JPS6348865B2 - - Google Patents
Info
- Publication number
- JPS6348865B2 JPS6348865B2 JP3206879A JP3206879A JPS6348865B2 JP S6348865 B2 JPS6348865 B2 JP S6348865B2 JP 3206879 A JP3206879 A JP 3206879A JP 3206879 A JP3206879 A JP 3206879A JP S6348865 B2 JPS6348865 B2 JP S6348865B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- chloro
- pyridone
- yloxy
- melting point
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- -1 methanol and ethanol Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- BYRJSCNPUHYZQE-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyridin-2-one Chemical class OC1=CC=C(C(F)(F)F)C=N1 BYRJSCNPUHYZQE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 2
- YFSCXLSUZZXNHW-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyridine-2-thione Chemical compound FC(F)(F)C1=CC=C(S)N=C1 YFSCXLSUZZXNHW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000005181 nitrobenzenes Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BGKIECJVXXHLDP-UHFFFAOYSA-N 1,2,3-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1Cl BGKIECJVXXHLDP-UHFFFAOYSA-N 0.000 description 1
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 1
- ZRJSABISRHPRSB-UHFFFAOYSA-N 2,6-difluorobenzoyl isocyanate Chemical compound FC1=CC=CC(F)=C1C(=O)N=C=O ZRJSABISRHPRSB-UHFFFAOYSA-N 0.000 description 1
- KCLWRVQIRVOVLJ-UHFFFAOYSA-N 3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl KCLWRVQIRVOVLJ-UHFFFAOYSA-N 0.000 description 1
- JHDCDEHVUADNKQ-UHFFFAOYSA-N 3-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=NC=CC=C1C(F)(F)F JHDCDEHVUADNKQ-UHFFFAOYSA-N 0.000 description 1
- UWHKLLYQUQPOQK-UHFFFAOYSA-N 3-bromo-5-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=NC=C(C(F)(F)F)C=C1Br UWHKLLYQUQPOQK-UHFFFAOYSA-N 0.000 description 1
- AJPOOWWMZOPUCG-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=NC=C(C(F)(F)F)C=C1Cl AJPOOWWMZOPUCG-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000500441 Plutellidae Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000004083 survival effect 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
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3206879A JPS55124763A (en) | 1979-03-19 | 1979-03-19 | 5-trifluoromethyl-2-pyridone derivative |
| GB8007881A GB2049666B (en) | 1979-03-19 | 1980-03-07 | Trifluoromethyl-2-(thio) pyridone compound and process forpreparing the same |
| DE19803008908 DE3008908A1 (de) | 1979-03-19 | 1980-03-07 | Trifluoromethyl-2-(thio)-pyridon- verbindungen und verfahren zu deren herstellung |
| CA000347559A CA1134833A (en) | 1979-03-19 | 1980-03-13 | Trifluoromethyl-2-(thio)pyridone compounds and process for the preparation of the same |
| CH203480A CH642355A5 (de) | 1979-03-19 | 1980-03-14 | Trifluormethyl-2-(thio)-pyridon-verbindungen und verfahren zu deren herstellung. |
| IT48176/80A IT1147077B (it) | 1979-03-19 | 1980-03-17 | Composti di tricloronetil-2-(tio)-piridone e procedimento per prepararli |
| FR8006030A FR2451917A1 (fr) | 1979-03-19 | 1980-03-18 | Composes de trifluoromethyl-2-(thio) pyridone et leur preparation |
| BE0/199840A BE882284A (fr) | 1979-03-19 | 1980-03-18 | COMPOSES DE TRIFLUOROMETHYL-2(THIO)pYRIDONE ET LEUR PROCEDE DE PREPARATION |
| NL8001618A NL8001618A (nl) | 1979-03-19 | 1980-03-19 | Trifluormethyl-2-(thio)pyridonverbindingen en werkwijze voor het bereiden en toepassen van deze verbindingen. |
| US06/131,719 US4546191A (en) | 1979-03-19 | 1980-03-19 | Trifluoromethyl-2-pyridinone or pyridinthione compounds and process for the preparation of the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3206879A JPS55124763A (en) | 1979-03-19 | 1979-03-19 | 5-trifluoromethyl-2-pyridone derivative |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16459486A Division JPS6226270A (ja) | 1986-07-15 | 1986-07-15 | ５−トリフルオロメチル−２−ピリドン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55124763A JPS55124763A (en) | 1980-09-26 |
| JPS6348865B2 true JPS6348865B2 (enExample) | 1988-09-30 |
Family
ID=12348551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3206879A Granted JPS55124763A (en) | 1979-03-19 | 1979-03-19 | 5-trifluoromethyl-2-pyridone derivative |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4546191A (enExample) |
| JP (1) | JPS55124763A (enExample) |
| BE (1) | BE882284A (enExample) |
| CA (1) | CA1134833A (enExample) |
| CH (1) | CH642355A5 (enExample) |
| DE (1) | DE3008908A1 (enExample) |
| FR (1) | FR2451917A1 (enExample) |
| GB (1) | GB2049666B (enExample) |
| IT (1) | IT1147077B (enExample) |
| NL (1) | NL8001618A (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3308800A1 (de) * | 1983-03-12 | 1984-09-13 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur herstellung von 3,5,6-trichlor-1h-pyridin-2-on |
| GB8523126D0 (en) * | 1985-09-19 | 1985-10-23 | Ici Plc | Aryl pyridones |
| GB8621217D0 (en) * | 1986-09-03 | 1986-10-08 | Ici Plc | Chemical compounds |
| US7517880B2 (en) * | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| US7329670B1 (en) | 1997-12-22 | 2008-02-12 | Bayer Pharmaceuticals Corporation | Inhibition of RAF kinase using aryl and heteroaryl substituted heterocyclic ureas |
| US20080269265A1 (en) * | 1998-12-22 | 2008-10-30 | Scott Miller | Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| EP1140840B1 (en) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | -g(v)-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ME00275B (me) | 1999-01-13 | 2011-02-10 | Bayer Corp | ω-KARBOKSIARIL SUPSTITUISANI DIFENIL KARBAMIDI KAO INHIBITORI RAF KINAZE |
| EP2298311B1 (en) | 1999-01-13 | 2012-05-09 | Bayer HealthCare LLC | w-Carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| WO2002012243A2 (en) * | 2000-08-09 | 2002-02-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | SYNTHESIS OF (R)-3-(4-BROMOBENZYL)-1-(3,5-DICHLOROPHENYL)-5-IODO-3-METHYL-1-H-IMIDAZO[1,2-a]IMIDAZOL-2-ONE |
| MXPA04005137A (es) * | 2001-12-03 | 2005-06-03 | Bayer Pharmaceuticals Corp | Compuestos de aril urea en combinacion con otros agentes citostaticos para el tratamiento de canceres humanos. |
| US20030207872A1 (en) * | 2002-01-11 | 2003-11-06 | Bayer Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ES2425739T3 (es) | 2002-02-11 | 2013-10-17 | Bayer Healthcare Llc | Sorafenib-tosilato para el tratamiento de enfermedades caracterizadas por angiogénesis anormal |
| DK1580188T3 (da) * | 2002-02-11 | 2012-02-06 | Bayer Healthcare Llc | Forbindelser af arylurea som kinaseinhibitorer |
| US7557129B2 (en) | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| CA2526636C (en) * | 2003-05-20 | 2012-10-02 | Bayer Pharmaceuticals Corporation | Diaryl ureas for diseases mediated by pdgfr |
| BR122016015715B8 (pt) | 2003-07-23 | 2021-05-25 | Bayer Healthcare Llc | composições farmacêuticas de metilamida de ácido 4[4-[3-(4-cloro-3-trifluorometilfenil)-ureido]-3-fluorofenóxi)-piridina-2-carboxílico |
| CN102875453B (zh) * | 2012-06-08 | 2016-02-03 | 上海泰坦化学有限公司 | 一种用于合成抗癌辅助类药物的吡啶类医药中间体的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3355278A (en) * | 1961-03-13 | 1967-11-28 | Hooker Chemical Corp | Herbicidal composition and method |
| US3634435A (en) * | 1968-07-10 | 1972-01-11 | Sandoz Ltd | Certain s-(n-methylene-pyridone - (2)-o o-dilower-alkyl mono and dithio phosphates and derivatives |
| US3682938A (en) * | 1970-12-18 | 1972-08-08 | Dow Chemical Co | Bis(trifluoro methyl)-2-pyridinols |
| AR208500A1 (es) * | 1972-06-14 | 1977-02-15 | Merck & Co Inc | Procedimiento para la preparacion de derivados de oxazolo(4,5-b)-piridinas |
| US3974166A (en) * | 1973-07-10 | 1976-08-10 | Ciba-Geigy Corporation | Process for the manufacture of bromopyridines |
| DE2531202C2 (de) * | 1975-07-12 | 1982-12-09 | Bayer Ag, 5090 Leverkusen | 2',4-Dichlor-4'-benzoylureido- diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| JPS5840946B2 (ja) * | 1976-10-29 | 1983-09-08 | 石原産業株式会社 | Ｎ−ベンゾイル−ｎ′−ピリジルオキシフエニルウレア系化合物、それらの製造方法及びそれらを含有する殺虫剤 |
| JPS5461182A (en) * | 1977-10-20 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-phenoxy-5-trifluoromethylpyridine compounds |
| JPS5461183A (en) * | 1977-10-21 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-substituted-5-trifluoromethyl pyridine compounds |
| BE862325A (fr) * | 1977-12-27 | 1978-06-27 | Ciba Geigy | Nouveaux derives d'acide pyridyloxy-phenoxypropionique ayant une action herbicide et phytoregulatrice |
| US4230864A (en) * | 1979-01-29 | 1980-10-28 | Reilly Tar & Chemical Corp. | Process for making 5-trifluoromethyl pyridone |
| US4249009A (en) * | 1979-01-29 | 1981-02-03 | Reilly Tar & Chemical Corp. | Processes for preparing 2-chloro-5-trifluoromethylpyridine |
-
1979
- 1979-03-19 JP JP3206879A patent/JPS55124763A/ja active Granted
-
1980
- 1980-03-07 DE DE19803008908 patent/DE3008908A1/de active Granted
- 1980-03-07 GB GB8007881A patent/GB2049666B/en not_active Expired
- 1980-03-13 CA CA000347559A patent/CA1134833A/en not_active Expired
- 1980-03-14 CH CH203480A patent/CH642355A5/de not_active IP Right Cessation
- 1980-03-17 IT IT48176/80A patent/IT1147077B/it active
- 1980-03-18 BE BE0/199840A patent/BE882284A/fr not_active IP Right Cessation
- 1980-03-18 FR FR8006030A patent/FR2451917A1/fr active Granted
- 1980-03-19 NL NL8001618A patent/NL8001618A/nl not_active Application Discontinuation
- 1980-03-19 US US06/131,719 patent/US4546191A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55124763A (en) | 1980-09-26 |
| FR2451917B1 (enExample) | 1983-04-22 |
| DE3008908C2 (enExample) | 1989-09-21 |
| BE882284A (fr) | 1980-07-16 |
| GB2049666B (en) | 1983-04-27 |
| GB2049666A (en) | 1980-12-31 |
| US4546191A (en) | 1985-10-08 |
| CA1134833A (en) | 1982-11-02 |
| IT8048176A0 (it) | 1980-03-17 |
| FR2451917A1 (fr) | 1980-10-17 |
| IT1147077B (it) | 1986-11-19 |
| NL8001618A (nl) | 1980-09-23 |
| DE3008908A1 (de) | 1980-10-02 |
| CH642355A5 (de) | 1984-04-13 |
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