CS196368B2 - Method of producing urea derivatives and metallic chelates thereof - Google Patents
Method of producing urea derivatives and metallic chelates thereof Download PDFInfo
- Publication number
- CS196368B2 CS196368B2 CS387677A CS387677A CS196368B2 CS 196368 B2 CS196368 B2 CS 196368B2 CS 387677 A CS387677 A CS 387677A CS 387677 A CS387677 A CS 387677A CS 196368 B2 CS196368 B2 CS 196368B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- urea
- formula
- divalent
- chelates
- iii
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 150000003672 ureas Chemical class 0.000 title claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000004202 carbamide Substances 0.000 claims abstract description 19
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 10
- 229910052742 iron Inorganic materials 0.000 claims abstract description 9
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 24
- 239000003337 fertilizer Substances 0.000 abstract description 15
- 239000013522 chelant Substances 0.000 abstract description 12
- 229910052751 metal Inorganic materials 0.000 abstract description 8
- 239000002184 metal Substances 0.000 abstract description 8
- YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical compound [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002426 superphosphate Substances 0.000 abstract description 3
- 239000011573 trace mineral Substances 0.000 abstract description 3
- 235000013619 trace mineral Nutrition 0.000 abstract description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 abstract description 2
- 208000006278 hypochromic anemia Diseases 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 229910052748 manganese Inorganic materials 0.000 abstract description 2
- AUQMULMWZOKOPN-UHFFFAOYSA-N 1,3-bis[(2-hydroxyphenyl)methyl]urea Chemical compound OC1=CC=CC=C1CNC(=O)NCC1=CC=CC=C1O AUQMULMWZOKOPN-UHFFFAOYSA-N 0.000 abstract 1
- 208000027219 Deficiency disease Diseases 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 description 14
- -1 N, N‘-disubstituted urea Chemical class 0.000 description 11
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 10
- 239000002738 chelating agent Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 235000015097 nutrients Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KATOLVAXCGIBLO-UHFFFAOYSA-N 1,3-dibenzylurea Chemical compound C=1C=CC=CC=1CNC(=O)NCC1=CC=CC=C1 KATOLVAXCGIBLO-UHFFFAOYSA-N 0.000 description 4
- DIZBQMTZXOUFTD-UHFFFAOYSA-N 2-(furan-2-yl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1C1=CC=CO1 DIZBQMTZXOUFTD-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 2
- 230000004720 fertilization Effects 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 150000004698 iron complex Chemical class 0.000 description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910001453 nickel ion Inorganic materials 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OCNWVUOTEMCHSM-UHFFFAOYSA-N (2-hydroxyphenyl)methylurea Chemical compound NC(=O)NCC1=CC=CC=C1O OCNWVUOTEMCHSM-UHFFFAOYSA-N 0.000 description 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical group CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZQBRTBJUHSVIBN-UHFFFAOYSA-N C1=CC(=C(C=C1C(=O)O)CNC(=O)N)O Chemical compound C1=CC(=C(C=C1C(=O)O)CNC(=O)N)O ZQBRTBJUHSVIBN-UHFFFAOYSA-N 0.000 description 1
- 206010022971 Iron Deficiencies Diseases 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- IPOJYSJCMKRFTL-UHFFFAOYSA-N OC(=O)C1=CC=C(O)C(CNC(=O)NCC=2C(=CC=C(C=2)C(O)=O)O)=C1 Chemical compound OC(=O)C1=CC=C(O)C(CNC(=O)NCC=2C(=CC=C(C=2)C(O)=O)O)=C1 IPOJYSJCMKRFTL-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical group [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- VRMWOQSSFPYAQD-UHFFFAOYSA-N [K].NC(N)=O Chemical compound [K].NC(N)=O VRMWOQSSFPYAQD-UHFFFAOYSA-N 0.000 description 1
- NJFMNPFATSYWHB-UHFFFAOYSA-N ac1l9hgr Chemical compound [Fe].[Fe] NJFMNPFATSYWHB-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 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
- 239000000356 contaminant Substances 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- CDUFCUKTJFSWPL-UHFFFAOYSA-L manganese(II) sulfate tetrahydrate Chemical compound O.O.O.O.[Mn+2].[O-]S([O-])(=O)=O CDUFCUKTJFSWPL-UHFFFAOYSA-L 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- DKGFIVSGQRBSOG-UHFFFAOYSA-M potassium;4-hydroxybenzoate Chemical compound [K+].OC1=CC=C(C([O-])=O)C=C1 DKGFIVSGQRBSOG-UHFFFAOYSA-M 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical group [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05D—INORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C; FERTILISERS PRODUCING CARBON DIOXIDE
- C05D9/00—Other inorganic fertilisers
- C05D9/02—Other inorganic fertilisers containing trace elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/20—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C275/24—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fertilizers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76PE00000991A HU172701B (hu) | 1976-06-24 | 1976-06-24 | Sposob poluchenija novykh proizvodnykh mocheviny i ikh metallnykh kelatov |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196368B2 true CS196368B2 (en) | 1980-03-31 |
Family
ID=11000475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS387677A CS196368B2 (en) | 1976-06-24 | 1977-06-13 | Method of producing urea derivatives and metallic chelates thereof |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3427980A1 (de) * | 1984-07-28 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | Mehrspurennaehrstoffduenger |
| ES2110894B1 (es) * | 1995-01-11 | 1998-08-16 | Agrides S A | Abono destinado a paliar la clorosis de los vegetales. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE511210C (de) * | 1927-12-12 | 1930-11-14 | Heinrich Von Diesbach Dr | Verfahren zur Herstellung von disubstituierten Harnstoffen und deren Umwandlungsprodukten |
| US3742002A (en) * | 1971-06-14 | 1973-06-26 | Grace W R & Co | Iron chelates useful for supplying iron to plants growing in calcareous soil |
-
1976
- 1976-06-24 HU HU76PE00000991A patent/HU172701B/hu unknown
-
1977
- 1977-03-24 AT AT204677A patent/AT351556B/de not_active IP Right Cessation
- 1977-06-07 FR FR7717328A patent/FR2355814A1/fr active Granted
- 1977-06-07 BG BG036531A patent/BG28046A3/xx unknown
- 1977-06-10 DE DE19772726114 patent/DE2726114A1/de not_active Ceased
- 1977-06-11 RO RO7790658A patent/RO70991A/ro unknown
- 1977-06-13 DD DD19946077A patent/DD131016A1/xx not_active IP Right Cessation
- 1977-06-13 CS CS387677A patent/CS196368B2/cs unknown
- 1977-06-16 SU SU772494205A patent/SU841584A3/ru active
- 1977-06-16 IT IT2474377A patent/IT1115529B/it active
- 1977-06-22 NL NL7706918A patent/NL7706918A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DD131016A1 (de) | 1978-05-24 |
| FR2355814A1 (fr) | 1978-01-20 |
| IT1115529B (it) | 1986-02-03 |
| AT351556B (de) | 1979-08-10 |
| NL7706918A (nl) | 1977-12-28 |
| BG28046A3 (bg) | 1980-02-25 |
| HU172701B (hu) | 1978-11-28 |
| SU841584A3 (ru) | 1981-06-23 |
| DE2726114A1 (de) | 1978-01-05 |
| RO70991A (ro) | 1982-02-01 |
| FR2355814B1 (enrdf_load_stackoverflow) | 1983-08-26 |
| ATA204677A (de) | 1979-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5504055A (en) | Metal amino acid chelate | |
| US3632637A (en) | Hydroxyaryl-containing aminocarboxylic chelating agents | |
| US20140360239A1 (en) | Composition of a magnesium sulfate/urea compound | |
| US20120160001A1 (en) | Chelated compositions and methods of making and using the same | |
| WO2014122669A1 (en) | A total foliar product for agriculture / horticulture / tissue culture and hydroponic cultivation | |
| US3758540A (en) | Ferric chelates of n-(2-hydroxybenzyl) substituted aminopoly carboxylic acids | |
| JPH0550477B2 (enrdf_load_stackoverflow) | ||
| RU2769464C2 (ru) | Новые фосфатные удобрения на основе алканоламиновых солей фосфорной кислоты | |
| CA2493215A1 (en) | Agrochemical composition containing phosphite and process for the preparation thereof | |
| EP0205748A1 (de) | Stabile Lösungen von Metallchelaten, Verfahren zu ihrer Herstellung und ihre Verwendung als Spurenelementdünger | |
| US20030101785A1 (en) | Micronutrient compositions including aminophosphonic acid and chelated metal ions | |
| Semenov et al. | Water-soluble cobalt complexes with 1-hydroxyethylydenediphosphonic acid and 2-aminoethanol | |
| PL199168B1 (pl) | Nawóz mikroelementowy, sposób wytwarzania nawozu mikroelementowego i zastosowanie nawozu mikroelementowego | |
| CS196368B2 (en) | Method of producing urea derivatives and metallic chelates thereof | |
| EP0173069B1 (de) | Mehrspurennährstoffdünger | |
| JPS6114190A (ja) | 土壌中に窒素を保存させるための組成物及び土壌処理法 | |
| RU2179162C1 (ru) | Способ получения питательных растворов, содержащих микроэлементы (микровит) | |
| CN109153618A (zh) | 用于灌溉施肥的包含基于硝酸盐的微量营养素的颗粒状硝酸钙组合物及其制备方法 | |
| US3507892A (en) | Heavy metal chelates of amino hydrazide chelating agents | |
| US3403992A (en) | Method of treating soil comprising adding a fertilizer and a chelating agent to the soil | |
| US3463799A (en) | Dimethylamino - bis - (2 - hydroxyphenyl) sulfonic and carboxylic acid and metal chelates thereof | |
| JPS59141478A (ja) | 液体肥料の製法 | |
| CN116063121A (zh) | 一种环境友好型螯合元素复合肥料及其制备方法 | |
| RU2582680C1 (ru) | КОМПЛЕКСОНАТЫ ЭТИЛЕНДИАМИН-β-ПРОПИОНОВЫХ КИСЛОТ С ДВУХВАЛЕНТНЫМИ МЕТАЛЛАМИ: МЕДЬЮ, ЦИНКОМ, НИКЕЛЕМ И КОБАЛЬТОМ, И СПОСОБЫ ИХ ПОЛУЧЕНИЯ | |
| JP5388861B2 (ja) | 鉄クロロシスの治療のための新規生成物 |