CS4492A3 - Piperidine derivatives, process of their preparation and use - Google Patents

Piperidine derivatives, process of their preparation and use Download PDF

Info

Publication number: CS4492A3
Authority: CS; Czechoslovakia
Prior art keywords: phenyl; compound; formula; alkyl; acid addition
Prior art date: 1991-01-10

Application number

CS9244A

Other languages

Czech (cs)

English (en)

Inventor

Paul Andrew Carter

Steven James Tapp

Nicholas John Daniels

Original Assignee

Shell Int Research

Priority date (The priority date 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 date listed.)

1991-01-10

Filing date

1992-01-08

Publication date

1992-07-15

1992-01-08 Application filed by Shell Int Research filed Critical Shell Int Research

1992-07-15 Publication of CS4492A3 publication Critical patent/CS4492A3/cs

Links

238000002360 preparation method Methods 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 13
150000003053 piperidines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 76
-1 4-tert-butylphenyl Chemical group 0.000 claims description 54
239000000203 mixture Substances 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 14
125000001624 naphthyl group Chemical group 0.000 claims description 12
239000004480 active ingredient Substances 0.000 claims description 11
230000000855 fungicidal effect Effects 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
239000004094 surface-active agent Substances 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000006501 nitrophenyl group Chemical group 0.000 claims description 7
241000233866 Fungi Species 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000004799 bromophenyl group Chemical group 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000001207 fluorophenyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000004802 cyanophenyl group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
125000004438 haloalkoxy group Chemical group 0.000 claims description 4
125000005059 halophenyl group Chemical group 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
230000002538 fungal effect Effects 0.000 claims description 3
239000000417 fungicide Substances 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000006038 hexenyl group Chemical group 0.000 claims description 2
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 claims description 2
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 claims description 2
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
125000006194 pentinyl group Chemical group 0.000 claims 1
210000001685 thyroid gland Anatomy 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
238000012360 testing method Methods 0.000 description 33
241000196324 Embryophyta Species 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 14
239000007921 spray Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000005507 spraying Methods 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
238000011156 evaluation Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000047 product Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000007788 liquid Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000008272 agar Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000001035 drying Methods 0.000 description 5
238000011081 inoculation Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
230000028070 sporulation Effects 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical compound C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000013068 control sample Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 3
PXNAZQBPHRKZRL-UHFFFAOYSA-N 1-benzyl-4-(4-bromophenyl)piperidine Chemical compound C1=CC(Br)=CC=C1C1CCN(CC=2C=CC=CC=2)CC1 PXNAZQBPHRKZRL-UHFFFAOYSA-N 0.000 description 3
MFTCGUGCAGUJHP-UHFFFAOYSA-N 1-benzyl-4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1CCN(CC=2C=CC=CC=2)CC1 MFTCGUGCAGUJHP-UHFFFAOYSA-N 0.000 description 3
GOEBEEJCYYXSFT-UHFFFAOYSA-N 2-phenylpentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C1=CC=CC=C1 GOEBEEJCYYXSFT-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
241001281803 Plasmopara viticola Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
240000003768 Solanum lycopersicum Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
230000003902 lesion Effects 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000003359 percent control normalization Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
WTQATTHFRGMBML-UHFFFAOYSA-N 1-phenylpiperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1C1=CC=CC=C1 WTQATTHFRGMBML-UHFFFAOYSA-N 0.000 description 2
DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical compound O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
VKQHTSSNSJIMAL-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1CCNCC1 VKQHTSSNSJIMAL-UHFFFAOYSA-N 0.000 description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
241000213004 Alternaria solani Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
241001668536 Oculimacula yallundae Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
240000006365 Vitis vinifera Species 0.000 description 2
235000014787 Vitis vinifera Nutrition 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
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230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
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239000002689 soil Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
ZKABWLFDCJKQRE-UHFFFAOYSA-N 4-(4-bromophenyl)piperidine Chemical compound C1=CC(Br)=CC=C1C1CCNCC1 ZKABWLFDCJKQRE-UHFFFAOYSA-N 0.000 description 1
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JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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239000011593 sulfur Substances 0.000 description 1
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238000001665 trituration Methods 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

CS9244A 1991-01-10 1992-01-08 Piperidine derivatives, process of their preparation and use CS4492A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB919100505A GB9100505D0 (en)	1991-01-10	1991-01-10	Piperidine derivatives

Publications (1)

Publication Number	Publication Date
CS4492A3 true CS4492A3 (en)	1992-07-15

Family

ID=10688228

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS9244A CS4492A3 (en)	1991-01-10	1992-01-08	Piperidine derivatives, process of their preparation and use

Country Status (12)

Country	Link
US (1)	US5489599A (tr)
EP (1)	EP0494717A1 (tr)
JP (1)	JPH06506441A (tr)
KR (1)	KR930703302A (tr)
CN (1)	CN1063101A (tr)
CS (1)	CS4492A3 (tr)
GB (1)	GB9100505D0 (tr)
HU (1)	HUT65119A (tr)
RU (1)	RU2097375C1 (tr)
TR (1)	TR28066A (tr)
WO (1)	WO1992012130A1 (tr)
ZA (1)	ZA92149B (tr)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994001403A1 (en) *	1992-07-08	1994-01-20	Shell Internationale Research Maatschappij B.V.	Piperidine derivatives
DE4335718A1 (de) *	1993-10-20	1995-04-27	Merck Patent Gmbh	Cyclische Aminderivate
ZA9610738B (en) *	1995-12-22	1997-06-24	Warner Lambert Co	Subtype selective nmda receptor ligands and the use thereof
EP0867183B1 (en) *	1996-07-22	2004-10-06	Daiichi Suntory Pharma Co., Ltd.	Arylpiperidinol and arylpiperidine derivatives and drugs containing the same
US5849802A (en) *	1996-09-27	1998-12-15	American Cyanamid Company	Fungicidal spirocyclic amines
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1991
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1992
- 1992-01-08 EP EP92200037A patent/EP0494717A1/en not_active Withdrawn
- 1992-01-08 WO PCT/EP1992/000040 patent/WO1992012130A1/en not_active Ceased
- 1992-01-08 HU HU9301987A patent/HUT65119A/hu unknown
- 1992-01-08 CS CS9244A patent/CS4492A3/cs unknown
- 1992-01-08 JP JP4501676A patent/JPH06506441A/ja active Pending
- 1992-01-08 US US08/081,298 patent/US5489599A/en not_active Expired - Fee Related
- 1992-01-08 RU RU9293051789A patent/RU2097375C1/ru active
- 1992-01-08 KR KR1019930702072A patent/KR930703302A/ko not_active Ceased
- 1992-01-09 ZA ZA92149A patent/ZA92149B/xx unknown
- 1992-01-10 TR TR00032/92A patent/TR28066A/tr unknown
- 1992-01-10 CN CN92100196A patent/CN1063101A/zh active Pending

Also Published As

Publication number	Publication date
RU2097375C1 (ru)	1997-11-27
ZA92149B (en)	1992-09-30
EP0494717A1 (en)	1992-07-15
CN1063101A (zh)	1992-07-29
WO1992012130A1 (en)	1992-07-23
HUT65119A (en)	1994-04-28
KR930703302A (ko)	1993-11-29
JPH06506441A (ja)	1994-07-21
US5489599A (en)	1996-02-06
TR28066A (tr)	1995-12-11
GB9100505D0 (en)	1991-02-20
HU9301987D0 (en)	1993-11-29

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AU2008258793A1 (en)	2008-12-11	Pyrazole carboxylic acid amides useful as microbiocides
CS266307B2 (en)	1989-12-13	Fungicide,herbicide or plant growth regulator
JPH04234370A (ja)	1992-08-24	テトラヒドロピリミジン誘導体
JPS59130287A (ja)	1984-07-26	ピリジルイソオキサゾリジン
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JPS6348866B2 (tr)	1988-09-30
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EP0191514B1 (en)	1991-04-03	Imidazole derivatives, their preparation and their use as fungicides
DK165553B (da)	1992-12-14	Imidazolderivater, fremgangsmaade til fremstilling heraf samt anvendelse af disse som fungicider
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US4355035A (en)	1982-10-19	Derivatives of certain pyridyliminomethylbenzenes
EP0621267A1 (en)	1994-10-26	Spiropiperidine derivatives and their use as fungicides
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