FI67558C - O-aryl-n-fosfonometylglycinnitriler deras anvaendning som herbicider och foerfarande foer framstaellning av dem - Google Patents
O-aryl-n-fosfonometylglycinnitriler deras anvaendning som herbicider och foerfarande foer framstaellning av dem Download PDFInfo
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- FI67558C FI67558C FI773495A FI773495A FI67558C FI 67558 C FI67558 C FI 67558C FI 773495 A FI773495 A FI 773495A FI 773495 A FI773495 A FI 773495A FI 67558 C FI67558 C FI 67558C
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- Finland
- Prior art keywords
- compound
- aryl
- effective amount
- herbicidally effective
- herbicidal
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- 150000008061 acetanilides Chemical class 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000007854 aminals Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FFVCBJCWQOHQCB-UHFFFAOYSA-N bis(1,3-benzodioxol-5-yl) hydrogen phosphite Chemical compound C1=C2OCOC2=CC(OP(OC=2C=C3OCOC3=CC=2)O)=C1 FFVCBJCWQOHQCB-UHFFFAOYSA-N 0.000 description 1
- QEASXYHBCOBLEU-UHFFFAOYSA-N bis(2,4,6-trimethylphenyl) hydrogen phosphite Chemical compound CC1=CC(C)=CC(C)=C1OP(O)OC1=C(C)C=C(C)C=C1C QEASXYHBCOBLEU-UHFFFAOYSA-N 0.000 description 1
- XAEQVLOIPHAOOW-UHFFFAOYSA-N bis(2-chlorophenyl) hydrogen phosphite Chemical compound C=1C=CC=C(Cl)C=1OP(O)OC1=CC=CC=C1Cl XAEQVLOIPHAOOW-UHFFFAOYSA-N 0.000 description 1
- ZUAGNRHSAPEJRW-UHFFFAOYSA-N bis(2-methoxyphenyl) hydrogen phosphite Chemical compound COC1=CC=CC=C1OP(O)OC1=CC=CC=C1OC ZUAGNRHSAPEJRW-UHFFFAOYSA-N 0.000 description 1
- PDPQEMNLXUGHNS-UHFFFAOYSA-N bis(3,4-dichlorophenyl) hydrogen phosphite Chemical compound C=1C=C(Cl)C(Cl)=CC=1OP(O)OC1=CC=C(Cl)C(Cl)=C1 PDPQEMNLXUGHNS-UHFFFAOYSA-N 0.000 description 1
- WAPALSKUZQDHKX-UHFFFAOYSA-N bis(3-methyl-4-nitrophenyl) hydrogen phosphite Chemical compound C1=C([N+]([O-])=O)C(C)=CC(OP(O)OC=2C=C(C)C(=CC=2)[N+]([O-])=O)=C1 WAPALSKUZQDHKX-UHFFFAOYSA-N 0.000 description 1
- ZJRNBGVJGIFZRO-UHFFFAOYSA-N bis(3-nitrophenyl) hydrogen phosphite Chemical compound C=1C=CC([N+]([O-])=O)=CC=1OP(O)OC1=CC=CC([N+]([O-])=O)=C1 ZJRNBGVJGIFZRO-UHFFFAOYSA-N 0.000 description 1
- ZOLLZXLIZDRUPF-UHFFFAOYSA-N bis(4-chlorophenyl) hydrogen phosphite Chemical compound C=1C=C(Cl)C=CC=1OP(O)OC1=CC=C(Cl)C=C1 ZOLLZXLIZDRUPF-UHFFFAOYSA-N 0.000 description 1
- PYJIFMCPFWRQKU-UHFFFAOYSA-N bis(4-methylsulfanylphenyl) hydrogen phosphite Chemical compound C1=CC(SC)=CC=C1OP(O)OC1=CC=C(SC)C=C1 PYJIFMCPFWRQKU-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- KRSMKPKTZALAAC-UHFFFAOYSA-N dinaphthalen-1-yl hydrogen phosphite Chemical compound C1=CC=C2C(OP(OC=3C4=CC=CC=C4C=CC=3)O)=CC=CC2=C1 KRSMKPKTZALAAC-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 201000004614 iritis Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XYQQPUALUKWVRH-UHFFFAOYSA-N phenoxy(phenylsulfanyl)phosphinous acid Chemical compound P(SC1=CC=CC=C1)(OC1=CC=CC=C1)O XYQQPUALUKWVRH-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229930000184 phytotoxin Natural products 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- WQQPDTLGLVLNOH-UHFFFAOYSA-M sodium;4-hydroxy-4-oxo-3-sulfobutanoate Chemical class [Na+].OC(=O)CC(C([O-])=O)S(O)(=O)=O WQQPDTLGLVLNOH-UHFFFAOYSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000005494 tarnishing Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 238000009736 wetting 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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
-
- 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
-
- 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
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic 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
- 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
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Claims (41)
1. Som herbicider användbara O-aryl-N-fosfonometylglycin-nitriler med formeln: Z (Aryl-Xa-0)2_b P - CH9 - N - CH9 - CN · R (I) I 2 2 X (0H)b där aryl är fenyl, naftyl eller bifenylyl, X är en substituent pa denna aryl och är halogen, C^-C^-alkyl, C^-C3~alkoxi, C^-C^-alkyl-tio, C2-C3-alkoxikarbonyl, metylendioxi, cyan, trifluormetyl eller nitro, Z är syre eller svavel, a är ett helt tai 0 - 3, b är ett helt tai 0 - 1, R är en stark syra som är i ständ att bilda ett sait med aminogruppen och x är 0 eller 1 med det förbehället att x maste vara 0 da b är 1.
2. Förening enligt patentkravet l,kännetecknad därav, att a är 0.
3. Förening enligt patentkravet 1, kännetecknad därav, att x är 1 och b är 0.
4. Förening enligt patentkravet 1, kännetecknad därav, att x är 0 och b är 1.
5. Förening enligt patentkravet 1,kännetecknad därav, att bade b och x är 0.
6. Förening enligt patentkravet 1,kännetecknad därav, att den starka syran har ett pK i vatten av 2,5 eller mindre. d
7. Förening enligt patentkravet 1,kännetecknad därav, att aryl är fenyl och Z är syre.
8. Förening enligt patentkravet 7,känneteckna d därav, att x är 1 och b är 0.
9. Förening enligt patentkravet 7., kännetecknad därav, att x är 0 och b är 1.
10. Förening enligt patentkravet 7,kännetecknad därav, att bade b och x är 0.
11. Förening enligt patentkravet 1, kännetecknad därav, att den är 0,O-difenyl-N-fosfonometylglycinnitril, 0,0-di(p-metoxifenyl)-N-fosfonometylglycinnitril, 0,0-di(p-fluorfenyl)-N- 52 67558 fosfonometylglycinnitril, 0-fenyl-N-fosfonometylglycinnitril, 0-m-nitrofenyl-N-fosfonometylglycinnitril, 0-o-klorfenyl-N-fosfonometylglycinnitril , bromvätesaltet av 0,0-difenyl-N-fosfonometylglycinnit-ril, trifluorättiksyrasaltet av 0 , 0-difenyl-N-fosfonometylglysin-nitril eller metansulfonsyrasaltet av G,O-difenyl-N-fosfonometyl-glys innitril.
12. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 1 ooh ett inert utspädningsmedel.
13. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 2 och ett inert utspädningsmedel.
14. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 3 och ett inert utspädningsmedel.
15. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 4 och ett inert utspädningsmedel.
16. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 5 och ett inert utspädningsmedel.
17. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 6 och ett inert utspädningsmedel.
18. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 7 och ett inert utspädningsmedel.
19. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 8 och ett inert utspädningsmedel.
20. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 9 och ett inert utspädningsmedel.
21. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 10 och ett inert utspädningsmedel. Il 53 6 7 5 5 8
22. Herbicid komposition, kännetecknad därav, att den bestär av en herbicidiskt effektiv mängd av en förening av patentkravet 11 och ett inert utspädningsmedel.
23. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 1.
24. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 2.
25. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 3.
26. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 4.
27. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 5.
28. Herbicid metod, kännet ecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 6.
29. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 7.
30. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 8.
31. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 9.
32. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 10.
33. Herbicid metod, kännetecknad därav, att en växt eller dess växtmedium bringas i kontakt med en herbicidiskt effektiv mängd av en förening av patentkravet 11. 54 67558
34. Förfarande för framställning av en diester med formeln: Aryl-'Xa~Os^^z H P-CH0NCH0CN Aryl-X^-0 där aryl är fenyl, naftyl eller bifenylyl, X är en substituent pä denna aryl och är halogen, C^-C^-alkyl, C]_"C3_ alkoxi, C^-C^-alkyltio, C2-C3-alkoxikarbonyl, metylendioxi, cyan, trifluormetyl eller nitro, Z är syre eller svavel och a är ett helt tai 0-3, kännetecknat därav, att diarylfosfit med formeln: Z (Aryl-Xa-0)2-P-H där X, Z och a har den ovan definierade betydelsen, omsätts med 1,3,5-tricyanmety1-hexahydro-l,3,5-triazin i bortvaro av en sur katalysator.
35. Förfarande enligt patentkravet 34, kännetecknat därav, att reaktionen genomförs vid en temperatur melian 25° och 110°C.
36. Förfarande enligt patentkravet 35, kännetecknat därav, att diarylfosfitet och triazinet reageras i närvaro av ett inert lösningsmedel.
37. Förfarande enligt patentkravet 34, kännetecknat därav, att diarylfosfitet är difenylfosfit, di-(m-klorfenyl)fos-fit, di-(p-metoxifenyl)fosfit, di-(3,4-dimetylfenyl)fosfit eller di-(p-fluorfenyl)fosfit.
38. Förfarande för f ramställning av ett sait med formeln: Z H (Aryl-Xa-0)2-P-CH2- N ® - CH? - CN R" » H där aryl, X, a och Z har samma betydelser som i patentkravet 1 och
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI833817A FI69469C (fi) | 1976-12-13 | 1983-10-19 | Foerfarande foer framstaellning av n-fosfonometylglycin eller dess tioanalog och deras salter |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/750,327 US4067719A (en) | 1976-12-13 | 1976-12-13 | O-Aryl N-phosphonomethylglycinonitriles and the herbicidal use thereof |
| US75032776 | 1976-12-13 | ||
| US05/756,521 US4083898A (en) | 1976-12-13 | 1977-01-03 | Process for preparing O-aryl, N-phosphonomethylglycinonitriles |
| US75652177 | 1977-01-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773495A FI773495A (fi) | 1978-06-14 |
| FI67558B FI67558B (fi) | 1984-12-31 |
| FI67558C true FI67558C (fi) | 1985-04-10 |
Family
ID=27115259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773495A FI67558C (fi) | 1976-12-13 | 1977-11-18 | O-aryl-n-fosfonometylglycinnitriler deras anvaendning som herbicider och foerfarande foer framstaellning av dem |
Country Status (36)
| Country | Link |
|---|---|
| JP (1) | JPS5373543A (sv) |
| AR (1) | AR223311A1 (sv) |
| AT (1) | AT359772B (sv) |
| AU (1) | AU510196B2 (sv) |
| BG (2) | BG28423A3 (sv) |
| BR (1) | BR7707676A (sv) |
| CA (1) | CA1098529A (sv) |
| CH (2) | CH636752A5 (sv) |
| CY (1) | CY1061A (sv) |
| DD (1) | DD145273A5 (sv) |
| DE (1) | DE2751631A1 (sv) |
| DK (1) | DK511677A (sv) |
| EG (1) | EG12818A (sv) |
| ES (1) | ES464216A1 (sv) |
| FI (1) | FI67558C (sv) |
| FR (1) | FR2373553A1 (sv) |
| GB (1) | GB1556322A (sv) |
| GR (1) | GR66150B (sv) |
| HU (1) | HU184655B (sv) |
| IE (1) | IE45917B1 (sv) |
| IL (1) | IL53425A (sv) |
| IN (1) | IN146347B (sv) |
| IT (1) | IT1088890B (sv) |
| KE (1) | KE3045A (sv) |
| MX (1) | MX4714E (sv) |
| NL (1) | NL7712653A (sv) |
| NO (1) | NO151547C (sv) |
| NZ (1) | NZ185720A (sv) |
| OA (1) | OA05804A (sv) |
| PH (2) | PH16387A (sv) |
| PL (1) | PL113273B1 (sv) |
| PT (1) | PT67295B (sv) |
| SE (7) | SE441451B (sv) |
| TR (1) | TR20178A (sv) |
| YU (1) | YU275677A (sv) |
| ZM (1) | ZM8377A1 (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR027024A1 (es) | 1999-12-23 | 2003-03-12 | Basf Ag | Procedimiento para la preparacion de n-fosfonometilglicina |
| CN110156838A (zh) * | 2013-05-14 | 2019-08-23 | 北京美倍他药物研究有限公司 | 磷酸/膦酸衍生物及其医药用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1445087A (en) * | 1972-11-08 | 1976-08-04 | Ici Ltd | Preparing n-phosphonomethylglycine and nitrile intermediates therefor |
| JPS5295640A (en) * | 1976-02-05 | 1977-08-11 | Nissan Chem Ind Ltd | N-(diphenylphosphonomethyl)aminoacetonitrile |
| JPS604840B2 (ja) * | 1976-11-04 | 1985-02-06 | 日産化学工業株式会社 | シアノメチルアミノメチルホスホネート誘導体および該誘導体を有効成分とする除草剤 |
-
1977
- 1977-11-16 EG EG643/77A patent/EG12818A/xx active
- 1977-11-17 ES ES464216A patent/ES464216A1/es not_active Expired
- 1977-11-17 NL NL7712653A patent/NL7712653A/xx not_active Application Discontinuation
- 1977-11-18 OA OA56318A patent/OA05804A/xx unknown
- 1977-11-18 DE DE19772751631 patent/DE2751631A1/de not_active Withdrawn
- 1977-11-18 CA CA291,165A patent/CA1098529A/en not_active Expired
- 1977-11-18 JP JP13800977A patent/JPS5373543A/ja active Granted
- 1977-11-18 AT AT825177A patent/AT359772B/de not_active IP Right Cessation
- 1977-11-18 PT PT67295A patent/PT67295B/pt unknown
- 1977-11-18 IN IN1627/CAL/77A patent/IN146347B/en unknown
- 1977-11-18 BR BR7707676A patent/BR7707676A/pt unknown
- 1977-11-18 NZ NZ185720A patent/NZ185720A/xx unknown
- 1977-11-18 PH PH20450A patent/PH16387A/en unknown
- 1977-11-18 IL IL53425A patent/IL53425A/xx unknown
- 1977-11-18 BG BG7737829A patent/BG28423A3/xx unknown
- 1977-11-18 GR GR54843A patent/GR66150B/el unknown
- 1977-11-18 NO NO773959A patent/NO151547C/no unknown
- 1977-11-18 HU HU77MO994A patent/HU184655B/hu unknown
- 1977-11-18 BG BG7839915A patent/BG36634A3/xx unknown
- 1977-11-18 ZM ZM7783A patent/ZM8377A1/xx unknown
- 1977-11-18 AU AU30754/77A patent/AU510196B2/en not_active Expired
- 1977-11-18 DD DD77214294A patent/DD145273A5/de unknown
- 1977-11-18 CY CY1061A patent/CY1061A/xx unknown
- 1977-11-18 IE IE2354/77A patent/IE45917B1/en unknown
- 1977-11-18 PL PL1977202250A patent/PL113273B1/pl unknown
- 1977-11-18 IT IT29814/77A patent/IT1088890B/it active
- 1977-11-18 SE SE7713047A patent/SE441451B/sv not_active IP Right Cessation
- 1977-11-18 FR FR7734834A patent/FR2373553A1/fr active Granted
- 1977-11-18 DK DK511677A patent/DK511677A/da not_active Application Discontinuation
- 1977-11-18 YU YU02756/77A patent/YU275677A/xx unknown
- 1977-11-18 FI FI773495A patent/FI67558C/fi not_active IP Right Cessation
- 1977-11-18 CH CH1411377A patent/CH636752A5/de not_active IP Right Cessation
- 1977-11-18 GB GB48084/77A patent/GB1556322A/en not_active Expired
- 1977-11-18 MX MX776570U patent/MX4714E/es unknown
- 1977-11-28 TR TR20178A patent/TR20178A/xx unknown
- 1977-12-12 AR AR270319A patent/AR223311A1/es active
-
1980
- 1980-04-28 KE KE3045A patent/KE3045A/xx unknown
-
1982
- 1982-03-30 CH CH196382A patent/CH636885A5/de not_active IP Right Cessation
-
1983
- 1983-03-30 SE SE8301805A patent/SE8301805D0/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301810A patent/SE8301810L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301808A patent/SE8301808L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301807A patent/SE8301807L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301809A patent/SE8301809L/sv not_active Application Discontinuation
- 1983-03-30 SE SE8301806A patent/SE8301806L/sv not_active Application Discontinuation
- 1983-07-14 PH PH29231A patent/PH18774A/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: MONSANTO COMPANY |