NL8500347A - Fenylpropargylaminederivaten, werkwijzen ter bereiding ervan, samenstellingen, die deze derivaten bevatten alsmede de toepassing daarvan. - Google Patents

Fenylpropargylaminederivaten, werkwijzen ter bereiding ervan, samenstellingen, die deze derivaten bevatten alsmede de toepassing daarvan. Download PDF

Info

Publication number: NL8500347A
Authority: NL; Netherlands
Prior art keywords: group; compound; general formula; carbon atoms; straight
Prior art date: 1984-02-08

Application number

NL8500347A

Other languages

English (en)

Dutch (nl)

Original Assignee

May & Baker Ltd

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.)

1984-02-08

Filing date

1985-02-07

Publication date

1985-09-02

1984-02-08 Priority claimed from GB848403362A external-priority patent/GB8403362D0/en

1984-12-12 Priority claimed from GB848431375A external-priority patent/GB8431375D0/en

1985-02-07 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1985-09-02 Publication of NL8500347A publication Critical patent/NL8500347A/nl

Links

239000000203 mixture Substances 0.000 title claims description 31
238000000034 method Methods 0.000 title claims description 21
IZKIWEYIOKPHLF-UHFFFAOYSA-N n-prop-2-ynylaniline Chemical class C#CCNC1=CC=CC=C1 IZKIWEYIOKPHLF-UHFFFAOYSA-N 0.000 title claims description 17
150000001875 compounds Chemical class 0.000 claims description 94
239000002253 acid Substances 0.000 claims description 53
150000003839 salts Chemical class 0.000 claims description 50
-1 benzoyl oxymethyl group Chemical group 0.000 claims description 49
239000007787 solid Substances 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 34
241000283984 Rodentia Species 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 23
239000012141 concentrate Substances 0.000 claims description 22
239000007788 liquid Substances 0.000 claims description 22
241000607479 Yersinia pestis Species 0.000 claims description 17
241001465754 Metazoa Species 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
241000700159 Rattus Species 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
239000000969 carrier Substances 0.000 claims description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
239000003128 rodenticide Substances 0.000 claims description 11
241000699670 Mus sp. Species 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
125000004849 alkoxymethyl group Chemical group 0.000 claims description 7
230000002429 anti-coagulating effect Effects 0.000 claims description 7
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 7
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
231100000518 lethal Toxicity 0.000 claims description 6
230000001665 lethal effect Effects 0.000 claims description 6
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
125000005042 acyloxymethyl group Chemical group 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000706 filtrate Substances 0.000 claims description 5
238000010348 incorporation Methods 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
235000001671 coumarin Nutrition 0.000 claims description 3
229960000956 coumarin Drugs 0.000 claims description 3
230000037406 food intake Effects 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
239000003146 anticoagulant agent Substances 0.000 claims description 2
229940127219 anticoagulant drug Drugs 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 7
WFFZGYRTVIPBFN-UHFFFAOYSA-N 3h-indene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)CC2=C1 WFFZGYRTVIPBFN-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
125000004970 halomethyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 40
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
235000008504 concentrate Nutrition 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
235000013312 flour Nutrition 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
RDZXCIVBEGJPON-UHFFFAOYSA-N 2-[1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]piperidin-4-yl]-2-methylpropan-1-ol Chemical compound C1CC(C(C)(CO)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 RDZXCIVBEGJPON-UHFFFAOYSA-N 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000843 powder Substances 0.000 description 7
231100000331 toxic Toxicity 0.000 description 7
230000002588 toxic effect Effects 0.000 description 7
235000013311 vegetables Nutrition 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
230000001119 rodenticidal effect Effects 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
206010061217 Infestation Diseases 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000010775 animal oil Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000019219 chocolate Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000002285 corn oil Substances 0.000 description 4
235000005687 corn oil Nutrition 0.000 description 4
230000034994 death Effects 0.000 description 4
231100000517 death Toxicity 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000008158 vegetable oil Substances 0.000 description 4
GIVBQOHFUXJZBB-UHFFFAOYSA-N 2-methyl-2-(1-prop-2-ynylpiperidin-4-yl)propan-1-ol Chemical compound OCC(C)(C)C1CCN(CC#C)CC1 GIVBQOHFUXJZBB-UHFFFAOYSA-N 0.000 description 3
229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
238000009826 distribution Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
235000014666 liquid concentrate Nutrition 0.000 description 3
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
239000006072 paste Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CSVCVIHEBDJTCJ-UHFFFAOYSA-N 1-bromo-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC(C(F)(F)F)=C1 CSVCVIHEBDJTCJ-UHFFFAOYSA-N 0.000 description 2
BCLSNCGBHPIGRS-UHFFFAOYSA-N 4-(1-methoxy-2-methylpropan-2-yl)-1-prop-2-ynylpiperidine Chemical compound COCC(C)(C)C1CCN(CC#C)CC1 BCLSNCGBHPIGRS-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699660 Mus musculus Species 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
208000005374 Poisoning Diseases 0.000 description 2
241000700161 Rattus rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QRSXNVRXUSKLFR-UHFFFAOYSA-N [2-[1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]piperidin-4-yl]-2-methylpropyl] benzoate Chemical compound C1CN(CC#CC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CCC1C(C)(C)COC(=O)C1=CC=CC=C1 QRSXNVRXUSKLFR-UHFFFAOYSA-N 0.000 description 2
TZZLQGDMAPUZID-UHFFFAOYSA-N acetic acid;2-methyl-2-piperidin-4-ylpropan-1-ol Chemical compound CC(O)=O.OCC(C)(C)C1CCNCC1 TZZLQGDMAPUZID-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000002411 adverse Effects 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000001684 chronic effect Effects 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
230000003370 grooming effect Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
150000002641 lithium Chemical group 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000012736 patent blue V Nutrition 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
231100000572 poisoning Toxicity 0.000 description 2
230000000607 poisoning effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000005871 repellent Substances 0.000 description 2
230000002940 repellent Effects 0.000 description 2
NZYOAGBNMCVQIV-UHFFFAOYSA-N sodium;chloro-(4-methylphenyl)sulfonylazanide;trihydrate Chemical compound O.O.O.[Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 NZYOAGBNMCVQIV-UHFFFAOYSA-N 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
229960005080 warfarin Drugs 0.000 description 2
PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
NABXACZOZGCLPK-UHFFFAOYSA-N 1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]-4-(1-methoxy-2-methylpropan-2-yl)piperidine Chemical compound C1CC(C(C)(C)COC)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NABXACZOZGCLPK-UHFFFAOYSA-N 0.000 description 1
SXWIKQBSRZFSOJ-UHFFFAOYSA-N 1-prop-1-ynyl-3,5-bis(trifluoromethyl)benzene Chemical compound CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SXWIKQBSRZFSOJ-UHFFFAOYSA-N 0.000 description 1
CLTALAKJDOMFRD-UHFFFAOYSA-N 2-[1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]piperidin-4-yl]-2-methylpropan-1-ol;hydrochloride Chemical compound Cl.C1CC(C(C)(CO)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CLTALAKJDOMFRD-UHFFFAOYSA-N 0.000 description 1
IFDRKCHWYJONEM-UHFFFAOYSA-N 2-[1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]piperidin-4-yl]-2-methylpropan-1-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1CC(C(C)(CO)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IFDRKCHWYJONEM-UHFFFAOYSA-N 0.000 description 1
BXUOQGOIJRWGMT-UHFFFAOYSA-N 2-[1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]piperidin-4-yl]-2-methylpropanal Chemical compound C1CC(C(C)(C=O)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BXUOQGOIJRWGMT-UHFFFAOYSA-N 0.000 description 1
YIFBPRIWDMZMLP-UHFFFAOYSA-N 2-[1-[3-[3,5-bis(trifluoromethyl)phenyl]prop-2-ynyl]piperidin-4-yl]-2-methylpropanal;hydrochloride Chemical compound Cl.C1CC(C(C)(C=O)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 YIFBPRIWDMZMLP-UHFFFAOYSA-N 0.000 description 1
OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 description 1
URRQEBTVGCKANT-UHFFFAOYSA-N 2-methyl-2-piperidin-4-ylpropan-1-ol Chemical compound OCC(C)(C)C1CCNCC1 URRQEBTVGCKANT-UHFFFAOYSA-N 0.000 description 1
NNHHDNWAQPDOHZ-UHFFFAOYSA-N 2-methyl-2-pyridin-4-ylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=NC=C1 NNHHDNWAQPDOHZ-UHFFFAOYSA-N 0.000 description 1
JTRKNMZRJOEYFJ-UHFFFAOYSA-N 4-(1-methoxy-2-methylpropan-2-yl)piperidine Chemical compound COCC(C)(C)C1CCNCC1 JTRKNMZRJOEYFJ-UHFFFAOYSA-N 0.000 description 1
UNJPFFMNIMCYKI-UHFFFAOYSA-N 4-(1-methoxy-2-methylpropan-2-yl)pyridine Chemical compound COCC(C)(C)C1=CC=NC=C1 UNJPFFMNIMCYKI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
235000003276 Apios tuberosa Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
OAXZEOQWVKJVCA-UHFFFAOYSA-N Cl.C1CC(C(C)(C)COC(=O)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 Chemical compound Cl.C1CC(C(C)(C)COC(=O)C)CCN1CC#CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OAXZEOQWVKJVCA-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
240000003133 Elaeis guineensis Species 0.000 description 1
235000001950 Elaeis guineensis Nutrition 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GCXMAHRQRKXJQN-UHFFFAOYSA-N P(=O)(O)(O)O.CC#C Chemical compound P(=O)(O)(O)O.CC#C GCXMAHRQRKXJQN-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
LXOBENKHDAKHJZ-UHFFFAOYSA-N [N+](=O)(O)[O-].C#CC Chemical compound [N+](=O)(O)[O-].C#CC LXOBENKHDAKHJZ-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
GFAHPTSAUYBTLD-UHFFFAOYSA-N acetic acid;prop-1-yne Chemical compound CC#C.CC(O)=O GFAHPTSAUYBTLD-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000002152 aqueous-organic solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
235000012970 cakes Nutrition 0.000 description 1
239000011111 cardboard Substances 0.000 description 1
239000004464 cereal grain Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
VXAPDXVBDZRZKP-UHFFFAOYSA-N nitric acid phosphoric acid Chemical compound O[N+]([O-])=O.OP(O)(O)=O VXAPDXVBDZRZKP-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
230000035764 nutrition Effects 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
235000014593 oils and fats Nutrition 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000000123 paper Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
235000015277 pork Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
UWECIPNAXRKCIZ-UHFFFAOYSA-N prop-1-yne;hydrochloride Chemical compound Cl.CC#C UWECIPNAXRKCIZ-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- 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
- C07D211/20—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- 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
- C07D211/26—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 with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—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 with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
- 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
- C07D211/30—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 with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NL8500347A 1984-02-08 1985-02-07 Fenylpropargylaminederivaten, werkwijzen ter bereiding ervan, samenstellingen, die deze derivaten bevatten alsmede de toepassing daarvan. NL8500347A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB848403362A GB8403362D0 (en)	1984-02-08	1984-02-08	Compositions of matter
GB8403362		1984-02-08
GB848431375A GB8431375D0 (en)	1984-12-12	1984-12-12	Compositions of matter
GB8431375		1984-12-12

Publications (1)

Publication Number	Publication Date
NL8500347A true NL8500347A (nl)	1985-09-02

Family

ID=26287301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8500347A NL8500347A (nl)	1984-02-08	1985-02-07	Fenylpropargylaminederivaten, werkwijzen ter bereiding ervan, samenstellingen, die deze derivaten bevatten alsmede de toepassing daarvan.

Country Status (15)

Country	Link
US (1)	US4871748A (da)
AU (1)	AU588795B2 (da)
BE (1)	BE901681A (da)
BR (1)	BR8500554A (da)
CA (1)	CA1280420C (da)
CH (1)	CH665836A5 (da)
DD (1)	DD235554A5 (da)
DE (1)	DE3504412A1 (da)
DK (1)	DK54085A (da)
FR (1)	FR2559149B1 (da)
GB (1)	GB2153827B (da)
IL (1)	IL74231A (da)
IT (1)	IT1183330B (da)
LU (1)	LU85762A1 (da)
NL (1)	NL8500347A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5252586A (en) *	1990-09-28	1993-10-12	The Du Pont Merck Pharmaceutical Company	Ether derivatives of alkyl piperidines and pyrrolidines as antipsychotic agents
ES2154570B1 (es) *	1998-10-23	2001-10-16	Almirall Prodesfarma Sa	Nuevos compuestos de peperidina y su uso como raticidas.
ATE327673T1 (de) *	2001-08-23	2006-06-15	Bayer Cropscience Sa	Substituierte propargylamine

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1483709A (fr) *	1962-07-11	1967-06-09		Composés basiques se rattachant au butane et leur préparation
GB1055548A (en) *	1965-08-23	1967-01-18	Acraf	New substituted 1-aryl-3-aminopropynes and process for their preparation
US4180574A (en) *	1978-12-26	1979-12-25	Abbott Laboratories	Certain ovicidal piperazines
US4285957A (en) *	1979-04-10	1981-08-25	Richardson-Merrell Inc.	1-Piperidine-alkanol derivatives, pharmaceutical compositions thereof, and method of use thereof
ZA813127B (en) *	1980-05-13	1982-05-26	May & Baker Ltd	A new phenylpropargylamine derivative
US4634699A (en) *	1983-11-30	1987-01-06	Burroughs Wellcome Co.	Branched chain phenothiazine

1985
- 1985-01-23 US US06/693,729 patent/US4871748A/en not_active Expired - Fee Related
- 1985-01-31 FR FR8501530A patent/FR2559149B1/fr not_active Expired
- 1985-02-03 IL IL74231A patent/IL74231A/xx unknown
- 1985-02-06 CA CA000473676A patent/CA1280420C/en not_active Expired - Fee Related
- 1985-02-06 AU AU38487/85A patent/AU588795B2/en not_active Ceased
- 1985-02-06 LU LU85762A patent/LU85762A1/fr unknown
- 1985-02-06 DK DK54085A patent/DK54085A/da not_active Application Discontinuation
- 1985-02-07 BE BE0/214473A patent/BE901681A/fr not_active IP Right Cessation
- 1985-02-07 BR BR8500554A patent/BR8500554A/pt unknown
- 1985-02-07 CH CH562/85A patent/CH665836A5/fr not_active IP Right Cessation
- 1985-02-07 NL NL8500347A patent/NL8500347A/nl not_active Application Discontinuation
- 1985-02-07 GB GB08503123A patent/GB2153827B/en not_active Expired
- 1985-02-08 DD DD85273149A patent/DD235554A5/de unknown
- 1985-02-08 DE DE19853504412 patent/DE3504412A1/de not_active Withdrawn
- 1985-02-08 IT IT19442/85A patent/IT1183330B/it active

Also Published As

Publication number	Publication date
CA1280420C (en)	1991-02-19
LU85762A1 (fr)	1986-09-02
AU588795B2 (en)	1989-09-28
DD235554A5 (de)	1986-05-14
IT1183330B (it)	1987-10-22
IL74231A (en)	1988-10-31
GB8503123D0 (en)	1985-03-13
BE901681A (fr)	1985-08-07
GB2153827A (en)	1985-08-29
BR8500554A (pt)	1985-09-24
DE3504412A1 (de)	1985-08-08
CH665836A5 (fr)	1988-06-15
US4871748A (en)	1989-10-03
GB2153827B (en)	1987-10-21
FR2559149B1 (fr)	1989-11-24
IT8519442A0 (it)	1985-02-08
AU3848785A (en)	1985-08-15
IL74231A0 (en)	1985-05-31
DK54085A (da)	1985-08-09
FR2559149A1 (fr)	1985-08-09
DK54085D0 (da)	1985-02-06

Legal Events

Date	Code	Title	Description
1992-04-01	BV	The patent application has lapsed

Publication	Publication Date	Title
WO2017075910A1 (zh)	2017-05-11	吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途
RO113988B1 (ro)	1998-12-30	Derivati de 1,2,4,5-tetrazina 3,6-disubstituiti si procedeu de obtinere a acestora
AT389800B (de)	1990-01-25	Fungizides mittel
EP0041324B1 (en)	1983-06-08	A new phenylpropargylamine derivative
IE59964B1 (en)	1994-05-04	Six-membered heterocyclic derivatives of n'-substituted-n, n'-diacylhydrazines
NL8500347A (nl)	1985-09-02	Fenylpropargylaminederivaten, werkwijzen ter bereiding ervan, samenstellingen, die deze derivaten bevatten alsmede de toepassing daarvan.
US4087534A (en)	1978-05-02	N-haloalkylmio urazole pesticides
CN110156685B (zh)	2020-07-17	芳香的环戊烯并吡啶及其合成方法和应用
JPS5925789B2 (ja)	1984-06-21	チアゾリリデン−オキソ−プロピオニトリル、その製造法並びに該化合物を含有する殺虫剤
JPS5933239A (ja)	1984-02-23	幼若ホルモン活性及び殺ダニ活性を有する１−フエノキシ（フエニルチオ）−４−アリ−ルアルキニルオキシベンゼン誘導体
US4156780A (en)	1979-05-29	3-Pyridylmethylthiocarbamates
US4233289A (en)	1980-11-11	3-Pyridylmethylthiocarbamates
AT388916B (de)	1989-09-25	Verfahren zur herstellung von neuen phenylpropargylaminderivaten und deren saeureadditionssalzen
US3966947A (en)	1976-06-29	Pyridyl phenyl-carbamate rodenticide
US4033972A (en)	1977-07-05	3-Pyridylmethyl-(N-substituted phenyl)-carbamate derivatives
NO143742B (no)	1980-12-29	Rodenticide 1-(3-pyridylmetyl)-3-(4`-substituert fenyl- eller -naftyl)-urinstoff-derivater
KR810000268B1 (ko)	1981-03-26	3-피리딜메틸 n-(4-치환된 페닐)티오카르바메이트의 제조방법
US4297342A (en)	1981-10-27	3-Pyridylmethylthiocarbamates
CH640698A5 (fr)	1984-01-31	Composition herbicide.
US3969357A (en)	1976-07-13	3-Pyridylmethyl phenyl urea metal salt complexes
CN101735199A (zh)	2010-06-16	邻甲酰胺基苯甲酰吡唑类化合物及其制备方法和应用
JPS60188369A (ja)	1985-09-25	新規なフエニルプロパルギルアミン誘導体
KR800000750B1 (ko)	1980-08-02	3-피리딜메틸페닐 우레아 금속복염의 제조방법
JPS6216921B2 (da)	1987-04-15
JPH06340508A (ja)	1994-12-13	軟体動物駆除剤