JPH06500310A - アミノメタンホスホン酸およびアミノメチル―ホスフィン酸の製造方法 - Google Patents
アミノメタンホスホン酸およびアミノメチル―ホスフィン酸の製造方法Info
- Publication number
- JPH06500310A JPH06500310A JP3513167A JP51316791A JPH06500310A JP H06500310 A JPH06500310 A JP H06500310A JP 3513167 A JP3513167 A JP 3513167A JP 51316791 A JP51316791 A JP 51316791A JP H06500310 A JPH06500310 A JP H06500310A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- phenyl
- formula
- alkyl
- water
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 title abstract description 10
- OHWRASKXEUIFFB-UHFFFAOYSA-N NCP(O)=O Chemical compound NCP(O)=O OHWRASKXEUIFFB-UHFFFAOYSA-N 0.000 title abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LFSFPNIUQADDIM-UHFFFAOYSA-N benzamidomethylphosphonic acid Chemical compound OP(O)(=O)CNC(=O)C1=CC=CC=C1 LFSFPNIUQADDIM-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- FDNUAHPLMXZWLS-UHFFFAOYSA-N (acetamidomethyl)phosphonic acid Chemical compound CC(=O)NCP(O)(O)=O FDNUAHPLMXZWLS-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical compound NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- ZVQSISKECFIRMH-UHFFFAOYSA-N acetamidomethyl(methyl)phosphinic acid Chemical compound CC(=O)NCP(C)(O)=O ZVQSISKECFIRMH-UHFFFAOYSA-N 0.000 description 1
- QLAUIXHXGPSZQW-UHFFFAOYSA-N aminomethyl(methyl)phosphinic acid Chemical compound CP(O)(=O)CN QLAUIXHXGPSZQW-UHFFFAOYSA-N 0.000 description 1
- NTYBHEKOVMEONU-UHFFFAOYSA-N benzamidomethyl(methyl)phosphinic acid Chemical compound CP(O)(=O)CNC(=O)C1=CC=CC=C1 NTYBHEKOVMEONU-UHFFFAOYSA-N 0.000 description 1
- BBPSHEVQDYJYJA-UHFFFAOYSA-N benzamidomethyl(phenyl)phosphinic acid Chemical compound C=1C=CC=CC=1P(=O)(O)CNC(=O)C1=CC=CC=C1 BBPSHEVQDYJYJA-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- BCDIWLCKOCHCIH-UHFFFAOYSA-N methylphosphinic acid Chemical compound CP(O)=O BCDIWLCKOCHCIH-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
- 1.式1 ▲数式、化学式、表等があります▼I 〔式中R1はヒドロキシ、C1〜C4−アルキルまたはフェニルを意味する。〕 で表される化合物の製造方法であって、一般式II▲数式、化学式、表等があり ます▼II〔式中R2は水素、炭素原子数1〜6のアルキル、ベンジル、あるい は置換されていないまたは、C1〜C4−アルキル、C1〜C4−アルコキシお よびハロゲンからなる群からの1つまたはそれ以上の基によって置換されている フェニルを意味しそしてR1は上記意味を有する。〕で表されるアシルアミノメ タンホスホン酸またはアシルアミノメチルホスフィン酸を、水と、80〜300 ℃で反応させることを特徴とする方法。
- 2.R1がヒドロキシを意味する、請求項1記載の方法。
- 3.R1がメチル、エチルまたはフェニルを意味する、請求項1記載の方法。
- 4.R2かH、C1〜C3−アルキル、ベンジルまたはフェニルを意味する、請 求項1、2または3記載の方法。
- 5.R2がフェニルを意味する、請求項1、2または3記載の方法。
- 6.反応温度が150〜250℃である、請求項1〜5のいずれか1項またはそ れ以上に記載の方法。
- 7.式IIで表される化合物1モルに対して、2〜30モルの過剰の水が使用さ れる、請求項1〜6のいずれか1項またはそれ以上に記載の方法。
- 8.反応時間が5〜40時間の範囲にある、請求項1〜7のいずれか1項または それ以上に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4026027.5 | 1990-08-17 | ||
DE4026027A DE4026027A1 (de) | 1990-08-17 | 1990-08-17 | Verfahren zur herstellung von aminomethanphosphonsaeure und aminomethyl-phosphinsaeuren |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH06500310A true JPH06500310A (ja) | 1994-01-13 |
JP3111076B2 JP3111076B2 (ja) | 2000-11-20 |
Family
ID=6412399
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP03513167A Expired - Fee Related JP3111076B2 (ja) | 1990-08-17 | 1991-08-07 | アミノメタンホスホン酸およびアミノメチル―ホスフィン酸の製造方法 |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0543845B1 (ja) |
JP (1) | JP3111076B2 (ja) |
KR (1) | KR100214903B1 (ja) |
CN (1) | CN1028996C (ja) |
AT (1) | ATE118008T1 (ja) |
AU (1) | AU653954B2 (ja) |
BR (1) | BR9106767A (ja) |
CA (1) | CA2089650C (ja) |
DE (2) | DE4026027A1 (ja) |
DK (1) | DK0543845T3 (ja) |
ES (1) | ES2069901T3 (ja) |
GR (1) | GR3015357T3 (ja) |
HU (1) | HU213457B (ja) |
IE (1) | IE912920A1 (ja) |
IL (1) | IL99203A (ja) |
PT (1) | PT98700B (ja) |
WO (1) | WO1992003449A1 (ja) |
ZA (1) | ZA916502B (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2683222B1 (fr) * | 1991-10-31 | 1995-05-19 | Rhone Poulenc Agrochimie | Procede de production d'acides, de sels et/ou esters aminoalcanephosphoniques. |
CN104744507B (zh) * | 2015-04-09 | 2016-11-09 | 泰索新材料科技(杭州)有限公司 | 一种氨甲基苯基次膦酸及其制备方法 |
CN104746168B (zh) * | 2015-04-09 | 2016-10-12 | 泰索新材料科技(杭州)有限公司 | 一种阻燃尼龙66纤维及其制备方法 |
CN104762688B (zh) * | 2015-04-09 | 2017-01-04 | 泰索新材料科技(杭州)有限公司 | 一种阻燃尼龙66及其制备方法 |
CN104762689B (zh) * | 2015-04-09 | 2017-01-04 | 泰索新材料科技(杭州)有限公司 | 一种阻燃尼龙6纤维及其制备方法 |
RU2613837C1 (ru) * | 2015-12-03 | 2017-03-21 | Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский технологический университет" "МИСиС" | Способ получения ионно-плазменного вакуумно-дугового керамикометаллического покрытия TiN-Ni для твердосплавного режущего инструмента расширенной области применения |
CN108927292B (zh) * | 2017-05-24 | 2021-10-22 | 中蓝连海设计研究院有限公司 | 一种氨基膦酸类化合物及其制备方法和用途 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3824961A1 (de) * | 1988-07-22 | 1990-01-25 | Basf Ag | Verfahren zur herstellung von bis(aminomethyl)-phosphinsaeure oder deren sauren oder basischen salzen |
HU203360B (en) * | 1988-11-25 | 1991-07-29 | Monsanto Co | Process for producing n-acylamino methylphosphonates |
-
1990
- 1990-08-17 DE DE4026027A patent/DE4026027A1/de not_active Withdrawn
-
1991
- 1991-08-07 DE DE59104516T patent/DE59104516D1/de not_active Expired - Fee Related
- 1991-08-07 CA CA002089650A patent/CA2089650C/en not_active Expired - Fee Related
- 1991-08-07 BR BR919106767A patent/BR9106767A/pt not_active Application Discontinuation
- 1991-08-07 AU AU83095/91A patent/AU653954B2/en not_active Ceased
- 1991-08-07 JP JP03513167A patent/JP3111076B2/ja not_active Expired - Fee Related
- 1991-08-07 AT AT91914121T patent/ATE118008T1/de not_active IP Right Cessation
- 1991-08-07 HU HU9300423A patent/HU213457B/hu unknown
- 1991-08-07 EP EP91914121A patent/EP0543845B1/de not_active Expired - Lifetime
- 1991-08-07 WO PCT/EP1991/001494 patent/WO1992003449A1/de active IP Right Grant
- 1991-08-07 ES ES91914121T patent/ES2069901T3/es not_active Expired - Lifetime
- 1991-08-07 DK DK91914121.8T patent/DK0543845T3/da active
- 1991-08-15 IL IL9920391A patent/IL99203A/en not_active IP Right Cessation
- 1991-08-16 ZA ZA916502A patent/ZA916502B/xx unknown
- 1991-08-16 CN CN91105718A patent/CN1028996C/zh not_active Expired - Fee Related
- 1991-08-16 IE IE292091A patent/IE912920A1/en unknown
- 1991-08-16 PT PT98700A patent/PT98700B/pt not_active IP Right Cessation
-
1993
- 1993-02-16 KR KR1019930700446A patent/KR100214903B1/ko not_active IP Right Cessation
-
1995
- 1995-03-10 GR GR950400515T patent/GR3015357T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
JP3111076B2 (ja) | 2000-11-20 |
IL99203A0 (en) | 1992-07-15 |
AU653954B2 (en) | 1994-10-20 |
CA2089650A1 (en) | 1992-02-18 |
HU9300423D0 (en) | 1993-05-28 |
ATE118008T1 (de) | 1995-02-15 |
DE59104516D1 (de) | 1995-03-16 |
CN1028996C (zh) | 1995-06-21 |
WO1992003449A1 (de) | 1992-03-05 |
AU8309591A (en) | 1992-03-17 |
KR100214903B1 (en) | 1999-08-02 |
HUT64355A (en) | 1993-12-28 |
GR3015357T3 (en) | 1995-06-30 |
EP0543845B1 (de) | 1995-02-01 |
HU213457B (en) | 1997-06-30 |
CN1059148A (zh) | 1992-03-04 |
EP0543845A1 (de) | 1993-06-02 |
DE4026027A1 (de) | 1992-02-20 |
ES2069901T3 (es) | 1995-05-16 |
BR9106767A (pt) | 1993-08-24 |
PT98700B (pt) | 1999-01-29 |
PT98700A (pt) | 1992-07-31 |
CA2089650C (en) | 2001-10-23 |
ZA916502B (en) | 1992-04-29 |
DK0543845T3 (da) | 1995-06-19 |
IE912920A1 (en) | 1992-02-26 |
IL99203A (en) | 1995-08-31 |
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