DE2437275A1 - Substituierte anilide - Google Patents
Substituierte anilideInfo
- Publication number
- DE2437275A1 DE2437275A1 DE19742437275 DE2437275A DE2437275A1 DE 2437275 A1 DE2437275 A1 DE 2437275A1 DE 19742437275 DE19742437275 DE 19742437275 DE 2437275 A DE2437275 A DE 2437275A DE 2437275 A1 DE2437275 A1 DE 2437275A1
- Authority
- DE
- Germany
- Prior art keywords
- spp
- substituted
- anilide
- acid
- methoxy
- 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.)
- Pending
Links
- 150000003931 anilides Chemical class 0.000 title description 5
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title description 4
- -1 halopropyl Chemical group 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229920005555 halobutyl Polymers 0.000 claims description 2
- 125000004968 halobutyl group Chemical group 0.000 claims description 2
- 125000004969 haloethyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- PBAJHDIBEJHZLU-UHFFFAOYSA-N n-(3,5-dichloro-4-ethoxyphenyl)cyclopropanecarboxamide Chemical compound C1=C(Cl)C(OCC)=C(Cl)C=C1NC(=O)C1CC1 PBAJHDIBEJHZLU-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 37
- 150000003839 salts Chemical class 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- 240000007594 Oryza sativa Species 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
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- 241000219146 Gossypium Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 235000013339 cereals Nutrition 0.000 description 6
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
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- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- 150000007513 acids Chemical class 0.000 description 4
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- 235000019438 castor oil Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- DHDUCYGPRJSVKL-UHFFFAOYSA-N ClC=1C=C(NC(C(C)C)=O)C=C(C1OC)Cl Chemical compound ClC=1C=C(NC(C(C)C)=O)C=C(C1OC)Cl DHDUCYGPRJSVKL-UHFFFAOYSA-N 0.000 description 3
- NXJWREHARJTWCL-UHFFFAOYSA-N ClC=1C=C(NC(C(CCC)C)=O)C=C(C1OC)Cl Chemical compound ClC=1C=C(NC(C(CCC)C)=O)C=C(C1OC)Cl NXJWREHARJTWCL-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000192043 Echinochloa Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001101998 Galium Species 0.000 description 3
- 244000100545 Lolium multiflorum Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XZSXUNOTSHOAEO-UHFFFAOYSA-N N-(3,5-dichloro-4-methoxyphenyl)cyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NC1=CC(=C(C(=C1)Cl)OC)Cl XZSXUNOTSHOAEO-UHFFFAOYSA-N 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000009973 maize Nutrition 0.000 description 3
- BDRBKTYHSXFGLC-UHFFFAOYSA-N n-(3,5-dichloro-4-methoxyphenyl)propanamide Chemical compound CCC(=O)NC1=CC(Cl)=C(OC)C(Cl)=C1 BDRBKTYHSXFGLC-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- 241000743985 Alopecurus Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
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- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- JLEBHXDGKBOVPZ-UHFFFAOYSA-N BrC=1C=C(NC(C(C)C)=O)C=C(C1OC)Br Chemical compound BrC=1C=C(NC(C(C)C)=O)C=C(C1OC)Br JLEBHXDGKBOVPZ-UHFFFAOYSA-N 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
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- 235000014750 Brassica kaber Nutrition 0.000 description 2
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- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 2
- 241000219193 Brassicaceae Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000219071 Malvaceae Species 0.000 description 2
- 241000219823 Medicago Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- 241000220259 Raphanus Species 0.000 description 2
- 235000004789 Rosa xanthina Nutrition 0.000 description 2
- 241000220222 Rosaceae Species 0.000 description 2
- 241000220261 Sinapis 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
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- 235000002634 Solanum Nutrition 0.000 description 2
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- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
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- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742437275 DE2437275A1 (de) | 1974-08-02 | 1974-08-02 | Substituierte anilide |
| PH17396A PH12823A (en) | 1974-08-02 | 1975-07-18 | Substituted anilides |
| JP8893375A JPS5135423A (ja) | 1974-08-02 | 1975-07-22 | Josozai |
| NL7508859A NL7508859A (nl) | 1974-08-02 | 1975-07-24 | Gesubstitueerde aniliden. |
| CH996775A CH595759A5 (enExample) | 1974-08-02 | 1975-07-30 | |
| SU752162206A SU591122A3 (ru) | 1974-08-02 | 1975-07-30 | Гербицидный состав |
| DD18759975A DD119122A5 (enExample) | 1974-08-02 | 1975-07-31 | |
| IT5075275A IT1041096B (it) | 1974-08-02 | 1975-07-31 | Anilidi sostituite |
| FR7523991A FR2280630A1 (fr) | 1974-08-02 | 1975-07-31 | Derives de substitution d'anilides utiles comme herbicides |
| BE158839A BE831996A (fr) | 1974-08-02 | 1975-07-31 | Derives de substitution d'anilides utiles comme herbicides |
| CS539175A CS198173B2 (en) | 1974-08-02 | 1975-08-01 | Herbicide |
| ES439923A ES439923A1 (es) | 1974-08-02 | 1975-08-01 | Procedimiento para la obtencion de una anilida sustituida. |
| GB3222075A GB1507545A (en) | 1974-08-02 | 1975-08-01 | Halo-substituted alkoxy anilides and their herbicidal use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742437275 DE2437275A1 (de) | 1974-08-02 | 1974-08-02 | Substituierte anilide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2437275A1 true DE2437275A1 (de) | 1976-02-12 |
Family
ID=5922273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742437275 Pending DE2437275A1 (de) | 1974-08-02 | 1974-08-02 | Substituierte anilide |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5135423A (enExample) |
| BE (1) | BE831996A (enExample) |
| CH (1) | CH595759A5 (enExample) |
| CS (1) | CS198173B2 (enExample) |
| DD (1) | DD119122A5 (enExample) |
| DE (1) | DE2437275A1 (enExample) |
| ES (1) | ES439923A1 (enExample) |
| FR (1) | FR2280630A1 (enExample) |
| GB (1) | GB1507545A (enExample) |
| IT (1) | IT1041096B (enExample) |
| NL (1) | NL7508859A (enExample) |
| PH (1) | PH12823A (enExample) |
| SU (1) | SU591122A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3373810D1 (de) * | 1982-07-27 | 1987-10-29 | Sumitomo Chemical Co | Fungicidal anilides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219947B (de) * | 1963-05-22 | 1966-06-30 | Bayer Ag | Verfahren zur Herstellung von Carbonsaeureaniliden |
| CH489198A (de) * | 1967-10-19 | 1970-04-30 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| CH489993A (de) * | 1967-12-19 | 1970-05-15 | Ciba Geigy | Das Pflanzenwachstum regulierendes und phytocides Mittel |
-
1974
- 1974-08-02 DE DE19742437275 patent/DE2437275A1/de active Pending
-
1975
- 1975-07-18 PH PH17396A patent/PH12823A/en unknown
- 1975-07-22 JP JP8893375A patent/JPS5135423A/ja active Pending
- 1975-07-24 NL NL7508859A patent/NL7508859A/xx not_active Application Discontinuation
- 1975-07-30 SU SU752162206A patent/SU591122A3/ru active
- 1975-07-30 CH CH996775A patent/CH595759A5/xx not_active IP Right Cessation
- 1975-07-31 FR FR7523991A patent/FR2280630A1/fr active Granted
- 1975-07-31 IT IT5075275A patent/IT1041096B/it active
- 1975-07-31 BE BE158839A patent/BE831996A/xx unknown
- 1975-07-31 DD DD18759975A patent/DD119122A5/xx unknown
- 1975-08-01 ES ES439923A patent/ES439923A1/es not_active Expired
- 1975-08-01 CS CS539175A patent/CS198173B2/cs unknown
- 1975-08-01 GB GB3222075A patent/GB1507545A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1041096B (it) | 1980-01-10 |
| ES439923A1 (es) | 1977-03-01 |
| FR2280630B1 (enExample) | 1978-09-01 |
| DD119122A5 (enExample) | 1976-04-12 |
| SU591122A3 (ru) | 1978-01-30 |
| GB1507545A (en) | 1978-04-19 |
| NL7508859A (nl) | 1976-02-04 |
| CH595759A5 (enExample) | 1978-02-28 |
| FR2280630A1 (fr) | 1976-02-27 |
| PH12823A (en) | 1979-08-31 |
| JPS5135423A (ja) | 1976-03-25 |
| CS198173B2 (en) | 1980-05-30 |
| BE831996A (fr) | 1976-02-02 |
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