KR840005158A - N-포스포노 메틸글리신의 제조방법 - Google Patents
N-포스포노 메틸글리신의 제조방법 Download PDFInfo
- Publication number
- KR840005158A KR840005158A KR1019830002953A KR830002953A KR840005158A KR 840005158 A KR840005158 A KR 840005158A KR 1019830002953 A KR1019830002953 A KR 1019830002953A KR 830002953 A KR830002953 A KR 830002953A KR 840005158 A KR840005158 A KR 840005158A
- Authority
- KR
- South Korea
- Prior art keywords
- phosphonomethylglycine
- producing
- formyl
- temperature
- reacting
- Prior art date
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims 14
- 238000000034 method Methods 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 claims 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- -1 diethylphosphonomethyl Chemical group 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 claims 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims 2
- 239000012312 sodium hydride Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- (a) 9∼10범위내의 pH로 포름알데히드를 포름아미드와 반응시켜 N-(히드록시메틸)포름 아미드를 형성하고; (b) N-(히드록시메틸) 포름아미드를 트리에틸 포스파이트와 반응시켜 디메틸, N-(포르밀) 아미노메틸포스포네이트를 형성하고; (c) 디에틸, N-(포르밀) 아미노메틸포스포네이트를 메틸클로로아세테이트와 반응시켜 N-(디에틸포스포노메틸), N-(포르밀) 글리신메틸 에스테르를 형성하고; (d) N-(디에틸포스포노메틸), N-(포르밀) 글리신메틸 에스테르를 가수분해제와 반응시켜 N-포스포노메틸 글리신을 형성하는 공정단계로 이루어지는 N-포스포노메틸글리신의 제조방법.
- 단계(a)는 약 20∼약 25℃ 범위내의 온도항에 반응이 완료되기에 충분한 시간동안 행하여지며, 포름알데히드에 대한 포름아미드의 분자비는 약 2-1인 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제조방법.
- 단계(b)는 약 120∼약 125℃ 범위내의 온도하에 반응이 완료되기에 충분한 시간동안 행하여지며, 트리에틸포스파이트에 대한 N-(히드록시메틸) 포름알데히드의 분자비는 약 1:1인 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제조방법.
- 단계(c)는 용제로서 수소화나트륨 및 테트라하이드로프란의 존재하에 행하여지며, 메틸클로로아세테이트에 대한 디에틸, N-(포르밀) 아미노메틸포스포네이트의 분자비는 약 1:1이고, 상기반응은 약 10∼약 25℃ 범위내의온도로 행하여지는 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제조방법.
- 단계(d)는 약 120∼약 125℃ 범위내의온도로 행하여지며, 염화수소산에 대한 N-(디에틸포스포노메틸), N-(포르밀) 글리신메틸 에스테르의 분자비는 약 1:5의 범위내인 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제조방법.
- 단계(c)에서 사용되는 용제는 테트라하이드로푸란, 톨루엔, 디메틸포름아미드 및 크실렌으로 구성되는 그루우프에서 선택되어지는 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제조방법.
- 단계(d)의 가수분해제는 염화수소산인 특허청구의 범위 1기재의 N-포스포노메틸글리신의 제조방법.
- (a) 유기용제 및 프로톤-추출염기의 존재하에 반응이 완료되기에 충분한 온도로 구조식.(식중, R은 포르밀, 아세틸, 메톡시카르보닐, 페닐옥시카르보닐, 및 벤질로 구성되는 그루우프에서 선택되며, R'은 메틸, 에틸, 프로필, 부틸, 펜틸 및 헥실로 구성되는 그루우프에서 선택된다)의 아미노메틸 포스포네이트를 메틸클로로아세테이트와 반응시켜 중간생성물, N-(디알킬포스포노메틸), N-(치환)글리신메틸에스테를 형성하고; (b) N-포스포노메틸글리신의 형성을 일으키기에 충분한 온도 및 충분한 반응시간동안, 상기 N-(디알킬포스포노메틸), N-(치환)-글리신메틸 에스테를 가수분해제와 반응시킴으로써 이루어지는 N-포스포노메틸글리신의 제조방법.
- 용제는 테트라하이드로푸란, 톨루엔, 메틸이소부틸케톤 및 디메틸포름아미드로 구성되는 그루우프에서 선택되는 특허청구의 범위 8기재의 N-포스포노메틸글리신의 제조방법.
- 프로톤-추출염기는 수소화나트륨인 특허청구의 범위 8기재의 N-포스포노메틸글리신의 제조방법.
- 가수분해제는 염화수소산인 특허청구의 범위 8기재의 N-포스포노메틸글리신의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/393,574 US4422982A (en) | 1982-06-30 | 1982-06-30 | Method for preparation of N-phosphonomethylglycine |
US393574 | 1982-06-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840005158A true KR840005158A (ko) | 1984-11-05 |
KR870001334B1 KR870001334B1 (ko) | 1987-07-18 |
Family
ID=23555297
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019830002953A KR870001334B1 (ko) | 1982-06-30 | 1983-06-29 | N-포스포노 메틸글리신의 제조방법 |
Country Status (18)
Country | Link |
---|---|
US (1) | US4422982A (ko) |
EP (1) | EP0098159B1 (ko) |
JP (1) | JPS5913795A (ko) |
KR (1) | KR870001334B1 (ko) |
AT (1) | ATE21903T1 (ko) |
AU (1) | AU555801B2 (ko) |
BR (1) | BR8303370A (ko) |
CA (1) | CA1205487A (ko) |
CS (2) | CS244939B2 (ko) |
DD (1) | DD212966A5 (ko) |
DE (1) | DE3365866D1 (ko) |
DK (1) | DK292283A (ko) |
ES (2) | ES523690A0 (ko) |
HU (1) | HU194256B (ko) |
IL (3) | IL69112A (ko) |
PL (1) | PL140912B1 (ko) |
RO (1) | RO86524B (ko) |
ZA (1) | ZA834740B (ko) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES534413A0 (es) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Procedimiento de preparacion de sulfonamidas con grupo ansinometilfosfonico |
FR2560198B1 (fr) * | 1984-02-23 | 1987-05-07 | Rhone Poulenc Agrochimie | Esters de la famille de la n-phosphonomethylglycine et leur utilisation pour la preparation d'herbicides connus |
US4548758A (en) * | 1984-08-30 | 1985-10-22 | Stauffer Chemical Company | Preparation of phosphonomethylated amino acids |
US4548759A (en) * | 1984-08-30 | 1985-10-22 | Stauffer Chemical Company | Preparation of phosphonomethylated amino acids |
US4921991A (en) * | 1985-02-22 | 1990-05-01 | Guy Lacroix | Preparation of esters of the N-phosphonomethylglycine and the N-phosphonomethyl glycines |
FR2611204B1 (fr) * | 1987-02-19 | 1989-05-05 | Rhone Poulenc Agrochimie | Composes intermediaires utiles pour la preparation d'herbicides |
US4830788A (en) * | 1987-11-20 | 1989-05-16 | Crompton & Knowles Corporation | Process for preparation of substituted-aminomethylphosphonic acids |
IN2015DN01080A (ko) | 2012-07-17 | 2015-06-26 | Straitmark Holding Ag | |
CN104812766B (zh) | 2012-07-17 | 2017-06-06 | 斯特雷特马克控股股份公司 | 用于合成氨基亚烷基膦酸的方法 |
EP2875038A1 (en) | 2012-07-17 | 2015-05-27 | Straitmark Holding AG | Method for the synthesis of n-phosphonomethyliminodiacetic acid |
US20150232493A1 (en) | 2012-07-17 | 2015-08-20 | Straitmark Holding Ag | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
CN110771607A (zh) * | 2019-10-09 | 2020-02-11 | 集美大学 | 一类n-羟甲基酰胺类抗菌剂及其制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE764270A (fr) * | 1970-03-20 | 1971-08-02 | Benckiser Gmbh Joh A | Acide niril-tris-(methylenephosphonique) et son procede de preparation |
US3853530A (en) * | 1971-03-10 | 1974-12-10 | Monsanto Co | Regulating plants with n-phosphonomethylglycine and derivatives thereof |
US4053505A (en) * | 1976-01-05 | 1977-10-11 | Monsanto Company | Preparation of n-phosphonomethyl glycine |
CH647528A5 (fr) * | 1978-10-27 | 1985-01-31 | Bcap Biolog Chem Act Pat | Procede pour la preparation de n-phosphonomethylglycine. |
HU184601B (en) * | 1979-07-09 | 1984-09-28 | Alkaloida Vegyeszeti Gyar | Process for producing n-/phosphono-methyl/-glycine |
-
1982
- 1982-06-30 US US06/393,574 patent/US4422982A/en not_active Expired - Fee Related
-
1983
- 1983-06-23 BR BR8303370A patent/BR8303370A/pt unknown
- 1983-06-24 DK DK292283A patent/DK292283A/da not_active Application Discontinuation
- 1983-06-28 PL PL1983242729A patent/PL140912B1/pl unknown
- 1983-06-28 AU AU16316/83A patent/AU555801B2/en not_active Ceased
- 1983-06-28 RO RO111440A patent/RO86524B/ro unknown
- 1983-06-28 JP JP58115298A patent/JPS5913795A/ja active Pending
- 1983-06-28 CA CA000431323A patent/CA1205487A/en not_active Expired
- 1983-06-29 DE DE8383303749T patent/DE3365866D1/de not_active Expired
- 1983-06-29 ES ES523690A patent/ES523690A0/es active Granted
- 1983-06-29 DD DD83252532A patent/DD212966A5/de unknown
- 1983-06-29 EP EP83303749A patent/EP0098159B1/en not_active Expired
- 1983-06-29 ZA ZA834740A patent/ZA834740B/xx unknown
- 1983-06-29 IL IL69112A patent/IL69112A/xx unknown
- 1983-06-29 IL IL80523A patent/IL80523A/xx unknown
- 1983-06-29 CS CS834849A patent/CS244939B2/cs unknown
- 1983-06-29 KR KR1019830002953A patent/KR870001334B1/ko not_active IP Right Cessation
- 1983-06-29 HU HU832357A patent/HU194256B/hu unknown
- 1983-06-29 AT AT83303749T patent/ATE21903T1/de not_active IP Right Cessation
-
1984
- 1984-04-20 CS CS843017A patent/CS244948B2/cs unknown
- 1984-11-30 ES ES538163A patent/ES538163A0/es active Granted
-
1986
- 1986-11-06 IL IL80523A patent/IL80523A0/xx unknown
Also Published As
Publication number | Publication date |
---|---|
BR8303370A (pt) | 1984-02-07 |
US4422982A (en) | 1983-12-27 |
RO86524A (ro) | 1985-03-15 |
ES8504209A1 (es) | 1985-04-01 |
PL242729A1 (en) | 1984-07-16 |
AU1631683A (en) | 1984-01-05 |
DK292283D0 (da) | 1983-06-24 |
IL80523A (en) | 1987-10-20 |
DE3365866D1 (en) | 1986-10-09 |
HU194256B (en) | 1988-01-28 |
EP0098159B1 (en) | 1986-09-03 |
ES8507565A1 (es) | 1985-09-01 |
ES538163A0 (es) | 1985-09-01 |
DD212966A5 (de) | 1984-08-29 |
KR870001334B1 (ko) | 1987-07-18 |
EP0098159A2 (en) | 1984-01-11 |
IL80523A0 (en) | 1987-02-27 |
ES523690A0 (es) | 1985-04-01 |
IL69112A0 (en) | 1983-10-31 |
JPS5913795A (ja) | 1984-01-24 |
ATE21903T1 (de) | 1986-09-15 |
ZA834740B (en) | 1984-04-25 |
CS244939B2 (en) | 1986-08-14 |
AU555801B2 (en) | 1986-10-09 |
CA1205487A (en) | 1986-06-03 |
RO86524B (ro) | 1985-03-30 |
CS244948B2 (en) | 1986-08-14 |
IL69112A (en) | 1987-10-20 |
DK292283A (da) | 1983-12-31 |
EP0098159A3 (en) | 1984-03-21 |
PL140912B1 (en) | 1987-06-30 |
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