SK279019B6 - N-acylované arylpyroly, spôsob ich prípravy a spôs - Google Patents
N-acylované arylpyroly, spôsob ich prípravy a spôs Download PDFInfo
- Publication number
- SK279019B6 SK279019B6 SK1350-91A SK135091A SK279019B6 SK 279019 B6 SK279019 B6 SK 279019B6 SK 135091 A SK135091 A SK 135091A SK 279019 B6 SK279019 B6 SK 279019B6
- Authority
- SK
- Slovakia
- Prior art keywords
- carbon atoms
- optionally substituted
- trifluoromethyl
- group
- alkyl
- Prior art date
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- 241000238631 Hexapoda Species 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 13
- 241000238876 Acari Species 0.000 title claims abstract description 11
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 125000005843 halogen group Chemical group 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- -1 cyano, fluoro, chloro, bromo, iodo Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 150000003233 pyrroles Chemical class 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- JGYVLLYMJIBXOV-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(2,2-dimethylpropanoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound BrC1=C(C(F)(F)F)N(C(=O)C(C)(C)C)C(C=2C=CC(Cl)=CC=2)=C1C#N JGYVLLYMJIBXOV-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- NQGLMIZWHNCTBA-UHFFFAOYSA-N 1-benzoyl-4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound C=1C=CC=CC=1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 NQGLMIZWHNCTBA-UHFFFAOYSA-N 0.000 claims description 4
- SZJGRBDLDWTJJV-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(2-methylbenzoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound CC1=CC=CC=C1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 SZJGRBDLDWTJJV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- NOPUKXMPLVHCNF-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(3-fluorobenzoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound FC1=CC=CC(C(=O)N2C(=C(Br)C(C#N)=C2C=2C=CC(Cl)=CC=2)C(F)(F)F)=C1 NOPUKXMPLVHCNF-UHFFFAOYSA-N 0.000 claims description 3
- JZNJFAAERPQKRO-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(4-methylbenzoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound C1=CC(C)=CC=C1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 JZNJFAAERPQKRO-UHFFFAOYSA-N 0.000 claims description 3
- LWCNBUZCNHGQQF-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(4-nitrobenzoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 LWCNBUZCNHGQQF-UHFFFAOYSA-N 0.000 claims description 3
- MAXDNBLZKNAWSJ-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(cyclohexanecarbonyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound C1CCCCC1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 MAXDNBLZKNAWSJ-UHFFFAOYSA-N 0.000 claims description 3
- SRHPFFXHPNQRNW-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1-[4-(trifluoromethyl)benzoyl]pyrrole-3-carbonitrile Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 SRHPFFXHPNQRNW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
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- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 claims description 2
- IVGLUUWEWOWMGI-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(2-methylprop-2-enoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound BrC1=C(C(F)(F)F)N(C(=O)C(=C)C)C(C=2C=CC(Cl)=CC=2)=C1C#N IVGLUUWEWOWMGI-UHFFFAOYSA-N 0.000 claims description 2
- KLUFMAVZQITMER-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-1-(3,4-dichlorobenzoyl)-5-(trifluoromethyl)pyrrole-3-carbonitrile Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=O)N1C(C(F)(F)F)=C(Br)C(C#N)=C1C1=CC=C(Cl)C=C1 KLUFMAVZQITMER-UHFFFAOYSA-N 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 2
- 238000009395 breeding Methods 0.000 claims 2
- 230000001488 breeding effect Effects 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
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- 150000001875 compounds Chemical class 0.000 abstract description 21
- 241000196324 Embryophyta Species 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
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- 208000031888 Mycoses Diseases 0.000 description 1
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- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
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- 239000012298 atmosphere Substances 0.000 description 1
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- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
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- 235000013339 cereals Nutrition 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
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- 230000009969 flowable effect Effects 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
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- 231100001225 mammalian toxicity Toxicity 0.000 description 1
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical class CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
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- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D207/42—Nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Multicomponent Fibers (AREA)
- Water Treatment By Sorption (AREA)
- Farming Of Fish And Shellfish (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52229990A | 1990-05-11 | 1990-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK279019B6 true SK279019B6 (sk) | 1998-05-06 |
Family
ID=24080318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1350-91A SK279019B6 (sk) | 1990-05-11 | 1991-05-08 | N-acylované arylpyroly, spôsob ich prípravy a spôs |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0484614B1 (cs) |
| JP (1) | JP3242943B2 (cs) |
| KR (1) | KR0176710B1 (cs) |
| AT (1) | ATE123020T1 (cs) |
| AU (1) | AU646454B2 (cs) |
| BG (1) | BG60282B2 (cs) |
| BR (2) | BR9101921A (cs) |
| CA (1) | CA2042243C (cs) |
| CZ (1) | CZ281576B6 (cs) |
| DE (1) | DE69110003T2 (cs) |
| DK (1) | DK0484614T3 (cs) |
| EG (1) | EG19326A (cs) |
| ES (1) | ES2072468T3 (cs) |
| FI (1) | FI103201B (cs) |
| HU (1) | HU213175B (cs) |
| IE (1) | IE911604A1 (cs) |
| IL (1) | IL97628A (cs) |
| MD (1) | MD1125C2 (cs) |
| NZ (1) | NZ238039A (cs) |
| PT (1) | PT97613B (cs) |
| RO (1) | RO110818B1 (cs) |
| RU (1) | RU2099326C1 (cs) |
| SK (1) | SK279019B6 (cs) |
| TR (1) | TR25658A (cs) |
| UA (1) | UA40563C2 (cs) |
| YU (1) | YU81891A (cs) |
| ZA (1) | ZA913559B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5306827A (en) * | 1991-12-04 | 1994-04-26 | American Cyanamid Company | Haloalkylthio, -sulfinyl and -sulfonyl arylpyrrole insecticidal and acaricidal agents |
| AU4950693A (en) * | 1992-09-01 | 1994-03-29 | Ciba-Geigy Ag | 3-cyano-4-halogeno-2-(subst.phenyl)-pyrroles as pesticides and fungicides |
| DE4233885A1 (de) * | 1992-10-08 | 1994-04-14 | Bayer Ag | Substituierte 2-Arylpyrrole |
| US5286743A (en) * | 1992-10-27 | 1994-02-15 | American Cyanamid Company | N-aminoalkylcarbonyloxyalkylpyrrole insecticidal acaricidal and molluscicidal agents |
| US5286741A (en) * | 1992-10-27 | 1994-02-15 | American Cyanamid Company | N-oxy- and thioalkylcarbonyloxyalkylpyrrole insecticidal, acaricidal and molluscicidal agents |
| US5232980A (en) * | 1992-10-27 | 1993-08-03 | American Cyanamid Company | N-substituted carbonyloxyalkylpyrrole insecticidal, acaricidal and molluscicidal agents |
| HU226640B1 (en) * | 1999-10-18 | 2009-05-28 | Egis Gyogyszergyar Nyilvanosan | Process for producing amorphous atorvastatin calcium salt |
| SI20425A (sl) * | 1999-12-10 | 2001-06-30 | LEK tovarna farmacevtskih in kemi�nih izdelkov d.d. | Priprava amorfnega atorvastatina |
| DE10063178A1 (de) * | 2000-12-18 | 2002-06-20 | Bayer Ag | Sulfonylpyrrole |
| MXPA04007396A (es) * | 2002-01-31 | 2004-10-11 | Novartis Ag | Proceso para la elaboracion de inhibidores de reductasa hmg-coa. |
| PE20070182A1 (es) | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5010098A (en) * | 1987-07-29 | 1991-04-23 | American Cyanamid Company | Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof |
| BR8906202A (pt) * | 1988-12-05 | 1990-09-25 | American Cyanamid Co | Processo e composicao para o controle de pragas de insetos,acaros e moluscos,composto para tal controle e processo para sua preparacao |
| DE69026906T2 (de) * | 1989-08-11 | 1996-11-28 | American Cyanamid Co., Wayne, N.J. | Arylpyrrol enthaltende insekticidale, acaricidale und nematicidale Mittel sowie Verfahren zu ihrer Herstellung |
-
1991
- 1991-03-14 EP EP91103923A patent/EP0484614B1/en not_active Expired - Lifetime
- 1991-03-14 DK DK91103923.8T patent/DK0484614T3/da active
- 1991-03-14 DE DE69110003T patent/DE69110003T2/de not_active Expired - Fee Related
- 1991-03-14 AT AT91103923T patent/ATE123020T1/de not_active IP Right Cessation
- 1991-03-14 ES ES91103923T patent/ES2072468T3/es not_active Expired - Lifetime
- 1991-03-21 IL IL9762891A patent/IL97628A/en not_active IP Right Cessation
- 1991-04-29 AU AU76055/91A patent/AU646454B2/en not_active Ceased
- 1991-05-01 TR TR91/0483A patent/TR25658A/xx unknown
- 1991-05-03 NZ NZ238039A patent/NZ238039A/xx unknown
- 1991-05-07 JP JP13027291A patent/JP3242943B2/ja not_active Expired - Fee Related
- 1991-05-08 CZ CS911350A patent/CZ281576B6/cs not_active IP Right Cessation
- 1991-05-08 RU SU914895406A patent/RU2099326C1/ru active
- 1991-05-08 EG EG27591A patent/EG19326A/xx active
- 1991-05-08 SK SK1350-91A patent/SK279019B6/sk unknown
- 1991-05-08 UA UA4895406A patent/UA40563C2/uk unknown
- 1991-05-09 PT PT97613A patent/PT97613B/pt not_active IP Right Cessation
- 1991-05-09 BG BG094385A patent/BG60282B2/bg unknown
- 1991-05-09 CA CA002042243A patent/CA2042243C/en not_active Expired - Fee Related
- 1991-05-10 IE IE160491A patent/IE911604A1/en not_active IP Right Cessation
- 1991-05-10 FI FI912291A patent/FI103201B/fi active
- 1991-05-10 KR KR1019910007570A patent/KR0176710B1/ko not_active Expired - Fee Related
- 1991-05-10 BR BR919101921A patent/BR9101921A/pt not_active Application Discontinuation
- 1991-05-10 ZA ZA913559A patent/ZA913559B/xx unknown
- 1991-05-10 YU YU81891A patent/YU81891A/sh unknown
- 1991-05-10 HU HU911570A patent/HU213175B/hu not_active IP Right Cessation
- 1991-05-10 RO RO147526A patent/RO110818B1/ro unknown
-
1994
- 1994-07-12 MD MD94-0288A patent/MD1125C2/ro unknown
-
1997
- 1997-04-30 BR BR1100378-2A patent/BR1100378A/pt active IP Right Grant
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