NO822038L - Monoestere og diestere av n-alkyl-substituert aminomethylfosfonsyre, fremgangsmaate ved deres fremstilling og herbicide preparater inneholdende samme - Google Patents
Monoestere og diestere av n-alkyl-substituert aminomethylfosfonsyre, fremgangsmaate ved deres fremstilling og herbicide preparater inneholdende sammeInfo
- Publication number
- NO822038L NO822038L NO822038A NO822038A NO822038L NO 822038 L NO822038 L NO 822038L NO 822038 A NO822038 A NO 822038A NO 822038 A NO822038 A NO 822038A NO 822038 L NO822038 L NO 822038L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- lower alkyl
- mol
- methyl
- hydrogen
- Prior art date
Links
- 150000005690 diesters Chemical class 0.000 title claims abstract description 8
- 239000004009 herbicide Substances 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 24
- 230000002363 herbicidal effect Effects 0.000 title claims description 12
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical class NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 title abstract description 3
- -1 2-ethoxyethyl Chemical group 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000004494 ethyl ester group Chemical group 0.000 claims description 28
- 239000004471 Glycine Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 239000003905 agrochemical Substances 0.000 claims 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- 241000282326 Felis catus Species 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 abstract description 2
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical class C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 1
- 108010077895 Sarcosine Proteins 0.000 abstract 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- 239000000047 product Substances 0.000 description 96
- 239000011541 reaction mixture Substances 0.000 description 60
- 238000004821 distillation Methods 0.000 description 44
- 238000004458 analytical method Methods 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 34
- 239000003480 eluent Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- 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 20
- 238000003756 stirring Methods 0.000 description 20
- 239000007788 liquid Substances 0.000 description 18
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 17
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 17
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- 239000000243 solution Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002250 absorbent Substances 0.000 description 6
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- 235000010980 cellulose Nutrition 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
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- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 6
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- AFGBMAMNFVKBKF-UHFFFAOYSA-N tris(1-cyanoethyl) phosphite Chemical compound N#CC(C)OP(OC(C)C#N)OC(C)C#N AFGBMAMNFVKBKF-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
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- 150000002148 esters Chemical class 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
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- 239000007921 spray Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 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 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical class OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 2
- 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 description 2
- 239000005745 Captan Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229940117949 captan Drugs 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002500 ions Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000003134 recirculating effect Effects 0.000 description 2
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- 239000003784 tall oil Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PAJVNEZTCILNQN-UHFFFAOYSA-N tris(2-cyanoethyl) phosphite Chemical compound N#CCCOP(OCCC#N)OCCC#N PAJVNEZTCILNQN-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- SRKGMGYADQTPBC-UHFFFAOYSA-N (cyanomethylamino)methylphosphonic acid Chemical compound OP(O)(=O)CNCC#N SRKGMGYADQTPBC-UHFFFAOYSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- KBNWJLSNOCDBPQ-UHFFFAOYSA-N 1,3,5-tris(prop-1-ynyl)-1,3,5-triazinane Chemical compound CC#CN1CN(C#CC)CN(C#CC)C1 KBNWJLSNOCDBPQ-UHFFFAOYSA-N 0.000 description 1
- GPBOXKOQAMLJKE-UHFFFAOYSA-N 12-(butylamino)dodecyl benzenesulfonate Chemical compound C(CCC)NCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GPBOXKOQAMLJKE-UHFFFAOYSA-N 0.000 description 1
- 125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 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
- ZDAIRKOKTKUUKW-UHFFFAOYSA-N 2-[2,4-bis(cyanomethyl)-1,2,4-triazinan-6-yl]acetonitrile Chemical compound N#CCC1CN(CC#N)CN(CC#N)N1 ZDAIRKOKTKUUKW-UHFFFAOYSA-N 0.000 description 1
- UTUBLJRGLLOMDP-UHFFFAOYSA-N 2-[2-acetyloxyethoxy(hydroxy)phosphanyl]oxyethyl acetate Chemical compound CC(=O)OCCOP(O)OCCOC(C)=O UTUBLJRGLLOMDP-UHFFFAOYSA-N 0.000 description 1
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- 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
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- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical group COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
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- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MNOBVOKDXIHUCP-UHFFFAOYSA-N bis(cyanomethyl) hydrogen phosphite Chemical compound N#CCOP(O)OCC#N MNOBVOKDXIHUCP-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- ZOZYWLQZNBIONE-UHFFFAOYSA-N diethyl 2-bis[(1,4-diethoxy-1,4-dioxobutan-2-yl)oxy]phosphanyloxybutanedioate Chemical compound CCOC(=O)CC(C(=O)OCC)OP(OC(CC(=O)OCC)C(=O)OCC)OC(CC(=O)OCC)C(=O)OCC ZOZYWLQZNBIONE-UHFFFAOYSA-N 0.000 description 1
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- KDKQSBWGLUZELU-UHFFFAOYSA-N ethyl 2-bis(2-ethoxy-2-oxoethoxy)phosphanyloxyacetate Chemical compound CCOC(=O)COP(OCC(=O)OCC)OCC(=O)OCC KDKQSBWGLUZELU-UHFFFAOYSA-N 0.000 description 1
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 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
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229920001821 foam rubber Polymers 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N methyl 2-hydroxypropionate Chemical compound COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- NMPZIVCWBOFUKT-UHFFFAOYSA-N pentyl 2-[3,5-bis(2-oxo-2-pentoxyethyl)-1,3,5-triazinan-1-yl]acetate Chemical compound CCCCCOC(=O)CN1CN(CC(=O)OCCCCC)CN(CC(=O)OCCCCC)C1 NMPZIVCWBOFUKT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([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
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 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
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ZHHOMIAGFRSWCU-UHFFFAOYSA-N thian-3-ol Chemical compound OC1CCCSC1 ZHHOMIAGFRSWCU-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- HYLCJGJLRAHQGK-UHFFFAOYSA-N tris(1-cyanopropyl) phosphite Chemical compound CCC(C#N)OP(OC(CC)C#N)OC(CC)C#N HYLCJGJLRAHQGK-UHFFFAOYSA-N 0.000 description 1
- YFIQIFMGKBEYKM-UHFFFAOYSA-N tris(2,2,2-trichloroethyl) phosphite Chemical compound ClC(Cl)(Cl)COP(OCC(Cl)(Cl)Cl)OCC(Cl)(Cl)Cl YFIQIFMGKBEYKM-UHFFFAOYSA-N 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 1
- UZEKABLVPXAVOE-UHFFFAOYSA-N tris(thian-3-yl) phosphite Chemical compound C1CCSCC1OP(OC1CSCCC1)OC1CSCCC1 UZEKABLVPXAVOE-UHFFFAOYSA-N 0.000 description 1
- LLAVUXNNNMKCKY-UHFFFAOYSA-N tris[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl] phosphite Chemical compound O1C(C)(C)OCC1COP(OCC1OC(C)(C)OC1)OCC1OC(C)(C)OC1 LLAVUXNNNMKCKY-UHFFFAOYSA-N 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
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27548781A | 1981-06-19 | 1981-06-19 | |
| US06/275,463 US4391625A (en) | 1981-06-19 | 1981-06-19 | Diesters of N-alkyl substituted amino methyl phosphonic acid useful as herbicides |
| US06/275,485 US4388102A (en) | 1981-06-19 | 1981-06-19 | Alkylphosphonate diesters of N-phosphonomethylglycinate as herbicides |
| US06/275,486 US4395275A (en) | 1981-06-19 | 1981-06-19 | Mono and diesters of N-phosphonomethylglycinates as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO822038L true NO822038L (no) | 1982-12-20 |
Family
ID=27501130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO822038A NO822038L (no) | 1981-06-19 | 1982-06-18 | Monoestere og diestere av n-alkyl-substituert aminomethylfosfonsyre, fremgangsmaate ved deres fremstilling og herbicide preparater inneholdende samme |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0068732B1 (pt) |
| KR (1) | KR840000574A (pt) |
| AT (1) | ATE15203T1 (pt) |
| AU (1) | AU549688B2 (pt) |
| BG (2) | BG37675A3 (pt) |
| BR (1) | BR8203590A (pt) |
| CA (1) | CA1212116A (pt) |
| CS (1) | CS238625B2 (pt) |
| DD (2) | DD209382A5 (pt) |
| DE (1) | DE3265835D1 (pt) |
| DK (1) | DK274182A (pt) |
| ES (1) | ES8304584A1 (pt) |
| FI (1) | FI822201L (pt) |
| GB (1) | GB2102002B (pt) |
| GR (1) | GR77553B (pt) |
| IE (1) | IE53128B1 (pt) |
| IL (1) | IL66083A0 (pt) |
| KE (1) | KE3538A (pt) |
| MY (1) | MY8600149A (pt) |
| NO (1) | NO822038L (pt) |
| PL (1) | PL236996A1 (pt) |
| PT (1) | PT75073B (pt) |
| RO (1) | RO85400B (pt) |
| SG (1) | SG38185G (pt) |
| TR (1) | TR21735A (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE56605B1 (en) * | 1983-01-28 | 1991-10-09 | Schering Corp | Phosphorous containing amide compounds,pharmaceutical compositions containing them,and processes for their preparation |
| CA2018470A1 (en) * | 1989-07-17 | 1991-01-17 | Scott Adams Biller | Phosphorus-containing squalene synthetase inhibitors and method |
| GB9307234D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Process |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
| US4008296A (en) * | 1972-11-08 | 1977-02-15 | Imperial Chemical Industries Limited | Esters of N-phosphonomethylglycinonitrile |
| CH606058A5 (pt) * | 1974-11-01 | 1978-10-13 | Sandoz Ag | |
| DE2848869A1 (de) * | 1978-11-10 | 1980-05-22 | Ciba Geigy Ag | Herbizides mittel und seine verwendung |
| US4221583A (en) * | 1978-12-22 | 1980-09-09 | Monsanto Company | N-Phosphonomethylglycinonitrile and certain derivatives thereof |
-
1982
- 1982-06-16 IE IE1454/82A patent/IE53128B1/en not_active IP Right Cessation
- 1982-06-17 DE DE8282303147T patent/DE3265835D1/de not_active Expired
- 1982-06-17 ES ES513197A patent/ES8304584A1/es not_active Expired
- 1982-06-17 EP EP82303147A patent/EP0068732B1/en not_active Expired
- 1982-06-17 AT AT82303147T patent/ATE15203T1/de not_active IP Right Cessation
- 1982-06-18 PT PT75073A patent/PT75073B/pt not_active IP Right Cessation
- 1982-06-18 IL IL66083A patent/IL66083A0/xx not_active IP Right Cessation
- 1982-06-18 KR KR1019820002717A patent/KR840000574A/ko unknown
- 1982-06-18 DD DD82240884A patent/DD209382A5/de unknown
- 1982-06-18 RO RO107923A patent/RO85400B/ro unknown
- 1982-06-18 NO NO822038A patent/NO822038L/no unknown
- 1982-06-18 AU AU85000/82A patent/AU549688B2/en not_active Ceased
- 1982-06-18 TR TR21735A patent/TR21735A/xx unknown
- 1982-06-18 BR BR8203590A patent/BR8203590A/pt unknown
- 1982-06-18 CA CA000405467A patent/CA1212116A/en not_active Expired
- 1982-06-18 CS CS824562A patent/CS238625B2/cs unknown
- 1982-06-18 DD DD82247628A patent/DD207205A5/de unknown
- 1982-06-18 GB GB08217631A patent/GB2102002B/en not_active Expired
- 1982-06-18 DK DK274182A patent/DK274182A/da not_active Application Discontinuation
- 1982-06-18 FI FI822201A patent/FI822201L/fi not_active Application Discontinuation
- 1982-06-18 GR GR68476A patent/GR77553B/el unknown
- 1982-06-18 PL PL23699682A patent/PL236996A1/xx unknown
- 1982-06-18 BG BG058281A patent/BG37675A3/xx unknown
- 1982-06-18 BG BG057045A patent/BG37529A3/xx unknown
-
1985
- 1985-05-23 SG SG381/85A patent/SG38185G/en unknown
- 1985-05-29 KE KE3538A patent/KE3538A/xx unknown
-
1986
- 1986-12-30 MY MY149/86A patent/MY8600149A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK274182A (da) | 1982-12-20 |
| DD209382A5 (de) | 1984-05-09 |
| DD207205A5 (de) | 1984-02-22 |
| KR840000574A (ko) | 1984-02-25 |
| KE3538A (en) | 1985-07-12 |
| RO85400A (ro) | 1985-03-15 |
| ES513197A0 (es) | 1983-03-01 |
| PT75073B (en) | 1985-05-31 |
| DE3265835D1 (en) | 1985-10-03 |
| PT75073A (en) | 1982-07-01 |
| IL66083A0 (en) | 1982-09-30 |
| AU8500082A (en) | 1982-12-23 |
| ATE15203T1 (de) | 1985-09-15 |
| FI822201A0 (fi) | 1982-06-18 |
| AU549688B2 (en) | 1986-02-06 |
| CA1212116A (en) | 1986-09-30 |
| BR8203590A (pt) | 1983-06-14 |
| BG37675A3 (en) | 1985-07-16 |
| BG37529A3 (en) | 1985-06-14 |
| GB2102002A (en) | 1983-01-26 |
| EP0068732A1 (en) | 1983-01-05 |
| TR21735A (tr) | 1985-05-20 |
| PL236996A1 (en) | 1983-01-31 |
| GR77553B (pt) | 1984-09-24 |
| SG38185G (en) | 1985-11-15 |
| IE53128B1 (en) | 1988-07-06 |
| MY8600149A (en) | 1986-12-31 |
| CS238625B2 (en) | 1985-12-16 |
| GB2102002B (en) | 1985-02-06 |
| RO85400B (ro) | 1985-03-30 |
| FI822201L (fi) | 1982-12-20 |
| ES8304584A1 (es) | 1983-03-01 |
| EP0068732B1 (en) | 1985-08-28 |
| IE821454L (en) | 1982-12-19 |
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