IE43517B1 - Substituted imidazoles and their use as fungicides - Google Patents
Substituted imidazoles and their use as fungicidesInfo
- Publication number
- IE43517B1 IE43517B1 IE226/76A IE22676A IE43517B1 IE 43517 B1 IE43517 B1 IE 43517B1 IE 226/76 A IE226/76 A IE 226/76A IE 22676 A IE22676 A IE 22676A IE 43517 B1 IE43517 B1 IE 43517B1
- Authority
- IE
- Ireland
- Prior art keywords
- substituted
- imidazole
- phenyl
- joined
- acid addition
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 92
- 239000000417 fungicide Substances 0.000 title claims abstract description 45
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 306
- 150000003839 salts Chemical class 0.000 claims abstract description 94
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 229910052751 metal Chemical class 0.000 claims abstract description 67
- 239000002184 metal Chemical class 0.000 claims abstract description 67
- 239000002253 acid Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 43
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract 3
- -1 pyrryl Chemical group 0.000 claims description 89
- 239000000203 mixture Substances 0.000 claims description 60
- 239000000460 chlorine Substances 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 230000000855 fungicidal effect Effects 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 10
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 230000003032 phytopathogenic effect Effects 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052793 cadmium Inorganic materials 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 5
- 239000011133 lead Substances 0.000 claims description 5
- 239000011777 magnesium Chemical group 0.000 claims description 5
- 229910052749 magnesium Inorganic materials 0.000 claims description 5
- 229940049920 malate Drugs 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 239000011135 tin Substances 0.000 claims description 5
- 229910052718 tin Inorganic materials 0.000 claims description 5
- 239000004563 wettable powder Substances 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- 229940022663 acetate Drugs 0.000 claims description 4
- 229910052788 barium Inorganic materials 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940001468 citrate Drugs 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000428 dust Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 4
- 230000009969 flowable effect Effects 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical group [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 4
- 229940039748 oxalate Drugs 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 230000009418 agronomic effect Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 claims 1
- 238000007429 general method Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 19
- 239000002243 precursor Substances 0.000 abstract description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 158
- 239000000243 solution Substances 0.000 description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 103
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 80
- 239000000047 product Substances 0.000 description 73
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 70
- 239000002904 solvent Substances 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 30
- 235000019341 magnesium sulphate Nutrition 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
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- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- YADYZZZSEQSSCD-UHFFFAOYSA-L zinc;1h-imidazole;dichloride Chemical compound [Cl-].[Cl-].[Zn+2].C1=CNC=N1 YADYZZZSEQSSCD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2637—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D233/91—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54729175A | 1975-02-05 | 1975-02-05 | |
| US55754675A | 1975-03-12 | 1975-03-12 | |
| US05/642,041 US4105762A (en) | 1975-02-05 | 1975-12-18 | Metal salt complexes of 1-substituted aralkyl imidazoles, and methods and compositions for controlling phytopathogenic fungi using them |
| US05/647,039 US4073921A (en) | 1975-03-12 | 1976-01-07 | Substituted arylcyanoalkyl and diarylcyanoalkylimidazoles and fungical compositions and methods utilizing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43517L IE43517L (en) | 1976-08-05 |
| IE43517B1 true IE43517B1 (en) | 1981-03-25 |
Family
ID=27504723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE226/76A IE43517B1 (en) | 1975-02-05 | 1976-02-04 | Substituted imidazoles and their use as fungicides |
Country Status (22)
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1590648A (en) * | 1976-12-01 | 1981-06-03 | Ciba Geigy Ag | N-((naphthothienyl or n-phenanthryl)alkyl) imidazoles their preparation and compositions containing them |
| FR2415095A1 (fr) * | 1978-01-20 | 1979-08-17 | Azote & Prod Chim | Procede d'alcoylation du phenylacetonitrile |
| JPS54157560A (en) * | 1978-06-01 | 1979-12-12 | Sumitomo Chem Co Ltd | Preparation of n-substituted imidazole derivative |
| DE2847441A1 (de) * | 1978-11-02 | 1980-05-22 | Basf Ag | Imidazol-kupferkomplexverbindungen |
| KR850000380B1 (ko) * | 1979-02-22 | 1985-03-23 | 더웰컴 화운데이숀 리미티드 | 이미다졸 유도체의 제조방법 |
| GR68076B (enrdf_load_stackoverflow) * | 1979-04-27 | 1981-10-30 | Chinoin Gyogyszer Es Vegyeszet | |
| DE3032326A1 (de) * | 1980-08-27 | 1982-04-08 | Bayer Ag, 5090 Leverkusen | Azolylalkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| ZA821577B (en) * | 1981-04-06 | 1983-03-30 | Boots Co Plc | Therapeutic agents |
| US4443449A (en) * | 1981-04-06 | 1984-04-17 | The Boots Company Limited | Arylcyclobutylalkylamines and anti-depression composition and methods using same |
| EP0064244A1 (en) * | 1981-04-24 | 1982-11-10 | Syntex (U.S.A.) Inc. | Spermicidal 1-bis(arylalkyl)alkylimidazoles |
| DE3121676A1 (de) * | 1981-06-01 | 1982-12-16 | Hoechst Ag, 6000 Frankfurt | "1,1-diaryl-2-azolyl-aethane, ihre herstellung, ihre verwendung und diese verbindungen enthaltende praeparationen" |
| DE3216301A1 (de) * | 1982-04-26 | 1983-10-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,2,4-triazol-1-yl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
| ZA835967B (en) * | 1982-08-14 | 1985-04-24 | Wellcome Found | Imidazole derivatives and salts thereof,their synthesis,and pharmaceutical formulations |
| GB2126218B (en) * | 1982-08-14 | 1986-01-22 | Wellcome Found | Imidazoles |
| IE56000B1 (en) * | 1982-09-30 | 1991-03-13 | Boots Co Plc | 1-arylcyclobutylalkylamine compounds |
| US4581370A (en) * | 1983-07-12 | 1986-04-08 | Schering A.G. | Antiarrhythmic imidazoliums |
| DE3329213A1 (de) * | 1983-08-10 | 1985-02-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | Azolyl-propannitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
| CA1227801A (en) * | 1983-11-10 | 1987-10-06 | Ted T. Fujimoto | .alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES |
| GB8501192D0 (en) * | 1985-01-17 | 1985-02-20 | Boots Co Plc | Therapeutic agents |
| GB8531071D0 (en) * | 1985-12-17 | 1986-01-29 | Boots Co Plc | Therapeutic compound |
| US5039978A (en) * | 1990-01-08 | 1991-08-13 | Kronberg James W | Analog graphic display method and apparatus |
| JP4773013B2 (ja) * | 1999-07-27 | 2011-09-14 | ロンザ アーゲー | １−（６−メチルピリジン−３−イル）−２−［４−（メチルスルホニル）フェニル］エタノンの製造方法 |
| BRPI0706365A2 (pt) | 2006-01-06 | 2011-03-22 | Sepracor Inc | Cicloalquilaminas como inibidores da recaptação de monoamina |
| EP2746264A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746255A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| WO2014095381A1 (en) * | 2012-12-19 | 2014-06-26 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
| WO2016136985A1 (ja) | 2015-02-27 | 2016-09-01 | 国立大学法人九州大学 | ピリジノン化合物およびその用途 |
| EP3519390A1 (en) | 2016-09-29 | 2019-08-07 | Bayer CropScience Aktiengesellschaft | 1,5-substituted imidazole derivatives as fungicides for crop protection. |
| EA201990783A1 (ru) | 2016-09-29 | 2019-10-31 | Производные 5-замещенного имидазолилметилоксирана в качестве фунгицидов | |
| CN109890795A (zh) | 2016-09-29 | 2019-06-14 | 拜耳作物科学股份公司 | 新的5-取代的咪唑衍生物 |
| BR112019006441A2 (pt) | 2016-09-29 | 2019-06-25 | Bayer Ag | derivados de 5-imidazol metil dioxolano substituídos como fungicidas |
| EP3519391A1 (en) | 2016-09-29 | 2019-08-07 | Bayer CropScience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| EP3519389A1 (en) | 2016-09-29 | 2019-08-07 | Bayer CropScience Aktiengesellschaft | Novel 5-substituted imidazolylmethyl derivatives |
| EP3519408A1 (en) | 2016-09-29 | 2019-08-07 | Bayer CropScience Aktiengesellschaft | 1 -[2-(1 -chlorocyclopropyl)-2-hydroxy-3-(3-phenyl-1,2-oxazol-5-yl)propyl]-1h-imidazole-5-carbonitrile derivatives and related compounds as fungicides for crop protection |
| CA3121445A1 (en) * | 2018-11-30 | 2020-06-04 | Kyushu University, National University Corporation | Dock1-inhibiting compound and use thereof |
-
1976
- 1976-01-22 SE SE7600674A patent/SE7600674L/xx unknown
- 1976-02-02 GB GB4011/76A patent/GB1530172A/en not_active Expired
- 1976-02-03 GR GR49944A patent/GR58522B/el unknown
- 1976-02-03 DE DE2604047A patent/DE2604047A1/de not_active Withdrawn
- 1976-02-04 IE IE226/76A patent/IE43517B1/en unknown
- 1976-02-04 OA OA55728A patent/OA05234A/xx unknown
- 1976-02-05 AR AR262172A patent/AR226407A1/es active
- 1976-02-05 FR FR7603195A patent/FR2300081A1/fr active Granted
- 1976-02-05 NZ NZ179937A patent/NZ179937A/xx unknown
- 1976-02-05 DD DD191120A patent/DD124098A5/xx unknown
- 1976-02-05 DK DK48076*#A patent/DK48076A/da unknown
- 1976-02-05 HU HU76RO877A patent/HU178950B/hu unknown
- 1976-02-05 BR BR7600736A patent/BR7600736A/pt unknown
- 1976-02-05 NL NL7601206A patent/NL7601206A/xx not_active Application Discontinuation
- 1976-02-05 TR TR18878A patent/TR18878A/xx unknown
- 1976-02-05 AU AU10873/76A patent/AU502679B2/en not_active Expired
- 1976-02-05 IT IT19924/76A patent/IT1061007B/it active
- 1976-02-05 JP JP51011810A patent/JPS51143667A/ja active Pending
- 1976-02-05 PT PT64778A patent/PT64778B/pt unknown
- 1976-02-05 IL IL48975A patent/IL48975A/xx unknown
- 1976-02-05 ES ES444918A patent/ES444918A1/es not_active Expired
- 1976-02-06 MX MX766654U patent/MX4047E/es unknown
-
1977
- 1977-04-16 ES ES458202A patent/ES458202A1/es not_active Expired
- 1977-10-12 AR AR269562A patent/AR220522A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| GR58522B (en) | 1977-10-29 |
| IL48975A (en) | 1980-03-31 |
| FR2300081A1 (fr) | 1976-09-03 |
| GB1530172A (en) | 1978-10-25 |
| NZ179937A (en) | 1978-09-25 |
| IT1061007B (it) | 1982-10-20 |
| AR220522A1 (es) | 1980-11-14 |
| NL7601206A (nl) | 1976-08-09 |
| PT64778B (en) | 1977-07-06 |
| SE7600674L (sv) | 1976-08-06 |
| AU1087376A (en) | 1977-08-11 |
| OA05234A (fr) | 1981-02-28 |
| AR226407A1 (es) | 1982-07-15 |
| AU502679B2 (en) | 1979-08-02 |
| DE2604047A1 (de) | 1976-09-16 |
| PT64778A (en) | 1976-03-01 |
| ES458202A1 (es) | 1978-08-16 |
| JPS51143667A (en) | 1976-12-10 |
| BR7600736A (pt) | 1976-08-31 |
| FR2300081B1 (enrdf_load_stackoverflow) | 1981-04-30 |
| DK48076A (da) | 1976-08-06 |
| TR18878A (tr) | 1977-10-13 |
| MX4047E (es) | 1981-11-23 |
| HU178950B (en) | 1982-07-28 |
| ES444918A1 (es) | 1977-11-01 |
| IE43517L (en) | 1976-08-05 |
| DD124098A5 (enrdf_load_stackoverflow) | 1977-02-02 |
| IL48975A0 (en) | 1976-04-30 |
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