NZ198608A - Phenyl derivatives of benzoyl urea - Google Patents
Phenyl derivatives of benzoyl ureaInfo
- Publication number
- NZ198608A NZ198608A NZ198608A NZ19860881A NZ198608A NZ 198608 A NZ198608 A NZ 198608A NZ 198608 A NZ198608 A NZ 198608A NZ 19860881 A NZ19860881 A NZ 19860881A NZ 198608 A NZ198608 A NZ 198608A
- Authority
- NZ
- New Zealand
- Prior art keywords
- chloro
- composition
- naphthoxy
- urea
- compound
- Prior art date
Links
- 239000004202 carbamide Substances 0.000 title claims description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 claims description 104
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 43
- 241000238631 Hexapoda Species 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- -1 nitro, cyano, amino, formamido Chemical group 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052727 yttrium Inorganic materials 0.000 claims description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- AAMVULSTDCRQRW-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-(4-chloronaphthalen-1-yl)oxy-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC=1C(Cl)=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl AAMVULSTDCRQRW-UHFFFAOYSA-N 0.000 claims description 2
- NFJGSLWTGOQLPO-UHFFFAOYSA-N 2-chloro-n-[[4-(4-chloronaphthalen-1-yl)oxy-3,5-dimethylphenyl]carbamoyl]benzamide Chemical compound C=1C(C)=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl NFJGSLWTGOQLPO-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 125000003118 aryl 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
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims 29
- 231100000518 lethal Toxicity 0.000 claims 19
- 230000001665 lethal effect Effects 0.000 claims 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- VYFLODDTFDNXTB-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-2,5-dimethylphenyl]carbamoyl]benzamide Chemical compound CC=1C(Cl)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl VYFLODDTFDNXTB-UHFFFAOYSA-N 0.000 claims 1
- OXRXJKZOMCROPA-UHFFFAOYSA-N 2-chloro-n-[[4-(4-chloronaphthalen-1-yl)oxy-3-methylphenyl]carbamoyl]benzamide Chemical compound C=1C=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl OXRXJKZOMCROPA-UHFFFAOYSA-N 0.000 claims 1
- 235000006629 Prosopis spicigera Nutrition 0.000 claims 1
- 240000000037 Prosopis spicigera Species 0.000 claims 1
- XAEXSWVTEJHRMH-UHFFFAOYSA-N chloropyrilene Chemical group C=1C=CC=NC=1N(CCN(C)C)CC1=CC=C(Cl)S1 XAEXSWVTEJHRMH-UHFFFAOYSA-N 0.000 claims 1
- 229950005434 chloropyrilene Drugs 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 description 88
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 230000000704 physical effect Effects 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 230000000749 insecticidal effect Effects 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000003672 ureas Chemical class 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 241001477931 Mythimna unipuncta Species 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 150000008047 benzoylureas Chemical class 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 241000462639 Epilachna varivestis Species 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000004611 spectroscopical analysis Methods 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
- 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 3
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 3
- RTYDKESMWNGDJB-UHFFFAOYSA-N 2-chloro-n-[[4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3,5-dimethylphenyl]carbamoyl]benzamide Chemical compound C=1C(C)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1Cl RTYDKESMWNGDJB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 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
- SSABAIUCBWJKMS-UHFFFAOYSA-N 1-(2-methyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=CC2=CC=CC=C12 SSABAIUCBWJKMS-UHFFFAOYSA-N 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- LUUUTJPAZKRAKM-UHFFFAOYSA-N 2-chloro-n-[[3-chloro-4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-5-methylphenyl]carbamoyl]-6-fluorobenzamide Chemical compound C=1C(Cl)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1Cl LUUUTJPAZKRAKM-UHFFFAOYSA-N 0.000 description 2
- AZPLDWUVJDZSRT-UHFFFAOYSA-N 3-chloro-4-(4-chloronaphthalen-1-yl)oxy-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 AZPLDWUVJDZSRT-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
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- OQSDXHCTGRTHMF-UHFFFAOYSA-N 4-(4-methoxynaphthalen-1-yl)oxy-3-methylaniline Chemical compound C12=CC=CC=C2C(OC)=CC=C1OC1=CC=C(N)C=C1C OQSDXHCTGRTHMF-UHFFFAOYSA-N 0.000 description 2
- BPMIFDLPVWMYNF-UHFFFAOYSA-N 7-(2-chloro-4-nitrophenoxy)-2,2-dimethyl-3h-1-benzofuran Chemical compound C=12OC(C)(C)CC2=CC=CC=1OC1=CC=C([N+]([O-])=O)C=C1Cl BPMIFDLPVWMYNF-UHFFFAOYSA-N 0.000 description 2
- 235000008744 Brassica perviridis Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 101000834981 Homo sapiens Testis, prostate and placenta-expressed protein Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 2
- 102100026164 Testis, prostate and placenta-expressed protein Human genes 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229940054066 benzamide antipsychotics Drugs 0.000 description 2
- 150000003936 benzamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- RRKCMGNZYOFYEA-UHFFFAOYSA-N n-[(4-naphthalen-2-yloxyphenyl)carbamoyl]benzamide Chemical compound C=1C=C(OC=2C=C3C=CC=CC3=CC=2)C=CC=1NC(=O)NC(=O)C1=CC=CC=C1 RRKCMGNZYOFYEA-UHFFFAOYSA-N 0.000 description 2
- FPUDCXCDKHUUCU-UHFFFAOYSA-N n-[[3-chloro-4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-5-methylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=1C(Cl)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F FPUDCXCDKHUUCU-UHFFFAOYSA-N 0.000 description 2
- BHFHZBRZXNSUHG-UHFFFAOYSA-N n-[[4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]-3,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C=1C(C)=C(OC=2C=3CCCCC=3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F BHFHZBRZXNSUHG-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- 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 1
- BSFHJMGROOFSRA-UHFFFAOYSA-N 1,4-dimethyl-2-nitrobenzene Chemical compound CC1=CC=C(C)C([N+]([O-])=O)=C1 BSFHJMGROOFSRA-UHFFFAOYSA-N 0.000 description 1
- CAKUTMRWSRMBOD-UHFFFAOYSA-N 1,6-dibromo-2-(2-chloro-4-nitrophenoxy)naphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(C=C(Br)C=C2)C2=C1Br CAKUTMRWSRMBOD-UHFFFAOYSA-N 0.000 description 1
- KDZHXLKVGPQVPZ-UHFFFAOYSA-N 1,6-dibromo-2-(2-methyl-4-nitrophenoxy)naphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(C=C(Br)C=C2)C2=C1Br KDZHXLKVGPQVPZ-UHFFFAOYSA-N 0.000 description 1
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- ZHOUOKMBHSWCST-UHFFFAOYSA-N n-[[4-(4-chloronaphthalen-1-yl)oxy-3-(trifluoromethyl)phenyl]carbamoyl]-2,4-dimethoxypyridine-3-carboxamide Chemical compound COC1=CC=NC(OC)=C1C(=O)NC(=O)NC(C=C1C(F)(F)F)=CC=C1OC1=CC=C(Cl)C2=CC=CC=C12 ZHOUOKMBHSWCST-UHFFFAOYSA-N 0.000 description 1
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- XTVPNPBPUQIEOO-UHFFFAOYSA-N n-[[4-[[4-(dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]-3,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound C1=2CCCCC=2C(N(C)C)=CC=C1OC(C(=C1)C)=C(C)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F XTVPNPBPUQIEOO-UHFFFAOYSA-N 0.000 description 1
- PPOSFCNLNROPTA-UHFFFAOYSA-N n-carbamoyl-2,6-difluorobenzamide Chemical compound NC(=O)NC(=O)C1=C(F)C=CC=C1F PPOSFCNLNROPTA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
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- 230000017448 oviposition Effects 0.000 description 1
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- 239000012312 sodium hydride Substances 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)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (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 |
|---|---|
| NZ198608A true NZ198608A (en) | 1985-07-31 |
Family
ID=26892983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ198608A NZ198608A (en) | 1980-10-16 | 1981-10-12 | Phenyl derivatives of benzoyl urea |
Country Status (23)
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5245071A (en) * | 1970-05-15 | 1993-09-14 | Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| US5342958A (en) * | 1970-05-15 | 1994-08-30 | Solvay 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 |
| DE3567642D1 (en) * | 1984-07-05 | 1989-02-23 | Duphar Int Res | Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same |
| 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 |
| WO1987000840A1 (en) * | 1985-08-05 | 1987-02-12 | Mitsui Petrochemical Industries, Ltd. | Novel urea derivatives, processes for production thereof and herbicide |
| 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 |
| US5189183A (en) * | 1987-02-05 | 1993-02-23 | Mitsui Petrochemical Industries, Ltd. | Aromatic amine derivatives |
| 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 |
| 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 |
| CA2291026A1 (en) | 1997-06-05 | 1998-12-10 | Takeda Chemical Industries, Ltd. | Heterocyclic compounds, their production and use |
| US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
| WO2013005168A2 (en) * | 2011-07-05 | 2013-01-10 | Lupin Limited | Cannabinoid receptor modulators |
| CA2919397C (en) | 2013-09-09 | 2021-05-18 | Peloton Therapeutics, Inc. | Aryl ethers as hif-2.alpha. inhibitors for the treatment of cancer |
| ES2737148T3 (es) | 2013-12-16 | 2020-01-10 | Peloton Therapeutics Inc | Análogos de sulfona y sulfoximina cíclicos y usos de los mismos |
| US10512626B2 (en) | 2015-03-11 | 2019-12-24 | Peloton Therapeautics, Inc. | Compositions for use in treating glioblastoma |
| EP3268362B1 (en) | 2015-03-11 | 2021-10-20 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
| US10807948B2 (en) | 2015-03-11 | 2020-10-20 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| EP3267792A4 (en) | 2015-03-11 | 2018-09-26 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
| US10335388B2 (en) | 2015-04-17 | 2019-07-02 | 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 |
|---|---|---|---|---|
| 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. |
| US3989842A (en) | 1970-05-15 | 1976-11-02 | U.S. Philips Corporation | Certain substituted benzoyl urea insecticides |
| 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 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 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 NZ NZ198608A patent/NZ198608A/en unknown
- 1981-10-12 GR GR66258A patent/GR75828B/el 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 EP EP81108380A patent/EP0050321B1/en not_active Expired
- 1981-10-15 HU HU812977A patent/HU189541B/hu not_active IP Right Cessation
- 1981-10-15 MX MX819714U patent/MX6917E/es unknown
- 1981-10-15 DE DE8181108380T patent/DE3171931D1/de not_active Expired
- 1981-10-15 DK DK457781A patent/DK457781A/da not_active Application Discontinuation
- 1981-10-15 RO RO105569A patent/RO83968B/ro unknown
- 1981-10-15 RO RO81113663A patent/RO88485A/ro unknown
- 1981-10-15 IN IN1136/CAL/81A patent/IN155350B/en unknown
- 1981-10-15 BR BR8106662A patent/BR8106662A/pt unknown
- 1981-10-15 PT PT73826A patent/PT73826B/pt unknown
- 1981-10-15 AR AR287098A patent/AR231972A1/es active
- 1981-10-15 KR KR1019810003917A patent/KR870000369B1/ko not_active Expired
- 1981-10-15 PH PH26351A patent/PH17880A/en unknown
- 1981-10-15 YU YU2468/81A patent/YU42732B/xx unknown
- 1981-10-16 DD DD81234166A patent/DD202377A5/de unknown
- 1981-10-16 TR TR21346A patent/TR21346A/xx 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 |
|---|---|
| DE3171931D1 (en) | 1985-09-26 |
| HU189541B (en) | 1986-07-28 |
| YU246881A (en) | 1984-02-29 |
| CA1190553A (en) | 1985-07-16 |
| KR870000369B1 (ko) | 1987-03-06 |
| MX6917E (es) | 1986-11-11 |
| EP0050321B1 (en) | 1985-08-21 |
| RO83968B (ro) | 1984-05-30 |
| AU7625081A (en) | 1982-04-22 |
| PH17880A (en) | 1985-01-14 |
| GR75828B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-02 |
| US4426385A (en) | 1984-01-17 |
| ZW24981A1 (en) | 1982-01-06 |
| DD202377A5 (de) | 1983-09-14 |
| IN155350B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-01-19 |
| TR21346A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-04-18 |
| RO83968A (ro) | 1984-04-12 |
| AU555928B2 (en) | 1986-10-16 |
| PT73826A (en) | 1981-11-01 |
| IL64069A0 (en) | 1982-01-31 |
| RO88485A (ro) | 1986-01-30 |
| AR231972A1 (es) | 1985-04-30 |
| EP0050321A3 (en) | 1982-10-13 |
| YU42732B (en) | 1988-12-31 |
| PT73826B (en) | 1983-01-17 |
| IL64069A (en) | 1985-01-31 |
| BR8106662A (pt) | 1982-06-29 |
| EP0050321A2 (en) | 1982-04-28 |
| DK457781A (da) | 1982-04-17 |
| MY8700103A (en) | 1987-12-31 |
| KR830007533A (ko) | 1983-10-21 |
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