NO143747B - Carboxyalkylestere av n-fosfonmethylglycin for anvendelse som herbicide midler - Google Patents
Carboxyalkylestere av n-fosfonmethylglycin for anvendelse som herbicide midler Download PDFInfo
- Publication number
- NO143747B NO143747B NO743973A NO743973A NO143747B NO 143747 B NO143747 B NO 143747B NO 743973 A NO743973 A NO 743973A NO 743973 A NO743973 A NO 743973A NO 143747 B NO143747 B NO 143747B
- Authority
- NO
- Norway
- Prior art keywords
- carboxyethyl
- methylgyline
- coolesters
- carboxyal
- phosphone
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 21
- 230000002363 herbicidal effect Effects 0.000 description 15
- 238000009472 formulation Methods 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- VLTQCAKAICGHKR-UHFFFAOYSA-N 3-[2-(phosphonomethylamino)acetyl]oxypropanoic acid Chemical compound C(=O)(O)CCOC(CNCP(=O)(O)O)=O VLTQCAKAICGHKR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- -1 carboxyalkyl ester Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- 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
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 241001290610 Abildgaardia Species 0.000 description 1
- XDARHTHZTUVHAH-UHFFFAOYSA-N C(C)N(CCO)CC.N(CCO)CCO Chemical compound C(C)N(CCO)CC.N(CCO)CCO XDARHTHZTUVHAH-UHFFFAOYSA-N 0.000 description 1
- 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 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 compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 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
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 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
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 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
- WSTNFGAKGUERTC-UHFFFAOYSA-N n-ethylhexan-1-amine Chemical compound CCCCCCNCC WSTNFGAKGUERTC-UHFFFAOYSA-N 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- KLJUVCXLKBGKOY-UHFFFAOYSA-N n-hexylheptan-1-amine Chemical compound CCCCCCCNCCCCCC KLJUVCXLKBGKOY-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
- 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
- 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
- 239000002245 particle Substances 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 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
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—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
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)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse angår nye carboxyalkylestere
av N-fosfonomethylglycin og salter derav, og herbicide komposisjoner inneholdende disse forbindelser.
De nye carboxyalkylestere ifolge oppfinnelsen har formelen
hvor M, M<1> og M" er hydrogen, alkalimetall, jordalkalimetall, ammonium eller en organisk ammoniumrest som er avledet av et organisk amin med en molekylvekt under 300 og inneholdende maksi-
mum 2 aminogrupper.
Fra BRD utlegningsskrift 2 152 826 og US patentskrift
3 556 762 er det kjent nær beslektede kjemiske forbindelser til de ifølge oppfinnelsen, og anvendt for samme formål.
På lignende måte som beskrevet i eksempel 4 i foreliggende be-skrivelse er representative forbindelser ifølge oppfinnelsen blitt sammenlignet med tre representative forbindelser kjent fra BRD-utlegningsskrift 2 152 826. Det fremgikk fra de erholdte data at de kjente forbindelser utviser generell herbicid aktivitet. De utrydder imidlertid ikke bare ugresset, men også
de verdifulle planter. Forbindelsene ifølge oppfinnelsen - selv når de anvendes i en høyere konsentrasjon - har moderat til kraftig herbicid aktivitet overfor utgress som finqerhirse, hønsehirse og meldestokk. Samtidig forårsaker forbindelsene ingen eller liten skade på nyttevekster slik som soyabønne, sukkerroe og ris.
Vedrørende US patentskrift 3 556 762 er forbindelser ifølge foreliggende eksempel 2 blitt sammenlignet med nitrilo (eddiksyre)di-(methylfosfonsyre) som sukkerroemodner og funnet å være overlegen sammenlignet med den kjente forbindelse.
De nye carboxyalkylestere ifolge oppfinnelsen fremstilles ved å omsette N-fosfonomethylglycin i en vanncp plosni ng med et lac-ton slik som propiolacton i nærvær av en base, hvorefter basen nøy-traliseres med saltsyre. De forskjellige salter fremstilles ved å behandle den frie syre med en passende base.
Reaksjonstemperaturen holdes normalt ved ca. 20°C, selvom hdyere eller lavere temperaturer er mulig.
Reaktantenes tilsetningsrekkefolge er kritisk. Det er ve-sentlig å tilsette lactonet til en basisk vannopplosning av N-fosfonomethylglycin. Av bekvemmelighetshensyn og med henblikk på iso-lering av produktet, carboxyalkylesteren, foretrekkes der å anvende like molare mengder av lactonet og N-fosfonomethylglycin.
Reaksjonen utfores normalt ved atmosfæretrykk selvom over-atmosfærisk og under-atmosfærisk trykk kan anvendes.
Uttrykket "alkalimeta11" omfatter lithium, natrium, kali-um, cesium og rubidium, og uttrykket "jordalkalimetall" omfatter beryllium, magnesium, kalsium, strontium og barium.
De organiske ammoniumsalter som innbefattes i den ovenfor angitte generelle formel er de som fremstilles fra organiske aminer med lav molekylvekt, dvs. med en molekylvekt under 300, og slike aminer innbefatter alkylaminer, alkylenaminer og alkanolaminer inneholdende ikke mere enn 2 aminogrupper, slik som
methylamin
ethylamin
n-propylamin
isopropylamin
n-butylamin,
isobutylamin
sek-butylamin
n-amylamin
isoamylamin
hexylamin
heptylamin
octylamin
nonylamin.
decylamin
undecylamin
dodecylamin
tridecylamin
te tradecylamin
pentadecylamin
hexadecylamin
heptadecylamin
oetadecylamin
methylethylamin
methylisopropylamin
methylhexylamin
methylnonylamin
methylpentadecylamin
methyloetadecylamin
ethylbutylamin
ethylheptylamin ••
ethyloetylamin
hexylheptylamin
hexyloetylamin
dime thylamin
diethylamin
di-n-propylamin
diisopropylamin
di-n-amylamin
diisoamylamin
dihexylamin
di-heptylamin
dioctylamin
trime thylamin
triethylamin
tri-n-propylamin
triisopropylamin
tri-n-butylamin
triisobutylamin
tri-sek-butylamin
tri-n-amylamin
ethanolamin
n-propanolamin
isopropanolamin
diethanolamin N,N-diethylethanolamin , N-ethylpropanolamin
N-butylethanolamin
allylamin
n-buteny1-2-amin,
n-penteny1-2-amin
2,3-dimethylbuteny1-2-amin di-buteny1-2-amin
n-hexeny1-2-amin
propylendiamin
De efterfSigende eksempler illustrerer oppfinnelsen. I eksemplene er alle deler og prosenter på vektbasis om ikke annet er angitt.
Eksempel 1
I en 500 ml rundkolbe ble innfort 17 g N-fosfonymethy1-glycin, 200 ml vann og 12 g natriumhydroxyd, og blandingen ble om-rort inntil der ble oppnådd en klar opplosning. Opplosningen ble kjolet til 20°C, og 8 g propiolacton ble tilsatt i lopet av en 15 minutters periode under omroring. Omrbringen ble fortsatt i 1 ti-me ved romtemperatur. Reaksjonsblandingen ble surgjort med saltsyre under hvilket tidsrom der ble dannet et fast materiale i form av en vandig oppslemming. Det faste materiale ble fjernet ved fil-trering og tørket. Det faste materiale ble identifisert som 2-carboxyethyl-N-fosfonmethylglycinat (forbindelse I) med smelte-punkt 211°C under spaltning og ga følgende elementæranalyse:
Eksempel 2
En vannopplbsning av bis(isopropylamin)salt av 2-carboxyethyl-n-fosfonomethylglycinat ble fremstillet som folger: 4,04 g 2-carboxyethy1-N-fosfonomethylglycinat ble oppslem-met i 5 g vann. Til blandingen ble under avkjoling tilsatt 1,92 g isopropylamin under dannelse av en vannopplbsning inneholdende bis-(isopropylamin)salt av 2-carboxyethy1-N-fosfonomethylglycinat (forbindelse II). (sm.p. 82 - 85°C).
Eksempel 3
En vannopplbsning av glycin, 2-carboxyethylester-N-(dina-triumfosfonomethyl) ble fremstillet som folger: 4,04 g 2-carboxyethyl-N-fosfonomethylglycinat ble oppslem-met i 5,28 g vann. Til blandingen ble under avkjoling tilsatt 1,36 g natriumhydroxyd under dannelse av en vannopplbsning inneholdende dinatrium(2-carboxyethyl)-N-(fosfonomethyl)glyeinat (forbindelse III). (sm.p. 75 - 85°C).
Ved å følge den i eksempler 2 og 3 angitte fremgangs-måte og anvende en egnet base eller ammoniumforbindelse, et forhold på 1 eller 2 ekvivalenter base for hver ekvivalent 2-carboxyethyl-N-f osf onmethylglycinat kan man fremstille andre salter som ligger innenfor oppfinnelsens ramme.
Eksempel 4
Den eftervirkende herbicide aktivitet til forbindelsene ifølge oppfinnelsen ble demonstrert som følger: De aktive bestanddeler ble påført i forstøvet form til 14 eller 21 dager gamle eksemplarer av de forskjellige plantearter. Sprøytemidlet, en vannopplosning inneholdende den aktive bestanddel og et overflateaktivt middel (35 deler butylaminsalt av dodecylbenzensulfonsyre og 65 deler tallolje kondensert med. ethylenoxyd i forholdet 11 mol ethylenoxyd til 1 mol tallolje) ble påfort plantene i forskjellige sett av potter ved flere konsentrasjoner (kg aktiv bestanddel pr. dekar). De behandlede planter ble plasert i et veksthus, og virkningen ble obserbert og nedtegnet efter ca. 2 uker og 4 uker som angitt i tabellen.
Den eftervirkende herbicide indeks som anvendes i tabellen er som folger:
For korthets og enkelthets skyld er uttrykket "aktiv bestanddel" anvendt herefter for å beskrive carboxyalkylesteren av N-fosfonomethylglycinderivatene ifolge oppfinnelsen.
I herbicide komposisjoner kan den aktive bestanddel blandes med ett eller flere tilsetningsstoffer som kan være faste eller flytende ekstendere, bærere, fortynnere, kondisjoneringsmidler og lignende. De herbicide formuleringer omfatter fuktbare pulvere, vandige suspensjoner, støvformuleringer, emulgerbare oljer og opp-løsninger i opplosningsmidler. Generelt kan disse formuleringer alle inneholde ett eller flere overflateaktive midler.
Overflateaktive midler som kan anvendes i herbicide formuleringer er vel kjent innen faget og er beskrevet i en rekke patent-skrifter og læreboker.
Fremstillingen, formuleringen og partikkelstørrelsen til de fuktbare pulvere, vandige suspensjoner, støv, emulgerbare oljer og opplosningsmidler i oppldsninger er også vel kjent innen faget.
Den aktive bestanddel foreligger vanligvis i den herbicide komposisjon i en konsentrasjon på fra 0,5 til 95 vektdeler pr. lOO vektdeler fuktbart pulver og stovformuleringer; fra 5 til 95 vektdeler pr. lOO vektdeler emulgerbare oljeformuleringer. Formuleringer inneholdende andre mengder av aktiv bestanddel enn hva som er angitt ovenfor kan lett fremstilles av fagmannen.
Påfdring av de herbicide komposisjoner ifolge oppfinnelsen til plantene er vel kjent innen faget. Påføring av flytende og par-tikkelformige faste herbicide formuleringer til de over-jordiske deler av plantene kan utfores efter kjente metoder, f.eks. ved pulver-forstovere, stativ og håndsproyter og pulversproyter.
Den aktive bestanddel kan blandes med ett eller flere hjel-pestoffer som kan være faste eller flytende ekstendere, bærere, fortynnere, kondisjoneringsmidler og lignende under dannelse av herbicide komposisjoner. Herbicide formuleringer inneholder de aktive bestanddeler ifolge oppfinnelsen med fuktbare pulvere, vandige suspensjoner, stovformuleringer, emulgerbare oljer og oppløsninger i opplosningsmidler. Generelt kan alle disse formuleringer inneholde ett eller flere overflateaktive midler. Herbicide blandinger påfø-res i en mengde av fra 1 til 50 deler pr. dekar av aktiv bestanddel for å oppnå en generell herbicid effekt.
Selv om illustrative utførelsesformer av oppfinnelsen er beskrevet, er det innlysende at forskjellige andre modifika-sjoner er mulige uten å avvike fra oppfinnelsens ramme.
Claims (3)
1. N-fosfonomethylglycin-carboxyalkylestere og salter derav for anvendelse som herbicide midler, karakterisert ved at de har formelen
hvor M, M<1> og M" er hydrogen, alkalimetall, jordalkalimetall, ammonium eller en organisk ammoniumrest som er avledet av et organisk amin med en molekylvekt under 300 og inneholdende maksimum 2 aminogrupper.
2. Kjemisk forbindelse ifølge krav 1, karakterisert ved at den er 3-carboxyethyl-N-fosfonomethylglycinat.
3. Kjemisk forbindelse ifølge krav 1, karakterisert ved at den er monoisopropylaminsaltet av |3-carboxyethyl-N-fosfonomethylglycinat.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US417858A US3868407A (en) | 1973-11-21 | 1973-11-21 | Carboxyalkyl esters of n-phosphonomethyl glycine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO743973L NO743973L (no) | 1975-06-16 |
| NO143747B true NO143747B (no) | 1980-12-29 |
| NO143747C NO143747C (no) | 1981-04-08 |
Family
ID=23655654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743973A NO143747C (no) | 1973-11-21 | 1974-11-05 | Carboxyalkylestere av n-fosfonmethylglycin for anvendelse som herbicide midler |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US3868407A (no) |
| JP (1) | JPS5242854B2 (no) |
| AR (1) | AR219688A1 (no) |
| AT (1) | AT341267B (no) |
| BE (1) | BE821879A (no) |
| BG (1) | BG26183A3 (no) |
| BR (1) | BR7409238A (no) |
| CA (1) | CA1048053A (no) |
| CH (1) | CH593013A5 (no) |
| CS (1) | CS178935B2 (no) |
| DD (2) | DD115686A5 (no) |
| DE (1) | DE2452460C3 (no) |
| DK (1) | DK139360B (no) |
| EG (1) | EG11241A (no) |
| ES (1) | ES431614A1 (no) |
| FI (1) | FI60020C (no) |
| FR (1) | FR2251569B1 (no) |
| GB (1) | GB1440847A (no) |
| HU (1) | HU171312B (no) |
| IL (1) | IL45989A (no) |
| IN (1) | IN140421B (no) |
| IT (1) | IT1049325B (no) |
| NL (1) | NL172065C (no) |
| NO (1) | NO143747C (no) |
| PH (1) | PH10683A (no) |
| PL (2) | PL93298B1 (no) |
| RO (1) | RO72710A (no) |
| SE (1) | SE421625B (no) |
| SU (1) | SU682097A3 (no) |
| YU (1) | YU40107B (no) |
| ZA (1) | ZA747107B (no) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988142A (en) * | 1972-02-03 | 1976-10-26 | Monsanto Company | Increasing carbohydrate deposition in plants with N-phosphono-methylglycine and derivatives thereof |
| US3948975A (en) * | 1974-08-05 | 1976-04-06 | Monsanto Company | Hydroxyalkyl esters of N-phosphonomethyl glycine |
| US4197254A (en) * | 1976-05-03 | 1980-04-08 | Monsanto Company | Derivatives of N-phosphonomethylglycine |
| US4159901A (en) * | 1977-05-16 | 1979-07-03 | Monsanto Company | Corrosion inhibited agricultural compositions |
| JPS5839127B2 (ja) * | 1978-03-09 | 1983-08-27 | 明治製菓株式会社 | 除草剤組成物 |
| US4226610A (en) * | 1978-04-15 | 1980-10-07 | Meiji Selka Kaisha, Ltd. | Herbicidal compounds, preparation thereof and herbicides containing the same |
| AU561761B2 (en) * | 1983-03-16 | 1987-05-14 | Monsanto Company | Glyphosate-type herbicidal compositions |
| ES8603901A1 (es) * | 1983-07-27 | 1986-01-01 | Rhone Poulenc Agrochimie | Procedimiento de preparacion de sulfonamidas con grupo ansinometilfosfonico |
| JPS60185443U (ja) * | 1984-05-21 | 1985-12-09 | 温泉青果農業協同組合 | 収穫用鋏 |
| US5580841A (en) * | 1985-05-29 | 1996-12-03 | Zeneca Limited | Solid, phytoactive compositions and method for their preparation |
| US5468718A (en) * | 1985-10-21 | 1995-11-21 | Ici Americas Inc. | Liquid, phytoactive compositions and method for their preparation |
| US5047079A (en) * | 1986-08-18 | 1991-09-10 | Ici Americas Inc. | Method of preparation and use of solid, phytoactive compositions |
| US5187292A (en) * | 1988-08-18 | 1993-02-16 | Rhone-Poulenc Agrochimie | N-sulfomethylglycinate, use in the preparation of herbicides of the glyphosate type |
| FR2635522B1 (fr) * | 1988-08-18 | 1990-11-16 | Rhone Poulenc Agrochimie | N-sulfonomethylglycinate procede de preparation, utilisation dans la preparation d'herbicides de type glyphosate |
| US6930075B1 (en) | 1990-11-02 | 2005-08-16 | Monsanto Technology, Llc | Fatty acid-based herbicidal composition |
| 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 |
| HU212802B (en) | 1991-07-19 | 1996-11-28 | Monsanto Europe Sa | Phytoactive sack-like composition containing glyphosate-izopropylamine salt |
| 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 |
| ITTO980048A1 (it) * | 1998-01-20 | 1999-07-20 | Ipici Spa | Composizioni erbicide, procedimenti per la loro preparazione ed impieghi |
| US6921834B2 (en) | 2002-05-22 | 2005-07-26 | Dow Agrosciences Llc | Continuous process for preparing N-phosphonomethyl glycine |
| AR037559A1 (es) * | 2002-11-19 | 2004-11-17 | Atanor S A | Una formulacion herbicida solida de n-fosfonometilglicina, bajo la forma de polvo, granulos o escamas, soluble o dispersable en agua, y el procedimiento para preparar dicha composicion |
| US8470741B2 (en) * | 2003-05-07 | 2013-06-25 | Croda Americas Llc | Homogeneous liquid saccharide and oil systems |
| NZ553629A (en) * | 2004-09-17 | 2010-12-24 | Monsanto Technology Llc | Glyphosate formulations with early burndown symptoms |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3799758A (en) * | 1971-08-09 | 1974-03-26 | Monsanto Co | N-phosphonomethyl-glycine phytotoxicant compositions |
-
1973
- 1973-11-21 US US417858A patent/US3868407A/en not_active Expired - Lifetime
-
1974
- 1974-11-04 IL IL45989A patent/IL45989A/en unknown
- 1974-11-04 SU SU742076318A patent/SU682097A3/ru active
- 1974-11-04 NL NLAANVRAGE7414338,A patent/NL172065C/xx not_active IP Right Cessation
- 1974-11-04 ES ES431614A patent/ES431614A1/es not_active Expired
- 1974-11-05 DK DK575274AA patent/DK139360B/da not_active IP Right Cessation
- 1974-11-05 IT IT29129/74A patent/IT1049325B/it active
- 1974-11-05 GB GB4783174A patent/GB1440847A/en not_active Expired
- 1974-11-05 DE DE2452460A patent/DE2452460C3/de not_active Expired
- 1974-11-05 YU YU2949/74A patent/YU40107B/xx unknown
- 1974-11-05 FI FI3227/74A patent/FI60020C/fi active
- 1974-11-05 BE BE150233A patent/BE821879A/xx not_active IP Right Cessation
- 1974-11-05 HU HU74MO00000919A patent/HU171312B/hu unknown
- 1974-11-05 PL PL1974187852A patent/PL93298B1/pl unknown
- 1974-11-05 NO NO743973A patent/NO143747C/no unknown
- 1974-11-05 CS CS7400007541A patent/CS178935B2/cs unknown
- 1974-11-05 BG BG028118A patent/BG26183A3/xx unknown
- 1974-11-05 DD DD182166A patent/DD115686A5/xx unknown
- 1974-11-05 DD DD189587A patent/DD121596A5/xx unknown
- 1974-11-05 JP JP49126653A patent/JPS5242854B2/ja not_active Expired
- 1974-11-05 PL PL1974175344A patent/PL92403B1/pl unknown
- 1974-11-05 FR FR7436746A patent/FR2251569B1/fr not_active Expired
- 1974-11-05 AT AT884674A patent/AT341267B/de not_active IP Right Cessation
- 1974-11-05 IN IN2419/CAL/1974A patent/IN140421B/en unknown
- 1974-11-05 BR BR9238/74A patent/BR7409238A/pt unknown
- 1974-11-05 SE SE7413853A patent/SE421625B/xx not_active IP Right Cessation
- 1974-11-05 AR AR256392A patent/AR219688A1/es active
- 1974-11-05 CH CH1476974A patent/CH593013A5/xx not_active IP Right Cessation
- 1974-11-05 ZA ZA00747107A patent/ZA747107B/xx unknown
- 1974-11-05 CA CA212,996A patent/CA1048053A/en not_active Expired
- 1974-11-05 RO RO7480433A patent/RO72710A/ro unknown
- 1974-11-08 PH PH16494A patent/PH10683A/en unknown
- 1974-11-20 EG EG515/74A patent/EG11241A/xx active
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