PL93298B1 - - Google Patents
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- PL93298B1 PL93298B1 PL1974187852A PL18785274A PL93298B1 PL 93298 B1 PL93298 B1 PL 93298B1 PL 1974187852 A PL1974187852 A PL 1974187852A PL 18785274 A PL18785274 A PL 18785274A PL 93298 B1 PL93298 B1 PL 93298B1
- Authority
- PL
- Poland
- Prior art keywords
- phosphonomethylglycine
- salt
- carboxyethyl
- carboxyethyl ester
- ester
- Prior art date
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229960000380 propiolactone Drugs 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- -1 carboxyalkyl ester Chemical class 0.000 description 16
- VLTQCAKAICGHKR-UHFFFAOYSA-N 3-[2-(phosphonomethylamino)acetyl]oxypropanoic acid Chemical compound C(=O)(O)CCOC(CNCP(=O)(O)O)=O VLTQCAKAICGHKR-UHFFFAOYSA-N 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- KGSVNOLLROCJQM-UHFFFAOYSA-N 2-(benzylamino)acetic acid Chemical compound OC(=O)CNCC1=CC=CC=C1 KGSVNOLLROCJQM-UHFFFAOYSA-N 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- QUIQKYAAGXIAFF-UHFFFAOYSA-N 2-(phosphonoamino)acetic acid Chemical compound OC(=O)CNP(O)(O)=O QUIQKYAAGXIAFF-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- YXSJAPUKSDAPST-UHFFFAOYSA-M [O-]C(CCOC(CNCP(O)(O)=O)=O)=O.[K+] Chemical compound [O-]C(CCOC(CNCP(O)(O)=O)=O)=O.[K+] YXSJAPUKSDAPST-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- RGSODMOUXWISAG-UHFFFAOYSA-N n-prop-2-ynylprop-2-yn-1-amine Chemical class C#CCNCC#C RGSODMOUXWISAG-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 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
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)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Opis patentowy opublikowano: 31.12.1977 93298 MKP C07f 9/40 Int, Cl.2 C07F 9/40 C£YTfclHtA Twórca wynalazku:— Uprawniony z patentu: Monsanto Company, St. Louis (Stany Zjednoczo¬ ne Ameryki) Sposób wytwarzania nowych estrów karboksyalkilowych N-fosfonometyloglicyny Przedmiotem wymalaziku jest sposób wytwarza¬ nia nowych es-trów karboiksyalkilowych N-fosfomo- metyloglicyny, ewentualnie w postaci ich soli.Nowe estiry karboksyalkilowe wytwarzane spo¬ sobem wedlug wynalazku maja wzór przedstawio¬ ny ma rysunku, w którym M, M' i M" oznaczaja niezaleznie od siebie atom wodoru, aitom metalu alkalicznego lub metalu zriem alkalicznych, kation amoniowy albo zasade organiczna. Korzystnymi zwiazkami sa takie, w których co najmniej jeden z podstawników M, M',lub M" oznacza atom wo¬ doru, atom metalu alkalicznego lub metalu ziem alkalicznych, kation amoniowy albo zasade orga¬ niczna.Estry karboksyalkilowe sposobem wedlug wyna¬ lazku otrzymuje sie w reakcji N-fosfonometylogli- cyny w srodowisku wodnym z laiktonem, takim jak propiolakton, w obecnosci zasady. Po zoboje- tnienu zasady kwasem solnym otrzymuje sie wol¬ ny kwas, z którego w reakcji z róznymi zasadami otrzymuje sie rozmaite sole.Reakcje prowadzi sie zwykle w temperaturze okolo 20°, aczkolwiek mozna stosowac wyzsze lub nizsze temperatury.Zasadnicze znaczenie ma kolejnosc dodawania reagentów i dlatego waznym jest by dodawac lak- ton do alkalicznego roztworu wodnego N-fosfono- metyloglicyny. Korzystnym jest stosowanie równo- molarnych ilosci laktonu i N-fosfonoglicyny, gdyz 2 ulatwia to pózniejsza izolacje otrzymiariego estru karboiksyalkilowego.Proces prowadzi sie zwykle pod cisnieniem at¬ mosferycznym, mozna jednak stosowac nadcisnie¬ nie lub podcisnienie.Okreslenie „metale alkaliczne" dotyczy litu. so¬ du, potasu, cezu i ruibidiu. Okreslenie ,^metale,ziem alkalicznych" dotyczy berylu, magnezu, wapnia, strontu i baru.Sole z zasadaimi organicznymi otrzymuje sie w re¬ akcji z aminami o ciezarze czasteczkowym nie prze¬ kraczajacym okolo 300. Do takich amin naleza, al- ikiloiaminy, alkilenoaminy i aminoalikohole zawiera¬ jace nie wiecej ,niz dwie grupy aminowe, takie jak metyloamina, etyloamiina, n-jjropyloaimiina, izopro^- pyloamina, n^butyloamina, izobutyloamina, II-rz.- nbutyloamina, n-amyloamina, izoamyloamina, he- ksyloamina, heptyloamina, oktyloaniina, nonylo- amiina, decyloamina, penitadecyloamiiria, heksadecy- loamiina, heptadecyloamina, oktadecyloamina, ety- lobutylo:amina, etyloheptyloamina, undecyloamina, dodecyloamina, trildecyloamina, tetradecyloamina, metyloetyloamiina, metyloizopropyloamina, metylo- heksyloamina, metylononyloaanina, metylopenta- decyloamiina, meftykaktadecyloamina, etylooiktylo- amiina, heksyloheptyloiamina, heksylooktyloaimiina, dwumetyloaimina, dwuietyloamina, dwu-n-propoylo- amina, dwu-n-aimyloamioa, dwuiizoamyloamrina, dwuheksyloamina, dwuheptyloamina, dwuototylo- amina, trójmetyloanrina, trójetyloamina, trój-n- «3 2»8-propyloaanina, itrójiizoparcpyloaflBp, torój-m-bii- tyloamikia, toójizobotylóarnAna^ Woj-II-rz.-butylo- aimlina, trój^n-iaimyloamiriia, etanoloamiina, n-propa- noloamina, izopropanoloamioa, dwuetamoloairiina, N,N-dwviietyloetanoloiamiinia, N-etylopropanoloamina,.N-butyftoetanoloamiria, alMoamiina, in-buetylo-2- wamiina nnpentanylo-2-amina, 2,3-dwumetylobuite- nyto-2-anilina, d(wubutanylo-2Haimina, . n-heksenylo- -2-iamina oraz propytenodwiiamina.Wynalazek ilustruja nastepujace przyklady, w których, jesli nie podano ioaazej, wszystkie czesci d procenty sa wielkosciami wagowymi.Przyklad I. Mieszanine 17• g N-fosfonomety- loglicynyj 200 ml wody i 12 g wodorotlenku sodo¬ wego miesza sie w kolbie okraglodeninej o pojem- inos-ei 500 ,ml az ^o otrzymania klarownego roztwo¬ ru. Pb ochlodizeniiu do temperatury 20°C dodaje sie w ciagu 15 minut 8 g propiolafctonu i calosc miesza, w oiggu 1 godiziny w temperaturze pokojowej. Po Bakwaszieniu kwasem solnym wytraca sie osad, któ¬ ry odsacza sie i suszy. Otrzymuje sie ester 2-kar- boksyetylowy N-fosfonometyloglicyny o tempera¬ turze topnienia 211°C (z rozikladem).Analiza elementarna: obtoczono: C —29,79; H —5,33; N —5,79; P —12,80; znaleziono: C —29,7«/o; H — 5,06%; N —5,712/s; P —12,63%.Przyklad II. Wodny roztwór soM dwuriziopro- pyloaminowej estru 2-karboksyetylowego N-fosfo¬ nometyloglicyny otrzymuje sie w nastepujacy spo¬ sób., Do zawiesiny 4,04 g esitru 2^karboksyetylowego N-fostfonometyloglicyny w 5,0 g wody dodaje sie i podczas chlodzenia 1,92 g izopropyloaminy. Otrzy¬ muje sie wodny roztwór zawierajacy sól dwuizo- propyloaminowa estru 2-karboksyetylowego N-fo¬ sfonometyloglicyny.Przyklad III. * Wodny roztwór soli dwusodo- wej estru 2Hkarboksyetyloweigo N-fenylometylogli- cyiny otrzymuje sie w sposób nastepujacy: Do zawiesiny 4,04 g estru 2-karboksyetylowego N-fosfonom^tyloglicyny w 2,28 g wody dodaje sie podiozas chlodzenia 1,36 g wodorotlenku sodowego.Otrzymuje §ie wodny roztwór zawierajacy sól dwu- sodowa estru 2-karboksyetylowego N-fosfonomety- logliicyny.Powtarzajac postepowanie opisane w przykladzie II i III oraz stosujac odpowiednia nasade w ilosci 1 lub 2 równowazniki zasady na 1 równowaznik eistai 2-karboiksyetylowego N-fenylometyloglicyny, , otrzymuje sie nastepujace sole: sól jtednobutyloamiinowa esitru 2-karboksyetylo- weglo N-fosfonoglicyny, sól jednoCtrójmetyloaminowa) estru 2-karboksy- etylawego-N-fosfonometyloglicyny, 298 4 sól jedno(idwuetylenotrójaimiinowa) esitru 2-toarbo- ksyetylowego. N-fosfonometyloglicyny, sól jednoizopiopyloaminowa esitru 2-karbolksyety¬ lowego NHfosfonometylogliicyny, s sól jedno-n-propyloamiinowa estru 2nkarbolksyety- lowego N-fosfonometyloglicyny, sól jtedno(dwupropargiloam!inowa) estru 2-karbo¬ ksyetylowego • N -fbsfonometyloglicyiny, sól jedinosodowa estru 2-karboksyetylowego N- -fosfonometyloiglicyny, sól jednopotasowa estru 2-karboksyetylowego N- fosfonometyloglicyny, sóljedno(dwuialkiloaminowa) estru 2-fcarboksyety- lowego N-fosfonometyloglicyny, sól jednolitowa estru 2-karboksyetylowego N-fo¬ sfonometyloglicyny, sól trójsodowa estru 2^karboksyetylowego N-fe- nylornetyloglicyny, sól jednocezowa estru 2-karboksyetylowego N- ao -fosionometyloglieyny, sól dwupotasowa estru 2-ikarboksyetylowego N- -tfosfonometyloglicyny, sól trójpotasowa es'tru 2-karboksyetylowego N- -fosfomametyloglicyny, sól jednocykloheksyloaminowa estru 2^arboksy- etylowego N-fosfonometyloglicyny, sól dwu(metyloiamiinowa) estru 2-karboksyetylo- wego N-fosfonometyloglicyny, sól dwu(etyloaminowa) estru 2-karboksyetylowe- go N-fosfonometyloglicyny, sól dwu(n-propyloamiinowa) estru 2-karboksyety¬ lowego N-fosfonometyloglicyny, sól dwui(izobutyloaminowa) estru 2-karboksyety¬ lowego N-fosfonometyloglicyny, sól jedno(heptadecynyloaminowa) estru 2-karbo- Iksyetylowego N-fosfonometyloglicyny, sól jednositearyloaminowa estru 2^karbdl$syetylo- wego N-fosfonometyloglicyny, sól jednotalloaminowa esitru 2-karboksyetylowe- 40 go N-fosfonometyloglicyny, sól jednometylobutyloaminowa estru 2-karbotay- etylowego N-fosfonometyloglicyny. W PL PL PL PL
Claims (2)
1. Zastrzezenia patentowe 45 1. Sposób wytwarzania nowych estrów karboksy- - alkilowych N-fosfonometyloglicyny o wzorze przed¬ stawionym na rysunku w którym M, M ii M" oeinia- ozaja niezaleznie od siiebie atom wodoru, atom me- 50 ftalu alkalicznego lub metalu ziem alkalicznych, ka¬ tion amoniowy albo zasade organiczna, znamienny tym, ze mieszanine N-fosfonometyloglicyny, wody i zasady poddaje sie reakcji z propiolakitonem.
2. Sposób wedlug zastrz. 4, znamienny tym, ze 55 proces prowadzi sie w itemperaturze okolo 20°C. /93 298 M1 \ O H O O \0 \ll i I II P-CH2-N-CH2C-0-(CH2)2-C-OM O / / M! PL PL PL PL
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US417858A US3868407A (en) | 1973-11-21 | 1973-11-21 | Carboxyalkyl esters of n-phosphonomethyl glycine |
Publications (1)
Publication Number | Publication Date |
---|---|
PL93298B1 true PL93298B1 (pl) | 1977-05-30 |
Family
ID=23655654
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1974187852A PL93298B1 (pl) | 1973-11-21 | 1974-11-05 | |
PL1974175344A PL92403B1 (pl) | 1973-11-21 | 1974-11-05 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1974175344A PL92403B1 (pl) | 1973-11-21 | 1974-11-05 |
Country Status (31)
Country | Link |
---|---|
US (1) | US3868407A (pl) |
JP (1) | JPS5242854B2 (pl) |
AR (1) | AR219688A1 (pl) |
AT (1) | AT341267B (pl) |
BE (1) | BE821879A (pl) |
BG (1) | BG26183A3 (pl) |
BR (1) | BR7409238A (pl) |
CA (1) | CA1048053A (pl) |
CH (1) | CH593013A5 (pl) |
CS (1) | CS178935B2 (pl) |
DD (2) | DD115686A5 (pl) |
DE (1) | DE2452460C3 (pl) |
DK (1) | DK139360B (pl) |
EG (1) | EG11241A (pl) |
ES (1) | ES431614A1 (pl) |
FI (1) | FI60020C (pl) |
FR (1) | FR2251569B1 (pl) |
GB (1) | GB1440847A (pl) |
HU (1) | HU171312B (pl) |
IL (1) | IL45989A (pl) |
IN (1) | IN140421B (pl) |
IT (1) | IT1049325B (pl) |
NL (1) | NL172065C (pl) |
NO (1) | NO143747C (pl) |
PH (1) | PH10683A (pl) |
PL (2) | PL93298B1 (pl) |
RO (1) | RO72710A (pl) |
SE (1) | SE421625B (pl) |
SU (1) | SU682097A3 (pl) |
YU (1) | YU40107B (pl) |
ZA (1) | ZA747107B (pl) |
Families Citing this family (23)
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 |
US3948975A (en) * | 1974-08-05 | 1976-04-06 | Monsanto Company | Hydroxyalkyl esters of N-phosphonomethyl glycine |
US4197254A (en) * | 1976-05-03 | 1980-04-08 | Monsanto Company | Derivatives of N-phosphonomethylglycine |
US4159901A (en) * | 1977-05-16 | 1979-07-03 | Monsanto Company | Corrosion inhibited agricultural compositions |
JPS5839127B2 (ja) * | 1978-03-09 | 1983-08-27 | 明治製菓株式会社 | 除草剤組成物 |
US4226610A (en) * | 1978-04-15 | 1980-10-07 | Meiji Selka Kaisha, Ltd. | Herbicidal compounds, preparation thereof and herbicides containing the same |
WO1984003607A1 (en) * | 1983-03-16 | 1984-09-27 | Chevron Res | Glyphosate-type herbicidal compositions |
ES8603901A1 (es) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Procedimiento de preparacion de sulfonamidas con grupo ansinometilfosfonico |
JPS60185443U (ja) * | 1984-05-21 | 1985-12-09 | 温泉青果農業協同組合 | 収穫用鋏 |
US5580841A (en) * | 1985-05-29 | 1996-12-03 | Zeneca Limited | Solid, phytoactive compositions and method for their preparation |
US5468718A (en) * | 1985-10-21 | 1995-11-21 | Ici Americas Inc. | Liquid, phytoactive compositions and method for their preparation |
US5047079A (en) * | 1986-08-18 | 1991-09-10 | Ici Americas Inc. | Method of preparation and use of solid, phytoactive compositions |
FR2635522B1 (fr) * | 1988-08-18 | 1990-11-16 | Rhone Poulenc Agrochimie | N-sulfonomethylglycinate procede de preparation, utilisation dans la preparation d'herbicides de type glyphosate |
US5187292A (en) * | 1988-08-18 | 1993-02-16 | Rhone-Poulenc Agrochimie | N-sulfomethylglycinate, use in the preparation of herbicides of the glyphosate type |
US6930075B1 (en) | 1990-11-02 | 2005-08-16 | Monsanto Technology, Llc | Fatty acid-based herbicidal composition |
IL101539A (en) | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing |
HU212802B (en) | 1991-07-19 | 1996-11-28 | Monsanto Europe Sa | Phytoactive sack-like composition containing glyphosate-izopropylamine salt |
WO1997031534A1 (de) * | 1996-02-28 | 1997-09-04 | Bayer Aktiengesellschaft | Verwendung von n-phosphonomethyl-glycinestern in wässriger lösung als herbizide und neue n-phosphonomethyl-glycinester |
ITTO980048A1 (it) * | 1998-01-20 | 1999-07-20 | Ipici Spa | Composizioni erbicide, procedimenti per la loro preparazione ed impieghi |
US6921834B2 (en) | 2002-05-22 | 2005-07-26 | Dow Agrosciences Llc | Continuous process for preparing N-phosphonomethyl glycine |
AR037559A1 (es) * | 2002-11-19 | 2004-11-17 | Atanor S A | Una formulacion herbicida solida de n-fosfonometilglicina, bajo la forma de polvo, granulos o escamas, soluble o dispersable en agua, y el procedimiento para preparar dicha composicion |
US8470741B2 (en) * | 2003-05-07 | 2013-06-25 | Croda Americas Llc | Homogeneous liquid saccharide and oil systems |
CA2579816C (en) * | 2004-09-17 | 2014-04-29 | Monsanto Technology Llc | Glyphosate formulations with early burndown symptoms |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
-
1973
- 1973-11-21 US US417858A patent/US3868407A/en not_active Expired - Lifetime
-
1974
- 1974-11-04 ES ES431614A patent/ES431614A1/es not_active Expired
- 1974-11-04 SU SU742076318A patent/SU682097A3/ru active
- 1974-11-04 IL IL45989A patent/IL45989A/en unknown
- 1974-11-04 NL NLAANVRAGE7414338,A patent/NL172065C/xx not_active IP Right Cessation
- 1974-11-05 IT IT29129/74A patent/IT1049325B/it active
- 1974-11-05 YU YU2949/74A patent/YU40107B/xx unknown
- 1974-11-05 CA CA212,996A patent/CA1048053A/en not_active Expired
- 1974-11-05 FR FR7436746A patent/FR2251569B1/fr not_active Expired
- 1974-11-05 CH CH1476974A patent/CH593013A5/xx not_active IP Right Cessation
- 1974-11-05 DK DK575274AA patent/DK139360B/da not_active IP Right Cessation
- 1974-11-05 AT AT884674A patent/AT341267B/de not_active IP Right Cessation
- 1974-11-05 IN IN2419/CAL/1974A patent/IN140421B/en unknown
- 1974-11-05 DE DE2452460A patent/DE2452460C3/de not_active Expired
- 1974-11-05 BR BR9238/74A patent/BR7409238A/pt unknown
- 1974-11-05 NO NO743973A patent/NO143747C/no unknown
- 1974-11-05 JP JP49126653A patent/JPS5242854B2/ja not_active Expired
- 1974-11-05 GB GB4783174A patent/GB1440847A/en not_active Expired
- 1974-11-05 RO RO7480433A patent/RO72710A/ro unknown
- 1974-11-05 ZA ZA00747107A patent/ZA747107B/xx unknown
- 1974-11-05 DD DD182166A patent/DD115686A5/xx unknown
- 1974-11-05 BE BE150233A patent/BE821879A/xx not_active IP Right Cessation
- 1974-11-05 BG BG7428118A patent/BG26183A3/xx unknown
- 1974-11-05 PL PL1974187852A patent/PL93298B1/pl unknown
- 1974-11-05 FI FI3227/74A patent/FI60020C/fi active
- 1974-11-05 HU HU74MO00000919A patent/HU171312B/hu unknown
- 1974-11-05 PL PL1974175344A patent/PL92403B1/pl unknown
- 1974-11-05 CS CS7400007541A patent/CS178935B2/cs unknown
- 1974-11-05 DD DD189587A patent/DD121596A5/xx unknown
- 1974-11-05 AR AR256392A patent/AR219688A1/es active
- 1974-11-05 SE SE7413853A patent/SE421625B/xx not_active IP Right Cessation
- 1974-11-08 PH PH16494A patent/PH10683A/en unknown
- 1974-11-20 EG EG515/74A patent/EG11241A/xx active
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