FI63761C - Som herbicider anvaendbara n-fosfonometylglycintriestrar och foerfarande foer framstaellning av dem - Google Patents
Som herbicider anvaendbara n-fosfonometylglycintriestrar och foerfarande foer framstaellning av dem Download PDFInfo
- Publication number
- FI63761C FI63761C FI763713A FI763713A FI63761C FI 63761 C FI63761 C FI 63761C FI 763713 A FI763713 A FI 763713A FI 763713 A FI763713 A FI 763713A FI 63761 C FI63761 C FI 63761C
- Authority
- FI
- Finland
- Prior art keywords
- ethyl
- glycinate
- phosphite
- benzene
- mol
- Prior art date
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 105
- -1 N-phosphonomethylglycine triesters Chemical class 0.000 claims description 58
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- 239000013638 trimer Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000008301 phosphite esters Chemical class 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 35
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- SPXOTSHWBDUUMT-UHFFFAOYSA-N 138-42-1 Chemical compound OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DPGUWLUQHWBGFB-UHFFFAOYSA-N [[(2-ethoxy-2-oxoethyl)amino]-bis(4-methoxyphenoxy)methyl]phosphonic acid Chemical compound C=1C=C(OC)C=CC=1OC(P(O)(O)=O)(NCC(=O)OCC)OC1=CC=C(OC)C=C1 DPGUWLUQHWBGFB-UHFFFAOYSA-N 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WPTKMZOZPKPYPJ-UHFFFAOYSA-N C=1C=C(F)C=CC=1OP(O)OC1=CC=C(F)C=C1 Chemical compound C=1C=C(F)C=CC=1OP(O)OC1=CC=C(F)C=C1 WPTKMZOZPKPYPJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 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 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 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 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- LRMSQVBRUNSOJL-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)F LRMSQVBRUNSOJL-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- YVWGGGZYGSZDKW-UHFFFAOYSA-N 2-(prop-2-enylazaniumyl)acetate Chemical compound OC(=O)CNCC=C YVWGGGZYGSZDKW-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
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- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QEASXYHBCOBLEU-UHFFFAOYSA-N bis(2,4,6-trimethylphenyl) hydrogen phosphite Chemical compound CC1=CC(C)=CC(C)=C1OP(O)OC1=C(C)C=C(C)C=C1C QEASXYHBCOBLEU-UHFFFAOYSA-N 0.000 description 1
- XAEQVLOIPHAOOW-UHFFFAOYSA-N bis(2-chlorophenyl) hydrogen phosphite Chemical compound C=1C=CC=C(Cl)C=1OP(O)OC1=CC=CC=C1Cl XAEQVLOIPHAOOW-UHFFFAOYSA-N 0.000 description 1
- ZUAGNRHSAPEJRW-UHFFFAOYSA-N bis(2-methoxyphenyl) hydrogen phosphite Chemical compound COC1=CC=CC=C1OP(O)OC1=CC=CC=C1OC ZUAGNRHSAPEJRW-UHFFFAOYSA-N 0.000 description 1
- CCNJNUGDZQIZBL-UHFFFAOYSA-N bis(2-methylphenyl) hydrogen phosphite Chemical compound CC1=CC=CC=C1OP(O)OC1=CC=CC=C1C CCNJNUGDZQIZBL-UHFFFAOYSA-N 0.000 description 1
- DXRRZSFVGCBWHI-UHFFFAOYSA-N bis(2-phenylphenyl) hydrogen phosphite Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1OP(O)OC1=CC=CC=C1C1=CC=CC=C1 DXRRZSFVGCBWHI-UHFFFAOYSA-N 0.000 description 1
- RKEKRPPUHVNPIX-UHFFFAOYSA-N bis(3,4-dimethylphenyl) hydrogen phosphite Chemical compound C1=C(C)C(C)=CC=C1OP(O)OC1=CC=C(C)C(C)=C1 RKEKRPPUHVNPIX-UHFFFAOYSA-N 0.000 description 1
- 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 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
- CWODEUGLCYQPFF-UHFFFAOYSA-N bis(4-chloro-3-methylphenyl) hydrogen phosphite Chemical compound C1=C(Cl)C(C)=CC(OP(O)OC=2C=C(C)C(Cl)=CC=2)=C1 CWODEUGLCYQPFF-UHFFFAOYSA-N 0.000 description 1
- LOEOWXVVVPWDCX-UHFFFAOYSA-N bis[(4-bromophenyl)methyl] hydrogen phosphite Chemical compound C=1C=C(Br)C=CC=1COP(O)OCC1=CC=C(Br)C=C1 LOEOWXVVVPWDCX-UHFFFAOYSA-N 0.000 description 1
- YMCNQAQIMNOULG-UHFFFAOYSA-N bis[(4-methylphenyl)methyl] hydrogen phosphite Chemical compound C1=CC(C)=CC=C1COP(O)OCC1=CC=C(C)C=C1 YMCNQAQIMNOULG-UHFFFAOYSA-N 0.000 description 1
- ZNMVHHAZNLWLEN-UHFFFAOYSA-N bis[3-(trifluoromethyl)phenyl] hydrogen phosphite Chemical compound C=1C=CC(C(F)(F)F)=CC=1OP(O)OC1=CC=CC(C(F)(F)F)=C1 ZNMVHHAZNLWLEN-UHFFFAOYSA-N 0.000 description 1
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- YHTBJFGFHUCNGS-UHFFFAOYSA-N ethyl 2-[bis[(4-tert-butylphenyl)peroxy]phosphorylmethylamino]acetate Chemical compound C=1C=C(C(C)(C)C)C=CC=1OOP(=O)(CNCC(=O)OCC)OOC1=CC=C(C(C)(C)C)C=C1 YHTBJFGFHUCNGS-UHFFFAOYSA-N 0.000 description 1
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- VXGABWCSZZWXPC-UHFFFAOYSA-N methyl 2-(methylamino)acetate Chemical compound CNCC(=O)OC VXGABWCSZZWXPC-UHFFFAOYSA-N 0.000 description 1
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- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle 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
- 239000010665 pine oil Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 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
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 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
- C07F9/4003—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
- 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)
- Medicines Containing Plant Substances (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64440675A | 1975-12-29 | 1975-12-29 | |
| US64440675 | 1975-12-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI763713A FI763713A (hu) | 1977-06-30 |
| FI63761B FI63761B (fi) | 1983-04-29 |
| FI63761C true FI63761C (fi) | 1983-08-10 |
Family
ID=24584785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI763713A FI63761C (fi) | 1975-12-29 | 1976-12-28 | Som herbicider anvaendbara n-fosfonometylglycintriestrar och foerfarande foer framstaellning av dem |
Country Status (40)
| Country | Link |
|---|---|
| US (1) | US4120689A (hu) |
| JP (2) | JPS5297949A (hu) |
| AR (1) | AR220309A1 (hu) |
| AT (1) | AT351858B (hu) |
| AU (1) | AU507499B2 (hu) |
| BE (1) | BE849907A (hu) |
| BG (2) | BG27736A3 (hu) |
| BR (1) | BR7608756A (hu) |
| CA (1) | CA1070704A (hu) |
| CH (1) | CH627922A5 (hu) |
| CS (1) | CS196338B2 (hu) |
| DD (2) | DD136696A5 (hu) |
| DE (1) | DE2659172C2 (hu) |
| DK (1) | DK144215C (hu) |
| EG (1) | EG12175A (hu) |
| ES (2) | ES454604A1 (hu) |
| FI (1) | FI63761C (hu) |
| FR (1) | FR2337142A1 (hu) |
| GB (1) | GB1538209A (hu) |
| GR (1) | GR62427B (hu) |
| HU (1) | HU185206B (hu) |
| IE (1) | IE44325B1 (hu) |
| IL (1) | IL51170A (hu) |
| IN (1) | IN145471B (hu) |
| IT (1) | IT1070047B (hu) |
| LU (1) | LU76475A1 (hu) |
| MX (1) | MX3898E (hu) |
| NL (1) | NL182881C (hu) |
| NO (3) | NO152861C (hu) |
| NZ (1) | NZ183000A (hu) |
| OA (1) | OA05523A (hu) |
| PH (2) | PH16654A (hu) |
| PL (2) | PL113916B1 (hu) |
| PT (1) | PT66022B (hu) |
| RO (1) | RO71484A (hu) |
| SE (1) | SE435386B (hu) |
| SU (2) | SU639416A3 (hu) |
| TR (1) | TR19596A (hu) |
| YU (1) | YU318176A (hu) |
| ZA (1) | ZA767654B (hu) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053505A (en) * | 1976-01-05 | 1977-10-11 | Monsanto Company | Preparation of n-phosphonomethyl glycine |
| 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 |
| US4300942A (en) | 1978-09-29 | 1981-11-17 | Monsanto Company | N-(Substituted carbonyl) derivatives of N-phos-phinylmethylglycinates and the herbicidal use thereof |
| US4251258A (en) | 1978-09-29 | 1981-02-17 | Monsanto Company | N-(Substituted carbonyl) derivatives of N-phosphinylmethylglycinates and the herbicidal use thereof |
| US4226611A (en) * | 1978-11-03 | 1980-10-07 | Monsanto Company | N-Phosphonomethylglycine thioester herbicides |
| US4211547A (en) * | 1978-12-22 | 1980-07-08 | Monsanto Company | N-Phosphonomethyliminodiacetonitrile and certain derivatives thereof |
| US4211548A (en) * | 1978-12-26 | 1980-07-08 | Monsanto Company | Esters of N-phosphinothioylmethylglycine and herbicidal method |
| 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 |
| US4322238A (en) * | 1980-08-13 | 1982-03-30 | Monsanto Company | N-Nitroso-N-phosphonomethylglycinonitrile esters and the herbicidal use thereof |
| US4322239A (en) * | 1980-08-13 | 1982-03-30 | Monsanto Company | N-Nitroso-N-phosphonomethylglycine esters and the herbicidal use thereof |
| US4395374A (en) * | 1981-01-02 | 1983-07-26 | Monsanto Company | Alkyl N-arylsulfenyl-N-diaryloxy-phosphinylmethylglycinates |
| US4666500A (en) * | 1981-01-02 | 1987-05-19 | Monsanto Company | Alkyl N-arylsulfenyl-N-diaryloxy-phosphinylmethylglycinates |
| US4401455A (en) * | 1981-10-05 | 1983-08-30 | Monsanto Company | Ester derivatives of N-alkylthio- N-cycloalkyl thio-N-phosphonomethylglycine and herbicidal methods using same |
| US4428765A (en) | 1981-10-05 | 1984-01-31 | Monsanto Company | Thiosulfenamide derivatives of N-phosphonomethylglycine triesters as herbicides |
| US4445928A (en) * | 1981-10-05 | 1984-05-01 | Monsanto Company | Herbicidal aminosulfenamide derivatives of N-phosphonomethylglycine triesters |
| US4401604A (en) * | 1981-10-05 | 1983-08-30 | Monsanto Company | Process for preparing thiosulfenamide derivatives of N-phosphonomethylglycine triesters |
| JPS5972094U (ja) * | 1982-11-06 | 1984-05-16 | オンキヨー株式会社 | スピ−カ−フレ−ム |
| EP0141794A1 (en) * | 1983-08-04 | 1985-05-15 | Monsanto Company | Aralower alkyl and substituted aralower alkyl esters of N-phosphonomethylglycines |
| US4471131A (en) * | 1983-09-27 | 1984-09-11 | Monsanto Company | Novel silyl esters of N-phosphonomethylglycine |
| US4519832A (en) * | 1984-04-27 | 1985-05-28 | Monsanto Company | Unsymmetrical aminosulfinamide derivatives of N-phosphonomethylglycine triesters, herbicidal compositions and use |
| JPS60188219U (ja) * | 1984-05-24 | 1985-12-13 | 川端 幸由 | 座金 |
| US4594093A (en) * | 1984-11-26 | 1986-06-10 | Monsanto Co. | Triester derivatives of N-phosphonomethylthionoglycine as herbicides |
| US4601744A (en) * | 1985-02-05 | 1986-07-22 | Monsanto Company | Esters of N,N'-methylene-bis-[N-[(diaryloxyphosphinyl)methyl]glycine] as herbicides |
| US5580841A (en) * | 1985-05-29 | 1996-12-03 | Zeneca Limited | Solid, phytoactive compositions and method for their preparation |
| US4634788A (en) * | 1985-06-06 | 1987-01-06 | Monsanto Company | Herbicidal glyphosate oxime derivatives |
| JPH0438127Y2 (hu) * | 1985-08-24 | 1992-09-07 | ||
| US5468718A (en) * | 1985-10-21 | 1995-11-21 | Ici Americas Inc. | Liquid, phytoactive compositions and method for their preparation |
| JPS6328933U (hu) * | 1986-08-11 | 1988-02-25 | ||
| ITTO980048A1 (it) * | 1998-01-20 | 1999-07-20 | Ipici Spa | Composizioni erbicide, procedimenti per la loro preparazione ed impieghi |
| US8470741B2 (en) * | 2003-05-07 | 2013-06-25 | Croda Americas Llc | Homogeneous liquid saccharide and oil systems |
| TWI635093B (zh) * | 2011-05-19 | 2018-09-11 | 基利科學股份有限公司 | 用於製備抗ｈｉｖ藥劑的方法與中間物 |
| PL3661937T3 (pl) | 2017-08-01 | 2021-12-20 | Gilead Sciences, Inc. | Formy krystaliczne ((s)-((((2r,5r)-5-(6-amino-9h-puryn-9-ylo)-4-fluoro-2,5-dihydrofuran-2-ylo)oksy)metylo)(fenoksy)fosforylo)-l-alaninianu etylu (gs-9131) do leczenia zakażeń wirusowych |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
| US3859183A (en) * | 1973-11-07 | 1975-01-07 | Monsanto Co | Process for producing n-phosphonomethyl glycine triesters |
| JPS5236627A (en) * | 1975-09-13 | 1977-03-22 | Nissan Chem Ind Ltd | Process for preparation of n- phosphonomethylglycine |
| JPS5272823A (en) * | 1975-12-16 | 1977-06-17 | Nissan Chem Ind Ltd | Herbicide |
-
1976
- 1976-12-17 MX MX765245U patent/MX3898E/es unknown
- 1976-12-23 IE IE2834/76A patent/IE44325B1/en unknown
- 1976-12-24 AU AU20895/76A patent/AU507499B2/en not_active Expired
- 1976-12-24 CA CA 268710 patent/CA1070704A/en not_active Expired
- 1976-12-27 NL NLAANVRAGE7614431,A patent/NL182881C/xx not_active IP Right Cessation
- 1976-12-27 ES ES454604A patent/ES454604A1/es not_active Expired
- 1976-12-28 DE DE2659172A patent/DE2659172C2/de not_active Expired
- 1976-12-28 AR AR266012A patent/AR220309A1/es active
- 1976-12-28 BE BE173679A patent/BE849907A/xx not_active IP Right Cessation
- 1976-12-28 DK DK584476A patent/DK144215C/da not_active IP Right Cessation
- 1976-12-28 BG BG035915A patent/BG27736A3/xx unknown
- 1976-12-28 PT PT66022A patent/PT66022B/pt unknown
- 1976-12-28 PL PL1976209063A patent/PL113916B1/pl unknown
- 1976-12-28 CS CS768703A patent/CS196338B2/cs unknown
- 1976-12-28 IN IN2280/CAL/76A patent/IN145471B/en unknown
- 1976-12-28 FI FI763713A patent/FI63761C/fi not_active IP Right Cessation
- 1976-12-28 JP JP15763776A patent/JPS5297949A/ja active Granted
- 1976-12-28 BG BG035032A patent/BG27533A3/xx unknown
- 1976-12-28 ZA ZA767654A patent/ZA767654B/xx unknown
- 1976-12-28 AT AT971076A patent/AT351858B/de not_active IP Right Cessation
- 1976-12-28 OA OA56025A patent/OA05523A/xx unknown
- 1976-12-28 CH CH1638176A patent/CH627922A5/de not_active IP Right Cessation
- 1976-12-28 PL PL1976194773A patent/PL106856B1/pl unknown
- 1976-12-28 DD DD76203329A patent/DD136696A5/xx unknown
- 1976-12-28 RO RO7688876A patent/RO71484A/ro unknown
- 1976-12-28 EG EG799/76A patent/EG12175A/xx active
- 1976-12-28 BR BR7608756A patent/BR7608756A/pt unknown
- 1976-12-28 IT IT30928/76A patent/IT1070047B/it active
- 1976-12-28 DD DD7600196654A patent/DD130857A5/xx unknown
- 1976-12-28 LU LU76475A patent/LU76475A1/xx unknown
- 1976-12-28 GR GR52489A patent/GR62427B/el unknown
- 1976-12-28 TR TR19596A patent/TR19596A/xx unknown
- 1976-12-28 NO NO764376A patent/NO152861C/no unknown
- 1976-12-28 HU HU76MO971A patent/HU185206B/hu not_active IP Right Cessation
- 1976-12-28 SE SE7614619A patent/SE435386B/xx not_active IP Right Cessation
- 1976-12-28 IL IL51170A patent/IL51170A/xx unknown
- 1976-12-28 FR FR7639274A patent/FR2337142A1/fr active Granted
- 1976-12-28 SU SU762436651A patent/SU639416A3/ru active
- 1976-12-28 PH PH19298A patent/PH16654A/en unknown
- 1976-12-29 GB GB54229/76A patent/GB1538209A/en not_active Expired
- 1976-12-29 YU YU03181/76A patent/YU318176A/xx unknown
-
1977
- 1977-01-06 NZ NZ183000A patent/NZ183000A/xx unknown
- 1977-03-16 NO NO770935A patent/NO152874C/no unknown
- 1977-07-12 PH PH19989A patent/PH14019A/en unknown
- 1977-09-09 SU SU772518560A patent/SU843755A3/ru active
- 1977-10-04 US US05/839,244 patent/US4120689A/en not_active Expired - Lifetime
- 1977-12-09 ES ES464928A patent/ES464928A1/es not_active Expired
-
1981
- 1981-06-24 JP JP56096797A patent/JPS5935919B2/ja not_active Expired
-
1983
- 1983-12-07 NO NO834498A patent/NO834498L/no unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: MONSANTO COMPANY |