GB1366379A - Herbicidal phosphonomethylglycine compounds and compositions containing them - Google Patents
Herbicidal phosphonomethylglycine compounds and compositions containing themInfo
- Publication number
- GB1366379A GB1366379A GB4926371A GB4926371A GB1366379A GB 1366379 A GB1366379 A GB 1366379A GB 4926371 A GB4926371 A GB 4926371A GB 4926371 A GB4926371 A GB 4926371A GB 1366379 A GB1366379 A GB 1366379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- prepared
- formula
- ammonium
- glycine
- 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.)
- Expired
Links
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical class OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 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)]
- C07F9/3804—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)]
- C07F9/3804—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)
Abstract
1366379 N-phosphonomethyl glycine and derivatives thereof MONSANTO CO 22 Oct 1971 [10 March 1971 9 Aug 1971] 49263/71 Heading C2P [Also in Division A5] Compounds of Formula I where R, R<SP>1</SP> and R<SP>2</SP> are each -OH; -NR<SP>4</SP>R<SP>5</SP> where R<SP>4</SP> and R<SP>5</SP> are each H, C 1-4 alkyl or hydroxyalkyl or C 2-4 alkenyl or R<SP>4</SP> and R<SP>5</SP> together with N form a heterocyclic ring; -OR<SP>3</SP> where R<SP>3</SP> is C 1-18 hydrocarbyl or hydrocarbyloxyhydrocarbyl optionally substituted by 1 to 3 halogen atoms, the hydrocarbyloxyhydrocarbyl groups also being optionally substituted by one or more hydrocarbyloxy groups, or a -C n H 2n -NR<SP>4</SP>R<SP>5</SP> group where n is 1 to 4; or -OR<SP>6</SP> where R<SP>6</SP> is alkali metal, alkaline earth metal, Cu, Zn, Mn, Ni, ammonium or organic ammonium, provided (i) that no more than 2 of R, R<SP>1</SP> and R<SP>2</SP> are selected from -NR<SP>4</SP>R<SP>5</SP> and -OR<SP>3</SP>, (ii) that when R<SP>6</SP> is arylammonium it is the cation of a primary amine, (iii) that no more than 2 of R, R<SP>1</SP> and R<SP>2</SP> are -OR<SP>6</SP> when R<SP>6</SP> is ammonium or organic ammonium, and (iv) that no more than 2 of R, R<SP>1</SP> and R<SP>2</SP> are -OH; and salts of the compound of Formula I in which R, R<SP>1</SP> and R<SP>2</SP> are each -OH with an acid having a pK of 2À5 or less are claimed per se. Compounds of Formula I, including the compound in which each of R, R<SP>1</SP> and R<SP>2</SP> is -OH (N-phosphonomethyl glycine), which compounds may be used as the active ingredients in conventional pesticidal compositions, may be prepared by phosphonomethylation of a glycine, by phosphite addition to azomethines or by oxidation of the corresponding phosphinic compounds. The amides and esters may also be prepared by reacting the corresponding acid halide or the methyl ester with the corresponding amine or alcohol. The salts may be prepared by partial or complete neutralization with the appropriate base.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12305771A | 1971-03-10 | 1971-03-10 | |
| US00170385A US3799758A (en) | 1971-08-09 | 1971-08-09 | N-phosphonomethyl-glycine phytotoxicant compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1366379A true GB1366379A (en) | 1974-09-11 |
Family
ID=26821180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4926371A Expired GB1366379A (en) | 1971-03-10 | 1971-10-22 | Herbicidal phosphonomethylglycine compounds and compositions containing them |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS566401B1 (en) |
| BE (1) | BE774349A (en) |
| BG (1) | BG18585A3 (en) |
| BR (1) | BR7107076D0 (en) |
| CA (1) | CA936865A (en) |
| CH (1) | CH571306A5 (en) |
| CY (1) | CY837A (en) |
| DD (1) | DD100868A6 (en) |
| DE (3) | DE2152826C3 (en) |
| DK (1) | DK140433B (en) |
| ES (1) | ES396223A1 (en) |
| FI (1) | FI57955C (en) |
| FR (1) | FR2129327A5 (en) |
| GB (1) | GB1366379A (en) |
| HU (1) | HU174479B (en) |
| IE (1) | IE35501B1 (en) |
| IL (3) | IL47972A (en) |
| IT (1) | IT946007B (en) |
| KE (1) | KE2599A (en) |
| MY (1) | MY7600110A (en) |
| NL (1) | NL146171B (en) |
| NO (1) | NO141090C (en) |
| OA (1) | OA03838A (en) |
| PH (2) | PH16509A (en) |
| PT (1) | PT56642A1 (en) |
| RO (2) | RO77018A (en) |
| SE (3) | SE400695B (en) |
| SU (3) | SU638238A3 (en) |
| TR (1) | TR18244A (en) |
| YU (1) | YU36532B (en) |
| ZM (1) | ZM15071A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997024931A1 (en) * | 1996-01-07 | 1997-07-17 | Yeda Research And Development Co. Ltd. | Use of glyphosate salts in seed dressing herbicidal compositions |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436843A (en) * | 1972-07-21 | 1976-05-26 | Ici Ltd | Preparation of n-phosphonomethyl-glycine |
| DE2717440C2 (en) * | 1976-05-17 | 1984-04-05 | Hoechst Ag, 6230 Frankfurt | Weed control with [(3-amino-3-carboxy) propyl-1] methylphosphinic acid derivatives |
| EG12897A (en) * | 1976-12-13 | 1980-07-31 | Monsanto Co | N,n,methylebebis-co,o-diaryl-n-phosphonomethylglycinonitrilles |
| US4140513A (en) * | 1978-01-03 | 1979-02-20 | Monsanto Company | Sodium sesquiglyphosate |
| EP0005321B1 (en) * | 1978-04-06 | 1982-04-14 | Monsanto Company | Derivatives of n-trifluoroacetyl n-phosphonomethylglycine dichloride, their preparation and their use as herbicides |
| US4359332A (en) * | 1978-07-10 | 1982-11-16 | Monsanto Company | Amide and hydrazide derivatives of N-trifluoroacetyl-N-phosphonomethylglycine as herbicides |
| US4218235A (en) * | 1978-07-10 | 1980-08-19 | Monsanto Company | Ester derivatives of n-trifluoroacetyl-n-phosphonomethylglycine and the herbicidal use thereof |
| US4175946A (en) * | 1978-07-10 | 1979-11-27 | Monsanto Company | Thio derivatives of N-trifluoroacetyl-N-phosphonomethylglycine |
| US4180394A (en) * | 1978-07-10 | 1979-12-25 | Monsanto Company | Derivatives of N-trifluoroacetyl-N-phosphonomethylglycinates and the herbicidal use thereof |
| US4414158A (en) * | 1980-04-29 | 1983-11-08 | Ciba-Geigy Corporation | Phosphonomethylglycylhydroxamic acid and novel herbicidally active salts thereof |
| ES534413A0 (en) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | SULFONAMIDES PREPARATION PROCEDURE WITH ANSYNOMETHYLPHOSPHONIC GROUP |
| DE3614788A1 (en) * | 1986-05-02 | 1987-11-05 | Hoechst Ag | HERBICIDE EMULSIONS |
| FR2644036B1 (en) * | 1989-03-07 | 1992-01-17 | Rhone Poulenc Agrochimie | HERBICIDE COMBINATION OF A WATER-SOLUBLE POLYMERIC PACKAGE AND AN N-PHOSPHONOMETHYLGLYCIN-CONTAINING HERBICIDE |
| DE19528060A1 (en) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Process for the preparation of N-phosphonomethyl-glycine esters |
| DE19528054A1 (en) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Process for the preparation of N-phosphonomethylglycine esters |
| WO1997031534A1 (en) * | 1996-02-28 | 1997-09-04 | Bayer Aktiengesellschaft | Use of n-phosphonomethylglycine esters in aqueous solution as herbicides, and new n-phosphonomethylglycine esters |
| AU2005235111B2 (en) | 2004-03-30 | 2010-10-28 | Monsanto Technology Llc | Methods for controlling plant pathogens using N-phosphonomethylglycine |
| EP2255650A3 (en) | 2005-06-09 | 2011-04-27 | Bayer CropScience AG | Agent combinations |
| DE102005026482A1 (en) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide |
| US10555527B2 (en) | 2009-05-18 | 2020-02-11 | Monsanto Technology Llc | Use of glyphosate for disease suppression and yield enhancement in soybean |
| US8987167B2 (en) | 2009-09-30 | 2015-03-24 | Basf Se | Low volatile amine salts of anionic pesticides |
| EP2460404A1 (en) | 2010-12-01 | 2012-06-06 | Basf Se | Compositions containing identical polyamine salts of mixed anionic pesticides |
| US11109591B2 (en) | 2017-04-24 | 2021-09-07 | Taminco Bvba | Single phase liquids of alkanolamine salts of dicamba |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160632A (en) * | 1961-01-30 | 1964-12-08 | Stauffer Chemical Co | Aminomethylenephosphinic acids, salts thereof, and process for their production |
-
1971
- 1971-10-11 PH PH12914A patent/PH16509A/en unknown
- 1971-10-15 SU SU711714528A patent/SU638238A3/en active
- 1971-10-21 HU HU71MO810A patent/HU174479B/en unknown
- 1971-10-21 ES ES396223A patent/ES396223A1/en not_active Expired
- 1971-10-21 NL NL717114487A patent/NL146171B/en not_active IP Right Cessation
- 1971-10-22 NO NO3926/71A patent/NO141090C/en unknown
- 1971-10-22 DK DK514071AA patent/DK140433B/en not_active IP Right Cessation
- 1971-10-22 IL IL47972A patent/IL47972A/en unknown
- 1971-10-22 DE DE2152826A patent/DE2152826C3/en not_active Expired
- 1971-10-22 ZM ZM150/71A patent/ZM15071A1/en unknown
- 1971-10-22 FI FI3000/71A patent/FI57955C/en active
- 1971-10-22 OA OA54402A patent/OA03838A/en unknown
- 1971-10-22 DD DD160070A patent/DD100868A6/xx unknown
- 1971-10-22 FR FR7138086A patent/FR2129327A5/fr not_active Expired
- 1971-10-22 BG BG018842A patent/BG18585A3/en unknown
- 1971-10-22 RO RO7199872A patent/RO77018A/en unknown
- 1971-10-22 RO RO7168548A patent/RO72460A/en unknown
- 1971-10-22 DE DE2167051A patent/DE2167051C2/en not_active Expired
- 1971-10-22 CH CH1539171A patent/CH571306A5/xx not_active IP Right Cessation
- 1971-10-22 JP JP8384671A patent/JPS566401B1/ja active Pending
- 1971-10-22 TR TR18244A patent/TR18244A/en unknown
- 1971-10-22 GB GB4926371A patent/GB1366379A/en not_active Expired
- 1971-10-22 IT IT30219/71A patent/IT946007B/en active
- 1971-10-22 CY CY837A patent/CY837A/en unknown
- 1971-10-22 IE IE1340/71A patent/IE35501B1/en unknown
- 1971-10-22 IL IL37993A patent/IL37993A/en unknown
- 1971-10-22 CA CA125905A patent/CA936865A/en not_active Expired
- 1971-10-22 DE DE2166573A patent/DE2166573C3/en not_active Expired
- 1971-10-22 BR BR7076/71A patent/BR7107076D0/en unknown
- 1971-10-22 YU YU02686/71A patent/YU36532B/en unknown
- 1971-10-22 BE BE774349A patent/BE774349A/en not_active IP Right Cessation
- 1971-10-22 SE SE7113473A patent/SE400695B/en unknown
- 1971-10-22 PT PT56642A patent/PT56642A1/en unknown
-
1972
- 1972-10-09 SU SU721834717A patent/SU665775A3/en active
- 1972-10-09 SU SU721834717D patent/SU963446A3/en active
-
1974
- 1974-02-28 SE SE7402719A patent/SE400158B/en not_active IP Right Cessation
- 1974-02-28 SE SE7402718A patent/SE399267B/en not_active IP Right Cessation
-
1975
- 1975-08-21 IL IL47972A patent/IL47972A0/en unknown
-
1976
- 1976-02-11 KE KE2599*UA patent/KE2599A/en unknown
- 1976-12-30 MY MY110/76A patent/MY7600110A/en unknown
-
1979
- 1979-10-16 PH PH23177A patent/PH13752A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997024931A1 (en) * | 1996-01-07 | 1997-07-17 | Yeda Research And Development Co. Ltd. | Use of glyphosate salts in seed dressing herbicidal compositions |
| US6096686A (en) * | 1996-01-07 | 2000-08-01 | Yeda Research And Development Co. Ltd. | Use of glyphosate salts in seed dressing herbicidal compositions |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| PE20 | Patent expired after termination of 20 years |