DE2339023A1 - Chinoxaline und sie enthaltende fungicide - Google Patents
Chinoxaline und sie enthaltende fungicideInfo
- Publication number
- DE2339023A1 DE2339023A1 DE2339023A DE2339023A DE2339023A1 DE 2339023 A1 DE2339023 A1 DE 2339023A1 DE 2339023 A DE2339023 A DE 2339023A DE 2339023 A DE2339023 A DE 2339023A DE 2339023 A1 DE2339023 A1 DE 2339023A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- amino
- chloro
- plants
- compound
- 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
- 239000000417 fungicide Substances 0.000 title claims description 6
- 150000003252 quinoxalines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 241000233866 Fungi Species 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- ZXXLWODXGLDCQG-UHFFFAOYSA-N n-(3-amino-6-chloroquinoxalin-2-yl)propanamide Chemical compound C1=C(Cl)C=C2N=C(N)C(NC(=O)CC)=NC2=C1 ZXXLWODXGLDCQG-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 26
- 241000221785 Erysiphales Species 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- -1 7-substituted diaminoquinoxalines Chemical class 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003359 percent control normalization Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- LUDZVVVPVCUUBP-UHFFFAOYSA-N quinoxaline-2,3-diamine Chemical compound C1=CC=C2N=C(N)C(N)=NC2=C1 LUDZVVVPVCUUBP-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical class N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- HUDLVTSAARMVED-GORDUTHDSA-N (e)-n-(3-aminoquinoxalin-2-yl)but-2-enamide Chemical compound C1=CC=C2N=C(N)C(NC(=O)/C=C/C)=NC2=C1 HUDLVTSAARMVED-GORDUTHDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- RQWVBQOUWJUMRS-UHFFFAOYSA-N 6-chloroquinoxaline-2,3-diamine Chemical compound C1=C(Cl)C=C2N=C(N)C(N)=NC2=C1 RQWVBQOUWJUMRS-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241001480059 Erysiphaceae Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- RKZXQQPEDGMHBJ-LIGJGSPWSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentakis[[(z)-octadec-9-enoyl]oxy]hexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RKZXQQPEDGMHBJ-LIGJGSPWSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Inorganic materials [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000005094 fruit set Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000011507 gypsum plaster Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- LAEPRBYXJDAHLX-UHFFFAOYSA-N n-(3-amino-6-chloroquinoxalin-2-yl)-3-bromopropanamide Chemical compound ClC1=CC=C2N=C(NC(=O)CCBr)C(N)=NC2=C1 LAEPRBYXJDAHLX-UHFFFAOYSA-N 0.000 description 1
- BTUHXJPSGFOXAQ-UHFFFAOYSA-N n-(3-amino-6-chloroquinoxalin-2-yl)prop-2-ynamide Chemical compound ClC1=CC=C2N=C(NC(=O)C#C)C(N)=NC2=C1 BTUHXJPSGFOXAQ-UHFFFAOYSA-N 0.000 description 1
- XLJHDMMTSGBZLN-UHFFFAOYSA-N n-(3-aminoquinoxalin-2-yl)acetamide Chemical compound C1=CC=C2N=C(N)C(NC(=O)C)=NC2=C1 XLJHDMMTSGBZLN-UHFFFAOYSA-N 0.000 description 1
- NRLVJQZRKYICRX-UHFFFAOYSA-N n-(3-aminoquinoxalin-2-yl)prop-2-enamide Chemical compound C1=CC=C2N=C(NC(=O)C=C)C(N)=NC2=C1 NRLVJQZRKYICRX-UHFFFAOYSA-N 0.000 description 1
- LDIKLDSKBJMACA-UHFFFAOYSA-N n-quinoxalin-2-ylpropanamide Chemical compound C1=CC=CC2=NC(NC(=O)CC)=CN=C21 LDIKLDSKBJMACA-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27760472A | 1972-08-01 | 1972-08-01 | |
| US36687773A | 1973-06-04 | 1973-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2339023A1 true DE2339023A1 (de) | 1974-02-14 |
Family
ID=26958587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2339023A Pending DE2339023A1 (de) | 1972-08-01 | 1973-08-01 | Chinoxaline und sie enthaltende fungicide |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4966830A (enExample) |
| AR (1) | AR198523A1 (enExample) |
| AU (1) | AU471863B2 (enExample) |
| BG (1) | BG21175A3 (enExample) |
| CH (1) | CH582991A5 (enExample) |
| DD (1) | DD107381A5 (enExample) |
| DE (1) | DE2339023A1 (enExample) |
| ES (1) | ES417395A1 (enExample) |
| FR (1) | FR2194705B1 (enExample) |
| GB (1) | GB1424602A (enExample) |
| IL (1) | IL42857A (enExample) |
| IT (1) | IT995103B (enExample) |
| NL (1) | NL7310659A (enExample) |
| RO (1) | RO69447A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4707261B2 (ja) * | 2001-05-15 | 2011-06-22 | 日本エンバイロケミカルズ株式会社 | キノキサリン系化合物および工業用殺菌組成物 |
-
1973
- 1973-07-30 CH CH1108973A patent/CH582991A5/xx not_active IP Right Cessation
- 1973-07-30 JP JP48085034A patent/JPS4966830A/ja active Pending
- 1973-07-30 AU AU58661/73A patent/AU471863B2/en not_active Expired
- 1973-07-30 ES ES417395A patent/ES417395A1/es not_active Expired
- 1973-07-31 AR AR249364A patent/AR198523A1/es active
- 1973-07-31 IL IL42857A patent/IL42857A/en unknown
- 1973-07-31 IT IT27344/73A patent/IT995103B/it active
- 1973-07-31 DD DD170575A patent/DD107381A5/xx unknown
- 1973-07-31 FR FR7328046A patent/FR2194705B1/fr not_active Expired
- 1973-08-01 DE DE2339023A patent/DE2339023A1/de active Pending
- 1973-08-01 GB GB3650073A patent/GB1424602A/en not_active Expired
- 1973-08-01 RO RO7375684A patent/RO69447A/ro unknown
- 1973-08-01 NL NL7310659A patent/NL7310659A/xx unknown
- 1973-08-01 BG BG024239A patent/BG21175A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5866173A (en) | 1975-01-30 |
| ES417395A1 (es) | 1976-07-16 |
| AR198523A1 (es) | 1974-06-28 |
| RO69447A (ro) | 1981-04-30 |
| JPS4966830A (enExample) | 1974-06-28 |
| IT995103B (it) | 1975-11-10 |
| FR2194705A1 (enExample) | 1974-03-01 |
| FR2194705B1 (enExample) | 1978-08-04 |
| IL42857A (en) | 1976-07-30 |
| CH582991A5 (enExample) | 1976-12-31 |
| GB1424602A (en) | 1976-02-11 |
| BG21175A3 (bg) | 1976-03-20 |
| AU471863B2 (en) | 1976-05-06 |
| IL42857A0 (en) | 1973-10-25 |
| NL7310659A (enExample) | 1974-02-05 |
| DD107381A5 (enExample) | 1974-08-05 |
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