CS196338B2 - Herbicide and method of producing the active constituent - Google Patents
Herbicide and method of producing the active constituent Download PDFInfo
- Publication number
- CS196338B2 CS196338B2 CS768703A CS870376A CS196338B2 CS 196338 B2 CS196338 B2 CS 196338B2 CS 768703 A CS768703 A CS 768703A CS 870376 A CS870376 A CS 870376A CS 196338 B2 CS196338 B2 CS 196338B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydroxy
- formula
- alkyl
- benzyl
- phosphonomethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 230000002363 herbicidal effect Effects 0.000 title claims description 20
- 239000004009 herbicide Substances 0.000 title abstract description 4
- 239000000470 constituent Substances 0.000 title 1
- -1 diaryl phosphite Chemical compound 0.000 claims abstract description 107
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 25
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 23
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000013638 trimer Substances 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 165
- 239000000203 mixture Substances 0.000 claims description 62
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 40
- 239000004480 active ingredient Substances 0.000 claims description 31
- 239000004471 Glycine Substances 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000008301 phosphite esters Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 32
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 239000011574 phosphorus Substances 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 177
- 239000000243 solution Substances 0.000 description 88
- 239000007787 solid Substances 0.000 description 75
- 239000003921 oil Substances 0.000 description 66
- 235000019198 oils Nutrition 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 229910052757 nitrogen Inorganic materials 0.000 description 51
- 229910052799 carbon Inorganic materials 0.000 description 43
- 238000004458 analytical method Methods 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 22
- 239000000725 suspension Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- 238000001914 filtration Methods 0.000 description 18
- KCNGRSQQOKXAKR-UHFFFAOYSA-N [(2-ethoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCOC(=O)CNCP(O)(O)=O KCNGRSQQOKXAKR-UHFFFAOYSA-N 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229960002449 glycine Drugs 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- ORZGBHNJZSALRU-UHFFFAOYSA-N ethyl 2-[3,5-bis(2-ethoxy-2-oxoethyl)-1,3,5-triazinan-1-yl]acetate Chemical compound CCOC(=O)CN1CN(CC(=O)OCC)CN(CC(=O)OCC)C1 ORZGBHNJZSALRU-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 150000005691 triesters Chemical class 0.000 description 6
- 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 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 241000132536 Cirsium Species 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-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
- 241000209072 Sorghum Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 231100000208 phytotoxic Toxicity 0.000 description 4
- 230000000885 phytotoxic effect Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 3
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- 241000254173 Coleoptera Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- LNRRZXVELGWOLM-UHFFFAOYSA-N methyl 2-[3,5-bis(2-methoxy-2-oxoethyl)-1,3,5-triazinan-1-yl]acetate Chemical compound COC(=O)CN1CN(CC(=O)OC)CN(CC(=O)OC)C1 LNRRZXVELGWOLM-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000006228 supernatant Substances 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
- DEHAVXIFVVRRRI-UHFFFAOYSA-N 2-[3,5-bis(carboxymethyl)-1,3,5-triazinan-1-yl]acetic acid Chemical compound OC(=O)CN1CN(CC(O)=O)CN(CC(O)=O)C1 DEHAVXIFVVRRRI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000021537 Beetroot Nutrition 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
- 101100421674 Drosophila melanogaster slou gene Proteins 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 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 2
- 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 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
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- 239000013078 crystal Substances 0.000 description 2
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- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- 230000001629 suppression Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
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- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
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- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
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- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 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
- 238000004519 manufacturing process Methods 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 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
- 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
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 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
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- LIXFJRLISFERDN-UHFFFAOYSA-N o-ethyl n,n-dipropylcarbamothioate Chemical compound CCCN(CCC)C(=S)OCC LIXFJRLISFERDN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052625 palygorskite Inorganic materials 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
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000015277 pork Nutrition 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
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002028 premature Effects 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry 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
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000001502 supplementing effect Effects 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
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- VKSSKWFHRVBVAD-UHFFFAOYSA-N trifluoro(hydroxysulfanyl)methane Chemical compound OSC(F)(F)F VKSSKWFHRVBVAD-UHFFFAOYSA-N 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 150000005219 trimethyl ethers Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000003828 vacuum filtration Methods 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
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64440675A | 1975-12-29 | 1975-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196338B2 true CS196338B2 (en) | 1980-03-31 |
Family
ID=24584785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS768703A CS196338B2 (en) | 1975-12-29 | 1976-12-28 | Herbicide and method of producing the active constituent |
Country Status (40)
| Country | Link |
|---|---|
| US (1) | US4120689A (de) |
| JP (2) | JPS5297949A (de) |
| AR (1) | AR220309A1 (de) |
| AT (1) | AT351858B (de) |
| AU (1) | AU507499B2 (de) |
| BE (1) | BE849907A (de) |
| BG (2) | BG27533A3 (de) |
| BR (1) | BR7608756A (de) |
| CA (1) | CA1070704A (de) |
| CH (1) | CH627922A5 (de) |
| CS (1) | CS196338B2 (de) |
| DD (2) | DD130857A5 (de) |
| DE (1) | DE2659172C2 (de) |
| DK (1) | DK144215C (de) |
| EG (1) | EG12175A (de) |
| ES (2) | ES454604A1 (de) |
| FI (1) | FI63761C (de) |
| FR (1) | FR2337142A1 (de) |
| GB (1) | GB1538209A (de) |
| GR (1) | GR62427B (de) |
| HU (1) | HU185206B (de) |
| IE (1) | IE44325B1 (de) |
| IL (1) | IL51170A (de) |
| IN (1) | IN145471B (de) |
| IT (1) | IT1070047B (de) |
| LU (1) | LU76475A1 (de) |
| MX (1) | MX3898E (de) |
| NL (1) | NL182881C (de) |
| NO (3) | NO152861C (de) |
| NZ (1) | NZ183000A (de) |
| OA (1) | OA05523A (de) |
| PH (2) | PH16654A (de) |
| PL (2) | PL113916B1 (de) |
| PT (1) | PT66022B (de) |
| RO (1) | RO71484A (de) |
| SE (1) | SE435386B (de) |
| SU (2) | SU639416A3 (de) |
| TR (1) | TR19596A (de) |
| YU (1) | YU318176A (de) |
| ZA (1) | ZA767654B (de) |
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 |
| US4175946A (en) * | 1978-07-10 | 1979-11-27 | Monsanto Company | Thio derivatives of N-trifluoroacetyl-N-phosphonomethylglycine |
| US4218235A (en) * | 1978-07-10 | 1980-08-19 | Monsanto Company | Ester derivatives of n-trifluoroacetyl-n-phosphonomethylglycine and the herbicidal use thereof |
| US4180394A (en) * | 1978-07-10 | 1979-12-25 | Monsanto Company | Derivatives of N-trifluoroacetyl-N-phosphonomethylglycinates 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 |
| US4300942A (en) | 1978-09-29 | 1981-11-17 | Monsanto Company | N-(Substituted carbonyl) derivatives of N-phos-phinylmethylglycinates 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 |
| 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 |
| 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 |
| 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 (de) * | 1983-08-04 | 1985-05-15 | Monsanto Company | Niedrigaralkyl- und substituierte Niedrigaralkylester von N-Phosphonomethylglycin |
| 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 (de) * | 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 (de) * | 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 |
| EP3661937B1 (de) | 2017-08-01 | 2021-07-28 | Gilead Sciences, Inc. | Kristalline formen von ethyl ((s)-((((2r,5r)-5-(6-amino-9h-purin-9-yl)-4-fluoro-2,5-dihydrofuran-2-yl)oxy)methyl)(phenoxy)phosphoryl)-l-alaninat (gs-9131) zur behandlung von viralen infektionen |
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 CA CA 268710 patent/CA1070704A/en not_active Expired
- 1976-12-24 AU AU20895/76A patent/AU507499B2/en not_active Expired
- 1976-12-27 ES ES454604A patent/ES454604A1/es not_active Expired
- 1976-12-27 NL NLAANVRAGE7614431,A patent/NL182881C/xx not_active IP Right Cessation
- 1976-12-28 PH PH19298A patent/PH16654A/en unknown
- 1976-12-28 DD DD7600196654A patent/DD130857A5/de unknown
- 1976-12-28 IT IT30928/76A patent/IT1070047B/it active
- 1976-12-28 GR GR52489A patent/GR62427B/el unknown
- 1976-12-28 CH CH1638176A patent/CH627922A5/de not_active IP Right Cessation
- 1976-12-28 JP JP15763776A patent/JPS5297949A/ja active Granted
- 1976-12-28 CS CS768703A patent/CS196338B2/cs unknown
- 1976-12-28 BR BR7608756A patent/BR7608756A/pt unknown
- 1976-12-28 PT PT66022A patent/PT66022B/pt unknown
- 1976-12-28 OA OA56025A patent/OA05523A/xx unknown
- 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 ZA ZA767654A patent/ZA767654B/xx unknown
- 1976-12-28 EG EG799/76A patent/EG12175A/xx active
- 1976-12-28 BG BG035032A patent/BG27533A3/xx unknown
- 1976-12-28 PL PL1976209063A patent/PL113916B1/pl unknown
- 1976-12-28 TR TR19596A patent/TR19596A/xx unknown
- 1976-12-28 NO NO764376A patent/NO152861C/no unknown
- 1976-12-28 DE DE2659172A patent/DE2659172C2/de not_active Expired
- 1976-12-28 PL PL1976194773A patent/PL106856B1/pl unknown
- 1976-12-28 FI FI763713A patent/FI63761C/fi not_active IP Right Cessation
- 1976-12-28 DD DD76203329A patent/DD136696A5/de unknown
- 1976-12-28 BG BG035915A patent/BG27736A3/xx unknown
- 1976-12-28 BE BE173679A patent/BE849907A/xx not_active IP Right Cessation
- 1976-12-28 LU LU76475A patent/LU76475A1/xx unknown
- 1976-12-28 IN IN2280/CAL/76A patent/IN145471B/en unknown
- 1976-12-28 SE SE7614619A patent/SE435386B/xx not_active IP Right Cessation
- 1976-12-28 HU HU76MO971A patent/HU185206B/hu not_active IP Right Cessation
- 1976-12-28 AR AR266012A patent/AR220309A1/es active
- 1976-12-28 RO RO7688876A patent/RO71484A/ro unknown
- 1976-12-28 AT AT971076A patent/AT351858B/de not_active IP Right Cessation
- 1976-12-28 DK DK584476A patent/DK144215C/da not_active IP Right Cessation
- 1976-12-29 YU YU03181/76A patent/YU318176A/xx unknown
- 1976-12-29 GB GB54229/76A patent/GB1538209A/en not_active Expired
-
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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