FI62842B - N-karboximetyl-n-fosfonometyl-amidsyror anvaendbara som ograesmedel - Google Patents
N-karboximetyl-n-fosfonometyl-amidsyror anvaendbara som ograesmedel Download PDFInfo
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- FI62842B FI62842B FI771387A FI771387A FI62842B FI 62842 B FI62842 B FI 62842B FI 771387 A FI771387 A FI 771387A FI 771387 A FI771387 A FI 771387A FI 62842 B FI62842 B FI 62842B
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- carbon atoms
- anhydride
- added
- compound according
- water
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- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
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- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
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- 150000001412 amines Chemical class 0.000 description 1
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- PXWUKZGIHQRDHL-UHFFFAOYSA-N atraton Chemical compound CCNC1=NC(NC(C)C)=NC(OC)=N1 PXWUKZGIHQRDHL-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- KYQRDNYMKKJUTH-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)C(C(=O)O)CC1C2 KYQRDNYMKKJUTH-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RMBGSBIZBRZJPK-UHFFFAOYSA-N butan-1-amine;2-dodecylbenzenesulfonic acid Chemical compound CCCCN.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O RMBGSBIZBRZJPK-UHFFFAOYSA-N 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 1
- IVUXTESCPZUGJC-UHFFFAOYSA-N chloroxuron Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1OC1=CC=C(Cl)C=C1 IVUXTESCPZUGJC-UHFFFAOYSA-N 0.000 description 1
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- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical class OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
- MMVFHENRSPTHHX-UHFFFAOYSA-L disodium;cyclohex-3-ene-1,2-dicarboxylate Chemical compound [Na+].[Na+].[O-]C(=O)C1CCC=CC1C([O-])=O MMVFHENRSPTHHX-UHFFFAOYSA-L 0.000 description 1
- PKVQSSWKJIPMRR-UHFFFAOYSA-L disodium;cyclohexane-1,2-dicarboxylate Chemical compound [Na+].[Na+].[O-]C(=O)C1CCCCC1C([O-])=O PKVQSSWKJIPMRR-UHFFFAOYSA-L 0.000 description 1
- BJTHMUJCKBTCFR-UHFFFAOYSA-L disodium;ethane-1,2-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCS([O-])(=O)=O BJTHMUJCKBTCFR-UHFFFAOYSA-L 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 238000005342 ion exchange Methods 0.000 description 1
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- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 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
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 235000019713 millet Nutrition 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- INFDPOAKFNIJBF-UHFFFAOYSA-N paraquat Chemical compound C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 INFDPOAKFNIJBF-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003123 plant toxin Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
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- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-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
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 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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- 239000000375 suspending agent Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- ZRQJSWOPZOITNN-UHFFFAOYSA-N urea;dihydrochloride Chemical compound Cl.Cl.NC(N)=O ZRQJSWOPZOITNN-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 238000009736 wetting 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)]
- C07F9/3804—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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
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)
Claims (17)
1. Som ogräsroedel användbara N^karboximetyl-N-fosfono-metylamidsyror med fonneln 0 0 . OH Y0-C-CHo-N-CHo-P , c=o ^ oz R-C-OZ II o väri Y är vätef lägre alkyl eller alkalimetall, Z är väte eller alkalimetall, och R är vinylen, metylvinylen, alkylen med en kedja med 2-3 kolatomer mellan de fria valenserna och sammanlagt av upp tili 8 kolatomer, ett monoklorderivat av nämnda vinylen eller alkylen, fenylen, karboxifenylen, 3-nitrofenylen, tolylen, cyklohexe-nylen, metylcyklohexenylen, cykloalkylen med 4^6 kolatomer, dikar-boxicykloalkylen med 4-6 ringkolatomer, dikarboxibentsoylfenylen, norbornenylen, norbornyliden, eller pyridyliden, med villkor att de fria valenserna pä de cykliska grupperna mäste stä i orto-ställ-ning tili varandra.
2, Förening enligt patentkravet l,känneteck n a d därav, att R är fenylen, cyklohexenylen eller alkylen där kedjan har 2-3 kolatomer mellan de fria valenserna och sammanlagt upp tili 5 kolatomer.
3, Förening enligt patentkravet 2, kännetecknad därav, att Y och Z är alkalimetaller.
4, Förening enligt patentkravet 2, kännetecknad därav, att Y är lägre alkyl,
5. Förening enligt patentkravet 2, kännetecknad därav, att R är fenylen.
6. Förening enligt patentkravet 2, kännetecknad därav , att R är cyklohexenylen. 62842 38
7, Förening enligt patentkravet 2, kännetecknad därav, att R är alkylen, där kedjan har 2-3 kolatomer mellan de fria valenserna och saromanlagt upp tili 5 kolatomer.
8, Förening enligt patentkravet 1, känneteck n a d därav, att R är cykloalkylen med 4-6 kolatomer.
9, Förening enligt patentkravet 1, känneteck n a d därav, att R är tolylen.
10. Förening enligt patentkravet 1, kännetecknad därav, att R är pyridyliden,
11. Förening enligt patentkravet 1, kännetecknad därav, att Y och Z är väte.
12. Förening enligt patentkravet 1, kännetecknad därav, att Y är lägre alkyl och Z är väte.
13. Förfarande för framställning av en förening med formeln: O O OH yo-c-ch2-n-ch2-p c=o \°z R-OOZ n o väri Y är väte, lägre alkyl eller alkalimetall, Z är väte eller alkalimetall, och R är vinylen, metylvinylen, alkylen med en kedja med 2-3 kolatomer mellan de fria valenserna och sammanlagt av upp tili 8 kolatomer, ett monoklorderivat av nämnda vinylen eller alkylen, fenylen, karboxifenylen, 3-nitrofenylen, tolylen, cyklohexe-nylen, metylcyklohexenylen, cykloalkylen med 4-6 kolatomer, dikar-boxicykloalkylen med 4-6 ringkolatomer, dikarboxibentsoylfenylen, norbornenylen, norbornyliden, eller pyridyliden med villkor att de fria valenserna pä de cykliska grupperna mäste st& i orto-ställ-ning tili varandra, kännetecknat därav, att man om-sätter ett di(alkalimetall)sait av N-fosfonometylglycin eller ett mono(alkalimetall)sait av lägre alkyl-N-fosfonometylglycinat med en anhydrid med formeln;
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68224376 | 1976-05-03 | ||
US05/682,243 US4197254A (en) | 1976-05-03 | 1976-05-03 | Derivatives of N-phosphonomethylglycine |
Publications (3)
Publication Number | Publication Date |
---|---|
FI771387A FI771387A (sv) | 1977-11-04 |
FI62842B true FI62842B (fi) | 1982-11-30 |
FI62842C FI62842C (fi) | 1983-03-10 |
Family
ID=24738842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI771387A FI62842C (fi) | 1976-05-03 | 1977-05-02 | N-karboximetyl-n-fosfonometyl-amidsyror anvaendbara som ograesmedel |
Country Status (43)
Country | Link |
---|---|
US (1) | US4197254A (sv) |
JP (1) | JPS52133928A (sv) |
AR (1) | AR218248A1 (sv) |
AT (1) | AT351860B (sv) |
AU (1) | AU510033B2 (sv) |
BE (1) | BE854167A (sv) |
BG (2) | BG27724A3 (sv) |
BR (1) | BR7702814A (sv) |
CA (1) | CA1085405A (sv) |
CH (1) | CH628905A5 (sv) |
CS (1) | CS193093B2 (sv) |
CY (1) | CY1022A (sv) |
DD (1) | DD131521A5 (sv) |
DE (1) | DE2719583A1 (sv) |
DK (1) | DK191877A (sv) |
EG (1) | EG13038A (sv) |
ES (1) | ES458316A1 (sv) |
FI (1) | FI62842C (sv) |
FR (1) | FR2350352A1 (sv) |
GB (1) | GB1532329A (sv) |
GR (1) | GR66155B (sv) |
HU (1) | HU184174B (sv) |
IE (1) | IE44829B1 (sv) |
IL (1) | IL51987A (sv) |
IN (1) | IN145362B (sv) |
IT (1) | IT1071331B (sv) |
KE (1) | KE2987A (sv) |
MX (1) | MX4664E (sv) |
MY (1) | MY8000125A (sv) |
NL (1) | NL7704710A (sv) |
NO (1) | NO153369C (sv) |
NZ (1) | NZ183984A (sv) |
OA (1) | OA05650A (sv) |
PH (2) | PH13654A (sv) |
PL (2) | PL106810B1 (sv) |
PT (1) | PT66498B (sv) |
RO (1) | RO72258A (sv) |
SE (2) | SE431213B (sv) |
SU (2) | SU665776A3 (sv) |
TR (1) | TR19644A (sv) |
YU (1) | YU111477A (sv) |
ZA (1) | ZA772622B (sv) |
ZM (1) | ZM3877A1 (sv) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5839127B2 (ja) * | 1978-03-09 | 1983-08-27 | 明治製菓株式会社 | 除草剤組成物 |
US4353731A (en) * | 1978-07-10 | 1982-10-12 | Monsanto Company | Amide and hydrazide derivatives of N-trifluoroacetyl-N-phosphonomethylglycine |
US4261727A (en) * | 1979-08-02 | 1981-04-14 | Monsanto Company | Herbicidal N-substituted triesters of N-phosphonomethylglycine |
US4340416A (en) * | 1979-08-02 | 1982-07-20 | Monsanto Company | N-Substituted triesters of N-phosphonomethylglycine |
US4364767A (en) * | 1981-07-27 | 1982-12-21 | Rhone-Poulenc Agrochimie | N(Carboxymethyl-N-(phosphonomethyl)-5-(2-chloro-4-trifluoromethyl phenoxy)-2-nitrobenzamide and salts thereof |
US4534902A (en) * | 1982-06-22 | 1985-08-13 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
US4444693A (en) * | 1982-09-07 | 1984-04-24 | Stauffer Chemical Company | Method for preparation of N-phosphonomethylglycine |
US5468718A (en) * | 1985-10-21 | 1995-11-21 | Ici Americas Inc. | Liquid, phytoactive compositions and method for their preparation |
US5087740A (en) * | 1989-08-17 | 1992-02-11 | Monsanto Company | Process for purifying N-phosphonomethylglycine |
KR20000068931A (ko) * | 1997-02-13 | 2000-11-25 | 죤 에이치. 뷰센 | 아미노 카르복실산의 제조방법 |
ITTO980048A1 (it) * | 1998-01-20 | 1999-07-20 | Ipici Spa | Composizioni erbicide, procedimenti per la loro preparazione ed impieghi |
JP4508394B2 (ja) * | 2000-09-20 | 2010-07-21 | 三菱瓦斯化学株式会社 | 有機ホスホン酸の精製方法 |
US6921834B2 (en) | 2002-05-22 | 2005-07-26 | Dow Agrosciences Llc | Continuous process for preparing N-phosphonomethyl glycine |
CN103524552A (zh) * | 2013-09-27 | 2014-01-22 | 中国农业大学 | 含磷酰基氨基酸结构的芳香酰胺类化合物及其制备方法与作为除草剂中的应用 |
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US2191738A (en) * | 1934-09-01 | 1940-02-27 | Ig Farbenindustrie Ag | High-molecular polycarboxylic acid amides and their production |
US2723991A (en) * | 1953-04-28 | 1955-11-15 | American Cyanamid Co | Production of n-arylmaleamic acids |
US3324033A (en) * | 1966-03-29 | 1967-06-06 | Ethyl Corp | Ester-amides of alkenyl succinic anhydride and diethanolamine as ashless dispersants |
US3455675A (en) * | 1968-06-25 | 1969-07-15 | Monsanto Co | Aminophosphonate herbicides |
DE2013371B1 (de) * | 1970-03-20 | 1971-11-04 | Joh A , Benckiser GmbH, Chemische Fabrik, 6700 Ludwigshafen | Verfahren zur Herstellung von Amino methylenphosphonsauren |
US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
US3853530A (en) * | 1971-03-10 | 1974-12-10 | Monsanto Co | Regulating plants with n-phosphonomethylglycine and derivatives thereof |
US3888915A (en) * | 1973-09-04 | 1975-06-10 | Monsanto Co | N-nitroso-n-phosphonomethyl glycine compounds and herbicidal use thereof |
US3868407A (en) * | 1973-11-21 | 1975-02-25 | Monsanto Co | Carboxyalkyl esters of n-phosphonomethyl glycine |
US3910969A (en) * | 1974-06-28 | 1975-10-07 | Monsanto Co | N-phenylsulfonamido-n-phosphonomethyl glycine and certain derivatives thereof |
US3933946A (en) * | 1974-11-19 | 1976-01-20 | Monsanto Company | N-hydroxy-N-phosphonomethylglycinates |
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1976
- 1976-05-03 US US05/682,243 patent/US4197254A/en not_active Expired - Lifetime
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1977
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- 1977-04-29 HU HU77MO981A patent/HU184174B/hu not_active IP Right Cessation
- 1977-04-29 SU SU772476270A patent/SU665776A3/ru active
- 1977-04-29 NL NL7704710A patent/NL7704710A/xx not_active Application Discontinuation
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- 1977-05-02 AU AU24756/77A patent/AU510033B2/en not_active Expired
- 1977-05-02 TR TR19644A patent/TR19644A/xx unknown
- 1977-05-02 FR FR7713245A patent/FR2350352A1/fr active Granted
- 1977-05-02 PT PT66498A patent/PT66498B/pt unknown
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- 1977-05-02 CA CA277,575A patent/CA1085405A/en not_active Expired
- 1977-05-02 CY CY1022A patent/CY1022A/xx unknown
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- 1977-05-02 BE BE177184A patent/BE854167A/xx not_active IP Right Cessation
- 1977-05-02 GB GB18237/77A patent/GB1532329A/en not_active Expired
- 1977-05-02 AT AT308477A patent/AT351860B/de not_active IP Right Cessation
- 1977-05-02 PL PL1977209094A patent/PL106810B1/pl unknown
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- 1977-05-02 IL IL51987A patent/IL51987A/xx unknown
- 1977-05-02 FI FI771387A patent/FI62842C/fi not_active IP Right Cessation
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- 1977-05-02 IT IT23084/77A patent/IT1071331B/it active
- 1977-05-02 AR AR267431A patent/AR218248A1/es active
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- 1977-05-02 DE DE19772719583 patent/DE2719583A1/de not_active Ceased
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- 1977-05-02 NZ NZ183984A patent/NZ183984A/xx unknown
- 1977-05-03 EG EG261/77A patent/EG13038A/xx active
- 1977-05-03 SE SE7705110A patent/SE431213B/sv not_active IP Right Cessation
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1979
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1980
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Legal Events
Date | Code | Title | Description |
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MM | Patent lapsed |
Owner name: MONSANTO COMPANY |