NO831287L - Fremgangsmaate for fremstilling av n-fosfonometylglycinderivater. - Google Patents

Fremgangsmaate for fremstilling av n-fosfonometylglycinderivater.

Info

Publication number: NO831287L
Authority: NO; Norway
Prior art keywords: salt; iminourea; salts; guanidine; general formula
Prior art date: 1982-06-25

Application number

NO831287A

Other languages

English (en)

Norwegian (no)

Inventor

Izhak Bakel

Original Assignee

Geshuri Lab Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-06-25

Filing date

1983-04-12

Publication date

1983-12-27

1982-06-25 Priority claimed from IL66137A external-priority patent/IL66137A/xx

1983-04-12 Application filed by Geshuri Lab Ltd filed Critical Geshuri Lab Ltd

1983-12-27 Publication of NO831287L publication Critical patent/NO831287L/no

Links

XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical class OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims description 48
238000000034 method Methods 0.000 title claims description 47
238000002360 preparation method Methods 0.000 title claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 32
229960004198 guanidine Drugs 0.000 claims description 28
238000007254 oxidation reaction Methods 0.000 claims description 22
-1 cation derivative of iminourea Chemical class 0.000 claims description 21
230000003647 oxidation Effects 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 17
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 15
239000000243 solution Substances 0.000 claims description 15
AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical class OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
239000007800 oxidant agent Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 9
150000004985 diamines Chemical class 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000007789 gas Substances 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
229910001882 dioxygen Inorganic materials 0.000 claims description 4
238000001914 filtration Methods 0.000 claims description 4
125000005059 halophenyl group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 3
230000002363 herbicidal effect Effects 0.000 claims description 3
JPBMIEMOIBASGJ-UHFFFAOYSA-N iminourea 2-(phosphonomethylamino)acetic acid Chemical compound NC(=O)N=N.OC(=O)CNCP(O)(O)=O JPBMIEMOIBASGJ-UHFFFAOYSA-N 0.000 claims description 3
239000012266 salt solution Substances 0.000 claims description 3
OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
229910052736 halogen Chemical group 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
ZWXVRALXNQWMEN-UHFFFAOYSA-N 1-azanylideneurea Chemical class NC(=O)N=N ZWXVRALXNQWMEN-UHFFFAOYSA-N 0.000 claims 3
ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical class CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 claims 2
WAGHPWVJCHOGJI-UHFFFAOYSA-N 1,1-bis(4-methylphenyl)guanidine Chemical compound C1=CC(C)=CC=C1N(C(N)=N)C1=CC=C(C)C=C1 WAGHPWVJCHOGJI-UHFFFAOYSA-N 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
239000000047 product Substances 0.000 description 17
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
FDQQNNZKEJIHMS-UHFFFAOYSA-N 3,4,5-trimethylphenol Chemical class CC1=CC(O)=CC(C)=C1C FDQQNNZKEJIHMS-UHFFFAOYSA-N 0.000 description 13
239000006227 byproduct Substances 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
239000001301 oxygen Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
238000006386 neutralization reaction Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
239000002245 particle Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
MRXYVMXWTBRRSB-UHFFFAOYSA-N 2-[2-(diaminomethylideneamino)ethyl]guanidine Chemical compound NC(N)=NCCN=C(N)N MRXYVMXWTBRRSB-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
239000000376 reactant Substances 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
FQQQSNAVVZSYMB-UHFFFAOYSA-N 1,1-diaminoguanidine Chemical compound NN(N)C(N)=N FQQQSNAVVZSYMB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ICBVWIUIDVBAFX-UHFFFAOYSA-N 2-[1-(diaminomethylideneamino)propan-2-yl]guanidine Chemical compound NC(=N)NC(C)CNC(N)=N ICBVWIUIDVBAFX-UHFFFAOYSA-N 0.000 description 2
VHVOMTORWFVJQJ-UHFFFAOYSA-N 2-[carboxymethyl(phosphonomethyl)amino]acetic acid iminourea Chemical class NC(=O)N=N.OC(=O)CN(CC(O)=O)CP(O)(O)=O VHVOMTORWFVJQJ-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
239000005700 Putrescine Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical class OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
150000001451 organic peroxides Chemical class 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
238000006485 reductive methylation reaction Methods 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
ISNICOKBNZOJQG-UHFFFAOYSA-N 1,1,2,3,3-pentamethylguanidine Chemical compound CN=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-N 0.000 description 1
AYRCKUXVQHNYRW-UHFFFAOYSA-N 1,1,2-triethylguanidine Chemical compound CCN=C(N)N(CC)CC AYRCKUXVQHNYRW-UHFFFAOYSA-N 0.000 description 1
NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
JNROUINNEHNBIZ-UHFFFAOYSA-N 1,1,3,3-tetraethylguanidine Chemical compound CCN(CC)C(=N)N(CC)CC JNROUINNEHNBIZ-UHFFFAOYSA-N 0.000 description 1
OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
FXQVBOJLSKRNLL-UHFFFAOYSA-N 1,2-bis(4-methylphenyl)guanidine Chemical compound C1=CC(C)=CC=C1NC(N)=NC1=CC=C(C)C=C1 FXQVBOJLSKRNLL-UHFFFAOYSA-N 0.000 description 1
JGGFDEJXWLAQKR-UHFFFAOYSA-N 1,2-diaminoguanidine Chemical class NNC(N)=NN JGGFDEJXWLAQKR-UHFFFAOYSA-N 0.000 description 1
MCMBEBOHGREEOP-UHFFFAOYSA-N 1,2-diethylguanidine Chemical compound CCNC(=N)NCC MCMBEBOHGREEOP-UHFFFAOYSA-N 0.000 description 1
LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
SGVDYFNFBJGOHB-UHFFFAOYSA-N 2-[methyl(phosphonomethyl)amino]acetic acid Chemical compound OC(=O)CN(C)CP(O)(O)=O SGVDYFNFBJGOHB-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 1
IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
238000006824 Eschweiler-Clarke methylation reaction Methods 0.000 description 1
WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
238000006547 Leuckart Thiophenol synthesis reaction Methods 0.000 description 1
XHXPXBSXMKMXOF-UHFFFAOYSA-N N-hydroxy-N-nitrosonitramide Chemical compound [N+](=O)([O-])N(O)N=O XHXPXBSXMKMXOF-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
239000011149 active material Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
150000003940 butylamines Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
150000004656 dimethylamines Chemical class 0.000 description 1
LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
150000003947 ethylamines Chemical class 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
CDEVLIRWDDNKAW-UHFFFAOYSA-N guanidine;prop-1-ene Chemical compound CC=C.NC(N)=N.NC(N)=N CDEVLIRWDDNKAW-UHFFFAOYSA-N 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
IUZZLNVABCISOI-UHFFFAOYSA-N n-ethylheptan-1-amine Chemical compound CCCCCCCNCC IUZZLNVABCISOI-UHFFFAOYSA-N 0.000 description 1
NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
OZIXTIPURXIEMB-UHFFFAOYSA-N n-methylnonan-1-amine Chemical compound CCCCCCCCCNC OZIXTIPURXIEMB-UHFFFAOYSA-N 0.000 description 1
SZEGKVHRCLBFKJ-UHFFFAOYSA-N n-methyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNC SZEGKVHRCLBFKJ-UHFFFAOYSA-N 0.000 description 1
CNCBAEHAEKNSPZ-UHFFFAOYSA-N n-methylpentadecan-1-amine Chemical compound CCCCCCCCCCCCCCCNC CNCBAEHAEKNSPZ-UHFFFAOYSA-N 0.000 description 1
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 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)]
- C07F9/44—Amides thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- 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

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Wood Science & Technology (AREA)
Dentistry (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NO831287A 1982-06-25 1983-04-12 Fremgangsmaate for fremstilling av n-fosfonometylglycinderivater. NO831287L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IL66137A IL66137A (en)	1982-06-25	1982-06-25	Process for producing n-phosphonomethylglycine isopropyl amine salt and herbicidal compositions prepared therewith
IL66824A IL66824A0 (en)	1982-06-25	1982-09-17	Process for producing n-phosphonomethylglycine derivatives and herbicidal compounds and compositions prepared thereby

Publications (1)

Publication Number	Publication Date
NO831287L true NO831287L (no)	1983-12-27

Family

ID=26321054

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO831287A NO831287L (no)	1982-06-25	1983-04-12	Fremgangsmaate for fremstilling av n-fosfonometylglycinderivater.

Country Status (13)

Country	Link
US (1)	US4486356A (da)
EP (1)	EP0098034A3 (da)
KR (1)	KR840005155A (da)
AU (1)	AU1350283A (da)
BR (1)	BR8303513A (da)
DK (1)	DK157683A (da)
FI (1)	FI831204L (da)
GR (1)	GR81421B (da)
IL (1)	IL66824A0 (da)
NO (1)	NO831287L (da)
PL (1)	PL242678A1 (da)
PT (1)	PT76635B (da)
RO (1)	RO87143A (da)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL68716A (en) *	1983-05-17	1987-03-31	Geshuri Lab Ltd	Process for producing n-phosphonomethylglycine
US4579689A (en) *	1985-02-11	1986-04-01	Monsanto Company	Oxidation with coated catalyst
US4582650A (en) *	1985-02-11	1986-04-15	Monsanto Company	Oxidation with encapsulated co-catalyst
HU204533B (en) *	1988-11-02	1992-01-28	Nitrokemia Ipartelepek	Process for producing n-phosphono-methyl-glycine
US5023369A (en) *	1990-06-25	1991-06-11	Monsanto Company	Process for producing N-phosphonomethylglycine
IL101539A (en) *	1991-04-16	1998-09-24	Monsanto Europe Sa	Mono-ammonium salts of the history of N phosphonomethyl glycyl which are not hygroscopes, their preparations and pesticides containing
US5948938A (en) *	1995-03-07	1999-09-07	Sankyo Company, Limited	Process for preparing N-phosphonomethylglycine
ITTO980048A1 (it) *	1998-01-20	1999-07-20	Ipici Spa	Composizioni erbicide, procedimenti per la loro preparazione ed impieghi
US6417133B1 (en)	1998-02-25	2002-07-09	Monsanto Technology Llc	Deeply reduced oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
WO2000001707A1 (en) *	1998-07-06	2000-01-13	Syngenta Participations Ag.	Preparation of n-phosphonomethylglycine salts
BR0111041A (pt) *	2000-05-22	2004-06-15	Monsanto Technology Llc	Sistemas de reação para produzir compostos de n-(fosfonometil)glicina
US8703639B2 (en) *	2004-09-15	2014-04-22	Monsanto Technology Llc	Oxidation catalyst and its use for catalyzing liquid phase oxidation reactions
US9615463B2 (en) *	2006-09-22	2017-04-04	Oscar Khaselev	Method for producing a high-aspect ratio conductive pattern on a substrate
US8252953B2 (en)	2008-05-01	2012-08-28	Monsanto Technology Llc	Metal utilization in supported, metal-containing catalysts
WO2010048164A2 (en) *	2008-10-20	2010-04-29	University Of South Florida	N,n'-di-p-bromophenyl guanidine treatment for stroke at delayed timepoints
RU2015103314A (ru) *	2012-07-17	2016-09-10	Страйтмарк Холдинг Аг	Способ синтеза N-фосфонометилиминодиуксусной кислоты
US11109591B2 (en) *	2017-04-24	2021-09-07	Taminco Bvba	Single phase liquids of alkanolamine salts of dicamba

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3853530A (en) *	1971-03-10	1974-12-10	Monsanto Co	Regulating plants with n-phosphonomethylglycine and derivatives thereof
US3977860A (en) *	1971-08-09	1976-08-31	Monsanto Company	Herbicidal compositions and methods employing esters of N-phosphonomethylglycine
US3950402A (en) *	1972-05-31	1976-04-13	Monsanto Company	Process for producing N-phosphonomethyl glycine
US3954848A (en) *	1972-05-31	1976-05-04	Monsanto Company	Process for producing N-phosphonomethyl glycine
US3969398A (en) *	1974-05-01	1976-07-13	Monsanto Company	Process for producing N-phosphonomethyl glycine
US3957431A (en) *	1975-03-28	1976-05-18	Basf Aktiengesellschaft	Process for easy-care finishing cellulosics
MX4703E (es) *	1976-12-20	1982-08-04	Monsanto Co	Procedimiento mejorado para la preparacion de mono y disales de n-fosfonometilglicina
CH634968A5 (de) *	1977-04-01	1983-03-15	Ciba Geigy Ag	Herbizides und pflanzenwuchsregulierendes mittel enthaltend eine neue phosphinsaeure oder deren salze, ester, amide oder hydrazide sowie verwendung derselben.
IL65187A (en) *	1982-03-08	1985-03-31	Geshuri Lab Ltd	N-phosphonomethylglycine derivatives,processes for their preparation and herbicidal compositions containing them

1982
- 1982-09-17 IL IL66824A patent/IL66824A0/xx unknown
1983
- 1983-04-11 FI FI831204A patent/FI831204L/fi not_active Application Discontinuation
- 1983-04-11 DK DK157683A patent/DK157683A/da not_active IP Right Cessation
- 1983-04-12 NO NO831287A patent/NO831287L/no unknown
- 1983-04-13 AU AU13502/83A patent/AU1350283A/en not_active Abandoned
- 1983-04-15 US US06/485,501 patent/US4486356A/en not_active Expired - Fee Related
- 1983-04-15 GR GR71101A patent/GR81421B/el unknown
- 1983-04-21 KR KR1019830001694A patent/KR840005155A/ko not_active Application Discontinuation
- 1983-04-22 EP EP83302314A patent/EP0098034A3/en not_active Withdrawn
- 1983-04-25 RO RO83110775A patent/RO87143A/ro unknown
- 1983-05-04 PT PT76635A patent/PT76635B/pt unknown
- 1983-06-24 BR BR8303513A patent/BR8303513A/pt unknown
- 1983-06-24 PL PL24267883A patent/PL242678A1/xx unknown

Also Published As

Publication number	Publication date
AU1350283A (en)	1984-01-05
FI831204L (fi)	1983-12-26
EP0098034A2 (en)	1984-01-11
BR8303513A (pt)	1984-02-07
RO87143A (ro)	1985-11-30
EP0098034A3 (en)	1984-03-28
KR840005155A (ko)	1984-11-03
DK157683D0 (da)	1983-04-11
GR81421B (da)	1984-12-11
PT76635A (en)	1983-06-01
DK157683A (da)	1983-12-26
PL242678A1 (en)	1984-07-02
FI831204A0 (fi)	1983-04-11
RO87143B (ro)	1985-10-31
PT76635B (en)	1985-12-20
IL66824A0 (en)	1982-12-31
US4486356A (en)	1984-12-04

Publication	Publication Date	Title
US4507250A (en)	1985-03-26	Process for producing N-phosphonomethylglycine acid
NO831287L (no)	1983-12-27	Fremgangsmaate for fremstilling av n-fosfonometylglycinderivater.
CA1090819A (en)	1980-12-02	Process for producing n-phosphonomethyglycine salts
EP0088180A1 (en)	1983-09-14	N-phosphonomethylglycine derivatives
US3005010A (en)	1961-10-17	Method for preparing dihydrocarbyloxyphosphinyl formamides
AU780040B2 (en)	2005-02-24	Process for the preparation of carboxylic acid salts from primary alcohols
KR930007995B1 (ko)	1993-08-25	N-포스포노 메틸글리신의 정제방법
CA1109482A (en)	1981-09-22	Process for the production of new phosphinic acids and derivatives thereof, as well as the use thereof
HU218307B (en)	2000-07-28	Processes for the preparation of n-phosphonomethylglycine from n-phosphonomethyliminodiacetic acid
EP0013554B1 (en)	1981-12-09	Process for production of 1,17-diamino-9-azaheptadecane
JP2550569B2 (ja)	1996-11-06	ソジウムジシアナミドの製造方法
US3713805A (en)	1973-01-30	Plant growth method and composition using 2-chloro-ethyl phosphonic diamide
US3424793A (en)	1969-01-28	Preparation of trimethyl chloro-substituted lower alkyl quaternary ammonium salts
US3787496A (en)	1974-01-22	Preparation of aromatic compounds via benzyne intermediates
Frank	1978	Synthesis and Properties of Tetrakis (ureidomethyl) phosphonium Salts
US3341583A (en)	1967-09-12	Synthesis of symmetrical ureas
KR810001326B1 (ko)	1981-10-14	N-포스포노 메틸글리신염의 제조방법
CA2053836C (en)	1996-07-02	Process for producing n-phosphonomethylglycine
JPH09110692A (ja)	1997-04-28	抗菌活性を有するビス第四アンモニウム塩化合物及びその製造方法
JPS597196A (ja)	1984-01-14	Ｎ−ホスホノメチルグリシン誘導体の製造方法、除草活性化合物および組成物
US3502706A (en)	1970-03-24	Amino thiocarbonate adducts and method of making same
JPH02160624A (ja)	1990-06-20	モリブデンの炭化水素可溶塩
SU1361148A1 (ru)	1987-12-23	Способ получени транс-21,25-диамино-2,3,11,12-дибенз-1,4,7,10,13,16-гексаоксациклооктадекадиена-2,11
JPS596301B2 (ja)	1984-02-10	チオカルバミン酸エステルの製造方法
IL35328A (en)	1972-11-28	Certain complexes of halogen and n,n1-hexaalkyl alkylene-diammonium dihalides and their use as herbicides