HU204022B - Nematocidal compositions comprising polyhalogen alkene derivatives and process for producing polyhalogen alkene derivatives - Google Patents
Nematocidal compositions comprising polyhalogen alkene derivatives and process for producing polyhalogen alkene derivatives Download PDFInfo
- Publication number
- HU204022B HU204022B HU863254A HU325486A HU204022B HU 204022 B HU204022 B HU 204022B HU 863254 A HU863254 A HU 863254A HU 325486 A HU325486 A HU 325486A HU 204022 B HU204022 B HU 204022B
- Authority
- HU
- Hungary
- Prior art keywords
- trifluoro
- butenylthio
- group
- phenyl
- liquid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 118
- 230000001069 nematicidal effect Effects 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 10
- 150000001344 alkene derivatives Chemical class 0.000 title description 3
- 239000007788 liquid Substances 0.000 claims description 174
- -1 3-butenyloxycarbonylmethyl group Chemical group 0.000 claims description 154
- 150000001875 compounds Chemical class 0.000 claims description 94
- 239000007787 solid Substances 0.000 claims description 74
- 239000004480 active ingredient Substances 0.000 claims description 66
- 239000000843 powder Substances 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- QZFAJVOLXLAUKV-UHFFFAOYSA-N 3-[(4-nitrophenyl)methylsulfanyl]-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,2,4-thiadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CSC1=NSC(SCCC(F)=C(F)F)=N1 QZFAJVOLXLAUKV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 3
- OMNSSWMGNYESQK-UHFFFAOYSA-N 2-(2,3,3-trifluoroprop-2-enylsulfanyl)-1,3-thiazole Chemical compound FC(F)=C(F)CSC1=NC=CS1 OMNSSWMGNYESQK-UHFFFAOYSA-N 0.000 claims description 3
- ZPTRFECGKAVAAK-UHFFFAOYSA-N 2-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3-thiazole Chemical compound FC(F)=C(F)CCSC1=NC=CS1 ZPTRFECGKAVAAK-UHFFFAOYSA-N 0.000 claims description 3
- QKJZICNKHLQSPQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound S1C(SCCC(F)=C(F)F)=NN=C1C1=CC=C(Cl)C=C1 QKJZICNKHLQSPQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 3
- MFVWSFXQWMYYSF-UHFFFAOYSA-L dipotassium;cyanoiminomethanedithiolate Chemical compound [K+].[K+].[S-]C([S-])=NC#N MFVWSFXQWMYYSF-UHFFFAOYSA-L 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- KMUBAWIIABCRHQ-UHFFFAOYSA-N 2-(3,4,4-trifluorobut-3-enylsulfanyl)-4,5-dihydro-1,3-thiazole Chemical compound FC(F)=C(F)CCSC1=NCCS1 KMUBAWIIABCRHQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- QSPUEWIFUYQAAT-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,2,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NC(C=2C=CC(Cl)=CC=2)=N1 QSPUEWIFUYQAAT-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 6
- DWSCEKFODWPGGM-UHFFFAOYSA-N 2-(4-bromophenyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NN=C1C1=CC=C(Br)C=C1 DWSCEKFODWPGGM-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- LOPWFUKSYMHJTA-UHFFFAOYSA-N 2-(2-fluoroethylsulfanyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound FCCSC1=NN=C(SCCC(F)=C(F)F)S1 LOPWFUKSYMHJTA-UHFFFAOYSA-N 0.000 claims 1
- CHHXONKNEPAZSR-UHFFFAOYSA-N 2-(2-phenylethyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NN=C1CCC1=CC=CC=C1 CHHXONKNEPAZSR-UHFFFAOYSA-N 0.000 claims 1
- GDDIGILLLKSABT-UHFFFAOYSA-N 2-(3,4,4-trifluorobut-3-enylsulfanyl)thiophene Chemical compound FC(F)=C(F)CCSC1=CC=CS1 GDDIGILLLKSABT-UHFFFAOYSA-N 0.000 claims 1
- BURVEPGWMINMPK-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NN=C1C1=CC=CC(Cl)=C1 BURVEPGWMINMPK-UHFFFAOYSA-N 0.000 claims 1
- YDIJFVWFEGCHNK-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NN=C1C1=CC=C(F)C=C1 YDIJFVWFEGCHNK-UHFFFAOYSA-N 0.000 claims 1
- IPBPSXFFRHFCGU-UHFFFAOYSA-N 2-(cyclopropylmethylsulfanyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound S1C(SCCC(F)=C(F)F)=NN=C1SCC1CC1 IPBPSXFFRHFCGU-UHFFFAOYSA-N 0.000 claims 1
- GRRUIEZGWRXFRA-UHFFFAOYSA-N 2-benzyl-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NN=C1CC1=CC=CC=C1 GRRUIEZGWRXFRA-UHFFFAOYSA-N 0.000 claims 1
- HOIJBDUGWKINMQ-UHFFFAOYSA-N 2-benzylsulfanyl-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound S1C(SCCC(F)=C(F)F)=NN=C1SCC1=CC=CC=C1 HOIJBDUGWKINMQ-UHFFFAOYSA-N 0.000 claims 1
- FUKUMEXGQDJJHT-UHFFFAOYSA-N 2-prop-2-enylsulfanyl-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound FC(F)=C(F)CCSC1=NN=C(SCC=C)S1 FUKUMEXGQDJJHT-UHFFFAOYSA-N 0.000 claims 1
- RVQVBLDBFYKPAL-UHFFFAOYSA-N 2-propylsulfanyl-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,3,4-thiadiazole Chemical compound CCCSC1=NN=C(SCCC(F)=C(F)F)S1 RVQVBLDBFYKPAL-UHFFFAOYSA-N 0.000 claims 1
- FUQAQQBHGRWLRN-UHFFFAOYSA-N 3-(4-nitrophenyl)-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,2,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NOC(SCCC(F)=C(F)F)=N1 FUQAQQBHGRWLRN-UHFFFAOYSA-N 0.000 claims 1
- GCGVCVCCRYLIRK-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-5-(3,4,4-trifluorobut-3-enylsulfanyl)-1,2,4-oxadiazole Chemical compound O1C(SCCC(F)=C(F)F)=NC(CC=2C=CC(F)=CC=2)=N1 GCGVCVCCRYLIRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 48
- 238000009472 formulation Methods 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 35
- 239000002689 soil Substances 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 29
- 241000244206 Nematoda Species 0.000 description 27
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
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- 239000003995 emulsifying agent Substances 0.000 description 20
- 239000000969 carrier Substances 0.000 description 18
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- 239000003795 chemical substances by application Substances 0.000 description 14
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- 241000243785 Meloidogyne javanica Species 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 239000008096 xylene Substances 0.000 description 12
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- 239000005645 nematicide Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
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- 150000001298 alcohols Chemical class 0.000 description 8
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 4
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/42—Halogenated unsaturated alcohols acyclic
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; 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
- 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
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; 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
- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/32—Cyclic imides of polybasic carboxylic acids or thio analogues 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
- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A01N43/74—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 five-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
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- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- 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
- C07C323/52—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 being acyclic and saturated
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/36—Sulfur atoms
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74714285A | 1985-06-20 | 1985-06-20 | |
| US74691185A | 1985-06-20 | 1985-06-20 | |
| PCT/US1986/001284 WO1986007590A1 (fr) | 1985-06-20 | 1986-06-12 | Derives de polyhaloalcene a effet pesticide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT42424A HUT42424A (en) | 1987-07-28 |
| HU204022B true HU204022B (en) | 1991-11-28 |
Family
ID=27114667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU863254A HU204022B (en) | 1985-06-20 | 1986-06-12 | Nematocidal compositions comprising polyhalogen alkene derivatives and process for producing polyhalogen alkene derivatives |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0228447A4 (fr) |
| KR (1) | KR910000247B1 (fr) |
| CN (1) | CN86104207A (fr) |
| AU (1) | AU601656B2 (fr) |
| BR (1) | BR8606746A (fr) |
| CA (1) | CA1277668C (fr) |
| DK (1) | DK84387D0 (fr) |
| HU (1) | HU204022B (fr) |
| IL (1) | IL79143A0 (fr) |
| MY (1) | MY102076A (fr) |
| OA (1) | OA08484A (fr) |
| WO (1) | WO1986007590A1 (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0263066A3 (fr) * | 1986-09-26 | 1988-06-01 | Ciba-Geigy Ag | Dérivés de 2-mercapto-oxadiazole et -thiadiazole, procédé pour leur préparation et nématicides les contenant |
| EP0290379A3 (fr) * | 1987-04-03 | 1989-02-22 | Ciba-Geigy Ag | 2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles et -1,3,4-thiadiazoles, procédé pour leur préparation et leur utilisation comme agents nematicides |
| DE3884031D1 (de) * | 1987-04-03 | 1993-10-21 | Ciba Geigy | 2-Mercapto-5-pyridyl-1,3,4-oxadiazole und -1,3,4-thiadiazole, Verfahren zu ihrer Herstellung und ihre Verwendung als nematizide Mittel. |
| ATE80878T1 (de) * | 1987-12-18 | 1992-10-15 | Ciba Geigy Ag | 2-thio-5-difluoromethylthio-1,3,4-thiadiazole und diese enthaltende nematizide mittel. |
| EP0323869A1 (fr) * | 1988-01-06 | 1989-07-12 | Shell Internationale Researchmaatschappij B.V. | Dérivés de saccharine |
| EP0364395A1 (fr) * | 1988-09-23 | 1990-04-18 | Ciba-Geigy Ag | Agents nématicides |
| DD295522A5 (de) * | 1989-07-26 | 1991-11-07 | �����@������������������k�� | 5-Alkyl-1,3,4-Thiadiazole, Verfahren zu ihrer Herstellung und Verwendung als Schädlingsbekämpfungsmittel |
| WO1992015555A2 (fr) * | 1991-03-01 | 1992-09-17 | Monsanto Company | Composes fluoroalcenyles et utilisation de ces composes comme insecticides |
| IL112721A0 (en) * | 1994-03-10 | 1995-05-26 | Zeneca Ltd | Azole derivatives |
| US5514717A (en) * | 1994-10-26 | 1996-05-07 | Monsanto Company | Fluoroalkenyl compounds and their use as pest control agents |
| DE4439334A1 (de) * | 1994-11-04 | 1996-05-09 | Bayer Ag | Dithiocarbazonsäurebutenylester |
| DE4445792A1 (de) * | 1994-12-21 | 1996-06-27 | Bayer Ag | Fluorbutenyl(thio)ether |
| US5811578A (en) * | 1995-05-23 | 1998-09-22 | Monsanto Company | Fluoroalkenyl compounds and their use as pest control agents |
| FR2786178A1 (fr) | 1998-11-25 | 2000-05-26 | Solvay | Monomeres trifluorovinyliques fonctionnels et leur copolymerisation avec des olefines fluorees |
| JP2001019685A (ja) | 1999-07-06 | 2001-01-23 | Nippon Bayer Agrochem Co Ltd | 殺センチュウ性トリフルオロブテン類 |
| DE10034132A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (lll) |
| DE10034130A1 (de) * | 2000-07-13 | 2002-01-24 | Bayer Ag | Heterocyclische Fluoralkenylthioether (lV) |
| JP2003113168A (ja) * | 2001-09-28 | 2003-04-18 | Bayer Ag | 殺センチュウ性トリフルオロブテン誘導体 |
| DE10229776A1 (de) | 2002-07-03 | 2004-01-22 | Bayer Cropscience Ag | Verfahren zum Herstellen von heterocyclischen Fluoralkenylsulfonen |
| WO2004013112A1 (fr) * | 2002-08-01 | 2004-02-12 | Basf Aktiengesellschaft | Derives d'alcene fluore antiparasitaires |
| DE10319591A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden, insektiziden und fungiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
| DE10319590A1 (de) | 2003-05-02 | 2004-11-18 | Bayer Cropscience Ag | Wirkstoffkombinationen mit nematiziden und insektiziden Eigenschaften basierend auf Trifluorbutenyl-Verbindungen |
| JP2005008567A (ja) * | 2003-06-19 | 2005-01-13 | Bayer Cropscience Ag | 殺センチュウ性チアゾリン含有フルオロブテン類 |
| JP2005089383A (ja) * | 2003-09-18 | 2005-04-07 | Bayer Cropscience Ag | 新規チアジアゾール含有ジフルオロアルケン類及び有害生物防除剤としての利用 |
| RU2017108785A (ru) | 2011-06-24 | 2019-01-22 | Доу Агросаенсиз Ллк | Пестицидные композиции и связанные с ними способы |
| CN102696609B (zh) * | 2012-01-10 | 2013-09-11 | 山东中农联合生物科技有限公司 | 一种含吡啶的三氟丁烯类杀虫剂 |
| CN102838593B (zh) * | 2012-10-08 | 2015-01-07 | 贵州大学 | 2-(4-甲基-1,2,3-噻二唑)-5-(取代基)-1,3,4-噁(噻)二唑类衍生物及其应用 |
| WO2014100206A1 (fr) * | 2012-12-19 | 2014-06-26 | Dow Agrosciences Llc | Compositions pesticides et leurs procédés associés |
| RU2667788C2 (ru) * | 2012-12-19 | 2018-09-24 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и связанные с ними способы |
| ES2667578T3 (es) | 2012-12-19 | 2018-05-11 | Dow Agrosciences Llc | Composiciones pesticidas y métodos relacionados con las mismas |
| RU2654336C2 (ru) * | 2012-12-19 | 2018-05-17 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и связанные с ними способы |
| EP2934142B1 (fr) | 2012-12-19 | 2018-01-31 | Dow AgroSciences LLC | Compositions de pesticide et leurs procédés associés |
| CN103193769A (zh) * | 2013-04-15 | 2013-07-10 | 南开大学 | 一类4-甲基-1,2,3-噻二唑-5-三唑类化合物及其制备方法和用途 |
| TWI667224B (zh) | 2014-06-09 | 2019-08-01 | 美商陶氏農業科學公司 | 殺蟲組成物及與其相關之方法 |
| CN106554335B (zh) * | 2015-09-30 | 2017-09-19 | 山东省联合农药工业有限公司 | 一种反式结构的含内酯环的杀线虫剂及其制备方法和用途 |
| JP6923535B2 (ja) | 2016-01-25 | 2021-08-18 | コルテバ アグリサイエンス エルエルシー | 農薬の効用を有する分子、ならびにこれに関連する中間体、組成物、及びプロセス |
| CN105646393A (zh) * | 2016-03-31 | 2016-06-08 | 贵州大学 | 含三氟丁烯的1,3,4-噁(噻)二唑硫醚(砜)类衍生物、其制备方法及应用 |
| CN106397420B (zh) * | 2016-09-05 | 2018-10-09 | 郑州大学 | 3-(5-芳基-1,3,4-噁二唑-2-基)细辛素类衍生物、其制备方法及应用 |
| TWI780112B (zh) | 2017-03-31 | 2022-10-11 | 美商科迪華農業科技有限責任公司 | 具有殺蟲效用之分子,及其相關之中間物、組成物暨方法 |
| CN107903338A (zh) * | 2017-11-23 | 2018-04-13 | 中国科学院海洋研究所 | 一种壳寡糖衍生物及其制备方法和应用 |
| BR112020012614A2 (pt) | 2017-12-20 | 2020-11-24 | Pi Industries Ltd | compostos de fluoralquenil, processo de preparação e utilização |
| IT201800004120A1 (it) * | 2018-03-30 | 2019-09-30 | Isagro Spa | Esteri di composti eterociclici ad attività nematocida, loro composizioni agronomiche e relativo uso |
| PY1980072A (es) | 2018-09-26 | 2020-06-05 | Adama Makhteshim Ltd | Proceso e intermedios para la preparación de fluensulfona |
| WO2020095161A1 (fr) | 2018-11-05 | 2020-05-14 | Pi Industries Ltd. | Composés nitrones et leur utilisation |
| CN113912495A (zh) * | 2020-07-09 | 2022-01-11 | 山东省联合农药工业有限公司 | 一种含氟丁烯酯类衍生物及其制备方法与用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3058990A (en) * | 1961-01-19 | 1962-10-16 | Monsanto Chemicals | Haloallylthiadiazoles |
| US3080405A (en) * | 1961-08-02 | 1963-03-05 | Dow Chemical Co | 3, 3-difluoroallyl esters |
| FR1528170A (fr) * | 1965-06-18 | 1968-06-07 | Agripat Sa | 3-oxo-1, 2-dithioles, leur préparation et leur application comme agents de lutte contre les micro-organismes |
| US3666818A (en) * | 1965-09-27 | 1972-05-30 | Stauffer Chemical Co | Trifluorobutenyl sulfides |
| US3513172A (en) * | 1965-09-27 | 1970-05-19 | Stauffer Chemical Co | 3-phenyl-5-(3,4,4-trifluoro-3-butenylthio)1,2,4-thiadiazole |
| US3463856A (en) * | 1967-04-05 | 1969-08-26 | Ihara Chem Co Ltd | Method for controlling phytopathogenic fungi and bacteria on plants by applying dichloroalkenylhydrophthalimides thereto |
| US3780050A (en) * | 1969-11-20 | 1973-12-18 | Stauffer Chemical Co | 2-thiobenzoxazolyl and 2-thiobenzothiazolyl trifluoro butenyl compounds |
| US3697536A (en) * | 1969-11-20 | 1972-10-10 | Stauffer Chemical Co | Composition of matter |
| JPS498259A (fr) * | 1972-05-10 | 1974-01-24 | ||
| AU1587683A (en) * | 1983-06-17 | 1984-12-20 | Merck & Co., Inc. | 2,3-dihalo-2,3-disubstituted propanoates |
| JPS6064940A (ja) * | 1983-09-21 | 1985-04-13 | Daikin Ind Ltd | 含フッ素オレフィン |
| FR2575156B1 (fr) * | 1984-12-26 | 1987-01-23 | Atochem | Telogenes fluores a terminaison ccl3, leur preparation et cotelomeres bisequences en derivant |
-
1986
- 1986-06-12 WO PCT/US1986/001284 patent/WO1986007590A1/fr not_active Ceased
- 1986-06-12 HU HU863254A patent/HU204022B/hu not_active IP Right Cessation
- 1986-06-12 KR KR1019870700146A patent/KR910000247B1/ko not_active Expired
- 1986-06-12 BR BR8606746A patent/BR8606746A/pt unknown
- 1986-06-12 EP EP19860904515 patent/EP0228447A4/en not_active Ceased
- 1986-06-12 AU AU61229/86A patent/AU601656B2/en not_active Ceased
- 1986-06-18 IL IL79143A patent/IL79143A0/xx unknown
- 1986-06-18 CA CA000511879A patent/CA1277668C/fr not_active Expired - Lifetime
- 1986-06-19 CN CN198686104207A patent/CN86104207A/zh active Pending
-
1987
- 1987-02-19 DK DK084387A patent/DK84387D0/da not_active Application Discontinuation
- 1987-02-20 OA OA59075A patent/OA08484A/fr unknown
- 1987-09-29 MY MYPI87002201A patent/MY102076A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1986007590A1 (fr) | 1986-12-31 |
| KR910000247B1 (ko) | 1991-01-23 |
| EP0228447A1 (fr) | 1987-07-15 |
| EP0228447A4 (en) | 1990-12-27 |
| CN86104207A (zh) | 1987-04-01 |
| DK84387A (da) | 1987-02-19 |
| OA08484A (fr) | 1988-07-29 |
| AU6122986A (en) | 1987-01-13 |
| BR8606746A (pt) | 1987-10-13 |
| KR870700589A (ko) | 1987-12-30 |
| DK84387D0 (da) | 1987-02-19 |
| AU601656B2 (en) | 1990-09-13 |
| MY102076A (en) | 1992-03-31 |
| HUT42424A (en) | 1987-07-28 |
| IL79143A0 (en) | 1986-09-30 |
| CA1277668C (fr) | 1990-12-11 |
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Legal Events
| Date | Code | Title | Description |
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| HMM4 | Cancellation of final prot. due to non-payment of fee |