C1CCCNC1=O CNMOHEDUVVUVPP-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-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
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
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- 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
- A01N35/06—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 keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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- 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
- A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
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- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- A—HUMAN NECESSITIES
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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-
- A—HUMAN NECESSITIES
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- 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
- A01N43/42—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 condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
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- 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
- A01N43/86—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 1,3
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/55—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C323/50—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 carboxyl groups bound to the same carbon skeleton
- C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—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 carboxyl groups 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 containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878703068A GB8703068D0 (en) | 1987-02-11 | 1987-02-11 | Compositions of matter |
| GB878707608A GB8707608D0 (en) | 1987-03-31 | 1987-03-31 | Compositions of matter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS83988A2 CS83988A2 (en) | 1990-06-13 |
| CS273340B2 true CS273340B2 (en) | 1991-03-12 |
Family
ID=26291891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS83988A CS273340B2 (en) | 1987-02-11 | 1988-02-10 | Herbicide and method of its active substances production |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5114461A (fr) |
| EP (1) | EP0278742A3 (fr) |
| KR (1) | KR880009929A (fr) |
| AU (2) | AU607183B2 (fr) |
| BG (1) | BG47342A3 (fr) |
| BR (1) | BR8800580A (fr) |
| CS (1) | CS273340B2 (fr) |
| DK (1) | DK68088A (fr) |
| FI (1) | FI880591A7 (fr) |
| HU (1) | HU203941B (fr) |
| IL (1) | IL85347A0 (fr) |
| MA (1) | MA21177A1 (fr) |
| NZ (1) | NZ223458A (fr) |
| OA (1) | OA08714A (fr) |
| PH (1) | PH25020A (fr) |
| PL (1) | PL270560A1 (fr) |
| PT (1) | PT86750B (fr) |
| TN (1) | TNSN88009A1 (fr) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4728745A (en) * | 1986-06-09 | 1988-03-01 | Stauffer Chemical Company | Substituted 4-benzoyl-3,5-dioxotetrahydropyrans and thiopyrans useful as herbicides |
| DE3850749D1 (de) * | 1987-11-28 | 1994-08-25 | Nippon Soda Co | Cyclohexenonderivate. |
| IL91200A0 (en) * | 1988-08-05 | 1990-03-19 | May & Baker Ltd | Herbicidal composition comprising bromoxynil and herbicidal methods employing the same |
| JPH0283305A (ja) * | 1988-08-05 | 1990-03-23 | May & Baker Ltd | アトラジンを用いる除草方法 |
| JPH0774126B2 (ja) * | 1989-10-18 | 1995-08-09 | ヘキスト・アクチェンゲゼルシャフト | イネにおける有害植物の防除方法 |
| US5306695A (en) * | 1991-03-06 | 1994-04-26 | Hoechst Aktiengesellschaft | Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators |
| WO1993001171A1 (fr) * | 1991-07-09 | 1993-01-21 | Nippon Soda Co., Ltd. | Derive de cyclohexanedione heterocyclique, production de celui-ci, et herbicide |
| JP3245421B2 (ja) * | 1992-08-18 | 2002-01-15 | 出光興産株式会社 | シクロヘキサンジオン誘導体 |
| AU5118693A (en) * | 1992-10-15 | 1994-05-09 | Idemitsu Kosan Co. Ltd | Cyclohexanedione derivative |
| US5840751A (en) * | 1993-11-19 | 1998-11-24 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
| TJ320B (en) * | 1993-11-19 | 2001-10-22 | Parke Davis & Co | 5,6-Dihydropyrone derivatives as protease inhibitors and antiviral agents |
| US5563280A (en) * | 1994-07-25 | 1996-10-08 | American Cyanamid Co. | 4-Phenoxycoumarins as herbicidal agents |
| EP0791572A4 (fr) * | 1994-11-07 | 1999-02-03 | Nippon Soda Co | Derive substitue de bicycloheptanedione, et herbicide |
| BR9714497A (pt) * | 1996-12-27 | 2000-03-21 | Nippon Soda Co | Derivados de piperidinadiona substituìda, e, herbicidas. |
| DE19700019A1 (de) | 1997-01-03 | 1998-07-09 | Basf Ag | Substituierte 2-Benzoyl-cyclohexan-1,3-dione |
| DE19700097A1 (de) | 1997-01-03 | 1998-07-09 | Basf Ag | 3-Aminocarbonyl/3-Aminothiocarbonyl-substituierte 2-Benzoyl-cyclohexan-1,3-dione |
| WO1998050377A1 (fr) * | 1997-05-07 | 1998-11-12 | Basf Aktiengesellschaft | 2-benzoyle-cyclohexane-1,3-diones substituees |
| CA2298574A1 (fr) * | 1997-08-07 | 1999-02-18 | Basf Aktiengesellschaft | 2-benzoyle-cyclohexane-1,3-diones |
| JP4592183B2 (ja) | 1997-08-07 | 2010-12-01 | ビーエーエスエフ ソシエタス・ヨーロピア | 2−ベンゾイルシクロヘキサン−1,3−ジオン |
| US6828460B2 (en) | 1999-03-22 | 2004-12-07 | Pfizer Inc. | Resorcinol derivatives |
| GT200100103A (es) | 2000-06-09 | 2002-02-21 | Nuevos herbicidas | |
| DE102004029309A1 (de) * | 2004-06-17 | 2005-12-29 | Bayer Cropscience Gmbh | Pyridinylisoxazole und ihre Verwendung als Herbizide |
| CN101287734B (zh) * | 2005-09-30 | 2011-07-20 | 诺华公司 | 2-氨基-7,8-二氢-6H-吡啶并[4,3-d]嘧啶-5-酮 |
| JO2783B1 (en) | 2005-09-30 | 2014-03-15 | نوفارتيس ايه جي | Compounds 2-Amino-7, 8-dihydro-6H-Bayredo (3,4-D) Pyrimidine-5-Ones |
| RU2584483C2 (ru) * | 2014-07-24 | 2016-05-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермская государственная сельскохозяйственная академия имени академика Д.Н. Прянишникова" | Стимулятор роста яровой пшеницы |
| CN104961704B (zh) * | 2015-07-09 | 2017-06-09 | 南开大学 | 含2‑(6‑硝基‑3‑氧杂‑2h‑苯并[1,4]噁嗪‑7‑羟基)环己烷‑1,3‑二酮类化合物及除草活性 |
| US12227501B2 (en) | 2019-02-07 | 2025-02-18 | Bayer Aktiengesellschaft | 3-amino-2-[2-(acylamino)pyridin-4-yl]-1,5,6,7-tetrahydro-4h-pyrrolo[3,2-c]pyridin-4-one as CSNK1 inhibitors |
| TW202543611A (zh) * | 2024-03-27 | 2025-11-16 | 美商費斯製藥有限公司 | Hpd抑制劑組成物及使用方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU562939B2 (en) * | 1983-09-16 | 1987-06-25 | Zeneca Ag Products Inc. | Herbicidal substituted benzoyl cyclohexanediones |
| TR22585A (tr) * | 1984-12-20 | 1987-12-07 | Stauffer Chemical Co | Bazi 2-(2'-alkilbenzoil)-1,3-sikloheksandion'lar |
| ES2014493B3 (es) * | 1986-04-24 | 1990-07-16 | Ciba-Geigy Ag | Acil-ciclohexandionas y sus eteres de oximas con efecto herbicida y regulador del crecimiento de las plantas. |
| US4808720A (en) * | 1986-06-09 | 1989-02-28 | Stauffer Chemical Company | Certain 3-benzoyl-4-oxolactams |
| US4741755A (en) * | 1986-06-09 | 1988-05-03 | Stauffer Chemical Company | Certain 4-oxo-3-benzoylvalerolactones and thiolactones |
-
1988
- 1988-02-08 MA MA21414A patent/MA21177A1/fr unknown
- 1988-02-08 IL IL85347A patent/IL85347A0/xx unknown
- 1988-02-09 NZ NZ223458A patent/NZ223458A/en unknown
- 1988-02-09 AU AU11454/88A patent/AU607183B2/en not_active Ceased
- 1988-02-09 FI FI880591A patent/FI880591A7/fi not_active IP Right Cessation
- 1988-02-10 OA OA59282A patent/OA08714A/xx unknown
- 1988-02-10 HU HU88607A patent/HU203941B/hu not_active IP Right Cessation
- 1988-02-10 CS CS83988A patent/CS273340B2/cs unknown
- 1988-02-10 EP EP88301103A patent/EP0278742A3/fr not_active Withdrawn
- 1988-02-10 TN TNTNSN88009A patent/TNSN88009A1/fr unknown
- 1988-02-10 PL PL27056088A patent/PL270560A1/xx unknown
- 1988-02-10 PH PH36478A patent/PH25020A/en unknown
- 1988-02-10 DK DK068088A patent/DK68088A/da not_active Application Discontinuation
- 1988-02-11 KR KR1019880001297A patent/KR880009929A/ko not_active Withdrawn
- 1988-02-11 BG BG082929A patent/BG47342A3/xx unknown
- 1988-02-11 BR BR8800580A patent/BR8800580A/pt unknown
- 1988-02-11 PT PT86750A patent/PT86750B/pt not_active IP Right Cessation
-
1989
- 1989-11-22 US US07/440,208 patent/US5114461A/en not_active Expired - Fee Related
-
1990
- 1990-11-23 AU AU66910/90A patent/AU6691090A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| FI880591A7 (fi) | 1988-08-12 |
| HU203941B (en) | 1991-11-28 |
| PL270560A1 (en) | 1989-09-04 |
| BG47342A3 (bg) | 1990-06-15 |
| PT86750B (pt) | 1992-04-30 |
| BR8800580A (pt) | 1988-09-27 |
| TNSN88009A1 (fr) | 1990-07-10 |
| HUT48092A (en) | 1989-05-29 |
| AU1145488A (en) | 1988-08-18 |
| DK68088D0 (da) | 1988-02-10 |
| KR880009929A (ko) | 1988-10-05 |
| AU6691090A (en) | 1991-06-27 |
| US5114461A (en) | 1992-05-19 |
| NZ223458A (en) | 1990-11-27 |
| AU607183B2 (en) | 1991-02-28 |
| OA08714A (en) | 1989-03-31 |
| PT86750A (pt) | 1988-03-01 |
| CS83988A2 (en) | 1990-06-13 |
| DK68088A (da) | 1988-08-12 |
| PH25020A (en) | 1991-01-28 |
| MA21177A1 (fr) | 1988-10-01 |
| IL85347A0 (en) | 1988-07-31 |
| EP0278742A2 (fr) | 1988-08-17 |
| FI880591A0 (fi) | 1988-02-09 |
| EP0278742A3 (fr) | 1989-11-15 |
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