DE2548231A1 - 1-(bis-trifluormethylphenyl)-2-oxo- pyrrolidin-4-carbonsaeurederivate, deren herstellung und verwendung als pflanzenwachstumsregulatoren und herbizide - Google Patents
1-(bis-trifluormethylphenyl)-2-oxo- pyrrolidin-4-carbonsaeurederivate, deren herstellung und verwendung als pflanzenwachstumsregulatoren und herbizideInfo
- Publication number
- DE2548231A1 DE2548231A1 DE19752548231 DE2548231A DE2548231A1 DE 2548231 A1 DE2548231 A1 DE 2548231A1 DE 19752548231 DE19752548231 DE 19752548231 DE 2548231 A DE2548231 A DE 2548231A DE 2548231 A1 DE2548231 A1 DE 2548231A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- formula
- bis
- trifluoromethylphenyl
- oxo
- 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.)
- Ceased
Links
- -1 BIS-TRIFLUOROMETHYLPHENYL Chemical class 0.000 title claims description 54
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000004009 herbicide Substances 0.000 title claims description 5
- 239000005648 plant growth regulator Substances 0.000 title description 2
- 239000004480 active ingredient Substances 0.000 claims description 65
- 241000196324 Embryophyta Species 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 10
- 235000013339 cereals Nutrition 0.000 claims description 10
- IVNOUUBBVOWAST-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 IVNOUUBBVOWAST-UHFFFAOYSA-N 0.000 claims description 9
- 241000209504 Poaceae Species 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 239000000969 carrier Substances 0.000 claims description 8
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- 150000002148 esters Chemical class 0.000 claims description 7
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 7
- 230000008635 plant growth Effects 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
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- 150000003839 salts Chemical class 0.000 claims description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- ZDGFPURRXYZUHZ-UHFFFAOYSA-N 1-[2,3-bis(trifluoromethyl)phenyl]-5-oxopyrrolidine-3-carboxylic acid Chemical class O=C1CC(C(=O)O)CN1C1=CC=CC(C(F)(F)F)=C1C(F)(F)F ZDGFPURRXYZUHZ-UHFFFAOYSA-N 0.000 claims description 3
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
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- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 3
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- 239000002585 base Substances 0.000 description 5
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- 241000219146 Gossypium Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- GZVHQYZRBCSHAI-UHFFFAOYSA-N 5-oxopyrrolidine-3-carboxylic acid Chemical compound OC(=O)C1CNC(=O)C1 GZVHQYZRBCSHAI-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
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- 159000000014 iron salts Chemical class 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BKXLGJXTKLGAAZ-UHFFFAOYSA-N methyl 1-[3,5-bis(trifluoromethyl)phenyl]-5-oxopyrrolidine-3-carboxylate Chemical compound O=C1CC(C(=O)OC)CN1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BKXLGJXTKLGAAZ-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- UIEGFKRJSQEKNB-UHFFFAOYSA-N naphthalene-1-sulfonic acid phenol Chemical compound Oc1ccccc1.OS(=O)(=O)c1cccc2ccccc12 UIEGFKRJSQEKNB-UHFFFAOYSA-N 0.000 description 1
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- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
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- 239000010695 polyglycol Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical class 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1459574A CH611773A5 (en, 2012) | 1974-10-31 | 1974-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2548231A1 true DE2548231A1 (de) | 1976-05-06 |
Family
ID=4402184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752548231 Ceased DE2548231A1 (de) | 1974-10-31 | 1975-10-28 | 1-(bis-trifluormethylphenyl)-2-oxo- pyrrolidin-4-carbonsaeurederivate, deren herstellung und verwendung als pflanzenwachstumsregulatoren und herbizide |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4013445A (en, 2012) |
| JP (1) | JPS51125745A (en, 2012) |
| AR (1) | AR217232A1 (en, 2012) |
| AT (1) | AT345317B (en, 2012) |
| AU (1) | AU507492B2 (en, 2012) |
| BE (1) | BE835040A (en, 2012) |
| BR (1) | BR7507116A (en, 2012) |
| CA (1) | CA1083574A (en, 2012) |
| CH (1) | CH611773A5 (en, 2012) |
| CS (1) | CS193531B2 (en, 2012) |
| DD (1) | DD124728A5 (en, 2012) |
| DE (1) | DE2548231A1 (en, 2012) |
| DK (1) | DK430975A (en, 2012) |
| ES (1) | ES442215A1 (en, 2012) |
| FR (1) | FR2289498A1 (en, 2012) |
| GB (1) | GB1522686A (en, 2012) |
| GR (1) | GR58590B (en, 2012) |
| IL (1) | IL48381A (en, 2012) |
| IT (1) | IT1044089B (en, 2012) |
| NL (1) | NL7512672A (en, 2012) |
| PL (1) | PL102551B1 (en, 2012) |
| SE (1) | SE405852B (en, 2012) |
| SU (1) | SU584739A3 (en, 2012) |
| TR (1) | TR18917A (en, 2012) |
| ZA (1) | ZA756836B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187185A (en) * | 1988-12-09 | 1993-02-16 | Rhone-Poulenc Ag Company | Pesticidal 1-arylpyrroles |
| CH618682A5 (en, 2012) * | 1975-11-07 | 1980-08-15 | Ciba Geigy Ag | |
| US4097260A (en) * | 1975-11-28 | 1978-06-27 | Monsanto Company | 2-Substituted-1,3(2H,4H)-isoquinolinediones as plant growth regulants |
| DE2928305A1 (de) * | 1979-07-13 | 1981-02-05 | Hoechst Ag | 2-dihalogenmethylen-3-halogen-3- carboalkoxy-5-oxopyrrolidine, verfahren zu ihrer herstellung und ihre verwendung als fungizide, bakterizide und algizide schaedlingsbekaempfungsmittel |
| US4344788A (en) * | 1980-07-15 | 1982-08-17 | Gaf Corporation | Method of plant growth regulation |
| US4643762A (en) * | 1984-08-27 | 1987-02-17 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(3-substituted-phenyl)-4-pyrroline and derivatives thereof |
| US4874422A (en) * | 1988-12-27 | 1989-10-17 | Ici Americas Inc. | 1-Phenyl-3-carboxyamidopyrrolidones and their use as herbicides |
| EP0397602A1 (de) * | 1989-05-12 | 1990-11-14 | Ciba-Geigy Ag | Neue N-Phenylpyrrolidine |
| CA2371618A1 (en) * | 1999-04-28 | 2000-11-09 | Yuji Ishihara | Cyclic amide compounds, their production and use |
| RU2195447C1 (ru) * | 2001-07-31 | 2002-12-27 | Кубанский государственный технологический университет | 1-(4-нитрофенил)-4-n-x-аминопирролидоны-2, проявляющие рострегулирующую и антистрессовую активность, и способ их получения |
| US7064211B2 (en) * | 2002-03-22 | 2006-06-20 | Eisai Co., Ltd. | Hemiasterlin derivatives and uses thereof |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| BRPI0512410A (pt) * | 2004-06-24 | 2008-03-04 | Incyte Corp | compostos de amido e seu uso como produtos farmacêuticos |
| EP1773773A4 (en) * | 2004-06-24 | 2009-07-29 | Incyte Corp | AMID COMPOUNDS AND THEIR USE AS MEDICAMENTS |
| JP2008504280A (ja) * | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | ２−メチルプロパンアミドおよびその医薬としての使用 |
| NZ551603A (en) | 2004-06-24 | 2010-11-26 | Incyte Corp | N-substituted piperidines and their use as pharmaceuticals |
| WO2006020598A2 (en) * | 2004-08-10 | 2006-02-23 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| US20070213311A1 (en) * | 2006-03-02 | 2007-09-13 | Yun-Long Li | Modulators of 11-beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| US20070208001A1 (en) * | 2006-03-03 | 2007-09-06 | Jincong Zhuo | Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| EP2013163A1 (en) * | 2006-05-01 | 2009-01-14 | Incyte Corporation | Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1 |
| JP2009537564A (ja) * | 2006-05-17 | 2009-10-29 | インサイト・コーポレイション | １１−βヒドロキシルステロイドデヒドロゲナーゼタイプＩの複素環阻害剤およびそれを用いる方法 |
| KR102070057B1 (ko) * | 2012-03-19 | 2020-01-29 | 제이에스알 가부시끼가이샤 | 포토레지스트 조성물, 화합물 및 그의 제조 방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1053635A (en, 2012) * | 1961-12-18 | |||
| US3149954A (en) * | 1962-02-16 | 1964-09-22 | Du Pont | Method of retarding the growth of vegetation |
-
1973
- 1973-10-28 TR TR18917A patent/TR18917A/xx unknown
-
1974
- 1974-10-31 CH CH1459574A patent/CH611773A5/xx not_active IP Right Cessation
-
1975
- 1975-09-25 DK DK430975A patent/DK430975A/da not_active Application Discontinuation
- 1975-10-07 SE SE7511210A patent/SE405852B/xx unknown
- 1975-10-23 US US05/625,234 patent/US4013445A/en not_active Expired - Lifetime
- 1975-10-23 SU SU7502183002A patent/SU584739A3/ru active
- 1975-10-28 FR FR7532902A patent/FR2289498A1/fr active Granted
- 1975-10-28 DE DE19752548231 patent/DE2548231A1/de not_active Ceased
- 1975-10-29 PL PL1975184337A patent/PL102551B1/pl unknown
- 1975-10-29 IL IL48381A patent/IL48381A/xx unknown
- 1975-10-29 CA CA238,543A patent/CA1083574A/en not_active Expired
- 1975-10-29 DD DD189104A patent/DD124728A5/xx unknown
- 1975-10-29 NL NL7512672A patent/NL7512672A/xx not_active Application Discontinuation
- 1975-10-29 AR AR260985A patent/AR217232A1/es active
- 1975-10-30 CS CS757331A patent/CS193531B2/cs unknown
- 1975-10-30 GR GR49243A patent/GR58590B/el unknown
- 1975-10-30 GB GB45066/75A patent/GB1522686A/en not_active Expired
- 1975-10-30 IT IT28845/75A patent/IT1044089B/it active
- 1975-10-30 ZA ZA00756836A patent/ZA756836B/xx unknown
- 1975-10-30 AT AT826575A patent/AT345317B/de not_active IP Right Cessation
- 1975-10-30 ES ES442215A patent/ES442215A1/es not_active Expired
- 1975-10-30 BR BR7507116*A patent/BR7507116A/pt unknown
- 1975-10-30 AU AU86194/75A patent/AU507492B2/en not_active Expired
- 1975-10-30 BE BE161395A patent/BE835040A/xx not_active IP Right Cessation
- 1975-10-31 JP JP50132080A patent/JPS51125745A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU507492B2 (en) | 1980-02-14 |
| DD124728A5 (en, 2012) | 1977-03-09 |
| NL7512672A (nl) | 1976-05-04 |
| IL48381A0 (en) | 1975-12-31 |
| GB1522686A (en) | 1978-08-23 |
| CA1083574A (en) | 1980-08-12 |
| DK430975A (da) | 1976-05-01 |
| IT1044089B (it) | 1980-03-20 |
| SU584739A3 (ru) | 1977-12-15 |
| SE7511210L (sv) | 1976-05-03 |
| IL48381A (en) | 1979-07-25 |
| ZA756836B (en) | 1976-10-27 |
| GR58590B (en) | 1977-11-10 |
| BR7507116A (pt) | 1976-08-03 |
| FR2289498B1 (en, 2012) | 1978-09-22 |
| JPS51125745A (en) | 1976-11-02 |
| CH611773A5 (en, 2012) | 1979-06-29 |
| BE835040A (fr) | 1976-04-30 |
| ES442215A1 (es) | 1977-04-16 |
| TR18917A (tr) | 1977-12-09 |
| AU8619475A (en) | 1977-05-05 |
| US4013445A (en) | 1977-03-22 |
| AR217232A1 (es) | 1980-03-14 |
| AT345317B (de) | 1978-09-11 |
| PL102551B1 (pl) | 1979-04-30 |
| SE405852B (sv) | 1979-01-08 |
| ATA826575A (de) | 1978-01-15 |
| CS193531B2 (en) | 1979-10-31 |
| FR2289498A1 (fr) | 1976-05-28 |
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| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |