IL37993A - N-phosphonomethylglycine phytotoxicant compositions - Google Patents
N-phosphonomethylglycine phytotoxicant compositionsInfo
- Publication number
- IL37993A IL37993A IL37993A IL3799371A IL37993A IL 37993 A IL37993 A IL 37993A IL 37993 A IL37993 A IL 37993A IL 3799371 A IL3799371 A IL 3799371A IL 37993 A IL37993 A IL 37993A
- Authority
- IL
- Israel
- Prior art keywords
- ammonium
- salt
- composition
- compound
- phosphonomethylglycine
- Prior art date
Links
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 2 5 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.
[GB1366379A]
Claims (30)
1. 37993/4 WHAT WE CLAIM IS : 1 . A compound of the formula: wherein R, R1 and R2 are Independently selected from -OH and -OR6, wherein R6 1s a salt-forming cation selected from the groups consisting of cations of alkal i metals , al kaline earth metal s , copper zinc, manganese, nickel , ammonium and organic ammonium selected from primary-, secondary- and tertlary-al kyl , al kenyl and al kynyl -amines, none of these having more than two amine groups ; primary aryl amines, primary aryl diamines and heterocycl ic amines and the add addition salts of strong acids of the above wherein R» R1 and R2 are OH; provided that no more than two of R, l and R2 are -OR6 when R6 designates ammonium or organic ammonium (as above defined) , and provided that when the organic group s an aryl group, the said ammonium salt 1s a primary amine salt, and mixtures of such salts, and provided that when said compound is other than an acid salt (said add having a p of 2.5 or less) , no more than two of the groups R, R1 and R2 are -OH.
2. A compound according to claim 1 wherein R and R2 are -OH and R1 is -OR6.
3. A compound according to claim 1 , wherein R2 or R Is -OH.
4. A compound as claimed 1n any of cl aims 1 to 3, wherein the -R6 substltuent 1s organic ammonium, as above defined.
5. A compound according to claim 4, wherein the organic ammonium group Is monoalkyl ammonium, dlaltylammonlum, dlalkenylammonlum, tria kyl ammonium, monoalkenyl ammonium, tr1 al kenyl ammonium, mono d - or tr1-alkynulammon1um, mono-, dl- or trial kanol ammonium, heterocyclic or monoaryl ammonium, said organic ammonl 57993/2
6. The mono-(methylamine) salt of H-phosphonomethylglycine*
7. The mono-("butylamine) salt of H-phosphonomethylglycine.
8. The mono-(ethanolamine)salt of H-phosphonomethylglycine.
9. The mono-(diethylamine)salt of H-phosphonomethylglycine.
10. The mono-ammonium salt of H-phosphonomethylglycine.
11. The sodium salt of H-phosphonomethylglycine.
12. The potassium salt of H-phosphonomethylglycine.
13. A compound accordin to claim 1, wherein one or two of R, R1, R2 are -OR6, the othe being -0¾¾
14. A compound according to claim 3.3, wherein the -R group is organic ammonium as defined in claim 5.
15. The disoddum salt of H-phosphonomethylglycine.
16. The trisodium salt of H-phosphonomethylglycine. - 24a
17. The lithium salt of N-phosphonomethylglycine .
18. A compound of claim 13 wherein R^ is selected from the class consisting of ammonium or organic ammonium selected from 1 the "group consisting of monoalkylammonium and monoalkanol-ammohlum.
19. A compound of claim 18 which is the mono(isopropylamine) salt of IT-phosphonomethylgl cine. , ,aaccccoorrddiinngq .ttoo .ccjlaaiim 1
20. Salts of N-phosphonomethylglyclneJ substantially as hereinbefore described and with reference to any of the Examples.
21. A phytotoxic composition comprising an adjuvant and an effective amount of one or more of the compounds claimed in any of claims 1 to 20 or N-phosphonomethylgl cine.
22. A composition in accordance with claim 21 wherein at least one of R, R and the remaining groups are -OH.
23. A composition in accordance with claim 21 in which at least one of R, R is an alkali metal and the remaining members of said group are -OH.
24. A composition in accordance with claim 22 wherein R is ammonium, or organic ammonium.
25. A composition of claim 24 wherein the organic ammonium group is selected from the group consisting of monoalkyl ammonium, dialkylammonium, tr^alkylammonium, monoalkenyl ammonium, dialkenylammonium, trialkenylammonium, monoalkynyl ammonium, diakynylammonium, trialkynylammoniu, monoalkanol ammonium, dialkanolammonium, trialkanolammonium, heterocyclic or monoarylammonium, said organic ammonium group containing from 1 to 18 carbon atoms.
26. A composition in accordance with claim 24 in which the compound is the mono-dimethylamine salt of N-phosphbno-methylglycine .
27. A composition in accordance with claim 24 in which the compound is the mono-ethanolamine salt of N-phosphonomethyl- l cine. V
28. A composition in accordance with claim 24 in which the compound is the mono-ammonium salt of N-phosphonomethylglycine.
29. A composition in accordance with flaim 24 in whic the compound is the mono(butylamine) salt of N-phosphonometh'yl- glycine.
30. A composition in accordanceχwith claim 24 in which the compound is the mono(methylamlne) salt of N-phosphonomethyl- glycine. 51. A composition in accordance with claim 23 :}.v. which is the monosfidlum salt of N-phosphonomethylglycine. 32. A composition in accordance with claim 23 which is the disodium slat of N-phosphonomethylglycine . 33. A composition in accordance with claim 23 which is the tris dium slat of N-phosphonomethylglycine. 34. A composition in accordance with claim 21 in which the compound is N-phosphonomethylglycine. 35. A composition af claim 21 wherein the compound is the mono (isopropylamine ) salt of N-phosphonomethylglycine . 36. A composition in accordance with claim 21 wherein the organic ammonium group is a monoalkylammonium group of a monoalkanolammohium group. 34 before the crop plant emerges from the soil. > before the growing vegetation is contacted vrith the composition. 40. A method of claim 37 wherein the crop seed is planted after contactin the growing vegetation with the composition. 41. A method which comprises exposing a plant to a phyto- toxic amount of a composition of claim 36. 42. Phytotoxic compositions of matter, comprising a compound as defined in claim' 1 , substantially as hereinbefore described. according to cl aim 37 or 38, 43·. A method of plant growth control/ substantially as hereinbefore described and with reference to the Examples.
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 (2)
| Publication Number | Publication Date |
|---|---|
| IL37993A0 IL37993A0 (en) | 1971-12-29 |
| IL37993A true IL37993A (en) | 1976-02-29 |
Family
ID=26821180
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL37993A IL37993A (en) | 1971-03-10 | 1971-10-22 | N-phosphonomethylglycine phytotoxicant compositions |
| IL47972A IL47972A (en) | 1971-03-10 | 1971-10-22 | N-phosphonomethylglycines and herbicidal compositions containing them |
| IL47972A IL47972A0 (en) | 1971-03-10 | 1975-08-21 | Novel n-phosphonomethylglycines and herbicidal compositions |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL47972A IL47972A (en) | 1971-03-10 | 1971-10-22 | N-phosphonomethylglycines and herbicidal compositions containing them |
| IL47972A IL47972A0 (en) | 1971-03-10 | 1975-08-21 | Novel n-phosphonomethylglycines and herbicidal compositions |
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) | DE2167051C2 (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) | IL37993A (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) |
Families Citing this family (25)
| 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 |
| ES479305A1 (en) * | 1978-04-06 | 1980-01-01 | Monsanto Co | Derivatives of N-trifluoroacetyl N-phosphonomethylglycine dichloride, their preparation and their use as herbicides. |
| 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 |
| 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 |
| 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 |
| DE19528054A1 (en) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Process for the preparation of N-phosphonomethylglycine esters |
| DE19528060A1 (en) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Process for the preparation of N-phosphonomethyl-glycine esters |
| IL116695A0 (en) * | 1996-01-07 | 1996-05-14 | Yeda Res & Dev | Seed dressing compositions |
| AU1790697A (en) * | 1996-02-28 | 1997-09-16 | Bayer Aktiengesellschaft | Use of n-phosphonomethylglycine esters in aqueous solution as herbicides, and new n-phosphonomethylglycine esters |
| MXPA06011412A (en) | 2004-03-30 | 2007-01-23 | Monsanto Technology Llc | Methods for controlling plant pathogens using n-phosphonomethylglycine. |
| EP2255648A3 (en) | 2005-06-09 | 2011-03-02 | 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 |
| RU2356229C2 (en) * | 2007-05-10 | 2009-05-27 | Государственное учреждение "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан" | Herbicidal agent and method of its preparation |
| WO2010135324A1 (en) | 2009-05-18 | 2010-11-25 | Monsanto Technology Llc | Use of glyphosate for disease suppression and yield enhancement in soybean |
| PL2638803T3 (en) | 2009-09-30 | 2017-08-31 | Basf Corporation | LOW VOLATILE AMINE SALTS OF ANIONAL 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 RO RO7199872A patent/RO77018A/en unknown
- 1971-10-22 IT IT30219/71A patent/IT946007B/en active
- 1971-10-22 RO RO7168548A patent/RO72460A/en unknown
- 1971-10-22 DE DE2167051A patent/DE2167051C2/en not_active Expired
- 1971-10-22 IL IL37993A patent/IL37993A/en unknown
- 1971-10-22 SE SE7113473A patent/SE400695B/en unknown
- 1971-10-22 OA OA54402A patent/OA03838A/en unknown
- 1971-10-22 PT PT56642A patent/PT56642A1/en unknown
- 1971-10-22 CA CA125905A patent/CA936865A/en not_active Expired
- 1971-10-22 DD DD160070A patent/DD100868A6/xx unknown
- 1971-10-22 IL IL47972A patent/IL47972A/en unknown
- 1971-10-22 BR BR7076/71A patent/BR7107076D0/en unknown
- 1971-10-22 NO NO3926/71A patent/NO141090C/en unknown
- 1971-10-22 FR FR7138086A patent/FR2129327A5/fr not_active Expired
- 1971-10-22 GB GB4926371A patent/GB1366379A/en not_active Expired
- 1971-10-22 ZM ZM150/71A patent/ZM15071A1/en unknown
- 1971-10-22 BE BE774349A patent/BE774349A/en not_active IP Right Cessation
- 1971-10-22 JP JP8384671A patent/JPS566401B1/ja active Pending
- 1971-10-22 FI FI3000/71A patent/FI57955C/en active
- 1971-10-22 CY CY837A patent/CY837A/en unknown
- 1971-10-22 TR TR18244A patent/TR18244A/en unknown
- 1971-10-22 BG BG018842A patent/BG18585A3/en unknown
- 1971-10-22 YU YU02686/71A patent/YU36532B/en unknown
- 1971-10-22 DE DE2166573A patent/DE2166573C3/en not_active Expired
- 1971-10-22 CH CH1539171A patent/CH571306A5/xx not_active IP Right Cessation
- 1971-10-22 IE IE1340/71A patent/IE35501B1/en unknown
- 1971-10-22 DE DE2152826A patent/DE2152826C3/en not_active Expired
- 1971-10-22 DK DK514071AA patent/DK140433B/en not_active IP Right Cessation
-
1972
- 1972-10-09 SU SU721834717D patent/SU963446A3/en active
- 1972-10-09 SU SU721834717A patent/SU665775A3/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
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