DE2553147A1 - Iminocarbonylphosphonatverbindungen und ihre herstellung und anwendung - Google Patents
Iminocarbonylphosphonatverbindungen und ihre herstellung und anwendungInfo
- Publication number
- DE2553147A1 DE2553147A1 DE19752553147 DE2553147A DE2553147A1 DE 2553147 A1 DE2553147 A1 DE 2553147A1 DE 19752553147 DE19752553147 DE 19752553147 DE 2553147 A DE2553147 A DE 2553147A DE 2553147 A1 DE2553147 A1 DE 2553147A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- alkyl
- carbon atoms
- methyl
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- -1 IMINOCARBONYL PHOSPHONATE COMPOUNDS Chemical class 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 239000011734 sodium Substances 0.000 claims description 28
- 230000012010 growth Effects 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 230000008635 plant growth Effects 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- MMRQGMGIQHPDBM-UHFFFAOYSA-N 1-diethoxyphosphoryl-n-(dimethylaminomethylidene)formamide Chemical compound CCOP(=O)(OCC)C(=O)N=CN(C)C MMRQGMGIQHPDBM-UHFFFAOYSA-N 0.000 claims description 5
- 238000005342 ion exchange Methods 0.000 claims description 5
- VNVRRNRPVIZREH-UHFFFAOYSA-N carbamoylphosphonic acid Chemical compound NC(=O)P(O)(O)=O VNVRRNRPVIZREH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- HIYGOFMMUZHWPO-UHFFFAOYSA-N bis(dimethylamino)methylidenecarbamoyl-methoxyphosphinic acid Chemical compound COP(O)(=O)C(=O)N=C(N(C)C)N(C)C HIYGOFMMUZHWPO-UHFFFAOYSA-N 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 230000000979 retarding effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 5
- FTBBSGAARDYJQV-UHFFFAOYSA-N [amino(methoxy)methylidene]carbamoyl-methoxyphosphinic acid Chemical compound COC(N)=NC(=O)P(O)(=O)OC FTBBSGAARDYJQV-UHFFFAOYSA-N 0.000 claims 2
- XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical compound C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 claims 1
- QRMXOPVEEFUBFN-UHFFFAOYSA-N dimethylaminomethylidenecarbamoyl(ethoxy)phosphinic acid Chemical compound CCOP(O)(=O)C(=O)N=CN(C)C QRMXOPVEEFUBFN-UHFFFAOYSA-N 0.000 claims 1
- 239000007954 growth retardant Substances 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- XOTREVBPKJHQEX-UHFFFAOYSA-M sodium;2-(3,3,6,6-tetramethyl-1,8-dioxo-9-phenyl-4,5,7,9-tetrahydro-2h-acridin-10-yl)acetate Chemical compound [Na+].C1C(C)(C)CC(=O)C2=C1N(CC([O-])=O)C(CC(C)(C)CC1=O)=C1C2C1=CC=CC=C1 XOTREVBPKJHQEX-UHFFFAOYSA-M 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 36
- 230000004044 response Effects 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 13
- RHUODGTXEYJWLD-UHFFFAOYSA-N NC(=O)OP(O)=O Chemical compound NC(=O)OP(O)=O RHUODGTXEYJWLD-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
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- 235000009518 sodium iodide Nutrition 0.000 description 6
- 208000006278 hypochromic anemia Diseases 0.000 description 5
- 231100001184 nonphytotoxic Toxicity 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- VITRIUYHBVKBDH-UHFFFAOYSA-N methyl dimethoxyphosphorylformate Chemical compound COC(=O)P(=O)(OC)OC VITRIUYHBVKBDH-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- BUMYXBYXDQLOGB-UHFFFAOYSA-N n-[bis(dimethylamino)methylidene]-1-dimethoxyphosphorylformamide Chemical compound COP(=O)(OC)C(=O)N=C(N(C)C)N(C)C BUMYXBYXDQLOGB-UHFFFAOYSA-N 0.000 description 3
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- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 3
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- YPLJCUIAAJHGGF-UHFFFAOYSA-L disodium;phosphonatoformamide Chemical compound [Na+].[Na+].NC(=O)P([O-])([O-])=O YPLJCUIAAJHGGF-UHFFFAOYSA-L 0.000 description 2
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- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
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- 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
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- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
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- UWLWFYZFOJIGMJ-UHFFFAOYSA-N OP(O)(=O)C(=O)N=C Chemical class OP(O)(=O)C(=O)N=C UWLWFYZFOJIGMJ-UHFFFAOYSA-N 0.000 description 1
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
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- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
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- 239000010871 livestock manure Substances 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- MLJVWFGPQCOELH-UHFFFAOYSA-N methyl diethoxyphosphorylformate Chemical compound CCOP(=O)(OCC)C(=O)OC MLJVWFGPQCOELH-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
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Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F27—FURNACES; KILNS; OVENS; RETORTS
- F27B—FURNACES, KILNS, OVENS OR RETORTS IN GENERAL; OPEN SINTERING OR LIKE APPARATUS
- F27B1/00—Shaft or like vertical or substantially vertical furnaces
- F27B1/10—Details, accessories or equipment specially adapted for furnaces of these types
- F27B1/18—Arrangements of dust collectors
-
- 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
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52735174A | 1974-11-26 | 1974-11-26 | |
| US62173175A | 1975-10-15 | 1975-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2553147A1 true DE2553147A1 (de) | 1976-08-12 |
Family
ID=27062390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752553147 Withdrawn DE2553147A1 (de) | 1974-11-26 | 1975-11-26 | Iminocarbonylphosphonatverbindungen und ihre herstellung und anwendung |
Country Status (6)
| Country | Link |
|---|---|
| AU (1) | AU8691475A (enExample) |
| CA (1) | CA1058628A (enExample) |
| DE (1) | DE2553147A1 (enExample) |
| FR (1) | FR2292712A1 (enExample) |
| GB (1) | GB1494018A (enExample) |
| SE (1) | SE7513227L (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3005010A (en) * | 1959-08-10 | 1961-10-17 | Monsanto Chemicals | Method for preparing dihydrocarbyloxyphosphinyl formamides |
-
1975
- 1975-11-24 GB GB4822075A patent/GB1494018A/en not_active Expired
- 1975-11-24 CA CA240,315A patent/CA1058628A/en not_active Expired
- 1975-11-25 SE SE7513227A patent/SE7513227L/ not_active Application Discontinuation
- 1975-11-25 FR FR7535942A patent/FR2292712A1/fr active Granted
- 1975-11-25 AU AU86914/75A patent/AU8691475A/en not_active Expired
- 1975-11-26 DE DE19752553147 patent/DE2553147A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA1058628A (en) | 1979-07-17 |
| AU8691475A (en) | 1977-06-02 |
| FR2292712B1 (enExample) | 1980-08-08 |
| SE7513227L (sv) | 1976-05-28 |
| GB1494018A (en) | 1977-12-07 |
| FR2292712A1 (fr) | 1976-06-25 |
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