HU189541B - Process for producing new bicyclo-oxy-phenyl-urea derivatives - Google Patents
Process for producing new bicyclo-oxy-phenyl-urea derivatives Download PDFInfo
- Publication number
- HU189541B HU189541B HU812977A HU297781A HU189541B HU 189541 B HU189541 B HU 189541B HU 812977 A HU812977 A HU 812977A HU 297781 A HU297781 A HU 297781A HU 189541 B HU189541 B HU 189541B
- Authority
- HU
- Hungary
- Prior art keywords
- chloro
- chlorine
- naphthoxy
- active ingredient
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 239000012948 isocyanate Substances 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 48
- 229910052801 chlorine Inorganic materials 0.000 claims description 46
- 239000004480 active ingredient Substances 0.000 claims description 38
- 229910052731 fluorine Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- -1 aryl isocyanate Chemical class 0.000 claims description 31
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
- 239000011737 fluorine Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 229910052794 bromium Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002270 dispersing agent Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 3
- 239000005909 Kieselgur Substances 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000003209 petroleum derivative Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 239000004202 carbamide Substances 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 2
- WKJLDFKGXKFHFD-UHFFFAOYSA-N 2-chloro-n-[[3,5-dichloro-4-(4-chloronaphthalen-1-yl)oxyphenyl]carbamoyl]benzamide Chemical group ClC1=CC=CC=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 WKJLDFKGXKFHFD-UHFFFAOYSA-N 0.000 claims 1
- QBSJUWMQKAFHCL-UHFFFAOYSA-N 2-chloro-n-[[3,5-dichloro-4-(4-methoxynaphthalen-1-yl)oxyphenyl]carbamoyl]benzamide Chemical group C12=CC=CC=C2C(OC)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=CC=CC=C1Cl QBSJUWMQKAFHCL-UHFFFAOYSA-N 0.000 claims 1
- NFJGSLWTGOQLPO-UHFFFAOYSA-N 2-chloro-n-[[4-(4-chloronaphthalen-1-yl)oxy-3,5-dimethylphenyl]carbamoyl]benzamide Chemical group 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 1
- LTHCYIQVUYXYAJ-UHFFFAOYSA-N 2-chloro-n-[[4-(4-chloronaphthalen-1-yl)oxy-3-methylphenyl]carbamoyl]-6-fluorobenzamide Chemical group C=1C=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1Cl LTHCYIQVUYXYAJ-UHFFFAOYSA-N 0.000 claims 1
- OXRXJKZOMCROPA-UHFFFAOYSA-N 2-chloro-n-[[4-(4-chloronaphthalen-1-yl)oxy-3-methylphenyl]carbamoyl]benzamide Chemical group 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
- DHTGVBJTTJYQEE-UHFFFAOYSA-N C1=CC=C2C(=C1)C=CC(=C2OC3=C(C=C(C=C3Cl)NC(=O)NC(=O)C4=C(C=CC=C4F)F)Cl)Cl Chemical group C1=CC=C2C(=C1)C=CC(=C2OC3=C(C=C(C=C3Cl)NC(=O)NC(=O)C4=C(C=CC=C4F)F)Cl)Cl DHTGVBJTTJYQEE-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- AZPRVODHUOOOOE-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-chloronaphthalen-1-yl)oxyphenyl]carbamoyl]-2-fluorobenzamide Chemical group FC1=CC=CC=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 AZPRVODHUOOOOE-UHFFFAOYSA-N 0.000 claims 1
- MFESPQTXJWRQEB-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-methoxynaphthalen-1-yl)oxyphenyl]carbamoyl]-2,6-difluorobenzamide Chemical group C12=CC=CC=C2C(OC)=CC=C1OC(C(=C1)Cl)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F MFESPQTXJWRQEB-UHFFFAOYSA-N 0.000 claims 1
- VMFMPVPWZMPKJC-UHFFFAOYSA-N n-[[4-(4-chloronaphthalen-1-yl)oxy-3,5-dimethylphenyl]carbamoyl]-2,6-difluorobenzamide Chemical group C=1C(C)=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=C(F)C=CC=C1F VMFMPVPWZMPKJC-UHFFFAOYSA-N 0.000 claims 1
- YWNMIDHXIDLQBN-UHFFFAOYSA-N n-[[4-(4-chloronaphthalen-1-yl)oxy-3,5-dimethylphenyl]carbamoyl]-2-fluorobenzamide Chemical group C=1C(C)=C(OC=2C3=CC=CC=C3C(Cl)=CC=2)C(C)=CC=1NC(=O)NC(=O)C1=CC=CC=C1F YWNMIDHXIDLQBN-UHFFFAOYSA-N 0.000 claims 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 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 abstract description 3
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 241001301805 Epilachna Species 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241001521235 Spodoptera eridania Species 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 244000046052 Phaseolus vulgaris Species 0.000 description 7
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000008744 Brassica perviridis Nutrition 0.000 description 5
- 241000712024 Brassica rapa var. perviridis Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 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
- 241000238876 Acari Species 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical class 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
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical class [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000256248 Spodoptera Species 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 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
- 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 2
- IVKRGQOBLBLKCF-UHFFFAOYSA-N 3,5-dichloro-4-[(4-chloro-5,6,7,8-tetrahydronaphthalen-1-yl)oxy]aniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=CC=C(Cl)C2=C1CCCC2 IVKRGQOBLBLKCF-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
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical class [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 2
- YWLCKABATDVTCV-UHFFFAOYSA-N 5-chloro-8-(2,6-dimethyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC(C)=C1OC1=CC=C(Cl)C2=C1CCCC2 YWLCKABATDVTCV-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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 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
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- 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 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
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- DNLQSKIYTYJCQJ-UHFFFAOYSA-N 5-chloro-8-(2,5-dimethyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=C(C)C=C1OC1=CC=C(Cl)C2=C1CCCC2 DNLQSKIYTYJCQJ-UHFFFAOYSA-N 0.000 description 1
- LRCBXQNSOURKMD-UHFFFAOYSA-N 5-chloro-8-(2,6-dibromo-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound BrC1=CC([N+](=O)[O-])=CC(Br)=C1OC1=CC=C(Cl)C2=C1CCCC2 LRCBXQNSOURKMD-UHFFFAOYSA-N 0.000 description 1
- ZKGKTHNQAWJJOO-UHFFFAOYSA-N 5-chloro-8-(2-chloro-3,6-dimethyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=C(C)C(Cl)=C1OC1=CC=C(Cl)C2=C1CCCC2 ZKGKTHNQAWJJOO-UHFFFAOYSA-N 0.000 description 1
- IDCIJNOVKWOFLG-UHFFFAOYSA-N 5-chloro-8-(2-chloro-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 IDCIJNOVKWOFLG-UHFFFAOYSA-N 0.000 description 1
- ZDSUDOHXBRYNIV-UHFFFAOYSA-N 5-chloro-8-(2-chloro-5-methyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OC=2C=3CCCCC=3C(Cl)=CC=2)=C1Cl ZDSUDOHXBRYNIV-UHFFFAOYSA-N 0.000 description 1
- CLNKSTRRSYPETQ-UHFFFAOYSA-N 5-chloro-8-(2-methyl-4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 CLNKSTRRSYPETQ-UHFFFAOYSA-N 0.000 description 1
- RYFXATWELZSPFI-UHFFFAOYSA-N 5-chloro-8-(4-nitrophenoxy)-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C2=C1CCCC2 RYFXATWELZSPFI-UHFFFAOYSA-N 0.000 description 1
- OQVOEMRETUJKMB-UHFFFAOYSA-N 7-(2,6-dichloro-4-nitrophenoxy)-2,2-dimethyl-3h-1-benzofuran Chemical compound C=12OC(C)(C)CC2=CC=CC=1OC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl OQVOEMRETUJKMB-UHFFFAOYSA-N 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 101000834981 Homo sapiens Testis, prostate and placenta-expressed protein Proteins 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- UHSOPOQMQPDVCG-UHFFFAOYSA-N N-[[4-(5,6,7,8-tetrahydronaphthalen-1-yloxy)phenyl]carbamoyl]benzamide Chemical class C=1C=C(OC=2C=3CCCCC=3C=CC=2)C=CC=1NC(=O)NC(=O)C1=CC=CC=C1 UHSOPOQMQPDVCG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 240000004072 Panicum sumatrense Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 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
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
- 102100026164 Testis, prostate and placenta-expressed protein Human genes 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- QMHAHUAQAJVBIW-UHFFFAOYSA-N [methyl(sulfamoyl)amino]methane Chemical compound CN(C)S(N)(=O)=O QMHAHUAQAJVBIW-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical class O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003278 egg shell Anatomy 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- XAXLGISKRWIHPM-UHFFFAOYSA-N n,n-dimethyl-4-(2-methyl-4-nitrophenoxy)-5,6,7,8-tetrahydronaphthalen-1-amine Chemical compound C1=2CCCCC=2C(N(C)C)=CC=C1OC1=CC=C([N+]([O-])=O)C=C1C XAXLGISKRWIHPM-UHFFFAOYSA-N 0.000 description 1
- CDGHAPLJIMFVFS-UHFFFAOYSA-N n-[[3,5-dichloro-4-(4-chloronaphthalen-1-yl)oxyphenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=C(Cl)C2=CC=CC=C12 CDGHAPLJIMFVFS-UHFFFAOYSA-N 0.000 description 1
- GVBHRBMWXDCRHZ-UHFFFAOYSA-N n-phenylpyridine-2-carboxamide Chemical class C=1C=CC=NC=1C(=O)NC1=CC=CC=C1 GVBHRBMWXDCRHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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 |
|---|---|
| HU189541B true HU189541B (en) | 1986-07-28 |
Family
ID=26892983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU812977A HU189541B (en) | 1980-10-16 | 1981-10-15 | Process for producing new bicyclo-oxy-phenyl-urea derivatives |
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 |
| 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. |
| US5342958A (en) * | 1970-05-15 | 1994-08-30 | Solvay Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| 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 |
| EP0131071B1 (en) * | 1983-01-24 | 1987-05-13 | Duphar International Research B.V | Benzoylurea compounds, and pesticidal and pharmaceutical compositions comprising same |
| US4783485A (en) * | 1983-01-24 | 1988-11-08 | Duphar International Research B.V. | Benzoylurea compounds, and insecticidal and acaricidal 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 |
| DE3569241D1 (de) * | 1984-06-22 | 1989-05-11 | Ciba Geigy Ag | Phenyl benzoyl ureas |
| 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 |
| EP0230475B1 (en) * | 1985-08-05 | 1992-03-18 | 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 |
| US7008950B1 (en) | 1997-06-05 | 2006-03-07 | Takeda Chemical Industries, Ltd. | Benzofurans as suppressors of neurodegeneration |
| 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 |
| CN105530923B (zh) * | 2013-09-09 | 2019-07-23 | 佩洛通治疗公司 | 芳基醚及其用途 |
| WO2015095048A1 (en) | 2013-12-16 | 2015-06-25 | Peloton Therapeutics, Inc. | Cyclic sulfone and sulfoximine analogs and uses thereof |
| US10155726B2 (en) | 2015-03-11 | 2018-12-18 | Peloton Therapeutics, Inc. | Substituted pyridines and uses thereof |
| EP3267792A4 (en) | 2015-03-11 | 2018-09-26 | Peloton Therapeutics, Inc. | Compositions for use in treating pulmonary arterial hypertension |
| WO2016145045A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Compositions for use in treating glioblastoma |
| WO2016144825A1 (en) | 2015-03-11 | 2016-09-15 | Peloton Therapeutics, Inc. | Aromatic compounds and uses thereof |
| 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 |
|---|---|---|---|---|
| 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 (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 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 DE DE8181108380T patent/DE3171931D1/de not_active Expired
- 1981-10-15 IN IN1136/CAL/81A patent/IN155350B/en unknown
- 1981-10-15 PT PT73826A patent/PT73826B/pt unknown
- 1981-10-15 RO RO81113663A patent/RO88485A/ro unknown
- 1981-10-15 MX MX819714U patent/MX6917E/es unknown
- 1981-10-15 YU YU2468/81A patent/YU42732B/xx unknown
- 1981-10-15 AR AR287098A patent/AR231972A1/es active
- 1981-10-15 BR BR8106662A patent/BR8106662A/pt unknown
- 1981-10-15 DK DK457781A patent/DK457781A/da not_active Application Discontinuation
- 1981-10-15 EP EP81108380A patent/EP0050321B1/en not_active Expired
- 1981-10-15 KR KR1019810003917A patent/KR870000369B1/ko not_active Expired
- 1981-10-15 PH PH26351A patent/PH17880A/en unknown
- 1981-10-15 HU HU812977A patent/HU189541B/hu not_active IP Right Cessation
- 1981-10-15 RO RO105569A patent/RO83968B/ro 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 |
|---|---|
| AR231972A1 (es) | 1985-04-30 |
| BR8106662A (pt) | 1982-06-29 |
| KR830007533A (ko) | 1983-10-21 |
| AU555928B2 (en) | 1986-10-16 |
| EP0050321A3 (en) | 1982-10-13 |
| IL64069A (en) | 1985-01-31 |
| IN155350B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-01-19 |
| KR870000369B1 (ko) | 1987-03-06 |
| GR75828B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-02 |
| RO83968B (ro) | 1984-05-30 |
| DE3171931D1 (en) | 1985-09-26 |
| PT73826B (en) | 1983-01-17 |
| IL64069A0 (en) | 1982-01-31 |
| DK457781A (da) | 1982-04-17 |
| US4426385A (en) | 1984-01-17 |
| AU7625081A (en) | 1982-04-22 |
| MY8700103A (en) | 1987-12-31 |
| MX6917E (es) | 1986-11-11 |
| NZ198608A (en) | 1985-07-31 |
| ZW24981A1 (en) | 1982-01-06 |
| YU246881A (en) | 1984-02-29 |
| TR21346A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-04-18 |
| PH17880A (en) | 1985-01-14 |
| EP0050321A2 (en) | 1982-04-28 |
| YU42732B (en) | 1988-12-31 |
| RO83968A (ro) | 1984-04-12 |
| DD202377A5 (de) | 1983-09-14 |
| CA1190553A (en) | 1985-07-16 |
| PT73826A (en) | 1981-11-01 |
| RO88485A (ro) | 1986-01-30 |
| EP0050321B1 (en) | 1985-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |