FI57955B - N-PHOSPHONOMETHYL GLASSINDERIVAT SOM KAN ANVAENDAS SOM HERBISIDISKT ELLER FYTOTOXISKT MEDEL - Google Patents
N-PHOSPHONOMETHYL GLASSINDERIVAT SOM KAN ANVAENDAS SOM HERBISIDISKT ELLER FYTOTOXISKT MEDEL Download PDFInfo
- Publication number
- FI57955B FI57955B FI3000/71A FI300071A FI57955B FI 57955 B FI57955 B FI 57955B FI 3000/71 A FI3000/71 A FI 3000/71A FI 300071 A FI300071 A FI 300071A FI 57955 B FI57955 B FI 57955B
- Authority
- FI
- Finland
- Prior art keywords
- phosphonomethylglycine
- salt
- phosphonomethyl
- mono
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 61
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical class OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 58
- -1 pyrrolidino, piperidino, morpholino Chemical group 0.000 claims description 29
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- 239000004009 herbicide Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- RGSODMOUXWISAG-UHFFFAOYSA-N n-prop-2-ynylprop-2-yn-1-amine Chemical compound C#CCNCC#C RGSODMOUXWISAG-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-O phenylazanium Chemical compound [NH3+]C1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-O 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000004471 Glycine Substances 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000508725 Elymus repens Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 241000894007 species Species 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000205407 Polygonum Species 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 240000002439 Sorghum halepense Species 0.000 description 3
- GDLMNBNILRDVJV-UHFFFAOYSA-N [(2-hexoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCCCCCOC(=O)CNCP(O)(O)=O GDLMNBNILRDVJV-UHFFFAOYSA-N 0.000 description 3
- YYGUXKOBRVTICK-UHFFFAOYSA-N [(2-methoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound COC(=O)CNCP(O)(O)=O YYGUXKOBRVTICK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 231100000208 phytotoxic Toxicity 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical class CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- DFRHETNXRZJTGA-UHFFFAOYSA-N 2-(phosphanylmethylamino)acetic acid Chemical compound OC(=O)CNCP DFRHETNXRZJTGA-UHFFFAOYSA-N 0.000 description 2
- DQNPFPHZAUMZHD-UHFFFAOYSA-N 2-aminoethanol;2-(phosphonomethylamino)acetic acid Chemical compound NCCO.OC(=O)CNCP(O)(O)=O DQNPFPHZAUMZHD-UHFFFAOYSA-N 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001148727 Bromus tectorum Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 240000001579 Cirsium arvense Species 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PDYXIVPKOMYDOK-UHFFFAOYSA-N Glyphosate-monoammonium Chemical compound [NH4+].OC(=O)CNCP(O)([O-])=O PDYXIVPKOMYDOK-UHFFFAOYSA-N 0.000 description 2
- 235000021506 Ipomoea Nutrition 0.000 description 2
- 241000207783 Ipomoea Species 0.000 description 2
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WNBFUSXJZJGYBP-UHFFFAOYSA-N OP(O)(=O)CNCC(=O)OCCOC1=CC=CC=C1 Chemical compound OP(O)(=O)CNCC(=O)OCCOC1=CC=CC=C1 WNBFUSXJZJGYBP-UHFFFAOYSA-N 0.000 description 2
- 244000088461 Panicum crus-galli Species 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000209072 Sorghum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 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
- 241001506766 Xanthium Species 0.000 description 2
- KCNGRSQQOKXAKR-UHFFFAOYSA-N [(2-ethoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCOC(=O)CNCP(O)(O)=O KCNGRSQQOKXAKR-UHFFFAOYSA-N 0.000 description 2
- IALUYLHSSRNCNE-UHFFFAOYSA-K [Li+].[Li+].[Li+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] Chemical compound [Li+].[Li+].[Li+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] IALUYLHSSRNCNE-UHFFFAOYSA-K 0.000 description 2
- YMWMBQGBGMVODB-UHFFFAOYSA-N [[2-(methylamino)-2-oxoethyl]amino]methylphosphonic acid Chemical compound CNC(=O)CNCP(O)(O)=O YMWMBQGBGMVODB-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 2
- UXAWAXMJQQWASI-UHFFFAOYSA-L copper;2-(phosphonomethylamino)acetate Chemical compound [Cu+2].OP(O)(=O)CNCC([O-])=O.OP(O)(=O)CNCC([O-])=O UXAWAXMJQQWASI-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 2
- SIQGBUJXKSJZAV-UHFFFAOYSA-L disodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].[Na+].OP(O)(=O)CNCC([O-])=O.OP(O)(=O)CNCC([O-])=O SIQGBUJXKSJZAV-UHFFFAOYSA-L 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XTVITOVZJPVCTQ-UHFFFAOYSA-L magnesium;2-(phosphonomethylamino)acetate Chemical compound [Mg+2].OP(O)(=O)CNCC([O-])=O.OP(O)(=O)CNCC([O-])=O XTVITOVZJPVCTQ-UHFFFAOYSA-L 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical class CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
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- 229960000278 theophylline Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XBKMYUZPSUAVAK-KHPLUVTOSA-N 1-[(3r,5r,6s,8r,9s,10r,13s,14s,17r)-3,6,17-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone Chemical compound C([C@H]1[C@@H](O)C2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@](C(=O)C)(O)[C@@]2(C)CC1 XBKMYUZPSUAVAK-KHPLUVTOSA-N 0.000 description 1
- MKPAXMWKNUWKTR-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;2-(phosphonomethylamino)acetic acid Chemical compound OCCNCCO.OC(=O)CNCP(O)(O)=O MKPAXMWKNUWKTR-UHFFFAOYSA-N 0.000 description 1
- HPNWUXSHPAXNKY-UHFFFAOYSA-N 2-(phosphonomethylamino)acetic acid;hydrate Chemical compound O.OC(=O)CNCP(O)(O)=O HPNWUXSHPAXNKY-UHFFFAOYSA-N 0.000 description 1
- JWLOLVQUOXPBMG-UHFFFAOYSA-N 2-(phosphonomethylamino)acetic acid;pyridine Chemical compound C1=CC=NC=C1.OC(=O)CNCP(O)(O)=O JWLOLVQUOXPBMG-UHFFFAOYSA-N 0.000 description 1
- RASUWBZHFDVNCQ-UHFFFAOYSA-N 2-(phosphonomethylamino)propanoic acid Chemical compound OC(=O)C(C)NCP(O)(O)=O RASUWBZHFDVNCQ-UHFFFAOYSA-N 0.000 description 1
- XPQDNNPZEVSCNB-UHFFFAOYSA-N 2-amino-n-(2-methoxyethyl)acetamide Chemical compound COCCNC(=O)CN XPQDNNPZEVSCNB-UHFFFAOYSA-N 0.000 description 1
- HLJQTSYXZPULQL-UHFFFAOYSA-N 2-amino-n-piperidin-1-ylacetamide Chemical compound NCC(=O)NN1CCCCC1 HLJQTSYXZPULQL-UHFFFAOYSA-N 0.000 description 1
- JDQBJMHNGNZBIO-UHFFFAOYSA-N 2-amino-n-prop-2-enylacetamide Chemical compound NCC(=O)NCC=C JDQBJMHNGNZBIO-UHFFFAOYSA-N 0.000 description 1
- LKCKUYRPMPUHTD-UHFFFAOYSA-N 2-amino-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CN LKCKUYRPMPUHTD-UHFFFAOYSA-N 0.000 description 1
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- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
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- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000282327 Felis silvestris Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical class CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- PCHMLYAWQBMTDG-UHFFFAOYSA-N N1=CC=CC=C1.N1=CC=CC=C1.N1C=CC=C1.N1C=CC=C1 Chemical compound N1=CC=CC=C1.N1=CC=CC=C1.N1C=CC=C1.N1C=CC=C1 PCHMLYAWQBMTDG-UHFFFAOYSA-N 0.000 description 1
- 241000209117 Panicum Species 0.000 description 1
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000985694 Polypodiopsida Species 0.000 description 1
- 244000275012 Sesbania cannabina Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- JZCSMMPWEAKXBU-UHFFFAOYSA-N [(2-aminoacetyl)amino]methylphosphonic acid Chemical compound NCC(=O)NCP(O)(O)=O JZCSMMPWEAKXBU-UHFFFAOYSA-N 0.000 description 1
- ZCZZPTBXXYBKHY-UHFFFAOYSA-N [(2-butoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCCCOC(=O)CNCP(O)(O)=O ZCZZPTBXXYBKHY-UHFFFAOYSA-N 0.000 description 1
- HMFXDADSTMJCNW-UHFFFAOYSA-N [(2-cyclohexyloxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound OP(O)(=O)CNCC(=O)OC1CCCCC1 HMFXDADSTMJCNW-UHFFFAOYSA-N 0.000 description 1
- CKUIMCVLTPVHEW-UHFFFAOYSA-N [(2-decoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCCCCCCCCCOC(=O)CNCP(O)(O)=O CKUIMCVLTPVHEW-UHFFFAOYSA-N 0.000 description 1
- ZSXJDYCJVGAPHZ-UHFFFAOYSA-N [(2-dodecoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCCCCCCCCCCCOC(=O)CNCP(O)(O)=O ZSXJDYCJVGAPHZ-UHFFFAOYSA-N 0.000 description 1
- ZGGNVSKWCFLTQB-UHFFFAOYSA-N [(2-octoxy-2-oxoethyl)amino]methylphosphonic acid Chemical compound CCCCCCCCOC(=O)CNCP(O)(O)=O ZGGNVSKWCFLTQB-UHFFFAOYSA-N 0.000 description 1
- GOUJWJDEWKEJHZ-UHFFFAOYSA-N [(2-oxo-2-propoxyethyl)amino]methylphosphonic acid Chemical compound CCCOC(=O)CNCP(O)(O)=O GOUJWJDEWKEJHZ-UHFFFAOYSA-N 0.000 description 1
- WTJXGSWRASYOOV-UHFFFAOYSA-K [K+].[K+].[K+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] Chemical compound [K+].[K+].[K+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] WTJXGSWRASYOOV-UHFFFAOYSA-K 0.000 description 1
- UTEQNDKCGRINAY-UHFFFAOYSA-N [K].[K].C(CCCCCCC)NC(CNCP(=O)(O)O)=O Chemical compound [K].[K].C(CCCCCCC)NC(CNCP(=O)(O)O)=O UTEQNDKCGRINAY-UHFFFAOYSA-N 0.000 description 1
- BDIRUEMDTWYHDH-UHFFFAOYSA-L [Li+].[Li+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] Chemical compound [Li+].[Li+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] BDIRUEMDTWYHDH-UHFFFAOYSA-L 0.000 description 1
- LLPIQRJDHHFHTJ-UHFFFAOYSA-N [NH4+].[NH4+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] Chemical compound [NH4+].[NH4+].P(=O)(O)(O)CNCC(=O)[O-].P(=O)(O)(O)CNCC(=O)[O-] LLPIQRJDHHFHTJ-UHFFFAOYSA-N 0.000 description 1
- XWYKDSIRZIVFES-UHFFFAOYSA-N [Na].P(=O)(O)(O)CNCC(=O)OCC Chemical compound [Na].P(=O)(O)(O)CNCC(=O)OCC XWYKDSIRZIVFES-UHFFFAOYSA-N 0.000 description 1
- PPNYNHCVCAGPIK-UHFFFAOYSA-N [[2-(2-chloroethoxy)-2-oxoethyl]amino]methylphosphonic acid Chemical compound OP(O)(=O)CNCC(=O)OCCCl PPNYNHCVCAGPIK-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- XQJHRCVXRAJIDY-UHFFFAOYSA-N aminophosphine Chemical class PN XQJHRCVXRAJIDY-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical class CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- RMBGSBIZBRZJPK-UHFFFAOYSA-N butan-1-amine;2-dodecylbenzenesulfonic acid Chemical compound CCCCN.CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O RMBGSBIZBRZJPK-UHFFFAOYSA-N 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- ZQNPDAVSHFGLIQ-UHFFFAOYSA-N calcium;hydrate Chemical compound O.[Ca] ZQNPDAVSHFGLIQ-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 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 1
- DKZFKSDUPOIUCA-UHFFFAOYSA-N ethanamine;2-(phosphonomethylamino)acetic acid Chemical compound CCN.OC(=O)CNCP(O)(O)=O DKZFKSDUPOIUCA-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 1
- 150000002333 glycines Chemical class 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- KICSSISQQYGDCL-UHFFFAOYSA-N magnesium;2-(phosphonomethylamino)acetic acid Chemical compound [Mg].OC(=O)CNCP(O)(O)=O KICSSISQQYGDCL-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- OTZTYSZKWXNPTG-UHFFFAOYSA-N methanamine;2-(phosphonomethylamino)acetic acid Chemical compound NC.OC(=O)CNCP(O)(O)=O OTZTYSZKWXNPTG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WGQXGEHRJAEFPO-UHFFFAOYSA-N n,n-diethylethanamine;2-(phosphonomethylamino)acetic acid Chemical compound CCN(CC)CC.OC(=O)CNCP(O)(O)=O WGQXGEHRJAEFPO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- 125000005447 octyloxy 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])O* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical class CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical class CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- KJIGOYRBSJXORZ-UHFFFAOYSA-M sodium 2-[carboxymethyl(phosphonomethyl)amino]acetate Chemical compound [Na+].P(=O)(O)(O)CN(CC(=O)O)CC(=O)[O-] KJIGOYRBSJXORZ-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 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
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- ONHIJCVRYPHITQ-UHFFFAOYSA-K trisodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CNCC([O-])=O.OP(O)(=O)CNCC([O-])=O.OP(O)(=O)CNCC([O-])=O ONHIJCVRYPHITQ-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
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)
Description
I55P1 Μ «ΐ)*υϋίϋΤϋβ|ϋι·*Α»βυ c 7 o ς ςI55P1 Μ «ΐ) * υϋίϋΤϋβ | ϋι · * Α» βυ c 7 o ς ς
JMTä l J 1 1 UTLÄGCNINOSSKRIFT 3 / V O OJMTä l J 1 1 UTLÄGCNINOSSKRIFT 3 / V O O
ejuf^Ce C (45) Patentti myönnetty 10 11 1930ejuf ^ Ce C (45) Patent granted on 10 11 1930
Patent meddelat y (51) Kr.lk.3/1nt.a.3 C 07 F 9/38 SUOMI—FINLAND (M) Paeea*·*···—P*«e*il*tat 3000/71 (22) HakamlspUvt—AnaBknlng^ag 22.10.71 (23) AltmplM—GlMghutadag 22.10.71 (41) Tulkit |ulklMksl — Bllvft offuntllg 11.09· 72Patent Meddelat y (51) Kr.lk.3 / 1nt.a.3 C 07 F 9/38 FINLAND — FINLAND (M) Paeea * · * ··· —P * «e * il * tat 3000/71 (22 ) HakamlspUvt — AnaBknlng ^ ag 22.10.71 (23) AltmplM — GlMghutadag 22.10.71 (41) Interpreters | ulklMksl - Bllvft offuntllg 11.09 · 72
Pttantti. ]· rekisterihallitus (44) NlhtiviiuipMWn,. kuaL|ullubunPttantti. ] · Registry Board (44) NlhtiviiuipMWn ,. Kual | ullubun
Patent- och registerstyrelsen ' AmMom uttafd oeh uci.skrMUn pubiicund 31.07.80 ^ (32)(33)(31) Eyydtty utuo)k«u« —Bugird prlorlt* 10.03.71 09-08.71 USA(US) 123057, 170385 (71) Monsanto Company, 800 North Lindbergh Boulevard, Saint Louis, Missouri " 63166, USA(US) (72) John Edward Franz, Crestwood, Missouri, USA(US) (7*0 Leizinger Oy (5*0 N-fosfonometyyliglysiinijohdannainen, jota voidaan käyttää herbisidisenä tai fytotoksisena aineena - N-fosfonometylglysinderivat, som kan användas som herbisidiskt eller iytotoxiskt medel Tämä keksintö koskee uutta N-fosfonometyyliglysiinijohdannaista, jota voidaan käyttää herbisidisenä tai fytotoksisena aineen ja jonka kaava °n OR1 /Patent and Registration Office AmMom uttafd oeh uci.skrMUn pubiicund 31.07.80 ^ (32) (33) (31) Eyydtty utuo) k «u« —Bugird prlorlt * 10.03.71 09-08.71 USA (US) 123057, 170385 ( 71) Monsanto Company, 800 North Lindbergh Boulevard, St. Louis, Missouri "63166, USA (US) (72) John Edward Franz, Crestwood, Missouri, USA (US) (7 * 0 Leizinger Oy (5 * 0 N-phosphonomethylglycine derivative, The present invention relates to a novel N-phosphonomethylglycine derivative which can be used as a herbicidal or phytotoxic substance and which has the formula OR1 / A which can be used as a herbicidal or phytotoxic substance.
R-CO-CH_-NH-CHn-P = OR-CO-CH_-NH-CHn-P = O
\r* jossa R voi olla amino, alkyyliamino, joka sisältää 1-8 hiiltä, pyrrolidino, piperidino, morfolino, hydroksialempialkyyliamino, (alempialkoksialem- pialkyyli)amino, allyyliamino, alkoksi, joka sisältää 1-12 hiiltä, syk- loheksyylioksi, allyylioksi, kloorialempialkyylioksi, alempialkoksialem- pialkoksi, (alempialkoksialempialkoksi)alempialkoksi, (kloorialempial- 3 3 koksi)alempialkoksi, fenoksietoksi tai ryhmä -OR , jossa R voi olla litium, natrium, kalium, kalsiumekvivalentti, magnesiumekvivalentti, kupariekvivalentti, sinkkiekvivalentti, ammonium, mono-, di- tai tri- alkyyliammonium, joka sisältää 1-8 hiiltä, mono- tai di(hydroksialem- pialkyyli)ammonium, mono- tai diallyyliammonium, mono- tai dipropar- gyyliammonium, anilinium, pyridinium tai piperidinium, 12 3 R tai R voi olla vety tai R sillä edellytyksellä, että molekyylissä 2 57955 on enintään kaksi ammoniumia tai substituoitua ammoniumia tarkoittavaa 3 R ryhmää; tai R voi olla OH sillä edellytyksellä, että ainoastaan 1 2 kaksi ryhmistä R, OR ja OR tarkoittavat OH-ryhmää.wherein R may be amino, alkylamino containing 1 to 8 carbons, pyrrolidino, piperidino, morpholino, hydroxy-lower alkylamino, (lower alkoxy-lower alkyl) amino, allylamino, alkoxy containing 1 to 12 carbons, cyclohexyloxy, allyloxy, chloroalkoxyloxy, lower alkoxy-lower alkoxy, (lower alkoxy-lower alkoxy) lower alkoxy, (chloro-lower-3 3 coke) lower alkoxy, phenoxyethoxy or the group -OR, where R can be lithium, sodium, potassium, calcium equivalent, magnesium equivalent, magnesium equivalent, copper equivalent, copper equivalent - or trialkylammonium containing 1 to 8 carbons, mono- or di (hydroxy-loweralkyl) ammonium, mono- or diallylammonium, mono- or dipropargylammonium, anilinium, pyridinium or piperidinium, 12 3 R or R may be hydrogen or R, provided that molecule 2 57955 contains up to two 3 R groups for ammonium or substituted ammonium; or R may be OH provided that only 1 2 two of R, OR and OR represent OH.
N-fosfonometyyliglysiinejä voidaan valmistaa fosfonometyloimalla gly-siiniä, mieluummin kloorimetyylifosfonihapolla. Niitä voidaan myös valmistaa fosfiittiadditiolla atsometiineihin. Esimerkiksi etyyliglysinaa-tin reaktio formaldehydin ja dietyylifosfiitin kanssa johtaa N-fosfono-metyyliglysiinin trietyyliesterin muodostumiseen. Kyseessä olevia yhdisteitä voidaan myös helposti valmistaa hapettamalla vastaavia amino-fosfiiniyhdisteitä käyttäen hyödyksi elohopea-2-kloridia tai muita hapettavia aineita. N-fosfonometyyliglysiinit ovat rakeisia tai kiteisiä kiinteitä aineita, jotka ovat yleensä liukenevia veteen.N-phosphonomethylglycines can be prepared by phosphonomethylation of Glycine, preferably with chloromethylphosphonic acid. They can also be prepared by phosphite addition to azomethines. For example, the reaction of ethyl glycinate with formaldehyde and diethyl phosphite results in the formation of triethyl ester of N-phosphonomethylglycine. The present compounds can also be readily prepared by oxidation of the corresponding aminophosphine compounds utilizing mercury-2-chloride or other oxidizing agents. N-phosphonomethylglycines are granular or crystalline solids that are generally soluble in water.
Vahvoja happoja, jotka muodostavat suoloja N-fosfonometyyliglysiinin kanssa, ovat ne, joiden pH-arvot ovat 2,5 tai alle, esimerkiksi suolahappo, rikkihappo, fosforihappo, trifluorietikkahappo, trikloorietikka-happo ja vastaavat. Eräissä tapauksissa nämä happosuolat eristettyinä ovat puolisuoloja, so. yksi molekyyli happoa yhtyy kahden molekyylin kanssa N-fosfonometyyliglysiiniä ja voi sisältää kidevettä.Strong acids which form salts with N-phosphonomethylglycine include those having pH values of 2.5 or less, for example, hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, trichloroacetic acid and the like. In some cases, these acid salts in isolation are semi-salts, i. one molecule of acid combines with two molecules of N-phosphonomethylglycine and may contain water of crystallization.
N-fosfonometyyliglysiinin happohalogenidit valmistetaan tunnetuilla menetelmillä. Esim. kloorijohdannaiset voidaan valmistaa N-fosfonometyyliglysiinin reaktiolla fosforipentakloridin tai tionyylikloridin kanssa vedettömässä liuottimessa kuten eetterissä, tai muussa orgaanisessa liuottimessa.The acid halides of N-phosphonomethylglycine are prepared by known methods. For example, chlorine derivatives can be prepared by the reaction of N-phosphonomethylglycine with phosphorus pentachloride or thionyl chloride in an anhydrous solvent such as ether, or another organic solvent.
N-fosfonometyyliglysiinin amideja tai estereitä voidaan valmistaa antamalla happohalogenidin reagoida liuottimessa sopivan amiinin tai alkoholin kanssa kun mukana on halogeenivetyakseptori kuten trietyyliamii-ni, pyridiini ja vastaava; tai vaihtoesteröimällä N-fosfonometyyli^ly-siini metyyliesterin kanssa.Amides or esters of N-phosphonomethylglycine can be prepared by reacting an acid halide in a solvent with a suitable amine or alcohol in the presence of a hydrogen halide acceptor such as triethylamine, pyridine and the like; or by transesterification with N-phosphonomethyl-lysine methyl ester.
N-fosfonometyyliglysiinin suolat valmsitetaan neutraloimalla happo osittain tai täydellisesti sopivalla emäksellä, emäksisellä karbonaatilla, ammoniakilla tai orgaanisella amiinilla.The salts of N-phosphonomethylglycine are prepared by partially or completely neutralizing the acid with a suitable base, basic carbonate, ammonia or organic amine.
N-fosfonometyyliglysiini on itse hyvin tehokas fytotoksinen aine tai herbisidi. Johtuen siitä, että se on suhteellisen liukenematon veteen ja tavanomaisiin orgaanisiin liuottimiin, sitä ei voida niin helposti 57955 soveltaa kaupallisiin formulaatioihin kuin useita muita sen johdannaisia. Yllättäen on nyt havaittu, että keksinnön mukaiset yhdisteet ovat veteen liukenevia, mutta niillä on kuitenkin suurusluokaltaan yhtä voimakas aktiivisuus kuin glysiinillä.N-phosphonomethylglycine itself is a very effective phytotoxic agent or herbicide. Due to its relative insolubility in water and conventional organic solvents, it cannot be applied as easily to commercial formulations as many of its other derivatives. Surprisingly, it has now been found that the compounds of the invention are soluble in water, yet have the same magnitude of activity as glycine.
On havaittu, että itävien siemenien, esiintunkeutuvien taimien, kehittyvien ja kehittyneiden puumaisten ja ruohomaisten kasvien ja vesikasvien kasvua voidaan säännöstellä asettamalla esiintunkeutuvat taimet tai kehittyvien ja kehittyneiden kasvien maanpäälliset osat tai vesikasvien osat alttiiksi tehokkaalle määrälle keksinnön mukaisia glysii-nejä. Yhdisteitä voidaan käyttää yksin, kahden tai useamman yhdisteen seoksina tai seoksina apuaineen kanssa. Nämä yhdisteet ovat tehokkaita pintaan tunkeutumisen jälkeisinä fytotoksisina aineina tai herbisidei-nä, esim. säännösteltäessä yhden tai useamman yksisirkkalehtisen lajin tai yhden tai useamman kaksisirkkalehtisen lajin kasvua selektiivisesti muiden sirkkalehtisten tai kaksisirkkalehtisten läsnäollessa. Edelleen näille yhdisteille on tunnusomaista, että niillä on laaja aktiivisuus, so. ne säännöstelevät hyvin erilaisten kasvien kasvua mukaanlukien saniaiset, havupuut (mänty, kuusi ja vastaavat) vesikasvit, yksisirkkai-set ja kaksisirkkaiset.It has been found that the growth of germinating seeds, emerging seedlings, developing and developed woody and herbaceous plants and aquatic plants can be regulated by exposing the emerging seedlings or above-ground parts of developing and developed plants or parts of aquatic plants to an effective amount of the glycines of the invention. The compounds may be used alone, as mixtures of two or more compounds, or as mixtures with an excipient. These compounds are effective as post-penetration phytotoxic agents or herbicides, e.g., by selectively regulating the growth of one or more monocotyledonous species or one or more dicotyledonous species in the presence of other cotyledons or dicotyledons. Furthermore, these compounds are characterized in that they have a wide range of activity, i. they regulate the growth of a wide variety of plants including ferns, conifers (pine, spruce and the like), aquatic plants, monocotyledons and dicotyledons.
Amerikkalaisessa patenttijulkaisussa 3 445 675 on kuvattu fytotoksisia yhdisteitä joiden kaava on 0 Γ o Il \\/m (MOC-CH-) -N— 0Ho-P z m z n.U.S. Pat. No. 3,445,675 describes phytotoxic compounds of the formula 0 Γ o Il \\ / m (MOC-CH-) -N-O-Ho-P z m z n.
OMOM
_ _ n jossa kaavassa M on alkalimetalli, vety- tai 1-4 hiiliatominen alkyyli-ryhmä, NH^ tai 1-4 hiiliatomisella alkyylillä substituoitu ammoniumryh-mä, m tai n ovat kokonaisluku 1 tai 2, jolloin n + m = 3.wherein M is an alkali metal, hydrogen or alkyl group having 1 to 4 carbon atoms, NH 4 or an ammonium group substituted with alkyl having 1 to 4 carbon atoms, m or n are an integer 1 or 2, wherein n + m = 3.
Amerikkalainen patenttijulkaisu 3 556 762 koskee kasvien kehityksen modifioimiseen tarkoitettuja yhdisteitä, joilla on seuraava kaava: 0 R R2 0 nMlU.S. Patent 3,556,762 relates to compounds for modifying plant development having the following formula: 0 R R2 0 nMl
I! I I II /0MI! I I II / 0M
MO - C - C ----N---- C-----PMO - C - C ---- N ---- C ----- P
R1 R3 N OH2 i_ Jm _ J n 4 57955R1 R3 N OH2 i_ Jm _ J n 4 57955
. 1 2 jossa m on kokonaisluku 0 - 2 ja n on kokonaisluku 1 - 3, R, R ja R. 1 2 where m is an integer from 0 to 2 and n is an integer from 1 to 3, R, R and R
ja R^ tarkoittavat vetyatomia tai 1-4-hiiliatomista alkyyliä ja M, 2 ja M tarkoittavat vetyä, 1-4-hiiliatomista alkyyliä tai suolan muodostavaa kationia.and R 1 represents a hydrogen atom or an alkyl having 1 to 4 carbon atoms, and M, 2 and M represent a hydrogen, an alkyl having 1 to 4 carbon atoms or a salt-forming cation.
On selvää, että oheisen keksinnön mukaiset yhdisteet eroavat näiden patenttijulkaisujen mukaisista yhdisteistä siten, että viimeksi mainitut eivät sisällä typpiatomiin sidottua vetyatomia. Tämä on hyvin tärkeä ero. On huomattava, että patenttijulkaisun 3 556 762 mukaisia yhdisteitä voidaan käyttää herbisideinä, jos niitä levitetään tähän tarkoitukseen riittävä määrä. Tätä vaikutusta ei tosin mainita patenttijulkaisussa .It is clear that the compounds of the present invention differ from the compounds of these patents in that the latter do not contain a hydrogen atom attached to a nitrogen atom. This is a very important difference. It should be noted that the compounds of U.S. Patent No. 3,556,762 can be used as herbicides if they are applied in sufficient amounts for this purpose. However, this effect is not mentioned in the patent publication.
Vertailukokeissa on saatu jäljempänä esitetyt tulokset. Keksinnön mukaiset yhdisteet ovat näiden kokeiden perusteella 8-16 kertaa niin tehokkaita kuin edellä mainittujen patenttijulkaisujen mukaiset yhdisteet. Huomionarvoista on, että substituoimalla alkyyliryhmällä yksi me-tyyliryhmien vetyatomeista saadaan niille yhdisteille, jotka sisältävät vetyatomin typpiatomissa, täydellinen epäaktiivisuus herbisidinä aina noin 4,5 kg/ha asti. Tämä osoittaa selvästi, että keksinnön mukaiseen seokseen sisältyvä yhdiste eroaa näiden kummankin patenttijulkaisun mukaisesta yhdisteestä.The following results have been obtained in comparative experiments. Based on these experiments, the compounds of the invention are 8 to 16 times as effective as the compounds of the above-mentioned patents. It is noteworthy that by substituting an alkyl group for one of the hydrogen atoms of the methyl groups, for those compounds which contain a hydrogen atom on the nitrogen atom, complete inactivity as a herbicide is obtained up to about 4.5 kg / ha. This clearly shows that the compound contained in the composition of the invention differs from the compound of both of these patents.
Vertailukoe keksinnön mukaisilla yhdisteillä ja aikaisemmin tunnetuil-la yhdisteillä_Comparative experiment with the compounds according to the invention and with previously known compounds_
Keksinnön mukaisena yhdisteenä käytettiin seuraavia: A. N-fosfonometyyliglysiinin mono-isopropyyliamiinisuola B. N-fosfonometyyliglysiinin mononatriumsuolaThe following were used as a compound of the invention: A. Mono-isopropylamine salt of N-phosphonomethylglycine B. Monosodium salt of N-phosphonomethylglycine
Aikaisemmin tunnettuina yhdisteinä käytettiin: M. N-fosfonometyyli-iminodietikkahapon mono-isopropyyliamiinisuola N. N-fosfonometyyli-iminodietikkahappo O. N-fosfonometyyli-iminodietikkahapon mono-natriumsuola P. Bis-N-fosfonometyyli-imino-etikkahapon isopropyyliamiinisuola Q. Bis-N-fosfonometyyli-imino-etikkahappo R. Bis-N-fosfonometyyli-imino-etikkahapon natriumsuola.The following were used as previously known compounds: M. N-phosphonomethyliminodiacetic acid monoisopropylamine salt N. N-phosphonomethyliminodiacetic acid O. N-phosphonomethyliminodiacetic acid monosodium salt P. Bis-N-phosphonomethylisopropylisopropylacetic acid phosphonomethyliminoacetic acid R. Sodium salt of bis-N-phosphonomethyliminoacetic acid.
5 5 7 9 5 55 5 7 9 5 5
Taulukko ITable I
Kg/ha Yhdiste A, Yhdiste M, Yhdiste P, herbisidi- herbisidi- herbisidi- _ vaikutus, % vaikutus, % vaikutus, %Kg / ha Compound A, Compound M, Compound P, herbicide- herbicide- herbicide _ effect,% effect,% effect,%
So As So Ag So Ag 1.12 100 100 76 95 80 75 0,56 100 100 35 70 30 65 0,28 100 98 35 65 30 50 0,14 90 100 30 55 20 30 0,07 65 70 25 0 15 30 0,03 35 50 20 0 15 20So As So Ag So Ag 1.12 100 100 76 95 80 75 0.56 100 100 35 70 30 65 0.28 100 98 35 65 30 50 0.14 90 100 30 55 20 30 0.07 65 70 25 0 15 30 0 , 03 35 50 20 0 15 20
Kg/ha Yhdiste B, Yhdiste N, Yhdiste Q, herbisidi- herbisidi, herbisidi- _ vaikutus, % vaikutus, % vaikutus, %Kg / ha Compound B, Compound N, Compound Q, herbicide herbicide, herbicide effect,% effect,% effect,%
So Ag So Ag So Ag 1.12 100 100 50 40 75 40 0,56 100 100 55 35 50 40 0,28 99 98 0 20 0 20 0,14 98 100 00 00 0,07 90 90 0 0 0 0 0,03 65 65 0 0 0 0So Ag So Ag So Ag 1.12 100 100 50 40 75 40 0.56 100 100 55 35 50 40 0.28 99 98 0 20 0 20 0.14 98 100 00 00 0.07 90 90 0 0 0 0 0.03 65 65 0 0 0 0
Kg/ha Yhdiste O, Yhdiste R, herbisidi- herbisidi- _ vaikutus, % vaikutus, %Kg / ha Compound O, Compound R, herbicide- herbicide _ effect,% effect,%
So Ag So Ag " 1,12 35 50 70 65 0,56 25 50 45 50 0,28 35 40 20 30 0,14 0 35 0 35 0,07 0 0 0 0 0,03 0 0 0 0So Ag So Ag "1.12 35 50 70 65 0.56 25 50 45 50 0.28 35 40 20 30 0.14 0 35 0 35 0.07 0 0 0 0 0.03 0 0 0 0
Edellä olevasta taulukosta I käy ilmi, että oheisen keksinnön mukaisilla yhdisteillä A ja B on 8 - 32 kertaa niin suuri herbisidinen vaikutus kuin aikaisemmin tunnetuilla yhdisteillä M, N, O, P, Q ja R. So on Sorghum halepense ja Ag on Agropyron repens.It can be seen from Table I above that the compounds A and B of the present invention have 8 to 32 times as much herbicidal activity as the previously known compounds M, N, O, P, Q and R. So is Sorghum halepense and Ag is Agropyron repens.
Tämän keksinnön mukaisten erilaisten yhdisteiden esiintunkeutumisen jälkeinen herbisidinen aktiviteetti osoitettiin seuraavasti. Aktiivisia aineosia levitettiin suihkumuodossa 14 - 21 päivän vanhoille eri- 57955 6 laisten kasvilajien yksilöille (kuten on osoitettu). Suihku, vesiliuos tai orgaaninen liuos - vesiliuos, joka sisälsi aktiivista aineosaa ja pinta-aktiivista ainetta (35 osaa dodekyylibentseeni-sulfonihapon bu-tyyliamiinisuolaa ja 65 osaa mäntyöljyä kondensoituna etyleenioksidin kanssa suhteessa 11 moolia etyleenioksidia yhtä mäntyöljymoolia kohti), kohdistetaan kasveihin aktiivisen aineosan määrien ollessa erilaisia (kiloa/hehtaari). Käsitellyt kasvit asetetaan kasvihuoneeseen ja vaikutukset huomioidaan ja merkitään muistiin noin kahden viikon ja noin neljän viikon kuluttua, kuten on osoitettu taulukon II viimeisessä sarakkeessa.The post-infiltration herbicidal activity of the various compounds of this invention was demonstrated as follows. The active ingredients were applied in spray form to 14-21 day old specimens of different plant species (as indicated). Spray, aqueous or organic solution - aqueous solution containing the active ingredient and a surfactant (35 parts of dodecylbenzenesulfonic acid butylamine salt and 65 parts of tall oil condensed with ethylene oxide in a ratio of 11 moles of ethylene oxide per mole of active ingredient per pine oil) (kilograms / hectare). The treated plants are placed in a greenhouse and the effects are noted and recorded after about two weeks and about four weeks, as shown in the last column of Table II.
Taulukossa II käytetään tunkeutumisen jälkeistä herbisidistä aktiviteetti-indeksiä seuraavasti:Table II uses the post-infestation herbicide activity index as follows:
Kasvin reaktio Indeksi Kasvin reaktio IndeksiPlant Reaction Index Plant Reaction Index
Ei vahingoittunut 0 Vakavasti vahingoittunut 3Not damaged 0 Severely damaged 3
Hieman vahingoittunut 1 Kuollut 4Slightly damaged 1 Died 4
Kohtalaisesti vahingoitt. 2 Näissä kokeissa käytetyt kasvilajit on esitetty kirjaimien avulla seuraavan selityksen mukaisesti:_ A - Soijapapu K - Polygonum B - Sokerijuurikas L - Abutilon theophrasti C - Vehnä M - Bromus D - Riisi N - Panicum Spp E - Sorgum O - Echinochloa crusgalli F - Xanthium p - Digitaria sanguinalis G - Villitatar Q - Cyperus x) H - Ipomoea r - Agropyron repens x) I - Sesbaniahamppu S - Sorghum halepense x) J - Cenopodium album T - Cirsium arvens x) x) Kasvatettu vegetatiivisista istukkaista.Moderately damaged. 2 The plant species used in these experiments are represented by letters as follows: _ A - Soybean K - Polygonum B - Sugar beet L - Abutilon theophrasti C - Wheat M - Bromine D - Rice N - Panicum Spp E - Sorghum O - Echinochloa crusgalli F - Xanthium p - Digitaria sanguinalis G - Wildcat Q - Cyperus x) H - Ipomoea r - Agropyron repens x) I - Sesbania hemp S - Sorghum halepense x) J - Cenopodium album T - Cirsium arvens x) x) Grown from vegetative cuttings.
Taulukko IITable II
Yhdiste Määrä ABCDEFGHIJKLMNOPQRST Viikkoa I 4,49 - 4-3-4444-4-444- 2 I 1,12 3443432334-44444- -- - 4 II 4,49 - -- -- 4-4-4-44 -- -443- 4 II 1,12 3444441234433444 ---- 2 7 57955Compound Amount ABCDEFGHIJKLMNOPQRST Weeks I 4.49 - 4-3-4444-4-444- 2 I 1.12 3443432334-44444- - - 4 II 4.49 - - - 4-4-4-44 - -443- 4 II 1,12 3444441234433444 ---- 2 7 57955
Yhdiste Määrä ABCDEFGHIJKLMNOPQRST Viikkoa III 4,49 -----4-3-4-44---4444 4 III 1,12 3434443344-44444 ---- 2 IV 4,49 -----4-3-4-44---444- 4 IV 1,12 2444442234-34444---- 2 V 4,49 -----4-4-4444-4-4444 4 V 1,12 3443443244-34444-- -- 2 VI 4,49 3-1-3222-3-1232 2 VII 4,49 -- - -- 3-2-3433-3-2443 2 VIII 4,49 3-3-4433-3-243- 2 IX 4,49 3-3-4444-4-3444 2 X 4,49 ---4-3-4443-4-33-4 2 XI 4,49 -----4-3-4444-4-24-4 4 XII x) 4,49 -----4-2-3-31-3-1213 2 XIII x) 4,49 03221102 10333---- 2 XIV x) 11,2 - ---- 1-1-4--2-4-1420 2 XV x) 4,49 --- -- 2-2-3232-2-1022 2 XVI 4,49 -----4-3-4-44-4-4444 2 XVII 4,49 3-1-4-33-3-233- 2 XVIII 4,49 -----3-2-3-33-2-234- 2 XIX 4,49 4-3-4-43-4-3444 2 XX 4,49 -4-3-4-33-3-44-4 2 XXI 4,49 -- -3-1-4-43-2-2143 2 XXII 4,49 -----4-3-4-33-4-4444 2 XXIII 4,49 -----4-2-4-34-4-344- 2 XXIV 4,49 -----4-2-4-44-4-4444 2 XXV 4,49 -----4-3-4-43-4-4444 xx) XXVI 4,49 -----4-2-4-43-4-3421 xx) XXVII 4,49 ---4-3-4-42-4-4443 xx) XXVIII 4,49 ---4-4-4-44-4-4444 2 XXIX 4,49 -----4-4-4-44-4-44-4 2 XXX 4,49 -----4-4-4-44-4-44-4 2 XXXI 4,49 --4-2-4-44-4-3444 2 XXXII 4,49 4-2-4-44-4-4444 2 x) Kohdistettu kolmen viikon vanhoihin kasveihin. Kaikki muut kokeet suoritettiin kaksiviikkoisilla kasveilla.Compound Amount ABCDEFGHIJKLMNOPQRST Week III 4.49 ----- 4-3-4-44 --- 4444 4 III 1.12 3434443344-44444 ---- 2 IV 4.49 ----- 4-3- 4-44 --- 444- 4 IV 1,12 2444442234-34444 ---- 2 V 4,49 ----- 4-4-4444-4-4444 4 V 1,12 3443443244-34444-- - - 2 VI 4,49 3-1-3222-3-1232 2 VII 4,49 - - - 3-2-3433-3-2443 2 VIII 4,49 3-3-4433-3-243- 2 IX 4.49 3-3-4444-4-3444 2 X 4.49 --- 4-3-4443-4-33-4 2 XI 4.49 ----- 4-3-4444-4- 24-4 4 XII x) 4.49 ----- 4-2-3-31-3-1213 2 XIII x) 4.49 03221102 10333 ---- 2 XIV x) 11.2 - --- - 1-1-4--2-4-1420 2 XV x) 4.49 --- - 2-2-3232-2-1022 2 XVI 4.49 ----- 4-3-4- 44-4-4444 2 XVII 4.49 3-1-4-33-3-233- 2 XVIII 4.49 ----- 3-2-3-33-2-234- 2 XIX 4.49 4 -3-4-43-4-3444 2 XX 4.49 -4-3-4-33-3-44-4 2 XXI 4.49 - -3-1-4-43-2-2143 2 XXII 4.49 ----- 4-3-4-33-4-4444 2 XXIII 4.49 ----- 4-2-4-34-4-344- 2 XXIV 4.49 ---- -4-2-4-44-4-4444 2 XXV 4.49 ----- 4-3-4-43-4-4444 xx) XXVI 4.49 ----- 4-2-4- 43-4-3421 xx) XXVII 4.49 --- 4-3-4-42-4-4443 xx) XXVIII 4.49 --- 4-4-4-44-4-4444 2 XXIX 4.49 ----- 4-4-4-44-4-44-4 2 XXX 4 , 49 ----- 4-4-4-44-4-44-4 2 XXXI 4.49 --4-2-4-44-4-3444 2 XXXII 4.49 4-2-4-44 -4-4444 2 x) Targeted to three-week-old plants. All other experiments were performed on two-week-old plants.
xx) Nämä lukemat tehtiin 11 päivän kuluttua.xx) These readings were taken after 11 days.
5 7 9 5 5 85 7 9 5 5 8
Keksinnön mukaisten yhdisteiden sekä tunnettujen yhdisteiden herbisidisiä «Muinaisuuksia verrattiin käsittelemällä kasvihuoneessa kasvatettuja yksi- ja monivuotisia taimia. (Monivuotiset lajit Cirsium arvense, Cyperus rotundus, Agropyron repens, Sorghum halopense; yksivuotiset lajit, Xanthium, Cissampelos pareira, Iponemde purpurea, Chenpodium album, Polygonum, Bromus tectorum, Exhinochloa Crusgasli).The herbicidal properties of the compounds according to the invention as well as the known compounds were compared by treating annual and perennial seedlings grown in a greenhouse. (Perennial species Cirsium arvense, Cyperus rotundus, Agropyron repens, Sorghum halopense; annual species, Xanthium, Cissampelos pareira, Iponemde purpurea, Chenpodium album, Polygonum, Bromus tectorum, Exhinochloa Crusgasli).
Kokeiltava yhdiste sekoitettiin 1 %:n kanssa pinta-aktiivista ainetta ja suih-kutettiin taimien päälle. Suihkutetun liuoksen määrä oli 0,02 1/m lukuunot-tamatta yhdistettä I jota liukoisuussyistä suihkutettiin 0,0U 1/m . Suihkutuk-sen jälkeen taimet pidettiin kasvihuoneessa ja niitä kasteltiin alhaaltapäin tarpeen mukaan. Käsittelyn jälkeen taimia tarkasteltiin kahden ja neljän viikon välein. Kokeissa käytettiin jokaisesta lajista useampia taimia ja seuraa-vassa taulukossa on annettu keskiarvot. Taulukossa mainitut koeyhdisteet ovat: 1 N-fosfonometyyli-iminodietikkahappo II N,N-bis(fosfonometyyli)glysiini III yhdisteen I monoisopropyyliamiinisuola IV yhdisteen II monoisopropyyliamiinisuola V N-fosfonometyyliglysiinin monoisopropyyliamiinisuola VI yhdisteen I mononatriumsuola VII yhdisteen II monomatriumsuola VIII N-fosfornometyyliglysiinin mononatriumsuolaThe test compound was mixed with 1% of surfactant and sprayed on the seedlings. The amount of the sprayed solution was 0.02 l / m except for compound I, which was sprayed with 0.0U 1 / m for solubility reasons. After spraying, the seedlings were kept in a greenhouse and watered from below as needed. After treatment, seedlings were examined every two and four weeks. Several seedlings of each species were used in the experiments and the following table gives the averages. The test compounds listed in the table are: 1 N-phosphonomethyliminodiacetic acid II N, N-bis (phosphonomethyl) glycine III monoisopropylamine salt of compound I monoisopropylamine salt of compound II monosol triolone
Seuraavassa taulukossa on annettu kokeissa saadut tulokset. Tästä selviää, että keksinnön mukaiset yhdisteet eli yhdisteet V, VIII ovat huomattavasti tehokkaampia kuin vertailuyhdisteet. Taulukossa on mainittu taimien kuolleisuus-? käsittelyn jälkeen.The following table gives the results obtained in the experiments. It is clear from this that the compounds according to the invention, i.e. compounds V, VIII, are considerably more potent than the reference compounds. The table mentions seedling mortality? after treatment.
9 579559 57955
TAULUKKO IIITABLE III
Taimien keskimäärinen kuolleisuus-# γπ Tr ~i·^ . I - - r r -~r ii---r- —Mean seedling mortality- # γπ Tr ~ i · ^. I - - r r - ~ r ii --- r- -
Aika Yhdiste Monivuotiset YksivuotisetTime Compound Perennial Annuals
Yhdisteiden pitoisuus (ρ-ϊ) 0,25 1,0 2,0 U,0 0,25 1,0 2,0 U,0Concentration of compounds (ρ-ϊ) 0.25 1.0 2.0 U, 0 0.25 1.0 2.0 U, 0
HAPOTACIDS
2 I 5 5 Uo 66 12 9 U2 82 2 II 15 35 U8 56 1T 55 76 77 U I 2 8 66 90 20 15 5U 88 U II 2U 6U 75 83 18 59 82 90 M0N0IS0PR0PYY—2 I 5 5 Uo 66 12 9 U2 82 2 II 15 35 U8 56 1T 55 76 77 U I 2 8 66 90 20 15 5U 88 U II 2U 6U 75 83 18 59 82 90 M0N0IS0PR0PYY—
LIAMIINI SUOLALAMINE SALT
2 III 2U 36 38 5U 26 36 56 67 2 IV 13 35 50 50 20 69 62 69 ^ 2 V 87 99 95 99 93 99 99 99 U III Ui 59 68 66 20 U7 69 75 U IV 19 68 70 85 23 71 76 73 UV 99 100 95 100 95 98 100 992 III 2U 36 38 5U 26 36 56 67 2 IV 13 35 50 50 20 69 62 69 ^ 2 V 87 99 95 99 93 99 99 99 U III Ui 59 68 66 20 U7 69 75 U IV 19 68 70 85 23 71 76 73 UV 99 100 95 100 95 98 100 99
M0N0NATRIUMM0N0NATRIUM
SUOLASALT
2 VI 36 61 59 71 39 62 79 8U2 VI 36 61 59 71 39 62 79 8U
2 VII Ui U5 U8 70 UO 5U 73 8U2 VII Ui U5 U8 70 UO 5U 73 8U
2 VIII 91 98 99 100 92 99 98 99 U VI 63 7U 75 78 51 78 75 85 U VII 6U 71 7U 87 51 6U 71 92 U VIII 9U 100 100 100 9U 100 99 992 VIII 91 98 99 100 92 99 98 99 U VI 63 7U 75 78 51 78 75 85 U VII 6U 71 7U 87 51 6U 71 92 U VIII 9U 100 100 100 9U 100 99 99
Seuraavassa vertailukokeessa on erästä keksinnön mukaista yhdistettä verrattu tunnettuihin fosforipitoisiin happoihin. Kuten taulukosta ilmenee keksinnön mukaisella yhdisteellä on ylivoimaisesti tehokkaimmat herbisidiset ominaisuudet kokeiltavista yh-^ disteistä. Kokeissa on käytetty sekä kapea- että leveälehtisiä kasveja ja kokeilta- vaa yhdistettä on levitetty noin 0,U g/m .In the following comparative experiment, a compound of the invention is compared with known phosphorus-containing acids. As can be seen from the table, the compound of the invention has by far the most effective herbicidal properties of the compounds tested. Both narrow and broadleaf plants have been used in the experiments and the test compound has been applied at about 0.1 U g / m 2.
TAULUKKO IVTABLE IV
" Yhdiste kapealehtiset leveälehtiset N-fosfonometyyliglysiinin“A compound of narrow-leaf broadleaf N-phosphonomethylglycine
isopropyyliamiinisuola U Uisopropylamine salt U U
N-fosfonometyyli-a-metyyliglysiini 0 0 N-foefonoraetyyli-a,e-dimetyyliglysiini 0 0 N-fosfonometyyli-a-isopropyyliglysiini 0 0 N-fo8fonometyyli-o-fenyyliglysiini 0 0 N-fosfono-isopropyylideeniglysiini 0 0N-phosphonomethyl-α-methylglycine 0 0 N-phosphonoethyl-α, ε-dimethylglycine 0 0 N-phosphonomethyl-α-isopropylglycine 0 0 N-phosphonomethyl-o-phenylglycine 0 0 N-phosphonoisopropylidene glycine 0 0
Herbisinen indeksi: U « kuollut; 3 * vakavasti vahingoittunut; 2 * kohtalaisesti vahingoittunut; 1 * hieman vahingoittunut 0 * vahingoittumaton 5 7 9 5 5 10Herbic index: U «dead; 3 * severely damaged; 2 * moderately damaged; 1 * slightly damaged 0 * undamaged 5 7 9 5 5 10
Seuraavassa on annettu taulukossa II roomalaisilla numeroilla esitetyt yhdisteet:The following are the compounds shown in Roman numerals in Table II:
Roomalainen Yhdisteen nimi numero_ _ I N-fosfonometyyliglysiinin natriumsuola II N-fosfonometyyliglysiinin dinatriumsuola III N-fosfonometyyliglysiinin trinatriumsuola IV N-fosfonometyyliglysiinin mono-etanoliamiinisuola V N-fosfonometyyliglysiinin mono-ammoniumsuola VI N-fosfonometyyliglysiinin kalsiumsuolan monohydraatti VII N-fosfonometyyliglysiinin magnesiumsuola VIII Magnesium-bis(N-fosfonometyyliglysinaatti) IX N-fosfonometyyliglysiinin kaliumsuola X N-fosfonometyyliglysiinin dimetyyliamiinisuola XI Kupari-bis-(N-fosfonometyyliglysinaatti) XII N-fosfonometyyliglysiinin dilitiumsuola XIII N-(fosfonometyyli)glysiinin sinkkisuola XIV N-fosfonometyyliglysiiniamiidi XV Metyyli-N-(fosfonometyyli)glysinaatti XVI Etyyli-N-(fosfonometyyli)glysinaatti XVII n-propyyli-N-(fosfonometyyli)glysinaatti XVIII n-butyyli-N-(fosfonometyyli)glysinaatti XIX n-heksyyli-N-(fosfonometyyli)glysinaatti XX Sykloheksyyli-N-(fosfonometyyli)glysinaatti XXI Oktyyli-N-(fosfonometyyli)glysinaatti XXII Dekyyli-N-(fosfonometyyli)glysinaatti XXIII Dodekyyli-N-(fosfonometyyli)glysinaatti XXIV Kloorietyyli-N-(fosfonometyyli)glysinaatti XXV N-fosfonometyyliglysiinin mono(metyyliamiini)suola XXVI N-fosfonometyyliglysiinin mono(di-isopropyyliamiini)- suola XXVII N-fosfonometyyliglysiinin mono(dietanoliamiini)suola XXVIII N-fosfonometyyliglysiinin mono(trietyyliamiini)suola XXIX N-fosfonometyyliglysiinin mono(pyridiini)suola XXX N-fosfonometyyliglysiinin mono(aniliini)suola XXXI N-fosfonometyyliglysiinin mono(isopropyyliamiini)suola XXXII N-fosfonometyyliglysiinin mono(n-butyyliamiini)suola Jäljempänä on annettu vielä 24 esimerkkiä valmistetuista yhdisteistä fysiologisine aktiivisuuksineen: 1. Pyrrolidiiniamido(N-fosfonometyyli)glysiini 5 795 5 2. (N-fosfonometyyli)glysiinin diallyyliamiinisuola 3. (N-fosfonometyyli)glysiinin dipropargyyliamiinisuola 4. Etyyli(N-fosfonometyyli)glysinaatin mononatriumsuola 5. (N-fosfonometyyli)glysiinin sekundäärinen butyyliamiinisuola 6. (N-fosfonometyyli)glysiinin etyyliamiinisuola 7. (N-fosfonometyyli)glysiinin butyroamidi 8. (N-fosfonometyyli)glysiinin allyyliamidi ^ 9. (N-fosfonometyyli)glysiinin morfoliinoamidi 10. (N-fosfonometyyli)glysiinin piperidinyyliamidi 11. (N-fosfonometyyli)glysiinin hydroksietyyliamidi 12. (N-fosfonometyyli)glysiinin metoksietyyliamidi 13. Allyyli(N-fosfonometyyli)glysinaatti 14. (N-fosfonometyyli)glysiinin isopropyyliamidi 15. Oktyylioksi(N-fosfonometyyli)glysinaatti 16. Dietyyli(N-fosfonometyyli)glysinaatin kaliumsuola 17. (N-fosfonometyyli)glysiinin di(etyyliamiini)suola 18. (N-fosfonometyyli)glysiinin di(monoisopropyyliamiini)suola 19. 2-metyylioksietyyli-N-(fosfonometyyli)glysinaatti 20. 2-fenoksietyyli-N-(fosfonometyyli)glysinaatti ^ 21. 2-(etoksietoksi)etyyli-N-(fosfonometyyli)glysinaatti 22. 2-(2-kloorietoksi)etyyli-N-(fosfonometyyli)glysinaatti 23. 2-(etoksi)etyyli-N-(fosfonometyyli)glysinaatti 24. 2-(butoksi)etyyli-N-(fosfonometyyli)glysinaatti Näiden 24 yhdisteen vaikutus selviää seuraavasti taulukosta III: / 57955 12Roman Compound name numero_ _ I of N-phosphonomethylglycine sodium salt II of N-phosphonomethylglycine disodium salt III N-phosphonomethylglycine trisodium salt IV N-phosphonomethylglycine mono-ethanolamine R N-phosphonomethylglycine mono-ammonium salt of VI N-phosphonomethylglycine of the calcium salt monohydrate VII of N-phosphonomethylglycine magnesium VIII, magnesium-bis ( N-phosphonomethylglycinate) IX Potassium salt of N-phosphonomethylglycine X Dimethylamine salt of N-phosphonomethylglycine XI Copper-bis- (N-phosphonomethylglycinate) XII N-phosphonomethylglycine N-phosphinyl XVI Ethyl N- (phosphonomethyl) glycinate XVII n-propyl N- (phosphonomethyl) glycinate XVIII n-butyl N- (phosphonomethyl) glycinate XIX n-hexyl-N- (phosphonomethyl) glycinate XX Cyclohexyl-N- (phosphonomethyl) glycinate XXI Octyl N- (phosphonomethyl) glycinate XXII Decyl-N- ( phosphonomethyl) glycinate XXIII Dodecyl N- (phosphonomethyl) glycinate XXIV Chloroethyl N- (phosphonomethyl) glycinate XXV N-phosphonomethylglycine mono (methylamine) salt XXVI N-phosphonomethylglycine mono (amine) amino-N-isopropylamine salt XXVIII Mono (triethylamine) salt of N-phosphonomethylglycine XXIX mono (pyridine) salt of N-phosphonomethylglycine XXX Mono (aniline) salt of N-phosphonomethylglycine XXXI N-phosphonomethylglycine mono (butopropylamine) given a further 24 examples of prepared compounds with physiological activities: 1. Pyrrolidinamido (N-phosphonomethyl) glycine 5,795 5 2. (N-phosphonomethyl) glycine diallylamine salt 3. (N-phosphonomethyl) glycine dipropargylamine salt 4. Ethyl (N-phosphinate) mono-5-phosphinethyl Secondary butylamine salt of (N-phosphonomethyl) glycine 6. Ethyl (N-phosphonomethyl) glycine ylamine salt 7. (N-phosphonomethyl) glycine butyramide 8. (N-phosphonomethyl) glycine allylamide ^ 9. (N-phosphonomethyl) glycine morpholinamide 10. (N-phosphonomethyl) glycine piperidinylamide 11. (N-phosphonomethyl) glycine 12 hydroxy N-phosphonomethyl) glycine methoxyethylamide 13. Allyl (N-phosphonomethyl) glycinate 14. (N-phosphonomethyl) glycine isopropylamide 15. Octyloxy (N-phosphonomethyl) glycinate 16. Diethyl (N-phosphonomethyl) glycinate potassium salt 17. (N-phosphonomethyl) di (ethylamine) salt of glycine 18. (N-phosphonomethyl) di (monoisopropylamine) salt of glycine 19. 2-methyloxyethyl N- (phosphonomethyl) glycinate 20. 2-phenoxyethyl N- (phosphonomethyl) glycinate ^ 21. 2- (ethoxyethoxy) ) ethyl N- (phosphonomethyl) glycinate 22. 2- (2-chloroethoxy) ethyl N- (phosphonomethyl) glycinate 23. 2- (ethoxy) ethyl N- (phosphonomethyl) glycinate 24. 2- (butoxy) ethyl N- (phosphonomethyl) glycinate The effect of these 24 compounds is shown in Table III as follows: / 57955 12
Taulukko IIITable III
Yhdiste n:o kg/ha TSt^SFLHJKMOCompound No. kg / ha TSt ^ SFLHJKMO
1 11,2 10232011-22 2 4,5 42344324--4 3 4,5 42324324--4 4 4,5 32443322-24 5 4,5 444-4424--4 6 4,5 4444443---4 7 4,5 10-20004-11 8 4,5 011-001 3 -01 9 4,5 10022011-02 10 4,5 11101011-01 11 4,5 01111011-01 12 4,5 12121323-14 13 4,5 32333223-14 14 4,5 00000010-00 15 4,5 40201311-13 16 4,5 00001012-01 17 4,5 33323324-23 18 4,5 33444324234 19 1,1 4-122423433 20 4,5 00112021222 21 4,5 43333233333 22 4,5 32433123223 23 4,5 44444434444 24 4,5 444424244441 11.2 10232011-22 2 4.5 42344324--4 3 4.5 42324324--4 4 4.5 32443322-24 5 4.5 444-4424--4 6 4.5 4444443 --- 4 7 4.5 10-20004-11 8 4,5 011-001 3 -01 9 4,5 10022011-02 10 4,5 11101011-01 11 4,5 01111011-01 12 4,5 12121323-14 13 4,5. 32333223-14 14 4,5 00000010-00 15 4,5 40201311-13 16 4,5 00001012-01 17 4,5 33323324-23 18 4,5 33444324234 19 1,1 4-122423433 20 4,5 00112021222 21 4. 5 43333233333 22 4.5 32433123223 23 4.5 44444434444 24 4.5 44442424444
Seuraavassa taulukossa IV on annettu lisää yhdisteitä herbisidisine aktiivisuuksineen: 13 57955Additional compounds with herbicidal activities are given in Table IV below: 13 57955
Taulukko IVTable IV
(Yhdisteille 1-19 annostus 11,2 kg/har ja yhdisteille 20 - 22 4,48 kg/har)(For compounds 1-19 the dosage is 11.2 kg / har and for compounds 20-22 4.48 kg / har)
YhdisteCompound
nro_ ABCDEFGHIJKno_ ABCDEFGHIJK
1 44444444444 2 44444444444 3 44444444444 4 44444444444 5 44444444444 6 44444444444 7 444444-4444 8 444344-4443 9 44444444443 10 44434444443 11 44444444444 12 44444444444 13 44444444444 14 444444-4444 15 44434444443 16 44434444443 17 01314411424 18 01324411434 19 12222122323 20 44434444444 21 00112021233 22 44434443434 Λ - Cirsium arvense B - Canthium C - Abutilon theophrasti 14 57955 D - Ipomoea E - Chenopodium album F - Polygonum G - Gyperus H - Agropyron repens I - Sorghum halepense J - Bromus tectorum K - Echinochloa crusgalli2 44444444444 1 44444444444 3 44444444444 4 44444444444 5 44444444444 6 44444444444 7 444444-4444 8 444344-4443 9 44444444443 10 44434444443 11 44444444444 12 44444444444 13 44444444444 14 444444-4444 15 44434444443 16 44434444443 17 01314411424 18 01324411434 19 12222122323 20 44434444444 21 00112021233 22 44434443434 Λ - Cirsium arvense B - Canthium C - Abutilon theophrasti 14 57955 D - Ipomoea E - Chenopodium album F - Polygonum G - Gyperus H - Agropyron repens I - Sorghum halepense J - Bromus tectorum K - Echinochloa crusgalli
Yhdisteet: 1. N-fosfonometyyliglysiinirt dikaliumsuola 2. N-fosfonometyyliglysiinin trikaliumsuola 3. N-fosfonometyyliglysiinin trilitiumsuola 4. N-fosfonometyyliglysiinin diammoniumsuola 5. N-fosfonometyyliglysiinin di(monometyyliamiini)-suola 6. N-fosfonometyyliglysiinin di(monoetyyliamiini)-suola 7. N-fosfonometyyliglysiinin di(monobutyyliamiini)-suola 8. N-fosfonometyyliglysiinin di(monopentyyliamiini)-suola 9. N-fosfonometyyliglysiinin di(monoheksyyliamiini)-suola 10. N-fosfonometyyliglysiinin di(mono-oktyyliamiini)-suola 11. N-fosfonometyyliglysiinin monopentyyliamiinisuola 12. N-fosfonometyyliglysiinin monoheksyyliamiinisuola 13. N-fosfonometyyliglysiinin monoheptyyliamiinisuola 14. N-fosfonometyyliglysiinin mono-oktyyliamiinisuola 15. N-fosfonometyyliglysiinin di(pyridiini)suola 16. N-fosfonometyyliglysiinin di(morfoliini) suola 17. N-fosfonometyyliglysiiniamidin isopropyyliamiinisuola 18. N-fosfonometyyliglysiinimetyyliamidin natriumsuola 19. N-fosfonometyyliglysiinioktyyliamidin dikaliumsuola 20. Etyyli-N-fosfonometyyliglysinaatin mononatriumsuola 21. Fenoksietyyli-N-fosfonometyyliglysinaatin monoisopropyyliamiini-suola 22. n-heksyyli-N-fosfonometyyliglysinaatin dinatriumsuolaCompounds: 1. N-phosphonomethylglycine and dipotassium salt 2. N-phosphonomethylglycine tripotassium salt 3. N-phosphonomethylglycine trilithium salt 4. N-phosphonomethylglycine diammonium salt 5. N-phosphonomethylglycine monoethylamine (dionomethylamine) Di (monobutylamine) salt of N-phosphonomethylglycine 8. Di (monopentylamine) salt of N-phosphonomethylglycine 9. Di (monohexylamine) salt of N-phosphonomethylglycine 10. Di (monooctylamine) salt of N-phosphonomethylglycine 12. Monohexylamine salt of N-phosphonomethylglycine 13. Monoheptylamine salt of N-phosphonomethylglycine 14. Monooctylamine salt of N-phosphonomethylglycine 15. N-phosphonomethylglycamine di-pyrrole-di (pyridine) salt of N-phosphonomethylglycine sodium salt of phosphonomethylglycine methylamide 19. N-phosphonomethylglycine octylamine din potassium salt 20. Monosodium salt of ethyl N-phosphonomethylglycinate 21. Monoisopropylamine salt of phenoxyethyl N-phosphonomethylglycinate 22. Disodium salt of n-hexyl-N-phosphonomethylglycinate
Seuraavissa esimerkeissä, jotka kuvaavat keksintöä, samoin kuin koko selvityksessä osat ja prosentit ovat paino-osia tai -prosentteja ellei toisin ole osoitettu.In the following examples, which illustrate the invention, as well as throughout the specification, parts and percentages are by weight unless otherwise indicated.
15 57955 Lähtöaineen valmistus; A. Seos, jossa oli noin 50 osaa glysiiniä, 92 osaa kloorimetyylifosfo-nihappoa, 150 osaa 50 %:sta vesipitoista natriumhydroksidia ja 100 osaa vettä, johdettiin reaktioastiaan ja pidettiin refluksointilämpö-tilassa samalla kun lisättiin edelleen 50 osaa 50 %:sta vesipitoista natriumhydroksidia. Reaktioseoksen pH pidettiin välillä 10 - 12 nat-riumhydroksidin avulla. Sen jälkeen kun kaikki emäsliuos oli lisätty, reaktioseosta refluksoitiin edelleen 20 tuntia, jäähdytettiin huoneen lämpötilaan ja suodatettiin. Sen jälkeen lisättiin noin 160 osaa väkevää suolahappoa ja seos suodatettiin, jolloin saatiin kirkas liuos, josta hitaasti N-fosfonometyyliglysiini saostui. Tämän aineen sulamispiste oli 230°C (hajosi).15 57955 Manufacture of starting materials; A. A mixture of about 50 parts of glycine, 92 parts of chloromethylphosphonic acid, 150 parts of 50% aqueous sodium hydroxide and 100 parts of water was introduced into a reaction vessel and kept at reflux temperature while further 50 parts of 50% aqueous sodium hydroxide were added. The pH of the reaction mixture was maintained between 10 and 12 with sodium hydroxide. After all the basic solution was added, the reaction mixture was further refluxed for 20 hours, cooled to room temperature and filtered. About 160 parts of concentrated hydrochloric acid were then added and the mixture was filtered to give a clear solution from which N-phosphonomethylglycine slowly precipitated. The melting point of this material was 230 ° C (decomposed).
Laskettu: CgHgNOgP: C 21,31 H 4,77 N 8,28Calculated: C 9 H 9 NO 9 P: C 21.31 H 4.77 N 8.28
Saatu: C 21,02 H 5,02 N 8,05 B. N-fosfonometyyliglysiini valmistettiin myös hapettamalla N-fosfi-nometyyliglysiiniä seuraavan menetelmän mukaisesti:Found: C 21.02 H 5.02 N 8.05 B. N-phosphonomethylglycine was also prepared by oxidizing N-phosphinomethylglycine according to the following procedure:
Seos, jossa oli noin 107 osaa fosfinometyyliglysiiniä, 624 osaa elo-hopea-II-kloridia ja 50 osaa vettä asetettiin reaktioastiaan ja pidettiin refluksointilämpötilassa noin kaksi tuntia. Reaktiosta syntynyt elohopea-I-kloridi saostui ja poistettiin suodattamalla. Suodos kyllästettiin rikkivedyllä ja syntynyt elohopea-II-sulfidi poistettiin liuoksesta suodattamalla, jolloin saatiin kirkas suodos, joka väkevöi-tiin alipaineessa, ja jäännös laimennettiin 10 osalla vettä. Kiteinen saostuma otettiin talteen ja pestiin metanolilla ja sen jälkeen die~ tyylieetterillä. Näin saatu tuote oli identtinen edeltävän esimerkin tuotteen kanssa.A mixture of about 107 parts of phosphinomethylglycine, 624 parts of mercury II chloride and 50 parts of water was placed in a reaction vessel and kept at reflux temperature for about two hours. The mercury I chloride formed from the reaction precipitated and was removed by filtration. The filtrate was saturated with hydrogen sulfide, and the resulting mercury II sulfide was removed from the solution by filtration to give a clear filtrate, which was concentrated under reduced pressure, and the residue was diluted with 10 parts of water. The crystalline precipitate was collected and washed with methanol followed by diethyl ether. The product thus obtained was identical to the product of the previous example.
Seuraavat esimerkit valaisevat keksinnön mukaisten yhdisteiden valmistus.The following examples illustrate the preparation of the compounds of the invention.
Esimerkki 1Example 1
Seosta, jossa oli noin 17 osaa N-fosfonometyyliglysiiniä 100 osaa vettä ja seitsemän osaa kaliumkarbonaattia, sekoitettiin reaktioasti-assa huoneen lämpötilassa. Sen jälkeen kun liukeneminen oli täydellinen, jota osoitti reaktioseoksen kirkastuminen, reaktioseos väkevöi- 57955 16 tiin höyryhauteella ja alipaineessa. Jäännös pestiin kuumalla metano-lilla ja sen jälkeen dietyylieetterillä. Näin saatu tuote on N-fosfo-nometyyliglysiinin monokaliumsuolan hemihydraatti.A mixture of about 17 parts of N-phosphonomethylglycine, 100 parts of water and seven parts of potassium carbonate was stirred in a reaction vessel at room temperature. After complete dissolution as indicated by the clarification of the reaction mixture, the reaction mixture was concentrated in a steam bath under reduced pressure. The residue was washed with hot methanol and then with diethyl ether. The product thus obtained is the hemihydrate of the monopotassium salt of N-phosphonomethylglycine.
Laskettu: C3H7N05PK·1/2H20: C 16,65 H 3,70 N 6,46Calculated for C3H7NO5PK · 1 / 2H2O: C 16.65 H 3.70 N 6.46
Saatu: C 16,67 H 3,85 N 6,32Found: C 16.67 H 3.85 N 6.32
Lisäämällä käytetyn kaliumkarbonaatin määrää voidaan valmistaa N-fos-fonometyyliglysiinin vastaavat dikalium- ja trikaliumsuolat. Vastaavat ammoniumsuolat ja muiden alkalimetallien ja maa-alkalimetallien _ samoin kuin kuparin, sinkin ja mangaanin ja nikkelin suolat voidaan helposti valmistaa olennaisesti samalla tavalla.By increasing the amount of potassium carbonate used, the corresponding dipotassium and tripotassium salts of N-phosphonomethylglycine can be prepared. The corresponding ammonium salts and salts of other alkali metals and alkaline earth metals as well as copper, zinc and manganese and nickel can easily be prepared in substantially the same manner.
Seuraavat suolat valmistettiin esimerkin 1 mukaisella tavalla, so. N-fosfonometyyliglysiini liuotettiin veteen ja liuokseen lisättiin 1, 2 tai 3 ekvivalenttia emästä, minkä jälkeen liuos haihdutettiin alipaineessa. Haihdutusjäännös pestiin metanolilla ja dietyylieetterillä ja kuumennettiin: N-fosfonometyyliglysiinin mononatriumsuola (sp. 220°C, hajoaa) N-fosfonometyyliglysiinin dinatriumsuola (sp. 150 - 155°C, hajoaa) N-fosfonometyyliglysiinin trinatriumsuola (sp. >300°C) N-fosfonometyyliglysiinin dilitiumsuola (sp. >300°C) N-fosfonometyyliglysiinin trilitiumsuola (sp. ?-300°C) N-fosfonometyyliglysiinin monoammoniumsuola (sp. 208 - 210°C, hajoaa) N-fosfonometyyliglysiinin monometyyliamiinisuola (sp. 83°C) N-fosfonometyyliglysiinin (dimetyyliamiini)suola (sp. 150 - 160°C, hajoaa) N-fosfonometyyliglysiini dietyyliamiinisuola (sp. 153 - 155°C, haojaa) N-fosfonometyyliglysiinin trietyyliamiinisuola (sp. 83°C) N-fosfonometyyliglysiinin di-isopropyyliami inisuola (sp. 0 5°C) 57955 17 N-fosfonometyyliglysiinin monoisopropyyliamiinisuola (sp. 95°C) N-fosfonometyyliglysiinin monoisobutyyliamiinisuola (sp. 89°C) N-fosfonometyyliglysiinin mono-sek.-butyyliamiinisuola (sp. 91 - 95°C) N-fosfonometyyliglysiinin monoetyyliamiinisuola (sp. 82°C) N-fosfonometyyliglysiinin monoetyleenidiamiinisuola (sp. 95°C) N-fosfonometyyliglysiinin monoaniliinisuola (sp. 210°C, hajoaa) ^ N-fosfonometyyliglysiinin monopiperidiinisuola (sp. 125°C) N-fosfonometyyliglysiinin monopropargyylisuola (sp. 55 - 60°C) N-fosfonometyyliglysiinin monoetanoliamiinisuola (sp. <25°C) N-fosfonometyyliglysiinin mono(dietanoliamiini)suola (sp. <25°C) N-fosfonometyyliglysiinin kuparisuola (sp. 216°C, hajoaa) N-fosfonometyyliglysiinin sinkkisuola (sp. >300°C) N-fosfonometyyliglysiiniamidin isopropyyliamiinisuola (sp. 175 - 177°C, hajoaa) N-fosfonometyyliglysiinimetyyliamidin natriumsuola (sp. 203 - 205°C, hajoaa) N-fosfonometyyliglysiinioktyyliamidin dikaliumsuola (sp. 200°C, hajoaa)The following salts were prepared according to Example 1, i. N-phosphonomethylglycine was dissolved in water, and 1, 2 or 3 equivalents of base were added to the solution, followed by evaporation of the solution under reduced pressure. The evaporation residue was washed with methanol and diethyl ether and heated: N-phosphonomethylglycine monosodium salt (m.p. 220 ° C, decomp.) N-phosphonomethylglycine disodium salt (m.p. 150-155 ° C, decomp.) N-phosphonomethylglycine (tri) trinat phosphonomethylglycine dilithium salt (m.p.> 300 ° C) N-phosphonomethylglycine trilithium salt (m.p. -300 ° C) N-phosphonomethylglycine monoammonium salt (m.p. 208-210 ° C, decomp.) N-phosphonomethylglycine N-phospholysin to monomethylamine -phosphonomethylglycine (dimethylamine) salt (m.p. 150-160 ° C, decomp.) N-phosphonomethylglycine diethylamine salt (m.p. 153-155 ° C, decomposes) N-phosphonomethylglycine triethylamine salt (m.p. 83 ° C) N-phosphinomethyl-di (m.p. 0 5 ° C) 57955 17 Monoisopropylamine salt of N-phosphonomethylglycine (m.p. 95 ° C) Monoisobutylamine salt of N-phosphonomethylglycine (m.p. 89 ° C) Mono-sec-butylamine salt of N-phosphonomethylglycine (m.p. 91-95 ° C) n-phosphonomethylglycine n monoethylamine salt (m.p. 82 ° C) Monoethylenediamine salt of N-phosphonomethylglycine (m.p. 95 ° C) Monoaniline salt of N-phosphonomethylglycine (m.p. 210 ° C, decomp.) Monopiperidine salt of N-phosphonomethylglycine (m.p. 125 ° C) ° C) N-phosphonomethylglycine monoethanolamine salt (m.p. <25 ° C) N-phosphonomethylglycine mono (diethanolamine) salt (m.p. <25 ° C) N-phosphonomethylglycine copper salt (m.p. 216 ° C, decomposes) N-phosphonomethylglycine > 300 ° C) N-phosphonomethylglycinamide isopropylamine salt (m.p. 175-177 ° C, dec.) Sodium salt of N-phosphonomethylglycine methylamide (m.p. 203-205 ° C, dec.) N-phosphonomethylglycine octylamide dipotassium salt, m.p. 200 ° C
Etyyli-N-fosfonometyyliglysinaatin mononatriumsuola (sp. 155°C, hajoaa)Ethyl N-phosphonomethylglycinate monosodium salt (m.p. 155 ° C, decomp.)
Fenoksietyyli-N-fosfonometyyliglysinaatin monoisopropyyliamiinisuola (sp. 90°C)Monoisopropylamine salt of phenoxyethyl N-phosphonomethylglycinate (m.p. 90 ° C)
Heksyyli-N-fosfonometyyliglysinaatin dinatriumsuola (sp. > 300°C) N-fosfonometyyliglysiinin kalsiumsuola (sp. 350°C) N-fosfonometyyliglysiinin di-isopropyyliamiinisuola (sp. 172 - 175°C, hajoaa) 57955 18 N-fosfonometyyliglysiinin hemimagnesiumsuola (sp. 150°C, hajoaa) N-fosfonometyyliglysiinin monopyridiinisuola (sp. 215°C, hajoaa) N-fosfonometyyliglysiinin magnesiumsuola (sp. >350°C)Disodium salt of hexyl N-phosphonomethylglycinate (m.p.> 300 ° C) Calcium salt of N-phosphonomethylglycine (m.p. 350 ° C) Diisopropylamine salt of N-phosphonomethylglycine (m.p. 172-175 ° C, decomp.) 57955 18 N-phosphinethyl 150 ° C, decomposes) N-phosphonomethylglycine monopyridine salt (m.p. 215 ° C, decomp.) N-phosphonomethylglycine magnesium salt (m.p.> 350 ° C)
Esimerkki 2Example 2
Noin 170 osaa N-fosfonometyyliglysiiniä lisättiin liuokseen, jossa oli 45 osaa dimetyyliamiinia liuotettuna 10 osaan vettä ja joka oli sopivassa reaktioastiassa. Reaktioseos selkeni lyhyen ajan kuluttua kun seosta sekoitettiin. Syntynyt liuos väkevöitiin sen jälkeen kuumentamalla 100 asteeseen alipaineessa. Jäännös oli viskoosinen öljy, josta saatiin kiteistä ainetta. Tuote tunnistettiin N-fosfonometyyliglysiinin mono-dimetyyliamiinisuolaksi, sp. 150°C (hajosi)About 170 parts of N-phosphonomethylglycine were added to a solution of 45 parts of dimethylamine dissolved in 10 parts of water in a suitable reaction vessel. The reaction mixture became clear after a short time when the mixture was stirred. The resulting solution was then concentrated by heating to 100 degrees under reduced pressure. The residue was a viscous oil which gave a crystalline substance. The product was identified as the mono-dimethylamine salt of N-phosphonomethylglycine, m.p. 150 ° C (decomposed)
Laskettu: c2Hi5N2 °5P: C 28'04 H 7>oe N 13,08 P 14,66Calculated: c 2 H 15 N 2 O 5 P: C 28'0 4 H 7> oe N 13.08 P 14.66
Saatu : C 27,88 H 6,92 N 12,88 P 14,22Found: C 27.88 H 6.92 N 12.88 P 14.22
Esimerkki 3Example 3
Kaasumaista kloorivetyä johdettiin suspension läpi, jossa oli 6 g (0,0355 moolia) N-fosfonometyyliglysiiniä ylimäärässä metyylialkoholia, kunnes saatiin kirkas liuos. Liuos väkevöitiin alipaineessa ja jäännökseen sekoitettiin metanoliliuosta, joka sisälsi vähintään yhden ekvivalentin trietyyliamiinia. Liuotin poistettiin alipaineessa ja jäännös uutettiin eetterillä, kunnes se oli rakeinen. Rakeinen kiinteä aine uutettiin lopuksi metanolilla trietyyliamiinihydro-kloridin poistamiseksi. Saatiin erinomaisella saannolla liukenematonta tuotetta, metyyli-N-fosfonometyyliglysinaattia. Uudelleen ki-teyttämisen jälkeen laimeasta metanolista tuote suli hajoten lämpötilassa 208,5°C.Gaseous hydrogen chloride was passed through a suspension of 6 g (0.0355 moles) of N-phosphonomethylglycine in excess methyl alcohol until a clear solution was obtained. The solution was concentrated under reduced pressure, and the residue was stirred with a methanol solution containing at least one equivalent of triethylamine. The solvent was removed under reduced pressure and the residue was extracted with ether until granular. The granular solid was finally extracted with methanol to remove triethylamine hydrochloride. An insoluble product, methyl N-phosphonomethylglycinate, was obtained in excellent yield. After recrystallization from dilute methanol, the product melted with decomposition at 208.5 ° C.
Laskettu: C2H1C)N05P: C 26,24 H 5,50Calculated for C 2 H 11 ClO 5 P: C 26.24 H 5.50
Saatu : C 26,15 H 5,43Found: C 26.15 H 5.43
Edellä olevan menettelyn mukaisesti valmistettiin seuraavat esterit (kaikki sulivat hajoten osoitetussa lämpötilassa): 19 5 7 9 5 5The following esters were prepared according to the above procedure (all melted with decomposition at the indicated temperature): 19 5 7 9 5 5
dodekyyli N-fosfonometyyliglysinaatti 197 - 200°Cdodecyl N-phosphonomethylglycinate 197-200 ° C
kloorietyyli N-fosfonometyyliglysinaatti 207°Cchloroethyl N-phosphonomethylglycinate 207 ° C
etyyli N-fosfonometyyliglysinaatti 203°Cethyl N-phosphonomethylglycinate 203 ° C
sykloheksyyli N-fosfonometyyliglysinaatti 195°Ccyclohexyl N-phosphonomethylglycinate 195 ° C
dekyyli N-fosfonometyyliglysinaatti 201 - 204°CDecyl N-phosphonomethylglycinate 201-204 ° C
heksyyli N-fosfonometyyliglysinaatti 202°Chexyl N-phosphonomethylglycinate 202 ° C
oktyyli N-fosfonometyyliglysinaatti 200°Coctyl N-phosphonomethylglycinate 200 ° C
n-butyyli N-fosfonometyyliglysinaatti 207 - 209°Cn-butyl N-phosphonomethylglycinate 207-209 ° C
propyyli N-fosfonometyyliglysinaatti 208,5°Cpropyl N-phosphonomethylglycinate 208.5 ° C
Esimerkki 4Example 4
Seosta, jossa oli 10 g (0,055 moolia) metyyli N-fosfonometyyliglysi-naattia ja ylimäärä väkevää vesipitoista ammoniumhydroksidia, kuumennettiin refluksointilämpötilassa kaksi tuntia. Sen jälkeen liuos väkevöitiin alipaineessa, jäännös pestiin eetterillä ja metanolilla ja rakeisen tuotteen kanssa sekoitettiin seosta, jossa oli ylimäärä jääetikkaa metanolissa. Saostunut kiinteä aine otettiin talteen, pestiin metanolilla ja kiteytettiin laimeasta etanolista. N-fosfonome-tyyliglysiiniamidin, sulamispiste 227°C (hajosi), saanto oli 8 g eli 87 % teoreettisesta määrästä.A mixture of 10 g (0.055 mol) of methyl N-phosphonomethylglycinate and an excess of concentrated aqueous ammonium hydroxide was heated at reflux for two hours. The solution was then concentrated under reduced pressure, the residue washed with ether and methanol, and a mixture of excess glacial acetic acid in methanol was mixed with the granular product. The precipitated solid was collected, washed with methanol and crystallized from dilute ethanol. The yield of N-phosphonomethylglycinamide, melting point 227 ° C (decomposed), was 8 g, or 87% of theory.
Laskettu: C^HgN^P: C 21,44 H 5,40Calculated: C 21 H 9 N 2 O 3: C 21.44 H 5.40
Saatu: C 21,26 H 5,39Found: C 21.26 H 5.39
Esimerkki 5Example 5
Liuosta, jossa oli 16,9 g (0,10 moolia) N-fosfonometyyliglysiiniä 300 ml:ssa kuumaa vettä, kuumennettiin refluksointilämpötilassa 5,6 g:n kanssa (0,10 moolia) kalsiumoksidia. Noin 10 minuutin kuluttua seos jäähdytettiin ja suodatettiin. Jäännös pestiin metanolilla ja eetterillä. Ilmakuivaamisen jälkeen N-fosfonometyyliglysiinihyd-raatin kalsiumsuolan saanto oli 17,5 g eli 84 % teoreettisesta saannosta.A solution of 16.9 g (0.10 moles) of N-phosphonomethylglycine in 300 ml of hot water was heated at reflux with 5.6 g (0.10 moles) of calcium oxide. After about 10 minutes, the mixture was cooled and filtered. The residue was washed with methanol and ether. After air drying, the yield of the calcium salt of N-phosphonomethylglycine hydrate was 17.5 g, or 84% of theory.
Laskettu: C^HgNC^PCa·1/2 H20: C 13,73 H 4,05 Ca 15,76Calculated: C 12 H 9 N 2 O 2 PCa · 1/2 H 2 O: C 13.73 H 4.05 Ca 15.76
Saatu: C 13,75 H 4,20 Ca 15,28Found: C 13.75 H 4.20 Ca 15.28
Esimerkki 6Example 6
Seosta, jossa oli 17 g (0,10 moolia) N-fosfonometyyliglysiiniä ja 50 5 7 9 5 5 2 g (0,05 moolia) magnesiumoksidia 300 ml:ssa vettä, kuumennettiin refluksointilämpötilassa 10 minuuttia. Liuos jäähdytettiin huoneen lämpötilaan ja suodatettiin pienen sedimenttimäärän poistamiseksi. Kirkas suodos väkevöitiin sen jälkeen alipaineessa ja rakeinen jäännös pestiin metanolilla ja eetterillä. Saatiin erinomaisella saannolla magnesium bis-N-fosfonometyyliglysinaattihydraattia.A mixture of 17 g (0.10 mol) of N-phosphonomethylglycine and 50 5 7 9 5 5 2 g (0.05 mol) of magnesium oxide in 300 ml of water was heated at reflux for 10 minutes. The solution was cooled to room temperature and filtered to remove a small amount of sediment. The clear filtrate was then concentrated under reduced pressure and the granular residue was washed with methanol and ether. Magnesium bis-N-phosphonomethylglycinate hydrate was obtained in excellent yield.
Laskettu: ceHi4N2°10P2Mg’21//2 H20: C 17,76 H 4,57 Mg 5,56Calculated: ceHi4N2 ° 10P2Mg'21 // 2 H2O: C 17.76 H 4.57 Mg 5.56
Saatu: C 17,80 H 4,69 Mg 6,00Found: C 17.80 H 4.69 Mg 6.00
Esimerkki 7Example 7
Seosta, jossa oli 20 g (0,11 moolia) metyyli N-fosfonometyyliglysi-naattia ja noin 23 g (0,33 moolia) pyrrolidiinia, kuumennettiin höy-ryhauteella kaksi tuntia. Sen jälkeen poistettiin ylimäärä amiinia alipaineessa ja jäännös pestiin eetterillä ja tetrahydrofuraanilla. Kumimaista tuotetta sekoitettiin seoksen kanssa, jossa oli ylimäärä jääetikkaa metanolissa, ja kiteinen saostuma otettiin talteen suodattamalla. Sen jälkeen kun oli pesty metanolilla ja eetterillä, saatiin tetrametyleeni N-fosfonometyyliglysiiniamidia, sulamispiste 243°C (hajosi), saannon ollessa 12 g eli 49 % teoreettisesta määrästä. Tuote kiteytettiin uudelleen laimeasta etanolista analyysia varten.A mixture of 20 g (0.11 moles) of methyl N-phosphonomethylglycinate and about 23 g (0.33 moles) of pyrrolidine was heated on a steam bath for two hours. Excess amine was then removed under reduced pressure and the residue was washed with ether and tetrahydrofuran. The gummy product was mixed with a mixture of excess glacial acetic acid in methanol, and the crystalline precipitate was collected by filtration. After washing with methanol and ether, tetramethylene N-phosphonomethylglycinamide was obtained, m.p. 243 ° C (decomposed), in a yield of 12 g, or 49% of theory. The product was recrystallized from dilute ethanol for analysis.
Laskettu: C-jH^N^P: C 37,84 H 6,81Calculated: C 11 H 19 N 2 O 3: C 37.84 H 6.81
Saatu: C 37,82 H 6,96Found: C 37.82 H 6.96
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI783501A FI58041C (en) | 1971-03-10 | 1978-11-16 | HERBICIDA BLANDNINGAR INNEHAOLLANDE VISSA N-PHOSPHONOMETYLGLYSINER SOM AKTIVA BESTAONDSDELAR |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12305771A | 1971-03-10 | 1971-03-10 | |
| US12305771 | 1971-03-10 | ||
| US17038571 | 1971-08-09 | ||
| US00170385A US3799758A (en) | 1971-08-09 | 1971-08-09 | N-phosphonomethyl-glycine phytotoxicant compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57955B true FI57955B (en) | 1980-07-31 |
| FI57955C FI57955C (en) | 1980-11-10 |
Family
ID=26821180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3000/71A FI57955C (en) | 1971-03-10 | 1971-10-22 | N-PHOSPHONOMETHYL GLASSINDERIVAT SOM KAN ANVAENDAS SOM HERBISIDISKT ELLER FYTOTOXISKT MEDEL |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS566401B1 (en) |
| BE (1) | BE774349A (en) |
| BG (1) | BG18585A3 (en) |
| BR (1) | BR7107076D0 (en) |
| CA (1) | CA936865A (en) |
| CH (1) | CH571306A5 (en) |
| CY (1) | CY837A (en) |
| DD (1) | DD100868A6 (en) |
| DE (3) | DE2167051C2 (en) |
| DK (1) | DK140433B (en) |
| ES (1) | ES396223A1 (en) |
| FI (1) | FI57955C (en) |
| FR (1) | FR2129327A5 (en) |
| GB (1) | GB1366379A (en) |
| HU (1) | HU174479B (en) |
| IE (1) | IE35501B1 (en) |
| IL (3) | IL47972A (en) |
| IT (1) | IT946007B (en) |
| KE (1) | KE2599A (en) |
| MY (1) | MY7600110A (en) |
| NL (1) | NL146171B (en) |
| NO (1) | NO141090C (en) |
| OA (1) | OA03838A (en) |
| PH (2) | PH16509A (en) |
| PT (1) | PT56642A1 (en) |
| RO (2) | RO72460A (en) |
| SE (3) | SE400695B (en) |
| SU (3) | SU638238A3 (en) |
| TR (1) | TR18244A (en) |
| YU (1) | YU36532B (en) |
| ZM (1) | ZM15071A1 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436843A (en) * | 1972-07-21 | 1976-05-26 | Ici Ltd | Preparation of n-phosphonomethyl-glycine |
| DE2717440C2 (en) * | 1976-05-17 | 1984-04-05 | Hoechst Ag, 6230 Frankfurt | Weed control with [(3-amino-3-carboxy) propyl-1] methylphosphinic acid derivatives |
| EG12897A (en) * | 1976-12-13 | 1980-07-31 | Monsanto Co | N,n,methylebebis-co,o-diaryl-n-phosphonomethylglycinonitrilles |
| US4140513A (en) * | 1978-01-03 | 1979-02-20 | Monsanto Company | Sodium sesquiglyphosate |
| DE2962495D1 (en) * | 1978-04-06 | 1982-05-27 | Monsanto Co | Derivatives of n-trifluoroacetyl n-phosphonomethylglycine dichloride, their preparation and their use as herbicides |
| 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 |
| US4359332A (en) * | 1978-07-10 | 1982-11-16 | Monsanto Company | Amide and hydrazide derivatives of N-trifluoroacetyl-N-phosphonomethylglycine as herbicides |
| US4180394A (en) * | 1978-07-10 | 1979-12-25 | Monsanto Company | Derivatives of N-trifluoroacetyl-N-phosphonomethylglycinates and the herbicidal use thereof |
| US4414158A (en) | 1980-04-29 | 1983-11-08 | Ciba-Geigy Corporation | Phosphonomethylglycylhydroxamic acid and novel herbicidally active salts thereof |
| ES8603901A1 (en) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Herbicides of the sulfon imide-type with an aminomethylphosphonic group. |
| DE3614788A1 (en) * | 1986-05-02 | 1987-11-05 | Hoechst Ag | HERBICIDE EMULSIONS |
| FR2644036B1 (en) * | 1989-03-07 | 1992-01-17 | Rhone Poulenc Agrochimie | HERBICIDE COMBINATION OF A WATER-SOLUBLE POLYMERIC PACKAGE AND AN N-PHOSPHONOMETHYLGLYCIN-CONTAINING HERBICIDE |
| DE19528054A1 (en) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Process for the preparation of N-phosphonomethylglycine esters |
| DE19528060A1 (en) * | 1995-07-31 | 1997-02-06 | Bayer Ag | Process for the preparation of N-phosphonomethyl-glycine esters |
| IL116695A0 (en) * | 1996-01-07 | 1996-05-14 | Yeda Res & Dev | Seed dressing compositions |
| AU1790697A (en) * | 1996-02-28 | 1997-09-16 | Bayer Aktiengesellschaft | Use of n-phosphonomethylglycine esters in aqueous solution as herbicides, and new n-phosphonomethylglycine esters |
| MXPA06011412A (en) | 2004-03-30 | 2007-01-23 | Monsanto Technology Llc | Methods for controlling plant pathogens using n-phosphonomethylglycine. |
| MX2007015376A (en) | 2005-06-09 | 2008-02-14 | Bayer Cropscience Ag | Active substance combinations. |
| DE102005026482A1 (en) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Active substance combination, useful e.g. for combating unwanted phytopathogenic fungus, comprises herbicides e.g. glyphosate and active substances e.g. strobilurin, triazoles, valinamide and carboxamide |
| WO2010135324A1 (en) | 2009-05-18 | 2010-11-25 | Monsanto Technology Llc | Use of glyphosate for disease suppression and yield enhancement in soybean |
| UA108623C2 (en) | 2009-09-30 | 2015-05-25 | LOWER-CELL AMIN ANTI-PESTICIDE SALTS | |
| EP2460404A1 (en) | 2010-12-01 | 2012-06-06 | Basf Se | Compositions containing identical polyamine salts of mixed anionic pesticides |
| US11109591B2 (en) | 2017-04-24 | 2021-09-07 | Taminco Bvba | Single phase liquids of alkanolamine salts of dicamba |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3160632A (en) * | 1961-01-30 | 1964-12-08 | Stauffer Chemical Co | Aminomethylenephosphinic acids, salts thereof, and process for their production |
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1971
- 1971-10-11 PH PH12914A patent/PH16509A/en unknown
- 1971-10-15 SU SU711714528A patent/SU638238A3/en active
- 1971-10-21 NL NL717114487A patent/NL146171B/en not_active IP Right Cessation
- 1971-10-21 HU HU71MO810A patent/HU174479B/en unknown
- 1971-10-21 ES ES396223A patent/ES396223A1/en not_active Expired
- 1971-10-22 CA CA125905A patent/CA936865A/en not_active Expired
- 1971-10-22 BE BE774349A patent/BE774349A/en not_active IP Right Cessation
- 1971-10-22 NO NO3926/71A patent/NO141090C/en unknown
- 1971-10-22 DE DE2167051A patent/DE2167051C2/en not_active Expired
- 1971-10-22 CY CY837A patent/CY837A/en unknown
- 1971-10-22 IE IE1340/71A patent/IE35501B1/en unknown
- 1971-10-22 BR BR7076/71A patent/BR7107076D0/en unknown
- 1971-10-22 SE SE7113473A patent/SE400695B/en unknown
- 1971-10-22 BG BG018842A patent/BG18585A3/en unknown
- 1971-10-22 GB GB4926371A patent/GB1366379A/en not_active Expired
- 1971-10-22 PT PT56642A patent/PT56642A1/en unknown
- 1971-10-22 IT IT30219/71A patent/IT946007B/en active
- 1971-10-22 JP JP8384671A patent/JPS566401B1/ja active Pending
- 1971-10-22 RO RO7168548A patent/RO72460A/en unknown
- 1971-10-22 DE DE2166573A patent/DE2166573C3/en not_active Expired
- 1971-10-22 DD DD160070A patent/DD100868A6/xx unknown
- 1971-10-22 ZM ZM150/71A patent/ZM15071A1/en unknown
- 1971-10-22 OA OA54402A patent/OA03838A/en unknown
- 1971-10-22 TR TR18244A patent/TR18244A/en unknown
- 1971-10-22 RO RO7199872A patent/RO77018A/en unknown
- 1971-10-22 IL IL47972A patent/IL47972A/en unknown
- 1971-10-22 DE DE2152826A patent/DE2152826C3/en not_active Expired
- 1971-10-22 IL IL37993A patent/IL37993A/en unknown
- 1971-10-22 FR FR7138086A patent/FR2129327A5/fr not_active Expired
- 1971-10-22 FI FI3000/71A patent/FI57955C/en active
- 1971-10-22 DK DK514071AA patent/DK140433B/en not_active IP Right Cessation
- 1971-10-22 CH CH1539171A patent/CH571306A5/xx not_active IP Right Cessation
- 1971-10-22 YU YU02686/71A patent/YU36532B/en unknown
-
1972
- 1972-10-09 SU SU721834717A patent/SU665775A3/en active
- 1972-10-09 SU SU721834717D patent/SU963446A3/en active
-
1974
- 1974-02-28 SE SE7402719A patent/SE400158B/en not_active IP Right Cessation
- 1974-02-28 SE SE7402718A patent/SE399267B/en not_active IP Right Cessation
-
1975
- 1975-08-21 IL IL47972A patent/IL47972A0/en unknown
-
1976
- 1976-02-11 KE KE2599*UA patent/KE2599A/en unknown
- 1976-12-30 MY MY110/76A patent/MY7600110A/en unknown
-
1979
- 1979-10-16 PH PH23177A patent/PH13752A/en unknown
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