DE2711928A1 - Acetanilidderivate, sie enthaltende herbizide mittel und ihre verwendung - Google Patents
Acetanilidderivate, sie enthaltende herbizide mittel und ihre verwendungInfo
- Publication number
- DE2711928A1 DE2711928A1 DE19772711928 DE2711928A DE2711928A1 DE 2711928 A1 DE2711928 A1 DE 2711928A1 DE 19772711928 DE19772711928 DE 19772711928 DE 2711928 A DE2711928 A DE 2711928A DE 2711928 A1 DE2711928 A1 DE 2711928A1
- Authority
- DE
- Germany
- Prior art keywords
- tert
- butyl
- acetanilide
- compounds
- group
- 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
- 230000002363 herbicidal effect Effects 0.000 title claims description 33
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 134
- 241000196324 Embryophyta Species 0.000 claims description 41
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 32
- 235000021536 Sugar beet Nutrition 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- -1 tert-butyl-2,6'-dichloro-N- (isobutoxymethyl) acetanilide Chemical compound 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229960001413 acetanilide Drugs 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 150000008061 acetanilides Chemical class 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 244000068988 Glycine max Species 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 5
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- 235000007164 Oryza sativa Nutrition 0.000 claims description 5
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 235000009566 rice Nutrition 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 240000006394 Sorghum bicolor Species 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- RKAMAEHVSGTUEI-UHFFFAOYSA-N C(C)(C)(C)C1=C(N(C(CCl)=O)COC(C)C)C(=CC=C1)Cl Chemical compound C(C)(C)(C)C1=C(N(C(CCl)=O)COC(C)C)C(=CC=C1)Cl RKAMAEHVSGTUEI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 244000045561 useful plants Species 0.000 claims description 2
- TUEZZFCIJOJMLB-UHFFFAOYSA-N CCCCC(C(N(COCC)C1=CC=CC=C1Cl)=O)Br Chemical compound CCCCC(C(N(COCC)C1=CC=CC=C1Cl)=O)Br TUEZZFCIJOJMLB-UHFFFAOYSA-N 0.000 claims 1
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- 230000000694 effects Effects 0.000 description 48
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
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- 238000004458 analytical method Methods 0.000 description 11
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- 239000003921 oil Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 241000287828 Gallus gallus Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000003931 anilides Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 6
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- SSKOQDSCQVSEGT-UHFFFAOYSA-N 2-tert-butyl-6-chloroaniline Chemical compound CC(C)(C)C1=CC=CC(Cl)=C1N SSKOQDSCQVSEGT-UHFFFAOYSA-N 0.000 description 4
- 235000011293 Brassica napus Nutrition 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 241000209510 Liliopsida Species 0.000 description 3
- MHIUHSXAIQZNPU-UHFFFAOYSA-N N-(2-tert-butyl-6-chlorophenyl)-2-chloro-N-(methoxymethyl)acetamide Chemical compound C(C)(C)(C)C1=C(N(C(CCl)=O)COC)C(=CC=C1)Cl MHIUHSXAIQZNPU-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 231100000208 phytotoxic Toxicity 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YXNAWCUIZOCJNG-UHFFFAOYSA-N 2-iodo-n-phenylacetamide Chemical class ICC(=O)NC1=CC=CC=C1 YXNAWCUIZOCJNG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 244000025254 Cannabis sativa 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 239000007900 aqueous suspension Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
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- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
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- GBXKJPOXVQNHEC-UHFFFAOYSA-N n-(2-tert-butyl-6-chlorophenyl)-2-chloroacetamide Chemical compound CC(C)(C)C1=CC=CC(Cl)=C1NC(=O)CCl GBXKJPOXVQNHEC-UHFFFAOYSA-N 0.000 description 2
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- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- QFMPPVCBYDNCLP-UHFFFAOYSA-N 2-bromo-n-(2-tert-butyl-6-chlorophenyl)acetamide Chemical class CC(C)(C)C1=CC=CC(Cl)=C1NC(=O)CBr QFMPPVCBYDNCLP-UHFFFAOYSA-N 0.000 description 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
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- KNVBYGNINQITJC-UHFFFAOYSA-N 2-chloro-n-(3-chlorophenyl)acetamide Chemical class ClCC(=O)NC1=CC=CC(Cl)=C1 KNVBYGNINQITJC-UHFFFAOYSA-N 0.000 description 1
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
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- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66877076A | 1976-03-19 | 1976-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2711928A1 true DE2711928A1 (de) | 1977-10-06 |
Family
ID=24683658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772711928 Pending DE2711928A1 (de) | 1976-03-19 | 1977-03-18 | Acetanilidderivate, sie enthaltende herbizide mittel und ihre verwendung |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS52113927A (cs) |
| AU (1) | AU2336677A (cs) |
| BE (1) | BE852621A (cs) |
| BR (1) | BR7701680A (cs) |
| CS (1) | CS193088B2 (cs) |
| DD (1) | DD130905A5 (cs) |
| DE (1) | DE2711928A1 (cs) |
| DK (1) | DK120377A (cs) |
| FR (1) | FR2344524A1 (cs) |
| GB (1) | GB1546029A (cs) |
| GR (1) | GR64413B (cs) |
| IT (1) | IT1113764B (cs) |
| LU (1) | LU76981A1 (cs) |
| NL (1) | NL7702888A (cs) |
| PL (1) | PL103793B1 (cs) |
| SE (1) | SE7703105L (cs) |
| SU (1) | SU659065A3 (cs) |
| TR (1) | TR19420A (cs) |
| ZA (1) | ZA771642B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153543B (da) * | 1979-04-24 | 1988-07-25 | Mta Mezoegazdasagi Kutato | Fremgangsmaade til fremstilling af 2',6'-dialkyl-n-alkoxymethyl-2-chlor-acetanilider |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK157189C (da) * | 1980-03-25 | 1990-04-23 | Monsanto Co | I 6'-stillingen eventuelt med alkyl substituerede n-(0-substitueret-oxy-methyl)-2'-trifluormethyl-2-chlor-acetanilider og herbicide blandinger indeholdende disse |
| WO1992017441A1 (en) * | 1991-04-04 | 1992-10-15 | Zeneca Limited | Process for conducting chemical reactions with formaldehyde |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788215A (fr) * | 1971-09-01 | 1973-02-28 | Ciba Geigy | Haloacetanilides utiles comme herbicides |
| CH579348A5 (cs) * | 1973-02-08 | 1976-09-15 | Ciba Geigy Ag |
-
1977
- 1977-03-15 PL PL1977196669A patent/PL103793B1/pl unknown
- 1977-03-17 NL NL7702888A patent/NL7702888A/xx not_active Application Discontinuation
- 1977-03-17 IT IT21387/77A patent/IT1113764B/it active
- 1977-03-17 TR TR19420A patent/TR19420A/xx unknown
- 1977-03-18 BE BE175903A patent/BE852621A/xx unknown
- 1977-03-18 JP JP3100477A patent/JPS52113927A/ja active Pending
- 1977-03-18 BR BR7701680A patent/BR7701680A/pt unknown
- 1977-03-18 DK DK120377A patent/DK120377A/da not_active IP Right Cessation
- 1977-03-18 AU AU23366/77A patent/AU2336677A/en not_active Expired
- 1977-03-18 ZA ZA00771642A patent/ZA771642B/xx unknown
- 1977-03-18 LU LU76981A patent/LU76981A1/xx unknown
- 1977-03-18 GB GB11507/77A patent/GB1546029A/en not_active Expired
- 1977-03-18 FR FR7708246A patent/FR2344524A1/fr not_active Withdrawn
- 1977-03-18 SU SU772460813A patent/SU659065A3/ru active
- 1977-03-18 CS CS771805A patent/CS193088B2/cs unknown
- 1977-03-18 GR GR53038A patent/GR64413B/el unknown
- 1977-03-18 DD DD7700197927A patent/DD130905A5/xx unknown
- 1977-03-18 DE DE19772711928 patent/DE2711928A1/de active Pending
- 1977-03-18 SE SE7703105A patent/SE7703105L/xx not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK153543B (da) * | 1979-04-24 | 1988-07-25 | Mta Mezoegazdasagi Kutato | Fremgangsmaade til fremstilling af 2',6'-dialkyl-n-alkoxymethyl-2-chlor-acetanilider |
Also Published As
| Publication number | Publication date |
|---|---|
| DD130905A5 (de) | 1978-05-17 |
| NL7702888A (nl) | 1977-09-21 |
| IT1113764B (it) | 1986-01-20 |
| FR2344524A1 (fr) | 1977-10-14 |
| PL196669A1 (pl) | 1978-01-02 |
| TR19420A (tr) | 1979-03-19 |
| AU2336677A (en) | 1978-09-21 |
| PL103793B1 (pl) | 1979-07-31 |
| DK120377A (da) | 1977-09-20 |
| CS193088B2 (en) | 1979-09-17 |
| BR7701680A (pt) | 1977-11-08 |
| LU76981A1 (cs) | 1977-10-03 |
| BE852621A (fr) | 1977-09-19 |
| ZA771642B (en) | 1978-02-22 |
| SU659065A3 (en) | 1979-04-25 |
| GR64413B (en) | 1980-03-21 |
| JPS52113927A (en) | 1977-09-24 |
| SE7703105L (sv) | 1977-09-20 |
| GB1546029A (en) | 1979-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |