DD153836A5 - Verfahren zur herstellung von neuen imidazolderivaten - Google Patents
Verfahren zur herstellung von neuen imidazolderivaten Download PDFInfo
- Publication number
- DD153836A5 DD153836A5 DD79223823A DD22382379A DD153836A5 DD 153836 A5 DD153836 A5 DD 153836A5 DD 79223823 A DD79223823 A DD 79223823A DD 22382379 A DD22382379 A DD 22382379A DD 153836 A5 DD153836 A5 DD 153836A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- compounds
- compound
- dicarboxamide
- dimethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- -1 alkali metal salt Chemical class 0.000 claims abstract description 15
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 244000299507 Gossypium hirsutum Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- NNWAARLSYSBVPB-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxamide Chemical compound NC(=O)C=1N=CNC=1C(N)=O NNWAARLSYSBVPB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QRIUCMULMILWJR-UHFFFAOYSA-N 1,2-dichloro-4-(dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=C(Cl)C(Cl)=C1 QRIUCMULMILWJR-UHFFFAOYSA-N 0.000 description 2
- UTYRZXNEFUYFCJ-UHFFFAOYSA-N 3,4-dibromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1Br UTYRZXNEFUYFCJ-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 240000006122 Chenopodium album Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 244000064622 Physalis edulis Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UHUMVLOMJGXNDW-UHFFFAOYSA-N 1,2-dibromo-4-(dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=C(Br)C(Br)=C1 UHUMVLOMJGXNDW-UHFFFAOYSA-N 0.000 description 1
- DOIFAFXAVXAEDA-UHFFFAOYSA-N 1,2-dichloro-4-(diethoxymethyl)benzene Chemical compound CCOC(OCC)C1=CC=C(Cl)C(Cl)=C1 DOIFAFXAVXAEDA-UHFFFAOYSA-N 0.000 description 1
- DCLMJYZEOSDVCL-UHFFFAOYSA-N 1-(chloromethyl)-4-ethoxybenzene Chemical compound CCOC1=CC=C(CCl)C=C1 DCLMJYZEOSDVCL-UHFFFAOYSA-N 0.000 description 1
- MRXDJZBMOMNNQJ-UHFFFAOYSA-N 1-(dimethoxymethyl)-2-(trifluoromethyl)benzene Chemical compound COC(C1=C(C=CC=C1)C(F)(F)F)OC MRXDJZBMOMNNQJ-UHFFFAOYSA-N 0.000 description 1
- AJXDWKRBWUECAG-UHFFFAOYSA-N 1-(dimethoxymethyl)-3-(trifluoromethyl)benzene Chemical compound COC(OC)C1=CC=CC(C(F)(F)F)=C1 AJXDWKRBWUECAG-UHFFFAOYSA-N 0.000 description 1
- BPLJLDNVDOXXGA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-(trifluoromethyl)benzene Chemical compound COC(OC)C1=CC=C(C(F)(F)F)C=C1 BPLJLDNVDOXXGA-UHFFFAOYSA-N 0.000 description 1
- WADFWGQKFNIIJI-UHFFFAOYSA-N 1-[chloro(methoxy)methyl]-4-(trifluoromethyl)benzene Chemical compound COC(Cl)C1=CC=C(C(F)(F)F)C=C1 WADFWGQKFNIIJI-UHFFFAOYSA-N 0.000 description 1
- RQDKAHBDYWLOFS-UHFFFAOYSA-N 1-chloro-3-(dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC(Cl)=C1 RQDKAHBDYWLOFS-UHFFFAOYSA-N 0.000 description 1
- YRNBYTFFWMWTGG-UHFFFAOYSA-N 1-chloro-4-(dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=C(Cl)C=C1 YRNBYTFFWMWTGG-UHFFFAOYSA-N 0.000 description 1
- ZEVWQFWTGHFIDH-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxylic acid Chemical compound OC(=O)C=1N=CNC=1C(O)=O ZEVWQFWTGHFIDH-UHFFFAOYSA-N 0.000 description 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- CASRSOJWLARCRX-UHFFFAOYSA-N 3,5-dichlorobenzaldehyde Chemical compound ClC1=CC(Cl)=CC(C=O)=C1 CASRSOJWLARCRX-UHFFFAOYSA-N 0.000 description 1
- NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 description 1
- SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
- BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
- UWRGQGVLSLNMLG-UHFFFAOYSA-N 4-chloro-2-(chloromethyl)-1-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1CCl UWRGQGVLSLNMLG-UHFFFAOYSA-N 0.000 description 1
- FDMDLNWXKUUKOU-UHFFFAOYSA-N 4-n,5-n-dimethyl-1h-imidazole-4,5-dicarboxamide Chemical compound CNC(=O)C=1N=CNC=1C(=O)NC FDMDLNWXKUUKOU-UHFFFAOYSA-N 0.000 description 1
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- 241001073385 Acanthospermum Species 0.000 description 1
- 241001073386 Acanthospermum hispidum Species 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 241000872049 Amsinckia intermedia Species 0.000 description 1
- 244000204909 Anoda cristata Species 0.000 description 1
- 241000602336 Anthemis arvensis Species 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000010662 Bidens pilosa Nutrition 0.000 description 1
- 244000104272 Bidens pilosa Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241001479535 Brillantaisia lamium Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000011498 Chenopodium album var missouriense Nutrition 0.000 description 1
- 235000013328 Chenopodium album var. album Nutrition 0.000 description 1
- 235000014052 Chenopodium album var. microphyllum Nutrition 0.000 description 1
- 235000014050 Chenopodium album var. stevensii Nutrition 0.000 description 1
- 235000013012 Chenopodium album var. striatum Nutrition 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 244000144786 Chrysanthemum segetum Species 0.000 description 1
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- 240000008853 Datura stramonium Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241001508646 Galeopsis tetrahit Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 241000207890 Ipomoea purpurea Species 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 235000009193 Lamium purpureum Nutrition 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000007846 Papaver rhoeas Nutrition 0.000 description 1
- 240000004674 Papaver rhoeas Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 235000002834 Sida rhombifolia Nutrition 0.000 description 1
- 240000003194 Sida rhombifolia Species 0.000 description 1
- 240000006410 Sida spinosa Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 240000003829 Sorghum propinquum Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 240000001261 Urtica urens Species 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000990144 Veronica persica Species 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- 244000090207 Vigna sesquipedalis Species 0.000 description 1
- 235000005072 Vigna sesquipedalis Nutrition 0.000 description 1
- 244000067505 Xanthium strumarium Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000021278 navy bean Nutrition 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7834671 | 1978-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD153836A5 true DD153836A5 (de) | 1982-02-03 |
Family
ID=10499286
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79223823A DD153836A5 (de) | 1978-08-25 | 1979-08-22 | Verfahren zur herstellung von neuen imidazolderivaten |
| DD79215123A DD145691A5 (de) | 1978-08-25 | 1979-08-22 | Herbicide zusammensetzung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79215123A DD145691A5 (de) | 1978-08-25 | 1979-08-22 | Herbicide zusammensetzung |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4246021A (enExample) |
| JP (1) | JPS5531097A (enExample) |
| KR (1) | KR830001244A (enExample) |
| AU (1) | AU5015679A (enExample) |
| BE (1) | BE878429A (enExample) |
| BR (1) | BR7905397A (enExample) |
| CU (1) | CU35128A (enExample) |
| DD (2) | DD153836A5 (enExample) |
| DE (1) | DE2933977A1 (enExample) |
| DK (1) | DK350779A (enExample) |
| ES (1) | ES483557A1 (enExample) |
| FR (1) | FR2434157A1 (enExample) |
| GR (1) | GR69725B (enExample) |
| IL (1) | IL58092A0 (enExample) |
| IT (1) | IT1207229B (enExample) |
| LU (1) | LU81624A1 (enExample) |
| MA (1) | MA18571A1 (enExample) |
| NL (1) | NL7906351A (enExample) |
| OA (1) | OA06327A (enExample) |
| PL (1) | PL217892A1 (enExample) |
| PT (1) | PT70099A (enExample) |
| SE (1) | SE7907014L (enExample) |
| ZA (1) | ZA794429B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8575359B2 (en) * | 2006-04-04 | 2013-11-05 | The Regents Of The University Of California | Acid-sensitive linkers for drug delivery |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE569663A (enExample) * | ||||
| US3336326A (en) * | 1964-04-16 | 1967-08-15 | Janssen Pharmaceutica Nv | Novel imidazole carboxamides |
| FR1585257A (enExample) * | 1967-08-31 | 1970-01-16 | ||
| JPS5320990B2 (enExample) * | 1973-02-26 | 1978-06-29 | ||
| GB1417363A (en) * | 1973-03-29 | 1975-12-10 | Nippon Soda Co | Process for the production of 4,5-imidazoledicarboxyamide |
| GB1599032A (en) * | 1977-03-04 | 1981-09-30 | May & Baker Ltd | Imidazole derivatives having herbicidal activity |
| FR2382443A1 (fr) * | 1978-03-02 | 1978-09-29 | May Et Baker | Derives herbicides de benzylimidazoles |
-
1979
- 1979-08-21 IT IT7925225A patent/IT1207229B/it active
- 1979-08-22 SE SE7907014A patent/SE7907014L/xx unknown
- 1979-08-22 BR BR7905397A patent/BR7905397A/pt unknown
- 1979-08-22 PT PT70099A patent/PT70099A/pt unknown
- 1979-08-22 US US06/068,681 patent/US4246021A/en not_active Expired - Lifetime
- 1979-08-22 JP JP10705679A patent/JPS5531097A/ja active Pending
- 1979-08-22 AU AU50156/79A patent/AU5015679A/en not_active Abandoned
- 1979-08-22 NL NL7906351A patent/NL7906351A/nl not_active Application Discontinuation
- 1979-08-22 DE DE19792933977 patent/DE2933977A1/de not_active Withdrawn
- 1979-08-22 ZA ZA00794429A patent/ZA794429B/xx unknown
- 1979-08-22 DD DD79223823A patent/DD153836A5/de unknown
- 1979-08-22 DD DD79215123A patent/DD145691A5/de unknown
- 1979-08-22 DK DK350779A patent/DK350779A/da unknown
- 1979-08-22 PL PL21789279A patent/PL217892A1/xx unknown
- 1979-08-22 IL IL58092A patent/IL58092A0/xx unknown
- 1979-08-22 ES ES483557A patent/ES483557A1/es not_active Expired
- 1979-08-23 MA MA18770A patent/MA18571A1/fr unknown
- 1979-08-23 LU LU81624A patent/LU81624A1/fr unknown
- 1979-08-24 FR FR7921959A patent/FR2434157A1/fr not_active Withdrawn
- 1979-08-24 OA OA56886A patent/OA06327A/xx unknown
- 1979-08-24 CU CU7935128A patent/CU35128A/es unknown
- 1979-08-24 BE BE0/196884A patent/BE878429A/fr unknown
- 1979-08-25 KR KR1019790002879A patent/KR830001244A/ko not_active Ceased
-
1980
- 1980-08-13 GR GR59881A patent/GR69725B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK350779A (da) | 1980-02-26 |
| DE2933977A1 (de) | 1980-03-13 |
| DD145691A5 (de) | 1981-01-07 |
| ES483557A1 (es) | 1980-04-16 |
| CU35128A (en) | 1981-12-04 |
| PT70099A (en) | 1979-09-01 |
| BE878429A (fr) | 1980-02-25 |
| ZA794429B (en) | 1980-08-27 |
| IT7925225A0 (it) | 1979-08-21 |
| AU5015679A (en) | 1980-02-28 |
| LU81624A1 (fr) | 1981-03-24 |
| JPS5531097A (en) | 1980-03-05 |
| NL7906351A (nl) | 1980-02-27 |
| OA06327A (fr) | 1981-06-30 |
| FR2434157A1 (fr) | 1980-03-21 |
| US4246021A (en) | 1981-01-20 |
| IT1207229B (it) | 1989-05-17 |
| KR830001244A (ko) | 1983-04-29 |
| SE7907014L (sv) | 1980-02-26 |
| IL58092A0 (en) | 1979-12-30 |
| PL217892A1 (enExample) | 1980-08-11 |
| GR69725B (enExample) | 1982-07-09 |
| BR7905397A (pt) | 1980-05-20 |
| MA18571A1 (fr) | 1980-04-01 |
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