DD262860A5 - Verfahren zur herstellung eines nikotinsaeurederivats - Google Patents
Verfahren zur herstellung eines nikotinsaeurederivats Download PDFInfo
- Publication number
- DD262860A5 DD262860A5 DD87308879A DD30887987A DD262860A5 DD 262860 A5 DD262860 A5 DD 262860A5 DD 87308879 A DD87308879 A DD 87308879A DD 30887987 A DD30887987 A DD 30887987A DD 262860 A5 DD262860 A5 DD 262860A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- formula
- halogen
- phenyl
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- -1 C ^ -alkyl Inorganic materials 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004692 metal hydroxides Chemical class 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 11
- 230000000855 fungicidal effect Effects 0.000 abstract description 7
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 150000003983 crown ethers Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- QIEFSGIIZDXFQK-UHFFFAOYSA-N octyl 2-cyanopyridine-3-carboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=CN=C1C#N QIEFSGIIZDXFQK-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WKJBWVWIKUPFHI-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-cyanopyridine-3-carboxylate Chemical compound CCOC(=O)COC(=O)C1=CC=CN=C1C#N WKJBWVWIKUPFHI-UHFFFAOYSA-N 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
- JGNFPTQBLAXJCJ-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-cyanopyridine-3-carboxylate Chemical compound ClC(Cl)(Cl)COC(=O)C1=CC=CN=C1C#N JGNFPTQBLAXJCJ-UHFFFAOYSA-N 0.000 description 1
- XKTPVUNCEFBYHP-UHFFFAOYSA-N 2-cyanopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C#N XKTPVUNCEFBYHP-UHFFFAOYSA-N 0.000 description 1
- JCGQFHHEGGKIKF-UHFFFAOYSA-N 2-cyanopyridine-3-carboxylic acid;n-propan-2-ylpropan-2-amine Chemical compound CC(C)[NH2+]C(C)C.[O-]C(=O)C1=CC=CN=C1C#N JCGQFHHEGGKIKF-UHFFFAOYSA-N 0.000 description 1
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 description 1
- MTRCYQLWASUJPX-UHFFFAOYSA-N 2-pyridin-2-ylethyl 2-cyanopyridine-3-carboxylate Chemical compound C=1C=CN=C(C#N)C=1C(=O)OCCC1=CC=CC=N1 MTRCYQLWASUJPX-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- BKBMACKZOSMMGT-UHFFFAOYSA-N methanol;toluene Chemical compound OC.CC1=CC=CC=C1 BKBMACKZOSMMGT-UHFFFAOYSA-N 0.000 description 1
- ANPYBZGPGODWJD-UHFFFAOYSA-N methyl 2-cyanopyridine-3-carboxylate Chemical compound COC(=O)C1=CC=CN=C1C#N ANPYBZGPGODWJD-UHFFFAOYSA-N 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- LOCWKKNHXBLMQP-UHFFFAOYSA-M potassium;2-cyanopyridine-3-carboxylate Chemical compound [K+].[O-]C(=O)C1=CC=CN=C1C#N LOCWKKNHXBLMQP-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8607260A FR2598708B1 (fr) | 1986-05-16 | 1986-05-16 | Compositions fongicides a base de derives nicotiniques, nouveaux derives nicotiniques et leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD262860A5 true DD262860A5 (de) | 1988-12-14 |
Family
ID=9335463
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87308879A DD262860A5 (de) | 1986-05-16 | 1987-05-14 | Verfahren zur herstellung eines nikotinsaeurederivats |
| DD87302773A DD260644A5 (de) | 1986-05-16 | 1987-05-14 | Fungizide zusammensetzungen und ihre verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87302773A DD260644A5 (de) | 1986-05-16 | 1987-05-14 | Fungizide zusammensetzungen und ihre verwendung |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4851396A (pt) |
| EP (1) | EP0246171A3 (pt) |
| JP (1) | JPS62277361A (pt) |
| KR (1) | KR870011096A (pt) |
| CN (1) | CN87103572A (pt) |
| AU (1) | AU601182B2 (pt) |
| BR (1) | BR8702502A (pt) |
| DD (2) | DD262860A5 (pt) |
| DK (1) | DK245787A (pt) |
| FI (1) | FI872151A (pt) |
| FR (1) | FR2598708B1 (pt) |
| HU (1) | HUT46669A (pt) |
| IL (1) | IL82409A0 (pt) |
| MA (1) | MA20975A1 (pt) |
| NZ (1) | NZ220329A (pt) |
| OA (1) | OA08599A (pt) |
| PL (1) | PL277031A1 (pt) |
| PT (1) | PT84883B (pt) |
| TN (1) | TNSN87067A1 (pt) |
| ZA (1) | ZA873510B (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999012907A1 (fr) * | 1997-09-10 | 1999-03-18 | Dainippon Ink And Chemicals, Inc. | Derives de 2,6-dichloro-4-pyridinemethanol et produits chimiques utilises en agriculture |
| AU7484400A (en) * | 1999-09-15 | 2001-04-17 | Summus Group, Ltd. | Methods for controlling a pest population |
| US9074289B2 (en) | 2011-11-08 | 2015-07-07 | Nalco Company | Environmentally friendly corrosion inhibitor |
| JP6212773B2 (ja) * | 2013-08-01 | 2017-10-18 | アグロカネショウ株式会社 | ２−アミノニコチン酸ベンジル誘導体およびこれを有効成分とする殺菌剤 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2623189B1 (fr) * | 1987-11-12 | 1990-02-23 | Rhone Poulenc Agrochimie | Derives nicotiniques fongicides |
| FR2623190B1 (fr) * | 1987-11-12 | 1990-02-23 | Rhone Poulenc Agrochimie | Nicotinates d'oximes fongicides |
-
1986
- 1986-05-16 FR FR8607260A patent/FR2598708B1/fr not_active Expired
-
1987
- 1987-05-01 IL IL82409A patent/IL82409A0/xx unknown
- 1987-05-12 MA MA21213A patent/MA20975A1/fr unknown
- 1987-05-14 DK DK245787A patent/DK245787A/da not_active Application Discontinuation
- 1987-05-14 DD DD87308879A patent/DD262860A5/de not_active IP Right Cessation
- 1987-05-14 DD DD87302773A patent/DD260644A5/de not_active IP Right Cessation
- 1987-05-14 EP EP87420126A patent/EP0246171A3/fr not_active Withdrawn
- 1987-05-15 AU AU72999/87A patent/AU601182B2/en not_active Ceased
- 1987-05-15 PT PT84883A patent/PT84883B/pt not_active IP Right Cessation
- 1987-05-15 FI FI872151A patent/FI872151A/fi not_active Application Discontinuation
- 1987-05-15 JP JP62118727A patent/JPS62277361A/ja active Pending
- 1987-05-15 ZA ZA873510A patent/ZA873510B/xx unknown
- 1987-05-15 BR BR8702502A patent/BR8702502A/pt unknown
- 1987-05-15 HU HU872189A patent/HUT46669A/hu unknown
- 1987-05-15 OA OA59123A patent/OA08599A/xx unknown
- 1987-05-15 CN CN198787103572A patent/CN87103572A/zh active Pending
- 1987-05-15 KR KR870004828A patent/KR870011096A/ko not_active Application Discontinuation
- 1987-05-15 NZ NZ220329A patent/NZ220329A/xx unknown
- 1987-05-15 PL PL27703187A patent/PL277031A1/xx unknown
- 1987-05-18 TN TNTNSN87067A patent/TNSN87067A1/fr unknown
- 1987-05-18 US US07/050,487 patent/US4851396A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU601182B2 (en) | 1990-09-06 |
| BR8702502A (pt) | 1988-02-23 |
| KR870011096A (ko) | 1987-12-19 |
| DD260644A5 (de) | 1988-10-05 |
| PT84883B (pt) | 1990-02-08 |
| OA08599A (fr) | 1988-11-30 |
| AU7299987A (en) | 1987-11-19 |
| EP0246171A2 (fr) | 1987-11-19 |
| FR2598708B1 (fr) | 1988-06-24 |
| US4851396A (en) | 1989-07-25 |
| FI872151A (fi) | 1987-11-17 |
| NZ220329A (en) | 1989-08-29 |
| CN87103572A (zh) | 1988-01-13 |
| FI872151A0 (fi) | 1987-05-15 |
| ZA873510B (en) | 1987-11-10 |
| JPS62277361A (ja) | 1987-12-02 |
| DK245787D0 (da) | 1987-05-14 |
| FR2598708A1 (fr) | 1987-11-20 |
| TNSN87067A1 (fr) | 1990-01-01 |
| PL277031A1 (en) | 1990-03-19 |
| MA20975A1 (fr) | 1987-12-31 |
| HUT46669A (en) | 1988-11-28 |
| EP0246171A3 (fr) | 1990-05-02 |
| PT84883A (fr) | 1987-06-01 |
| IL82409A0 (en) | 1987-11-30 |
| DK245787A (da) | 1987-11-17 |
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