JP5388861B2 - 鉄クロロシスの治療のための新規生成物 - Google Patents
鉄クロロシスの治療のための新規生成物 Download PDFInfo
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- JP5388861B2 JP5388861B2 JP2009542075A JP2009542075A JP5388861B2 JP 5388861 B2 JP5388861 B2 JP 5388861B2 JP 2009542075 A JP2009542075 A JP 2009542075A JP 2009542075 A JP2009542075 A JP 2009542075A JP 5388861 B2 JP5388861 B2 JP 5388861B2
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- compound
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- hydroxyphenyl
- iron
- Prior art date
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 title claims description 114
- 229910052742 iron Inorganic materials 0.000 title claims description 32
- 208000006278 hypochromic anemia Diseases 0.000 title claims description 21
- 238000011282 treatment Methods 0.000 title description 27
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 phospho, sulfo Chemical group 0.000 claims description 54
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 239000013522 chelant Substances 0.000 claims description 22
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000010949 copper Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000002738 chelating agent Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 206010022971 Iron Deficiencies Diseases 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000002739 metals Chemical class 0.000 claims description 8
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229960003330 pentetic acid Drugs 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 239000012872 agrochemical composition Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 3
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000008139 complexing agent Substances 0.000 claims description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000006839 xylylene group Chemical group 0.000 claims description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 3
- KMBSSXSNDSJXCG-UHFFFAOYSA-N 1-[2-(2-hydroxyundecylamino)ethylamino]undecan-2-ol Chemical compound CCCCCCCCCC(O)CNCCNCC(O)CCCCCCCCC KMBSSXSNDSJXCG-UHFFFAOYSA-N 0.000 claims description 2
- QDAYZTZGLPEDOB-UHFFFAOYSA-N 2-(2-hydroxyanilino)acetic acid Chemical compound OC(=O)CNC1=CC=CC=C1O QDAYZTZGLPEDOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 241000196324 Embryophyta Species 0.000 description 31
- 239000000243 solution Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 239000002262 Schiff base Substances 0.000 description 20
- 150000004753 Schiff bases Chemical class 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 235000015097 nutrients Nutrition 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- RKIJFCVAHRSRQM-UHFFFAOYSA-N 2-(2-aminoethylamino)-2-(2-hydroxyphenyl)acetic acid;hydrochloride Chemical compound Cl.NCCNC(C(O)=O)C1=CC=CC=C1O RKIJFCVAHRSRQM-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000004448 titration Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000011785 micronutrient Substances 0.000 description 7
- 235000013369 micronutrients Nutrition 0.000 description 7
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- GEJZURNJVYJJHR-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-[2-[(2-hydroxyphenyl)methylamino]ethylamino]acetic acid Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNCC1=CC=CC=C1O GEJZURNJVYJJHR-UHFFFAOYSA-N 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- PZZHMLOHNYWKIK-UHFFFAOYSA-N eddha Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNC(C(O)=O)C1=CC=CC=C1O PZZHMLOHNYWKIK-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 239000000797 iron chelating agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 229930002875 chlorophyll Natural products 0.000 description 4
- 235000019804 chlorophyll Nutrition 0.000 description 4
- 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 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 3
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- 239000011575 calcium Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
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- 230000008020 evaporation Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 235000021073 macronutrients Nutrition 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000003918 potentiometric titration Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UQQKFIZVFWSJAP-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-[2-(1h-pyrrol-2-ylmethylamino)ethylamino]acetic acid Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNCC1=CC=CN1 UQQKFIZVFWSJAP-UHFFFAOYSA-N 0.000 description 2
- WXTJMUIJQMDSJA-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-[2-(pyridin-2-ylmethylamino)ethylamino]acetic acid Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNCC1=CC=CC=N1 WXTJMUIJQMDSJA-UHFFFAOYSA-N 0.000 description 2
- HQFMGLGFAKRJCF-UHFFFAOYSA-N 2-[2-[(2-hydroxynaphthalen-1-yl)methylamino]ethylamino]-2-(2-hydroxyphenyl)acetic acid Chemical compound OC=1C=CC2=CC=CC=C2C=1CNCCNC(C(=O)O)C1=CC=CC=C1O HQFMGLGFAKRJCF-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- IIDGQOMMSWYZBE-UHFFFAOYSA-N 2-(2-aminoethylamino)-2-(2-hydroxy-4-methylphenyl)acetic acid;hydrochloride Chemical compound Cl.CC1=CC=C(C(NCCN)C(O)=O)C(O)=C1 IIDGQOMMSWYZBE-UHFFFAOYSA-N 0.000 description 1
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- ACQVWSUUDRPXIT-UHFFFAOYSA-N 2-(2-hydroxy-4-methylphenyl)-2-[2-[(2-hydroxyphenyl)methylamino]ethylamino]acetic acid Chemical compound OC1=CC(C)=CC=C1C(C(O)=O)NCCNCC1=CC=CC=C1O ACQVWSUUDRPXIT-UHFFFAOYSA-N 0.000 description 1
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- KZTPODPKARJIPS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-[2-(1h-imidazol-2-ylmethylamino)ethylamino]acetic acid Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNCC1=NC=CN1 KZTPODPKARJIPS-UHFFFAOYSA-N 0.000 description 1
- DXGQDOFHTALVNO-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-[2-(piperidin-2-ylmethylamino)ethylamino]acetic acid Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNCC1CCCCN1 DXGQDOFHTALVNO-UHFFFAOYSA-N 0.000 description 1
- VNEFYZXAOLNFFQ-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-[2-(pyrrolidin-2-ylmethylamino)ethylamino]acetic acid Chemical compound C=1C=CC=C(O)C=1C(C(=O)O)NCCNCC1CCCN1 VNEFYZXAOLNFFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
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- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- KZNDGAGWQPGYTB-UHFFFAOYSA-N tert-butyl 2-formylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1C=O KZNDGAGWQPGYTB-UHFFFAOYSA-N 0.000 description 1
- YDBPZCVWPFMBDH-UHFFFAOYSA-N tert-butyl 2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1C=O YDBPZCVWPFMBDH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
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Images
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
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/76—Metal complexes of amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06127041A EP1939157A1 (en) | 2006-12-22 | 2006-12-22 | New products for the treatment of the iron chlorosis |
| EP06127041.9 | 2006-12-22 | ||
| PCT/EP2007/064370 WO2008077897A1 (en) | 2006-12-22 | 2007-12-20 | New products for the treatment of the iron chlorosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010513409A JP2010513409A (ja) | 2010-04-30 |
| JP2010513409A5 JP2010513409A5 (enExample) | 2011-01-06 |
| JP5388861B2 true JP5388861B2 (ja) | 2014-01-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009542075A Expired - Fee Related JP5388861B2 (ja) | 2006-12-22 | 2007-12-20 | 鉄クロロシスの治療のための新規生成物 |
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| Country | Link |
|---|---|
| US (1) | US7943797B2 (enExample) |
| EP (2) | EP1939157A1 (enExample) |
| JP (1) | JP5388861B2 (enExample) |
| KR (1) | KR20090097889A (enExample) |
| CN (1) | CN101616880B (enExample) |
| BR (1) | BRPI0720697A2 (enExample) |
| EC (1) | ECSP099533A (enExample) |
| EG (1) | EG27036A (enExample) |
| IL (1) | IL199149A (enExample) |
| MA (1) | MA31098B1 (enExample) |
| MX (1) | MX2009006727A (enExample) |
| WO (1) | WO2008077897A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT201900022833A1 (it) * | 2019-12-03 | 2021-06-03 | Valagro Spa | Processo per la preparazione di acidi poliamminocarbossilici e loro composti chelati |
| US20220394981A1 (en) * | 2021-06-10 | 2022-12-15 | Trademark Nitrogen Corp. | Micronutrient formulations that control plant pathogens |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3903119A (en) * | 1973-08-24 | 1975-09-02 | Ciba Geigy Corp | Iron complexes of ethylene-bis-({60 -2-hydroxyaryl acetic acids |
| DE3329028A1 (de) | 1983-08-11 | 1985-02-28 | Cassella Ag, 6000 Frankfurt | Substituierte (2-amino-2-imidazolin-1-yl)-essigsaeurederivate, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende pharmazeutische zubereitungen |
| DE4222980A1 (de) * | 1992-07-13 | 1994-01-20 | Cassella Ag | Verwendung von 2-(N-(2-Aminoethyl)amino)-essigsäure-derivaten |
| ES2132662T3 (es) | 1994-05-04 | 1999-08-16 | Novartis Ag | Amidas de n-sulfonil y n-sulfinil-aminoacidos como microbiocidas. |
| JP3650571B2 (ja) * | 2000-06-30 | 2005-05-18 | 株式会社 日立インダストリイズ | ドレン浄化装置 |
| AU2002346787A1 (en) * | 2002-12-05 | 2004-06-23 | Kemira Agro Oy | Nutrient composition comprising an iron chelate |
| BRPI0509526A (pt) * | 2004-04-02 | 2007-09-18 | Syngenta Participations Ag | nutriente de planta baseado em o,p-etileno(bis)hidroxifenilglicinas |
| WO2006045852A1 (es) | 2004-10-14 | 2006-05-04 | Cambium, S.L. | Procedimiento para la preparación de aminoácidos fenólicos a partir de productos industriales |
-
2006
- 2006-12-22 EP EP06127041A patent/EP1939157A1/en not_active Withdrawn
-
2007
- 2007-12-20 CN CN2007800475719A patent/CN101616880B/zh not_active Expired - Fee Related
- 2007-12-20 BR BRPI0720697-6A2A patent/BRPI0720697A2/pt not_active IP Right Cessation
- 2007-12-20 US US12/520,450 patent/US7943797B2/en not_active Expired - Fee Related
- 2007-12-20 KR KR1020097012738A patent/KR20090097889A/ko not_active Withdrawn
- 2007-12-20 JP JP2009542075A patent/JP5388861B2/ja not_active Expired - Fee Related
- 2007-12-20 EP EP07857989A patent/EP2125671A1/en not_active Withdrawn
- 2007-12-20 WO PCT/EP2007/064370 patent/WO2008077897A1/en not_active Ceased
- 2007-12-20 MX MX2009006727A patent/MX2009006727A/es active IP Right Grant
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2009
- 2009-06-04 IL IL199149A patent/IL199149A/en active IP Right Grant
- 2009-06-12 EG EG2009060954A patent/EG27036A/xx active
- 2009-07-16 MA MA32098A patent/MA31098B1/fr unknown
- 2009-07-22 EC EC2009009533A patent/ECSP099533A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL199149A (en) | 2014-04-30 |
| EP2125671A1 (en) | 2009-12-02 |
| CN101616880B (zh) | 2012-09-05 |
| CN101616880A (zh) | 2009-12-30 |
| WO2008077897A1 (en) | 2008-07-03 |
| MA31098B1 (fr) | 2010-01-04 |
| ECSP099533A (es) | 2009-11-30 |
| EP1939157A1 (en) | 2008-07-02 |
| AU2007338021A1 (en) | 2008-07-03 |
| JP2010513409A (ja) | 2010-04-30 |
| BRPI0720697A2 (pt) | 2014-02-18 |
| US20100022394A1 (en) | 2010-01-28 |
| US7943797B2 (en) | 2011-05-17 |
| KR20090097889A (ko) | 2009-09-16 |
| EG27036A (en) | 2015-04-14 |
| MX2009006727A (es) | 2009-07-07 |
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