DE2751631A1 - O-aryl-n-phosphonmethylglycinnitrile, verfahren zu ihrer herstellung und ihre verwendung - Google Patents
O-aryl-n-phosphonmethylglycinnitrile, verfahren zu ihrer herstellung und ihre verwendungInfo
- Publication number
- DE2751631A1 DE2751631A1 DE19772751631 DE2751631A DE2751631A1 DE 2751631 A1 DE2751631 A1 DE 2751631A1 DE 19772751631 DE19772751631 DE 19772751631 DE 2751631 A DE2751631 A DE 2751631A DE 2751631 A1 DE2751631 A1 DE 2751631A1
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- compound according
- nitrile
- phosphonmethylglycine
- herbicidally effective
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000002825 nitriles Chemical class 0.000 claims description 78
- -1 biphenylyl Chemical group 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 230000002363 herbicidal effect Effects 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 17
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 239000004606 Fillers/Extenders Substances 0.000 claims description 16
- 150000005690 diesters Chemical class 0.000 claims description 15
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical group C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 3
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- 125000003277 amino group Chemical group 0.000 claims description 3
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- 239000007864 aqueous solution Substances 0.000 claims description 2
- LEEIJMDGSPFENF-UHFFFAOYSA-N bis(3-chlorophenyl) hydrogen phosphite Chemical compound C=1C=CC(Cl)=CC=1OP(O)OC1=CC=CC(Cl)=C1 LEEIJMDGSPFENF-UHFFFAOYSA-N 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
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- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 2
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 239000010985 leather Chemical group 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 83
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- 239000007787 solid Substances 0.000 description 59
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- 238000004458 analytical method Methods 0.000 description 44
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- 238000002844 melting Methods 0.000 description 35
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
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- 229960001701 chloroform Drugs 0.000 description 28
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- 239000000047 product Substances 0.000 description 21
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- 239000013078 crystal Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
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- 241000894007 species Species 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 5
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
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- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- XYQQPUALUKWVRH-UHFFFAOYSA-N phenoxy(phenylsulfanyl)phosphinous acid Chemical compound P(SC1=CC=CC=C1)(OC1=CC=CC=C1)O XYQQPUALUKWVRH-UHFFFAOYSA-N 0.000 description 1
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- WQQPDTLGLVLNOH-UHFFFAOYSA-M sodium;4-hydroxy-4-oxo-3-sulfobutanoate Chemical compound [Na+].OC(=O)CC(C([O-])=O)S(O)(=O)=O WQQPDTLGLVLNOH-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
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- 239000013638 trimer Substances 0.000 description 1
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- 238000007738 vacuum evaporation Methods 0.000 description 1
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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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- 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
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/750,327 US4067719A (en) | 1976-12-13 | 1976-12-13 | O-Aryl N-phosphonomethylglycinonitriles and the herbicidal use thereof |
| US05/756,521 US4083898A (en) | 1976-12-13 | 1977-01-03 | Process for preparing O-aryl, N-phosphonomethylglycinonitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2751631A1 true DE2751631A1 (de) | 1978-06-15 |
Family
ID=27115259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772751631 Withdrawn DE2751631A1 (de) | 1976-12-13 | 1977-11-18 | O-aryl-n-phosphonmethylglycinnitrile, verfahren zu ihrer herstellung und ihre verwendung |
Country Status (36)
| Country | Link |
|---|---|
| JP (1) | JPS5373543A (xx) |
| AR (1) | AR223311A1 (xx) |
| AT (1) | AT359772B (xx) |
| AU (1) | AU510196B2 (xx) |
| BG (2) | BG28423A3 (xx) |
| BR (1) | BR7707676A (xx) |
| CA (1) | CA1098529A (xx) |
| CH (2) | CH636752A5 (xx) |
| CY (1) | CY1061A (xx) |
| DD (1) | DD145273A5 (xx) |
| DE (1) | DE2751631A1 (xx) |
| DK (1) | DK511677A (xx) |
| EG (1) | EG12818A (xx) |
| ES (1) | ES464216A1 (xx) |
| FI (1) | FI67558C (xx) |
| FR (1) | FR2373553A1 (xx) |
| GB (1) | GB1556322A (xx) |
| GR (1) | GR66150B (xx) |
| HU (1) | HU184655B (xx) |
| IE (1) | IE45917B1 (xx) |
| IL (1) | IL53425A (xx) |
| IN (1) | IN146347B (xx) |
| IT (1) | IT1088890B (xx) |
| KE (1) | KE3045A (xx) |
| MX (1) | MX4714E (xx) |
| NL (1) | NL7712653A (xx) |
| NO (1) | NO151547C (xx) |
| NZ (1) | NZ185720A (xx) |
| OA (1) | OA05804A (xx) |
| PH (2) | PH16387A (xx) |
| PL (1) | PL113273B1 (xx) |
| PT (1) | PT67295B (xx) |
| SE (7) | SE441451B (xx) |
| TR (1) | TR20178A (xx) |
| YU (1) | YU275677A (xx) |
| ZM (1) | ZM8377A1 (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6818793B2 (en) | 1999-12-23 | 2004-11-16 | Basf Aktiengesellschaft | Method for production of n-phosphonomethylglycine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110156838A (zh) * | 2013-05-14 | 2019-08-23 | 北京美倍他药物研究有限公司 | 磷酸/膦酸衍生物及其医药用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923877A (en) * | 1972-11-08 | 1975-12-02 | Ici Ltd | Preparation of N-phosphonomethyl glycine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5295640A (en) * | 1976-02-05 | 1977-08-11 | Nissan Chem Ind Ltd | N-(diphenylphosphonomethyl)aminoacetonitrile |
| JPS604840B2 (ja) * | 1976-11-04 | 1985-02-06 | 日産化学工業株式会社 | シアノメチルアミノメチルホスホネート誘導体および該誘導体を有効成分とする除草剤 |
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1977
- 1977-11-16 EG EG643/77A patent/EG12818A/xx active
- 1977-11-17 ES ES464216A patent/ES464216A1/es not_active Expired
- 1977-11-17 NL NL7712653A patent/NL7712653A/xx not_active Application Discontinuation
- 1977-11-18 OA OA56318A patent/OA05804A/xx unknown
- 1977-11-18 DE DE19772751631 patent/DE2751631A1/de not_active Withdrawn
- 1977-11-18 CA CA291,165A patent/CA1098529A/en not_active Expired
- 1977-11-18 JP JP13800977A patent/JPS5373543A/ja active Granted
- 1977-11-18 AT AT825177A patent/AT359772B/de not_active IP Right Cessation
- 1977-11-18 PT PT67295A patent/PT67295B/pt unknown
- 1977-11-18 IN IN1627/CAL/77A patent/IN146347B/en unknown
- 1977-11-18 BR BR7707676A patent/BR7707676A/pt unknown
- 1977-11-18 NZ NZ185720A patent/NZ185720A/xx unknown
- 1977-11-18 PH PH20450A patent/PH16387A/en unknown
- 1977-11-18 IL IL53425A patent/IL53425A/xx unknown
- 1977-11-18 BG BG7737829A patent/BG28423A3/xx unknown
- 1977-11-18 GR GR54843A patent/GR66150B/el unknown
- 1977-11-18 NO NO773959A patent/NO151547C/no unknown
- 1977-11-18 HU HU77MO994A patent/HU184655B/hu unknown
- 1977-11-18 BG BG7839915A patent/BG36634A3/xx unknown
- 1977-11-18 ZM ZM7783A patent/ZM8377A1/xx unknown
- 1977-11-18 AU AU30754/77A patent/AU510196B2/en not_active Expired
- 1977-11-18 DD DD77214294A patent/DD145273A5/de unknown
- 1977-11-18 CY CY1061A patent/CY1061A/xx unknown
- 1977-11-18 IE IE2354/77A patent/IE45917B1/en unknown
- 1977-11-18 PL PL1977202250A patent/PL113273B1/pl unknown
- 1977-11-18 IT IT29814/77A patent/IT1088890B/it active
- 1977-11-18 SE SE7713047A patent/SE441451B/sv not_active IP Right Cessation
- 1977-11-18 FR FR7734834A patent/FR2373553A1/fr active Granted
- 1977-11-18 DK DK511677A patent/DK511677A/da not_active Application Discontinuation
- 1977-11-18 YU YU02756/77A patent/YU275677A/xx unknown
- 1977-11-18 FI FI773495A patent/FI67558C/fi not_active IP Right Cessation
- 1977-11-18 CH CH1411377A patent/CH636752A5/de not_active IP Right Cessation
- 1977-11-18 GB GB48084/77A patent/GB1556322A/en not_active Expired
- 1977-11-18 MX MX776570U patent/MX4714E/es unknown
- 1977-11-28 TR TR20178A patent/TR20178A/xx unknown
- 1977-12-12 AR AR270319A patent/AR223311A1/es active
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1980
- 1980-04-28 KE KE3045A patent/KE3045A/xx unknown
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1982
- 1982-03-30 CH CH196382A patent/CH636885A5/de not_active IP Right Cessation
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1983
- 1983-03-30 SE SE8301805A patent/SE8301805D0/xx not_active Application Discontinuation
- 1983-03-30 SE SE8301810A patent/SE8301810L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301808A patent/SE8301808L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301807A patent/SE8301807L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301809A patent/SE8301809L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301806A patent/SE8301806L/sv not_active Application Discontinuation
- 1983-07-14 PH PH29231A patent/PH18774A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923877A (en) * | 1972-11-08 | 1975-12-02 | Ici Ltd | Preparation of N-phosphonomethyl glycine |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6818793B2 (en) | 1999-12-23 | 2004-11-16 | Basf Aktiengesellschaft | Method for production of n-phosphonomethylglycine |
| US6855841B2 (en) | 1999-12-23 | 2005-02-15 | Basf Aktiengesellschaft | Process for the preparation of N-phosphonomethylglycine |
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