DD145273A5 - Verfahren zur herstellung von o-aryl-n-phosphonomethylglycinnitrilen - Google Patents
Verfahren zur herstellung von o-aryl-n-phosphonomethylglycinnitrilen Download PDFInfo
- Publication number
- DD145273A5 DD145273A5 DD77214294A DD21429477A DD145273A5 DD 145273 A5 DD145273 A5 DD 145273A5 DD 77214294 A DD77214294 A DD 77214294A DD 21429477 A DD21429477 A DD 21429477A DD 145273 A5 DD145273 A5 DD 145273A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acid
- aryl
- phosphite
- solution
- mol
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- -1 methylenedioxy Chemical group 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 16
- 150000005690 diesters Chemical class 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- CTTRIWVSECLRDA-UHFFFAOYSA-N 2-[3,5-bis(cyanomethyl)-1,3,5-triazinan-1-yl]acetonitrile Chemical compound N#CCN1CN(CC#N)CN(CC#N)C1 CTTRIWVSECLRDA-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- MWZWOLDTGUGECQ-UHFFFAOYSA-N bis(4-methoxyphenyl) hydrogen phosphite Chemical compound C1=CC(OC)=CC=C1OP(O)OC1=CC=C(OC)C=C1 MWZWOLDTGUGECQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- 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
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- 229950005499 carbon tetrachloride Drugs 0.000 description 6
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- 241000132536 Cirsium Species 0.000 description 1
- 241001547427 Cissampelos pareira Species 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
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- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- PDPQEMNLXUGHNS-UHFFFAOYSA-N bis(3,4-dichlorophenyl) hydrogen phosphite Chemical compound C=1C=C(Cl)C(Cl)=CC=1OP(O)OC1=CC=C(Cl)C(Cl)=C1 PDPQEMNLXUGHNS-UHFFFAOYSA-N 0.000 description 1
- WAPALSKUZQDHKX-UHFFFAOYSA-N bis(3-methyl-4-nitrophenyl) hydrogen phosphite Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OP(O)OC=2C=C(C)C(=CC=2)[N+]([O-])=O)=C1 WAPALSKUZQDHKX-UHFFFAOYSA-N 0.000 description 1
- VZOSMKZCDPKGHW-UHFFFAOYSA-N bis(3-methylphenyl) hydrogen phosphite Chemical compound CC1=CC=CC(OP(O)OC=2C=C(C)C=CC=2)=C1 VZOSMKZCDPKGHW-UHFFFAOYSA-N 0.000 description 1
- ZJRNBGVJGIFZRO-UHFFFAOYSA-N bis(3-nitrophenyl) hydrogen phosphite Chemical compound C=1C=CC([N+]([O-])=O)=CC=1OP(O)OC1=CC=CC([N+]([O-])=O)=C1 ZJRNBGVJGIFZRO-UHFFFAOYSA-N 0.000 description 1
- ZOLLZXLIZDRUPF-UHFFFAOYSA-N bis(4-chlorophenyl) hydrogen phosphite Chemical compound C=1C=C(Cl)C=CC=1OP(O)OC1=CC=C(Cl)C=C1 ZOLLZXLIZDRUPF-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 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
- 150000003940 butylamines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- JNXDHIIQYKMEDV-UHFFFAOYSA-N dinaphthalen-2-yl hydrogen phosphite Chemical compound C1=CC=CC2=CC(OP(OC=3C=C4C=CC=CC4=CC=3)O)=CC=C21 JNXDHIIQYKMEDV-UHFFFAOYSA-N 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 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
- 239000003208 petroleum Substances 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
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 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
- 238000004382 potting Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 239000011343 solid material Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 239000011345 viscous material Substances 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)]
- C07F9/40—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)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (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 |
---|---|
DD145273A5 true DD145273A5 (de) | 1980-12-03 |
Family
ID=27115259
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD77214294A DD145273A5 (de) | 1976-12-13 | 1977-11-18 | Verfahren zur herstellung von o-aryl-n-phosphonomethylglycinnitrilen |
Country Status (36)
Country | Link |
---|---|
JP (1) | JPS5373543A (fr) |
AR (1) | AR223311A1 (fr) |
AT (1) | AT359772B (fr) |
AU (1) | AU510196B2 (fr) |
BG (2) | BG36634A3 (fr) |
BR (1) | BR7707676A (fr) |
CA (1) | CA1098529A (fr) |
CH (2) | CH636752A5 (fr) |
CY (1) | CY1061A (fr) |
DD (1) | DD145273A5 (fr) |
DE (1) | DE2751631A1 (fr) |
DK (1) | DK511677A (fr) |
EG (1) | EG12818A (fr) |
ES (1) | ES464216A1 (fr) |
FI (1) | FI67558C (fr) |
FR (1) | FR2373553A1 (fr) |
GB (1) | GB1556322A (fr) |
GR (1) | GR66150B (fr) |
HU (1) | HU184655B (fr) |
IE (1) | IE45917B1 (fr) |
IL (1) | IL53425A (fr) |
IN (1) | IN146347B (fr) |
IT (1) | IT1088890B (fr) |
KE (1) | KE3045A (fr) |
MX (1) | MX4714E (fr) |
NL (1) | NL7712653A (fr) |
NO (1) | NO151547C (fr) |
NZ (1) | NZ185720A (fr) |
OA (1) | OA05804A (fr) |
PH (2) | PH16387A (fr) |
PL (1) | PL113273B1 (fr) |
PT (1) | PT67295B (fr) |
SE (7) | SE441451B (fr) |
TR (1) | TR20178A (fr) |
YU (1) | YU275677A (fr) |
ZM (1) | ZM8377A1 (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR027024A1 (es) | 1999-12-23 | 2003-03-12 | Basf Ag | Procedimiento para la preparacion de n-fosfonometilglicina |
CN104151360B (zh) * | 2013-05-14 | 2019-02-22 | 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 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1445087A (en) * | 1972-11-08 | 1976-08-04 | Ici Ltd | Preparing n-phosphonomethylglycine and nitrile intermediates therefor |
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 |
-
1977
- 1977-11-16 EG EG643/77A patent/EG12818A/xx active
- 1977-11-17 NL NL7712653A patent/NL7712653A/xx not_active Application Discontinuation
- 1977-11-17 ES ES464216A patent/ES464216A1/es not_active Expired
- 1977-11-18 PL PL1977202250A patent/PL113273B1/pl unknown
- 1977-11-18 AT AT825177A patent/AT359772B/de not_active IP Right Cessation
- 1977-11-18 FI FI773495A patent/FI67558C/fi not_active IP Right Cessation
- 1977-11-18 HU HU77MO994A patent/HU184655B/hu unknown
- 1977-11-18 IL IL53425A patent/IL53425A/xx unknown
- 1977-11-18 NO NO773959A patent/NO151547C/no unknown
- 1977-11-18 CY CY1061A patent/CY1061A/xx unknown
- 1977-11-18 CA CA291,165A patent/CA1098529A/fr not_active Expired
- 1977-11-18 BG BG7839915A patent/BG36634A3/xx unknown
- 1977-11-18 NZ NZ185720A patent/NZ185720A/xx unknown
- 1977-11-18 AU AU30754/77A patent/AU510196B2/en not_active Expired
- 1977-11-18 YU YU02756/77A patent/YU275677A/xx unknown
- 1977-11-18 IT IT29814/77A patent/IT1088890B/it active
- 1977-11-18 OA OA56318A patent/OA05804A/fr unknown
- 1977-11-18 DD DD77214294A patent/DD145273A5/de unknown
- 1977-11-18 SE SE7713047A patent/SE441451B/sv not_active IP Right Cessation
- 1977-11-18 DE DE19772751631 patent/DE2751631A1/de not_active Withdrawn
- 1977-11-18 GB GB48084/77A patent/GB1556322A/en not_active Expired
- 1977-11-18 CH CH1411377A patent/CH636752A5/de not_active IP Right Cessation
- 1977-11-18 DK DK511677A patent/DK511677A/da not_active Application Discontinuation
- 1977-11-18 GR GR54843A patent/GR66150B/el unknown
- 1977-11-18 PT PT67295A patent/PT67295B/pt unknown
- 1977-11-18 PH PH20450A patent/PH16387A/en unknown
- 1977-11-18 JP JP13800977A patent/JPS5373543A/ja active Granted
- 1977-11-18 BR BR7707676A patent/BR7707676A/pt unknown
- 1977-11-18 IE IE2354/77A patent/IE45917B1/en unknown
- 1977-11-18 ZM ZM7783A patent/ZM8377A1/xx unknown
- 1977-11-18 FR FR7734834A patent/FR2373553A1/fr active Granted
- 1977-11-18 MX MX776570U patent/MX4714E/es unknown
- 1977-11-18 IN IN1627/CAL/77A patent/IN146347B/en unknown
- 1977-11-18 BG BG7737829A patent/BG28423A3/xx unknown
- 1977-11-28 TR TR20178A patent/TR20178A/xx unknown
- 1977-12-12 AR AR270319A patent/AR223311A1/es active
-
1980
- 1980-04-28 KE KE3045A patent/KE3045A/xx unknown
-
1982
- 1982-03-30 CH CH196382A patent/CH636885A5/de not_active IP Right Cessation
-
1983
- 1983-03-30 SE SE8301807A patent/SE8301807L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301808A patent/SE8301808L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301805A patent/SE8301805L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301810A patent/SE8301810D0/xx not_active Application Discontinuation
- 1983-03-30 SE SE8301806A patent/SE8301806D0/xx not_active Application Discontinuation
- 1983-03-30 SE SE8301809A patent/SE8301809D0/xx not_active Application Discontinuation
- 1983-07-14 PH PH29231A patent/PH18774A/en unknown
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