DD202377A5 - Pestizide zusammensetzungen - Google Patents
Pestizide zusammensetzungen Download PDFInfo
- Publication number
- DD202377A5 DD202377A5 DD81234166A DD23416681A DD202377A5 DD 202377 A5 DD202377 A5 DD 202377A5 DD 81234166 A DD81234166 A DD 81234166A DD 23416681 A DD23416681 A DD 23416681A DD 202377 A5 DD202377 A5 DD 202377A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- chloro
- chlorine
- item
- composition according
- urea
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 239000000575 pesticide Substances 0.000 title claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 85
- 239000001257 hydrogen Substances 0.000 claims abstract description 60
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000006684 polyhaloalkyl group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 665
- 229910052801 chlorine Inorganic materials 0.000 claims description 86
- -1 ureo Chemical group 0.000 claims description 71
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 48
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 44
- 239000011737 fluorine Chemical group 0.000 claims description 44
- 229910052731 fluorine Chemical group 0.000 claims description 44
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 43
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 40
- 239000004202 carbamide Substances 0.000 claims description 36
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 229910052727 yttrium Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- ZGOLQMOPAHHQCC-UHFFFAOYSA-N n-carbamoyl-2-chlorobenzamide Chemical compound NC(=O)NC(=O)C1=CC=CC=C1Cl ZGOLQMOPAHHQCC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 16
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000002498 deadly effect Effects 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 231100000518 lethal Toxicity 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- 235000013877 carbamide Nutrition 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
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- 238000002360 preparation method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
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- 235000019198 oils Nutrition 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 241001521235 Spodoptera eridania Species 0.000 description 11
- 235000013601 eggs Nutrition 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 7
- 241000462639 Epilachna varivestis Species 0.000 description 7
- 150000008047 benzoylureas Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000003672 ureas Chemical class 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- IEEFFONXXSQVOQ-UHFFFAOYSA-N 1-chloro-4-(2,6-dichloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 IEEFFONXXSQVOQ-UHFFFAOYSA-N 0.000 description 4
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- 241000254173 Coleoptera Species 0.000 description 4
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- 230000009467 reduction Effects 0.000 description 4
- 238000004611 spectroscopical analysis Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
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- HHLCSFGOTLUREE-UHFFFAOYSA-N 1,2,3-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 HHLCSFGOTLUREE-UHFFFAOYSA-N 0.000 description 2
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 2
- ZLDPOHAKONFWBU-UHFFFAOYSA-N 1-chloro-4-(4-nitrophenoxy)naphthalene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C2=CC=CC=C12 ZLDPOHAKONFWBU-UHFFFAOYSA-N 0.000 description 2
- KXOLGDVYYIQCIO-UHFFFAOYSA-N 3-chloro-4-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]aniline Chemical compound C=12OC(C)(C)CC2=CC=CC=1OC1=CC=C(N)C=C1Cl KXOLGDVYYIQCIO-UHFFFAOYSA-N 0.000 description 2
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- 101000834981 Homo sapiens Testis, prostate and placenta-expressed protein Proteins 0.000 description 2
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- PRVZBFHPBBIILN-UHFFFAOYSA-N n-[(4-naphthalen-1-yloxyphenyl)carbamoyl]benzamide Chemical compound C=1C=C(OC=2C3=CC=CC=C3C=CC=2)C=CC=1NC(=O)NC(=O)C1=CC=CC=C1 PRVZBFHPBBIILN-UHFFFAOYSA-N 0.000 description 2
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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- OAGXKEOTRBGZAD-UHFFFAOYSA-N 1-(2-chloro-6-methyl-4-nitrophenoxy)-4-methoxynaphthalene Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC1=C(C)C=C([N+]([O-])=O)C=C1Cl OAGXKEOTRBGZAD-UHFFFAOYSA-N 0.000 description 1
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- SEGARSYGUBYPOK-UHFFFAOYSA-N 1-(4-nitrophenoxy)naphthalene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC2=CC=CC=C12 SEGARSYGUBYPOK-UHFFFAOYSA-N 0.000 description 1
- YPECNVBQNYHRLT-UHFFFAOYSA-N 1-[4-nitro-2-(trifluoromethyl)phenoxy]naphthalene Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC2=CC=CC=C12 YPECNVBQNYHRLT-UHFFFAOYSA-N 0.000 description 1
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- MEYLVPCYDKRADV-UHFFFAOYSA-N 1-chloro-4-(2-chloro-6-methyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 MEYLVPCYDKRADV-UHFFFAOYSA-N 0.000 description 1
- KXERKSDYTLPGID-UHFFFAOYSA-N 1-chloro-4-(2-methyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C2=CC=CC=C12 KXERKSDYTLPGID-UHFFFAOYSA-N 0.000 description 1
- VSQARESDJRIKSA-UHFFFAOYSA-N 1-methoxy-4-(2-methoxy-4-nitrophenoxy)naphthalene Chemical compound COC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(OC)C2=CC=CC=C12 VSQARESDJRIKSA-UHFFFAOYSA-N 0.000 description 1
- CWPBIPCCFYWQGJ-UHFFFAOYSA-N 1-methoxy-4-(2-methyl-4-nitrophenoxy)naphthalene Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1C CWPBIPCCFYWQGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- PWHRHEPKJREJHR-UHFFFAOYSA-N 2,4-dichloro-1-(2-chloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C2=CC=CC=C12 PWHRHEPKJREJHR-UHFFFAOYSA-N 0.000 description 1
- ZBOJAMGIFGSVFF-UHFFFAOYSA-N 2,6-difluoro-n-(phenylcarbamoyl)benzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=CC=C1 ZBOJAMGIFGSVFF-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
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- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
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- BVAGHBKNJRIOBV-UHFFFAOYSA-N n-[[3-chloro-4-(4-chloronaphthalen-1-yl)oxy-5-methylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=1C(Cl)=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F BVAGHBKNJRIOBV-UHFFFAOYSA-N 0.000 description 1
- GJYSBFCULPWYQH-UHFFFAOYSA-N n-[[3-chloro-4-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=12OC(C)(C)CC2=CC=CC=1OC(C(=C1)Cl)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F GJYSBFCULPWYQH-UHFFFAOYSA-N 0.000 description 1
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- 239000010502 orange oil Substances 0.000 description 1
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- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
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- 235000002020 sage Nutrition 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
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- 230000000392 somatic effect Effects 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/02—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds
- C07C273/06—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds from cyanamide or calcium cyanamide
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- 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
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/16—Derivatives of isocyanic acid having isocyanate groups acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19759580A | 1980-10-16 | 1980-10-16 | |
| US06/305,951 US4426385A (en) | 1980-10-16 | 1981-09-28 | Insecticidal bicyclooxyphenyl ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD202377A5 true DD202377A5 (de) | 1983-09-14 |
Family
ID=26892983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81234166A DD202377A5 (de) | 1980-10-16 | 1981-10-16 | Pestizide zusammensetzungen |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4426385A (OSRAM) |
| EP (1) | EP0050321B1 (OSRAM) |
| KR (1) | KR870000369B1 (OSRAM) |
| AR (1) | AR231972A1 (OSRAM) |
| AU (1) | AU555928B2 (OSRAM) |
| BR (1) | BR8106662A (OSRAM) |
| CA (1) | CA1190553A (OSRAM) |
| DD (1) | DD202377A5 (OSRAM) |
| DE (1) | DE3171931D1 (OSRAM) |
| DK (1) | DK457781A (OSRAM) |
| GR (1) | GR75828B (OSRAM) |
| HU (1) | HU189541B (OSRAM) |
| IL (1) | IL64069A (OSRAM) |
| IN (1) | IN155350B (OSRAM) |
| MX (1) | MX6917E (OSRAM) |
| MY (1) | MY8700103A (OSRAM) |
| NZ (1) | NZ198608A (OSRAM) |
| PH (1) | PH17880A (OSRAM) |
| PT (1) | PT73826B (OSRAM) |
| RO (2) | RO83968B (OSRAM) |
| TR (1) | TR21346A (OSRAM) |
| YU (1) | YU42732B (OSRAM) |
| ZW (1) | ZW24981A1 (OSRAM) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5342958A (en) * | 1970-05-15 | 1994-08-30 | Solvay Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| US5245071A (en) * | 1970-05-15 | 1993-09-14 | Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
| US4880838A (en) * | 1982-06-30 | 1989-11-14 | Rhone-Poulenc | Pesticidal 1-(4-Phenoxyphenyl)-5-Benzoyl urea compounds and process for preparation |
| CA1205483A (en) * | 1982-06-30 | 1986-06-03 | David T. Chou | Pesticidal 1-(alkyl phenoxyaryl)-3-benzoyl ureas and process for preparation |
| US4783485A (en) * | 1983-01-24 | 1988-11-08 | Duphar International Research B.V. | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| EP0131071B1 (en) * | 1983-01-24 | 1987-05-13 | Duphar International Research B.V | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| US4665097A (en) * | 1983-03-31 | 1987-05-12 | Union Carbide Corporation | Novel bicyclooxyaryl thioureas and process for preparation |
| US4873264A (en) * | 1983-05-20 | 1989-10-10 | Rhone-Poulenc Nederlands B.V. | Novel pesticidal 1-(alkyl-phenoxy-aryl)-3-benzoyl ureas and process for preparation |
| US4602021A (en) * | 1984-06-22 | 1986-07-22 | Ciba-Geigy Corporation | Phenylbenzoylureas useful as pesticides |
| ATE40111T1 (de) * | 1984-07-05 | 1989-02-15 | Duphar Int Res | Benzoylharnstoffverbindungen sowie solche enthaltende insektizide und akarizide zusammensetzungen. |
| DE3431221A1 (de) * | 1984-08-24 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Benzoylharnstoffe |
| US4638088A (en) * | 1984-11-15 | 1987-01-20 | Union Carbide Corporation | Pesticidal biphenylyloxy and biphenylylalkoxy aryl acyl urea compounds |
| US5135953A (en) * | 1984-12-28 | 1992-08-04 | Ciba-Geigy | Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals |
| DE3684445D1 (de) * | 1985-08-05 | 1992-04-23 | Mitsui Petrochemical Ind | Neue harnstoffderivate, verfahren zu ihrer herstellung und herbizide. |
| US4705554A (en) * | 1985-12-03 | 1987-11-10 | Mitsubishi Chemical Industries Limited | Benzofuranyloxyphenylurea derivative and herbicidal composition containing it as an active ingredient |
| DE3545068A1 (de) * | 1985-12-19 | 1987-06-25 | Kuka Schweissanlagen & Roboter | Getriebekopf fuer manipulatoren |
| JP2514945B2 (ja) * | 1987-02-05 | 1996-07-10 | 三井石油化学工業株式会社 | 芳香族アミン誘導体 |
| US5189183A (en) * | 1987-02-05 | 1993-02-23 | Mitsui Petrochemical Industries, Ltd. | Aromatic amine derivatives |
| US4959092A (en) * | 1987-06-03 | 1990-09-25 | Mitsubishi Kasei Corporation | Substituted phenyl (or pyridyl) urea compound and herbicidal composition containing the same as active ingredient |
| FR2686341B1 (fr) * | 1992-01-22 | 1995-05-12 | Poudres & Explosifs Ste Nale | N-pyridylcarbonyl-n'-phenylurees, procedes pour leur preparation et leur utilisation comme pesticides. |
| KR950003497B1 (ko) * | 1992-08-07 | 1995-04-13 | 재단법인 한국화학연구소 | 제초성 시클로헥산-1,3-디온 유도체와 그 제조방법 |
| EP0988289A2 (en) * | 1997-06-05 | 2000-03-29 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds, their production and use |
| US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
| IN2014MN00226A (OSRAM) * | 2011-07-05 | 2015-09-25 | Lupin Ltd | |
| SG11201601616SA (en) | 2013-09-09 | 2016-04-28 | Peloton Therapeutics Inc | Aryl ethers and uses thereof |
| US9884843B2 (en) | 2013-12-16 | 2018-02-06 | Peloton Therapeutics, Inc. | Cyclic sulfone and sulfoximine analogs and uses thereof |
| US10278942B2 (en) | 2015-03-11 | 2019-05-07 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
| US10807948B2 (en) | 2015-03-11 | 2020-10-20 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| WO2016144826A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
| WO2016145045A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating glioblastoma |
| WO2016168510A1 (en) | 2015-04-17 | 2016-10-20 | Peloton Therapeutics, Inc. | Combination therapy of a hif-2-alpha inhibitor and an immunotherapeutic agent and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3989842A (en) | 1970-05-15 | 1976-11-02 | U.S. Philips Corporation | Certain substituted benzoyl urea insecticides |
| NL160809C (nl) | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
| US3993908A (en) | 1973-06-22 | 1976-11-23 | Ervin Kaplan | System for whole body imaging and count profiling with a scintillation camera |
| DE2438747C2 (de) | 1974-08-13 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Benzoylureido-diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| DE2504983C2 (de) | 1975-02-06 | 1982-10-21 | Bayer Ag, 5090 Leverkusen | Benzoylureido-nitro-diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| US4148902A (en) | 1977-05-13 | 1979-04-10 | The Dow Chemical Company | N-[(optionally substituted phenylamino)carbonyl] pyridine carboxamides and insecticidal use thereof |
| GR73690B (OSRAM) | 1979-01-15 | 1984-04-02 | Celamerck Gmbh & Co Kg |
-
1981
- 1981-09-28 US US06/305,951 patent/US4426385A/en not_active Expired - Fee Related
- 1981-10-12 ZW ZW249/81A patent/ZW24981A1/xx unknown
- 1981-10-12 GR GR66258A patent/GR75828B/el unknown
- 1981-10-12 NZ NZ198608A patent/NZ198608A/en unknown
- 1981-10-12 AU AU76250/81A patent/AU555928B2/en not_active Ceased
- 1981-10-14 CA CA000387884A patent/CA1190553A/en not_active Expired
- 1981-10-15 DK DK457781A patent/DK457781A/da not_active Application Discontinuation
- 1981-10-15 YU YU2468/81A patent/YU42732B/xx unknown
- 1981-10-15 DE DE8181108380T patent/DE3171931D1/de not_active Expired
- 1981-10-15 BR BR8106662A patent/BR8106662A/pt unknown
- 1981-10-15 EP EP81108380A patent/EP0050321B1/en not_active Expired
- 1981-10-15 MX MX819714U patent/MX6917E/es unknown
- 1981-10-15 KR KR1019810003917A patent/KR870000369B1/ko not_active Expired
- 1981-10-15 PH PH26351A patent/PH17880A/en unknown
- 1981-10-15 AR AR287098A patent/AR231972A1/es active
- 1981-10-15 RO RO105569A patent/RO83968B/ro unknown
- 1981-10-15 IN IN1136/CAL/81A patent/IN155350B/en unknown
- 1981-10-15 HU HU812977A patent/HU189541B/hu not_active IP Right Cessation
- 1981-10-15 RO RO81113663A patent/RO88485A/ro unknown
- 1981-10-15 PT PT73826A patent/PT73826B/pt unknown
- 1981-10-16 TR TR21346A patent/TR21346A/xx unknown
- 1981-10-16 DD DD81234166A patent/DD202377A5/de unknown
- 1981-10-18 IL IL64069A patent/IL64069A/xx unknown
-
1987
- 1987-12-30 MY MY103/87U patent/MY8700103A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZW24981A1 (en) | 1982-01-06 |
| KR870000369B1 (ko) | 1987-03-06 |
| MY8700103A (en) | 1987-12-31 |
| US4426385A (en) | 1984-01-17 |
| YU42732B (en) | 1988-12-31 |
| EP0050321A3 (en) | 1982-10-13 |
| IL64069A0 (en) | 1982-01-31 |
| KR830007533A (ko) | 1983-10-21 |
| AR231972A1 (es) | 1985-04-30 |
| PH17880A (en) | 1985-01-14 |
| NZ198608A (en) | 1985-07-31 |
| AU555928B2 (en) | 1986-10-16 |
| EP0050321A2 (en) | 1982-04-28 |
| AU7625081A (en) | 1982-04-22 |
| DE3171931D1 (en) | 1985-09-26 |
| DK457781A (da) | 1982-04-17 |
| EP0050321B1 (en) | 1985-08-21 |
| RO83968A (ro) | 1984-04-12 |
| GR75828B (OSRAM) | 1984-08-02 |
| RO88485A (ro) | 1986-01-30 |
| IN155350B (OSRAM) | 1985-01-19 |
| RO83968B (ro) | 1984-05-30 |
| CA1190553A (en) | 1985-07-16 |
| YU246881A (en) | 1984-02-29 |
| TR21346A (OSRAM) | 1984-04-18 |
| PT73826A (en) | 1981-11-01 |
| IL64069A (en) | 1985-01-31 |
| BR8106662A (pt) | 1982-06-29 |
| MX6917E (es) | 1986-11-11 |
| HU189541B (en) | 1986-07-28 |
| PT73826B (en) | 1983-01-17 |
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