EP0000373B1 - Imidazolcarbonsäuren und deren Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Pflanzenwachstumsregulierung bzw. zum Pflanzenschutz - Google Patents
Imidazolcarbonsäuren und deren Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Pflanzenwachstumsregulierung bzw. zum Pflanzenschutz Download PDFInfo
- Publication number
- EP0000373B1 EP0000373B1 EP78100314A EP78100314A EP0000373B1 EP 0000373 B1 EP0000373 B1 EP 0000373B1 EP 78100314 A EP78100314 A EP 78100314A EP 78100314 A EP78100314 A EP 78100314A EP 0000373 B1 EP0000373 B1 EP 0000373B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- compound
- benzhydryl
- imidazole
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 10
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical class OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 title claims 2
- 239000011814 protection agent Substances 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 230000008635 plant growth Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 61
- -1 cyano, phenyl Chemical group 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000003931 anilides Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000007970 thio esters Chemical class 0.000 claims description 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000006477 desulfuration reaction Methods 0.000 claims description 3
- 230000023556 desulfurization Effects 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical class SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 150000003378 silver Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000007031 hydroxymethylation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000005648 plant growth regulator Substances 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 description 42
- 230000008018 melting Effects 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YAFNMRRNLCZOEL-UHFFFAOYSA-N methyl 3-benzhydrylimidazole-4-carboxylate Chemical compound COC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YAFNMRRNLCZOEL-UHFFFAOYSA-N 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- HDQHJQBNQMYPTR-UHFFFAOYSA-N methyl 3-benzhydryl-2-sulfanylidene-1h-imidazole-4-carboxylate Chemical compound COC(=O)C1=CNC(=S)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 HDQHJQBNQMYPTR-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 9
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000003630 growth substance Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- GFKDNUWSCWFASZ-UHFFFAOYSA-N 3-benzhydrylimidazole-4-carboxylic acid Chemical compound OC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GFKDNUWSCWFASZ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- PWOOTQHFSITPQC-UHFFFAOYSA-N dimethyl 3-benzhydryl-2-sulfanylidene-1h-imidazole-4,5-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)NC(=S)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 PWOOTQHFSITPQC-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YIXIBLSSCYRKQG-UHFFFAOYSA-M [Na+].C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C=NC=C1C(=O)[O-] Chemical compound [Na+].C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C=NC=C1C(=O)[O-] YIXIBLSSCYRKQG-UHFFFAOYSA-M 0.000 description 4
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 4
- QZEGJXWBYBPSCN-UHFFFAOYSA-N benzyl 3-benzhydrylimidazole-4-carboxylate Chemical compound C=1N=CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 QZEGJXWBYBPSCN-UHFFFAOYSA-N 0.000 description 4
- QNUJCHFYRKTQNN-UHFFFAOYSA-N butyl 3-benzhydrylimidazole-4-carboxylate Chemical compound CCCCOC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 QNUJCHFYRKTQNN-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- KRCZPXUHOPWKJG-UHFFFAOYSA-N dimethyl 1-benzhydrylimidazole-4,5-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)N=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 KRCZPXUHOPWKJG-UHFFFAOYSA-N 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WYBFILQJNCJXKI-UHFFFAOYSA-N 3-benzhydryl-2-sulfanylidene-1h-imidazole-4-carboxylic acid Chemical compound OC(=O)C1=CNC(=S)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 WYBFILQJNCJXKI-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000003032 phytopathogenic effect Effects 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- GJGLZEWXTIUIBR-UHFFFAOYSA-N propyl 3-benzhydrylimidazole-4-carboxylate Chemical compound CCCOC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GJGLZEWXTIUIBR-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- MMHYHJKQSYMAQY-UHFFFAOYSA-N (3-benzhydryl-2-sulfanylidene-1h-imidazol-4-yl)-pyrrolidin-1-ylmethanone Chemical compound C=1NC(=S)N(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1C(=O)N1CCCC1 MMHYHJKQSYMAQY-UHFFFAOYSA-N 0.000 description 2
- VUUHUBXXCBRGQG-UHFFFAOYSA-N (3-benzhydrylimidazol-4-yl)-pyrrolidin-1-ylmethanone Chemical compound C=1N=CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1C(=O)N1CCCC1 VUUHUBXXCBRGQG-UHFFFAOYSA-N 0.000 description 2
- 0 *c1cnc[n]1 Chemical compound *c1cnc[n]1 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RVIRRVZNILOIDS-UHFFFAOYSA-N 1-(3-benzhydrylimidazol-4-yl)ethanethione Chemical compound CC(=S)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 RVIRRVZNILOIDS-UHFFFAOYSA-N 0.000 description 2
- VLDZKISIMOJIIB-UHFFFAOYSA-N 1-benzhydrylimidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 VLDZKISIMOJIIB-UHFFFAOYSA-N 0.000 description 2
- HMBGOZIBJJKYCN-UHFFFAOYSA-N 1-benzhydrylimidazole-4,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C(=O)O)N=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HMBGOZIBJJKYCN-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- UIKMGAYCFAVIOA-UHFFFAOYSA-N 1-chloro-3-dimethylphosphorylpropane Chemical compound CP(C)(=O)CCCCl UIKMGAYCFAVIOA-UHFFFAOYSA-N 0.000 description 2
- BLJQGZXRECZHOS-UHFFFAOYSA-N 2-benzhydryl-1h-imidazole Chemical class C1=CNC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 BLJQGZXRECZHOS-UHFFFAOYSA-N 0.000 description 2
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 2
- PZCVHZZTXONODG-UHFFFAOYSA-N 3-benzhydryl-2-sulfanylidene-1h-imidazole-4-carbohydrazide Chemical compound NNC(=O)C1=CNC(=S)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 PZCVHZZTXONODG-UHFFFAOYSA-N 0.000 description 2
- PFZGCEYOJBOPQY-UHFFFAOYSA-N 3-benzhydryl-2-sulfanylidene-1h-imidazole-4-carboxamide Chemical compound NC(=O)C1=CNC(=S)N1C(C=1C=CC=CC=1)C1=CC=CC=C1 PFZGCEYOJBOPQY-UHFFFAOYSA-N 0.000 description 2
- FQKKHVHOIAPAAJ-UHFFFAOYSA-N 3-benzhydryl-n',n'-dimethylimidazole-4-carbohydrazide Chemical compound CN(C)NC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 FQKKHVHOIAPAAJ-UHFFFAOYSA-N 0.000 description 2
- USNWIWDBVKHOST-UHFFFAOYSA-N 3-benzhydryl-n'-methylimidazole-4-carbohydrazide Chemical compound CNNC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 USNWIWDBVKHOST-UHFFFAOYSA-N 0.000 description 2
- MCRGNOWREZEHBA-UHFFFAOYSA-N 3-benzhydrylimidazole-4-carbohydrazide Chemical compound NNC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 MCRGNOWREZEHBA-UHFFFAOYSA-N 0.000 description 2
- HSCITHKSTWXZFP-UHFFFAOYSA-N 3-benzhydrylimidazole-4-carboxamide Chemical compound NC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 HSCITHKSTWXZFP-UHFFFAOYSA-N 0.000 description 2
- FGKZAEXREUNCBE-UHFFFAOYSA-N 3-dimethylphosphorylpropyl 3-benzhydrylimidazole-4-carboxylate Chemical compound CP(C)(=O)CCCOC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 FGKZAEXREUNCBE-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- BCEIUDAMUFAQMG-UHFFFAOYSA-M CC(C)(C)O[Cr](O)(=O)=O Chemical compound CC(C)(C)O[Cr](O)(=O)=O BCEIUDAMUFAQMG-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229930182764 Polyoxin Natural products 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
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- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 2
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- CBQMVTGJYSHIRG-UHFFFAOYSA-N methyl 1-acetylimidazole-4-carboxylate Chemical compound COC(=O)C1=CN(C(C)=O)C=N1 CBQMVTGJYSHIRG-UHFFFAOYSA-N 0.000 description 1
- RCWZJJKWHUJFTE-UHFFFAOYSA-N methyl 2-amino-3-oxo-4,4-diphenylbutanoate Chemical compound C=1C=CC=CC=1C(C(=O)C(N)C(=O)OC)C1=CC=CC=C1 RCWZJJKWHUJFTE-UHFFFAOYSA-N 0.000 description 1
- WSOZJHKFURWKEN-UHFFFAOYSA-N methyl 3-benzhydrylimidazole-4-carboxylate;nitric acid Chemical compound O[N+]([O-])=O.COC(=O)C1=CN=CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 WSOZJHKFURWKEN-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- FFACJJSUQMXDRE-UHFFFAOYSA-N phenyl 3-methylbut-2-enoate Chemical compound CC(C)=CC(=O)OC1=CC=CC=C1 FFACJJSUQMXDRE-UHFFFAOYSA-N 0.000 description 1
- 239000012165 plant wax Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
Definitions
- DE-OS 2 130 673 discloses benzhydryl imidazole derivatives with alkyl substitution in the imidazole ring.
- 1-benzyl- and 1-tetrahydronaphthyl-imidazole- (5) -carboxylic acids and their esters have already been described (J. Med. Chem. 15, 336-337 (1972)).
- Benzhydryl-imidazole derivatives with a carboxyl function in the imidazole radical are not yet known.
- compounds of the formula I which contain hydrogen or a carbalkoxy group in the 4-position of the imidazole ring and an —SH group in the 2-position.
- the latter can be dehydrated in a known manner, for example by means of iodine, oxygen, hydrogen peroxide or sulfuryl chloride, disulfides of the formula III being obtained.
- the SH group can also be eliminated from the compounds obtained in the first stage by desulfurization, for example by 15 percent nitric acid at 30 to 35 ° C. or nickel at 50-100 ° C.
- the desulfurized compounds can then be halogenated or hydroxymethylated in the 2-position in the usual way.
- the hydroxymethyl group can be introduced, for example, by using methanolic or aqueous formaldehyde solution at elevated temperature, preferably 130 to 140 ° C. in the pressure vessel.
- the group -CO-Rg serves as a protective group, which prevents a double reaction on both nitrogen atoms of the imidazole ring.
- the starting materials of the formula V can be obtained by acylation of compounds of the formula VIII on nitrogen atom 1.
- the reaction of the compounds of the formula V with those of the formula VI results in a quaternization on the nitrogen atom 3.
- X generally represents a group which enables the quaternization of the imidazole ring; as such halogen (CI, Br) or an alkyl or arylsulfonyl group (mesyl, tosyl) is preferred.
- esters can be saponified to free acids or their salts in a known manner.
- Free acids such as those formed according to a) to f) by saponification of ester groups or according to g) by saponification of cyano groups, can furthermore, optionally via the acid chlorides, into other esters, thiolesters, amides, anilides or hydrazides of the formula - CO-R to be transferred. If two ester groups are present, one of them can be saponified and decarboxylated.
- the nitrate was suspended in 100 ml of chloroform. After adding about 60 ml of a 1N sodium hydroxide solution, the entire nitrate went into solution. 17.8 g (61% of theory) of 1-benzhydryl-5-methoxycarbonyl-imidazole could be isolated from the chloroform solution.
- the compounds according to the invention can be used in many ways as plant treatment agents in agriculture and horticulture. They are effective growth regulators, herbicides and fungicides. They can also be used to control moss, phytopathogenic bacteria and as antifungals
- the invention therefore also relates to agents for use in agriculture and horticulture and as antifungals, plant growth-regulating and herbicidal agents and agents for combating fungi and phytopathogenic bacteria.
- the active compounds according to the invention are converted, in a manner known per se, alone or in combination with other active compounds or nutrients into the customary formulations, such as powders, dusts, pastes, granules, solutions, foams, emulsions and suspensions.
- Solvents, liquefied gases, emulsifiers, dispersants, foam generators and solid carrier materials such as those available for processing non-crop protection agents or pharmaceuticals are suitable for mixing and stretching the active ingredients.
- the compounds can be used within a substantial concentration range of about 0.00005 to 2%.
- the active ingredients can also be used in higher concentrations, even in pure form, e.g. microfine ground, find use.
- the active ingredient concentration per ha of soil is generally 0.01 kg of active ingredient.
- 20 to 50 percent wettable powders which contain the usual proportions of inert, cell pitch and wetting agents, and possibly also adhesives, 15 to 30 percent emulsion concentrates and 5 percent granules in addition to dusts of different active ingredient concentrations are preferred.
- Preparations for the treatment of skin fungi usually contain 0.5 to 2% of the active ingredient.
- the compounds according to the invention show excellent growth-inhibiting activity, e.g. for cereals, broad beans and ornamental turf as well as in the germ test for linseed and oat grains.
- the harvest can be facilitated and the yield increased while the quality of the harvested products can be increased.
- the nutrient supply to the ears is improved and storage losses can be avoided.
- the protein content in cereals and soybeans as well as the sugar content in sugar beet and cane can be increased by using growth regulators.
- Other areas of application are, for example, the optimization of cuttings and leaf growth in tobacco plants.
- the growth of lawn, herbs and woody plants can be controlled, which reduces the maintenance costs.
- the use of mechanical harvesting aids is made possible or at least made cheaper by the use of growth regulators.
- good adaptation to the qualitative and time requirements of the market can be achieved.
- the compounds according to the invention also have very good herbicidal properties, particularly in the pre-emergence, against a large number of economically important harmful grasses and dicotyledon weeds. On the other hand, they are compatible with some crops of agricultural and horticultural importance, such as cotton, corn, rapeseed, beans, etc., so that they are suitable for selective weed control.
- the compounds also have an excellent, partially systemic action against phytopathogenic fungi and are therefore outstandingly suitable as crop protection agents. They show a good fungicidal activity e.g. against rust fungi, Phytophthora infestans, Plasmopara viticola, Venturia inaequalis, Phoma betae and Botrytis cinerea as well as against skin fungi such as Trichophone mentagrophytes and Microsporium canis.
- the compounds have an excellent fungicidal action against Piricularia oryzae and powdery mildew on cucumber, cereals (wheat and barley), apples and ornamental plants. Of particular note is the excellent fungicidal activity of the compounds against benzimidazole-resistant mildew species.
- the fungicidal agents can be used in a conventional manner e.g. be formulated as dusts, wettable powders, dispersions and emulsion concentrates. Their total active substance content is preferably 10 to 90% by weight. They also contain the usual adhesives, wetting agents, dispersing agents, fillers and carriers.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2732531 | 1977-07-19 | ||
| DE19772732531 DE2732531A1 (de) | 1977-07-19 | 1977-07-19 | Imidazolcarbonsaeuren und deren derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0000373A1 EP0000373A1 (de) | 1979-01-24 |
| EP0000373B1 true EP0000373B1 (de) | 1981-01-07 |
Family
ID=6014260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP78100314A Expired EP0000373B1 (de) | 1977-07-19 | 1978-07-06 | Imidazolcarbonsäuren und deren Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Pflanzenwachstumsregulierung bzw. zum Pflanzenschutz |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4182624A (da) |
| EP (1) | EP0000373B1 (da) |
| JP (1) | JPS5422367A (da) |
| AT (1) | AT367601B (da) |
| AU (1) | AU516238B2 (da) |
| BR (1) | BR7804613A (da) |
| CA (1) | CA1095910A (da) |
| DD (1) | DD138877A5 (da) |
| DE (2) | DE2732531A1 (da) |
| DK (1) | DK320678A (da) |
| EG (1) | EG13351A (da) |
| ES (7) | ES471660A1 (da) |
| GR (1) | GR74141B (da) |
| IL (1) | IL55149A (da) |
| IT (1) | IT1097833B (da) |
| PH (1) | PH14312A (da) |
| PT (1) | PT68316A (da) |
| ZA (1) | ZA784094B (da) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217094A1 (de) * | 1982-05-07 | 1983-11-10 | Hoechst Ag, 6230 Frankfurt | 1-substituierte imidazol-5-carbonsaeurederivate, ihre herstellung sowie ihre verwendung als biozide |
| DE3301717A1 (de) * | 1983-01-20 | 1984-07-26 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von imidazol-4,5-dicarbonsaeure |
| US4820335A (en) * | 1983-11-02 | 1989-04-11 | Hoechst Ag | 1-substituted imidazole-5-carboxylic acid derivatives, their preparation and their use as biocides |
| DE3442690A1 (de) * | 1984-11-23 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | Salze von 1-phenyl-imidazol-5-carbonsaeuren, ein verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| GB8502398D0 (en) * | 1985-01-31 | 1985-03-06 | Shell Int Research | Imidazole derivatives |
| GB8516573D0 (en) * | 1985-07-01 | 1985-08-07 | Janssen Pharmaceuticaa Nv | Controlling weeds |
| DE3537290A1 (de) * | 1985-10-19 | 1987-04-23 | Hoechst Ag | 1,2,5-substituierte imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| US4813998A (en) * | 1986-02-27 | 1989-03-21 | Janssen Pharmaceutica N.V. | Herbicidal 1H-imidazole-5-carboxylic acid derivatives |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4749713A (en) * | 1986-03-07 | 1988-06-07 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| PL149675B1 (pl) * | 1986-03-10 | 1990-03-31 | Sposób wytwarzania nowych pochodnych kwasu 1-metyl0-1h-imidaz0l0karb0ksyl0weg0-5 | |
| US4770689A (en) * | 1986-03-10 | 1988-09-13 | Janssen Pharmaceutica N.V. | Herbicidal imidazole-5-carboxylic acid derivatives |
| DE3614364A1 (de) * | 1986-04-28 | 1987-10-29 | Hoechst Ag | 1-phenyl-imidazolverbindungen, verfahren zu ihrer herstellung und ihre verwendung als wachstumsregulatoren |
| US5246915A (en) * | 1986-06-20 | 1993-09-21 | Janssen Pharmaceutica N.V. | Method for controlling weeds |
| GB8631020D0 (en) * | 1986-12-30 | 1987-02-04 | Janssen Pharmaceutica Nv | 1-methyl-1h-imidazole-5-carboxylic acid derivatives |
| DE3720245A1 (de) * | 1987-06-19 | 1988-12-29 | Hoechst Ag | Verfahren zur herstellung von n-alkoxycarbonylmethyl-n-formyl-aminen und -anilinen |
| IL84809A (en) * | 1987-11-06 | 1992-12-01 | Ciba Geigy | Process for the synthesis of 1-substituted imidazole- 5-carboxylic acids and derivatives thereof |
| LT4013B (en) | 1994-10-04 | 1996-08-26 | Univ Kauno Tech | Growth regulator |
| KR20010102073A (ko) | 1999-02-11 | 2001-11-15 | 실버스타인 아써 에이. | 항암제로 유용한 헤테로아릴-치환된 퀴놀린-2-온 유도체 |
| FR2793796A1 (fr) * | 1999-04-14 | 2000-11-24 | Hoechst Marion Roussel Inc | Nouveaux derives d'imidazoles, leur procede de preparation et les intermediaires de ce procede, leur application comme medicaments et les compositions pharmaceutiques les contenant |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519310A (en) * | 1948-12-01 | 1950-08-15 | American Cyanamid Co | Preparation of 2-mercaptoimidazole |
| FR1184709A (fr) * | 1957-09-21 | 1959-07-24 | Cfmc | Nouveaux dérivés imidazoliques, utilisables comme agents de protection contre les rayons ultra-violets et leurs procédés de fabrication |
| NL294421A (da) * | 1962-06-22 | |||
| US3354173A (en) * | 1964-04-16 | 1967-11-21 | Janssen Pharmaceutica Nv | Imidazole carboxylates |
| US3485917A (en) * | 1966-04-14 | 1969-12-23 | Janssen Pharmaceutica Nv | Composition and method for combating fungus with imidazole carboxylates |
| DE1908991B2 (de) * | 1969-02-22 | 1977-05-26 | Bayer Ag, 5090 Leverkusen | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
| US4018924A (en) * | 1969-05-21 | 1977-04-19 | Bayer Aktiengesellschaft | Phenyl-imidazolyl-acetamide derivatives |
| BE756663A (fr) * | 1969-09-27 | 1971-03-25 | Bayer Ag | Composition destinee a la regulation de la croissance des vegetaux |
| US3993647A (en) * | 1972-09-26 | 1976-11-23 | Bayer Aktiengesellschaft | Imidazolylacetic acid amides |
| US4038286A (en) * | 1975-03-10 | 1977-07-26 | Janssen Pharmaceutica N.V. | Racemates and optical isomers of 1-(1-phenylethyl)-1h-imidazole-5-carboylic acid derivatives |
| US4020064A (en) * | 1975-05-30 | 1977-04-26 | E. R. Squibb & Sons, Inc. | 3-[Substituted-2-(methylamino) phenyl]-4-[2-oxo-2-(hetero-cyclic) ethyl]-5-substituted-1,2,4-triazoles |
| US4118461A (en) * | 1975-12-18 | 1978-10-03 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
-
1977
- 1977-07-19 DE DE19772732531 patent/DE2732531A1/de not_active Withdrawn
-
1978
- 1978-07-06 EP EP78100314A patent/EP0000373B1/de not_active Expired
- 1978-07-06 DE DE7878100314T patent/DE2860407D1/de not_active Expired
- 1978-07-12 ES ES471660A patent/ES471660A1/es not_active Expired
- 1978-07-17 PH PH21387A patent/PH14312A/en unknown
- 1978-07-17 US US05/925,546 patent/US4182624A/en not_active Expired - Lifetime
- 1978-07-17 IL IL55149A patent/IL55149A/xx unknown
- 1978-07-17 EG EG445/78A patent/EG13351A/xx active
- 1978-07-17 IT IT25809/78A patent/IT1097833B/it active
- 1978-07-17 GR GR56806A patent/GR74141B/el unknown
- 1978-07-17 DD DD78206766A patent/DD138877A5/xx unknown
- 1978-07-18 PT PT68316A patent/PT68316A/pt unknown
- 1978-07-18 BR BR7804613A patent/BR7804613A/pt unknown
- 1978-07-18 DK DK320678A patent/DK320678A/da unknown
- 1978-07-18 AT AT0518878A patent/AT367601B/de not_active IP Right Cessation
- 1978-07-18 CA CA307,637A patent/CA1095910A/en not_active Expired
- 1978-07-18 AU AU38116/78A patent/AU516238B2/en not_active Expired
- 1978-07-18 JP JP8684478A patent/JPS5422367A/ja active Pending
- 1978-07-18 ZA ZA00784094A patent/ZA784094B/xx unknown
-
1979
- 1979-03-31 ES ES479158A patent/ES479158A1/es not_active Expired
- 1979-03-31 ES ES479160A patent/ES479160A1/es not_active Expired
- 1979-03-31 ES ES479163A patent/ES479163A1/es not_active Expired
- 1979-03-31 ES ES479161A patent/ES479161A1/es not_active Expired
- 1979-03-31 ES ES479159A patent/ES479159A1/es not_active Expired
- 1979-03-31 ES ES479162A patent/ES479162A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES479161A1 (es) | 1980-01-16 |
| GR74141B (da) | 1984-06-06 |
| DE2732531A1 (de) | 1979-02-01 |
| IL55149A0 (en) | 1978-09-29 |
| PT68316A (en) | 1978-08-01 |
| AU3811678A (en) | 1980-01-24 |
| DE2860407D1 (en) | 1981-02-26 |
| IT7825809A0 (it) | 1978-07-17 |
| ES479160A1 (es) | 1980-01-16 |
| AU516238B2 (en) | 1981-05-21 |
| ES479158A1 (es) | 1980-01-16 |
| ATA518878A (de) | 1981-12-15 |
| CA1095910A (en) | 1981-02-17 |
| BR7804613A (pt) | 1979-05-22 |
| ES479159A1 (es) | 1980-01-16 |
| EG13351A (en) | 1981-06-30 |
| DD138877A5 (de) | 1979-11-28 |
| PH14312A (en) | 1981-05-20 |
| IL55149A (en) | 1982-07-30 |
| ZA784094B (en) | 1979-07-25 |
| JPS5422367A (en) | 1979-02-20 |
| IT1097833B (it) | 1985-08-31 |
| EP0000373A1 (de) | 1979-01-24 |
| AT367601B (de) | 1982-07-26 |
| US4182624A (en) | 1980-01-08 |
| DK320678A (da) | 1979-01-20 |
| ES479162A1 (es) | 1980-01-16 |
| ES479163A1 (es) | 1980-02-16 |
| ES471660A1 (es) | 1979-10-01 |
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