DD213221A5 - Methode zur darstellung von n-phosphonomethyl-glycin - Google Patents

Methode zur darstellung von n-phosphonomethyl-glycin Download PDF

Info

Publication number: DD213221A5
Authority: DD; German Democratic Republic
Prior art keywords: item; groups; reaction; formula; alkyl group
Prior art date: 1982-08-30

Application number

DD83254313A

Other languages

German (de)

English (en)

Inventor

Raymond A Felix

Original Assignee

Stauffer Chemical Co

Priority date (The priority date 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 date listed.)

1982-08-30

Filing date

1983-08-29

Publication date

1984-09-05

1982-08-30 Priority claimed from US06/412,624 external-priority patent/US4425284A/en

1983-08-29 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1984-09-05 Publication of DD213221A5 publication Critical patent/DD213221A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title claims abstract description 12
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title abstract description 7
230000007062 hydrolysis Effects 0.000 claims abstract description 9
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 9
-1 phosphonate compound Chemical class 0.000 claims abstract description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 7
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract description 6
150000001408 amides Chemical class 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
125000001931 aliphatic group Chemical group 0.000 claims description 9
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
150000001263 acyl chlorides Chemical class 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
239000003377 acid catalyst Substances 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
239000003054 catalyst Substances 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 13
150000004820 halides Chemical class 0.000 abstract description 6
150000001266 acyl halides Chemical class 0.000 abstract description 3
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract 1
150000003918 triazines Chemical class 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
KCZIRQGMWBGPRP-UHFFFAOYSA-N 2-(2-hydroxyacetyl)oxyethyl 2-hydroxyacetate Chemical compound OCC(=O)OCCOC(=O)CO KCZIRQGMWBGPRP-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
QCMYYKRYFNMIEC-UHFFFAOYSA-N COP(O)=O Chemical compound COP(O)=O QCMYYKRYFNMIEC-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000589614 Pseudomonas stutzeri Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 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 description 1
150000003949 imides Chemical class 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
KZZUBAQVMPHDHM-UHFFFAOYSA-N n-(chloromethyl)propanamide Chemical compound CCC(=O)NCCl KZZUBAQVMPHDHM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-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
239000011541 reaction mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005406 washing 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
- C07F9/38—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
- 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
- C07C233/45—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 carboxyl groups
- C07C233/46—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- 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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD83254313A 1982-08-30 1983-08-29 Methode zur darstellung von n-phosphonomethyl-glycin DD213221A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/412,624 US4425284A (en)	1982-08-30	1982-08-30	Method for preparation of N-phosphonomethylglycine
US06/468,223 US4482504A (en)	1982-08-30	1983-02-22	Method for preparation of N-phosphonomethylglycine

Publications (1)

Publication Number	Publication Date
DD213221A5 true DD213221A5 (de)	1984-09-05

Family

ID=27021837

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83254313A DD213221A5 (de)	1982-08-30	1983-08-29	Methode zur darstellung von n-phosphonomethyl-glycin

Country Status (12)

Country	Link
US (1)	US4482504A (da)
EP (1)	EP0104775B1 (da)
AU (1)	AU554999B2 (da)
BR (1)	BR8304711A (da)
CA (1)	CA1205488A (da)
DD (1)	DD213221A5 (da)
DE (1)	DE3365452D1 (da)
DK (1)	DK394783A (da)
ES (1)	ES8502707A1 (da)
HU (1)	HU194257B (da)
IL (1)	IL69583A (da)
MX (1)	MX157972A (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4569802A (en) *	1983-06-27	1986-02-11	Stauffer Chemical Company	Method for preparation of N-phosphonomethylglycine
ES8603901A1 (es) *	1983-07-27	1986-01-01	Rhone Poulenc Agrochimie	Procedimiento de preparacion de sulfonamidas con grupo ansinometilfosfonico
IL76842A0 (en) *	1984-12-28	1986-02-28	Monsanto Co	Novel n-acyl-n-isopropyl-glycine derivatives
US5041627A (en) *	1988-11-25	1991-08-20	Monsanto Company	Preparation of N-acyl-aminomethylphosphonates
AR027024A1 (es) *	1999-12-23	2003-03-12	Basf Ag	Procedimiento para la preparacion de n-fosfonometilglicina
DE10130135A1 (de) *	2001-06-22	2003-01-02	Basf Ag	Verfahren zur Herstellung von N-Phosphonomethylglycin

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3988142A (en) *	1972-02-03	1976-10-26	Monsanto Company	Increasing carbohydrate deposition in plants with N-phosphono-methylglycine and derivatives thereof
GB1445087A (en) *	1972-11-08	1976-08-04	Ici Ltd	Preparing n-phosphonomethylglycine and nitrile intermediates therefor
US4053505A (en) *	1976-01-05	1977-10-11	Monsanto Company	Preparation of n-phosphonomethyl glycine

1983
- 1983-02-22 US US06/468,223 patent/US4482504A/en not_active Expired - Fee Related
- 1983-08-26 DE DE8383304951T patent/DE3365452D1/de not_active Expired
- 1983-08-26 EP EP83304951A patent/EP0104775B1/en not_active Expired
- 1983-08-29 CA CA000435543A patent/CA1205488A/en not_active Expired
- 1983-08-29 IL IL69583A patent/IL69583A/xx unknown
- 1983-08-29 MX MX198527A patent/MX157972A/es unknown
- 1983-08-29 HU HU833017A patent/HU194257B/hu not_active IP Right Cessation
- 1983-08-29 DD DD83254313A patent/DD213221A5/de not_active IP Right Cessation
- 1983-08-30 AU AU18526/83A patent/AU554999B2/en not_active Ceased
- 1983-08-30 ES ES525235A patent/ES8502707A1/es not_active Expired
- 1983-08-30 DK DK394783A patent/DK394783A/da unknown
- 1983-08-30 BR BR8304711A patent/BR8304711A/pt unknown

Also Published As

Publication number	Publication date
CA1205488A (en)	1986-06-03
AU554999B2 (en)	1986-09-11
AU1852683A (en)	1984-03-08
DK394783A (da)	1984-03-01
HU194257B (en)	1988-01-28
US4482504A (en)	1984-11-13
DK394783D0 (da)	1983-08-30
IL69583A0 (en)	1983-11-30
ES525235A0 (es)	1985-01-16
MX157972A (es)	1988-12-28
ES8502707A1 (es)	1985-01-16
DE3365452D1 (en)	1986-09-25
EP0104775B1 (en)	1986-08-20
BR8304711A (pt)	1984-04-10
IL69583A (en)	1986-11-30
EP0104775A1 (en)	1984-04-04

Legal Events

Date	Code	Title	Description
2001-04-26	ENJ	Ceased due to non-payment of renewal fee

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DE869956C (de)	1953-03-09	Verfahren zur Herstellung von Organodisiloxanen
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EP0132733B1 (de)	1986-06-11	Neue Fluorpivalsäurefluoride und Verfahren zu ihrer Herstellung
DD210055A5 (de)	1984-05-30	Verfahren zur herstellung von n-phosphonomethylglycin
US3260712A (en)	1966-07-12	Alkyl phosphonic and thiophosphonic aryl ester amides
EP0123199B1 (de)	1987-09-16	2-Methacrylamido-2-methyl-propanphosphonsäure und ihre Salze, Verfahren zu deren Herstellung und ihre Verwendung zur Herstellung von Copolymeren
US4482504A (en)	1984-11-13	Method for preparation of N-phosphonomethylglycine
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