DD207143A5 - Agrochemisches schaedlingsbekaempfungsmittel - Google Patents

Info

Publication number

DD207143A5

DD207143A5 DD82239803A DD23980382A DD207143A5 DD 207143 A5 DD207143 A5 DD 207143A5 DD 82239803 A DD82239803 A DD 82239803A DD 23980382 A DD23980382 A DD 23980382A DD 207143 A5 DD207143 A5 DD 207143A5

Authority

DD

German Democratic Republic

Prior art keywords

alkyl

item

independently

formula

halogen

Prior art date

1981-05-12

Links

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• 239000003905 agrochemical Substances 0.000 title claims abstract description 18
• 239000003795 chemical substances by application Substances 0.000 title claims abstract description 17
• 150000001875 compounds Chemical class 0.000 claims abstract description 136
• 239000000203 mixture Substances 0.000 claims abstract description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
• 239000001257 hydrogen Substances 0.000 claims abstract description 61
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 59
• 150000002367 halogens Chemical class 0.000 claims abstract description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 52
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 39
• 241000233866 Fungi Species 0.000 claims abstract description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
• 244000005700 microbiome Species 0.000 claims abstract description 10
• 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 9
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
• 239000000460 chlorine Chemical group 0.000 claims description 437
• 150000003839 salts Chemical class 0.000 claims description 114
• -1 C 1 -C 3 -alkoxy Chemical group 0.000 claims description 96
• 238000002360 preparation method Methods 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 30
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 229910052751 metal Chemical class 0.000 claims description 19
• 239000002184 metal Chemical class 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 239000007787 solid Substances 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 15
• 239000007788 liquid Substances 0.000 claims description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
• 206010061217 Infestation Diseases 0.000 claims description 14
• 239000000654 additive Substances 0.000 claims description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
• 229910052794 bromium Inorganic materials 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 11
• 239000004094 surface-active agent 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
• 239000000969 carrier Substances 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 239000011737 fluorine Chemical group 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 239000000575 pesticide Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 239000011593 sulfur Substances 0.000 claims description 4
• 230000000996 additive effect Effects 0.000 claims description 3
• 230000003449 preventive effect Effects 0.000 claims description 3
• MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• 239000002671 adjuvant Substances 0.000 claims description 2
• 244000038559 crop plants Species 0.000 claims description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 239000013256 coordination polymer Substances 0.000 claims 2
• ZAGUSKAXELYWCE-UHFFFAOYSA-N 1,3-dioxolan-2-ylmethanol Chemical compound OCC1OCCO1 ZAGUSKAXELYWCE-UHFFFAOYSA-N 0.000 claims 1
• HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 claims 1
• ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 claims 1
• 229940125904 compound 1 Drugs 0.000 claims 1
• 229910000365 copper sulfate Inorganic materials 0.000 claims 1
• 230000003641 microbiacidal effect Effects 0.000 abstract description 9
• 230000000843 anti-fungal effect Effects 0.000 abstract description 7
• 230000000949 anxiolytic effect Effects 0.000 abstract description 7
• 229940124561 microbicide Drugs 0.000 abstract description 7
• 241001465754 Metazoa Species 0.000 abstract description 6
• 230000002082 anti-convulsion Effects 0.000 abstract description 5
• 150000002170 ethers Chemical class 0.000 abstract description 5
• 229940121375 antifungal agent Drugs 0.000 abstract description 4
• 239000002249 anxiolytic agent Substances 0.000 abstract description 4
• 230000003071 parasitic effect Effects 0.000 abstract description 4
• 208000019901 Anxiety disease Diseases 0.000 abstract description 3
• 206010026749 Mania Diseases 0.000 abstract description 3
• 230000036506 anxiety Effects 0.000 abstract description 3
• 229940079593 drug Drugs 0.000 abstract description 3
• 239000003814 drug Substances 0.000 abstract description 3
• 206010015037 epilepsy Diseases 0.000 abstract description 3
• 239000002855 microbicide agent Substances 0.000 abstract description 3
• 238000001228 spectrum Methods 0.000 abstract description 3
• 230000005284 excitation Effects 0.000 abstract description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 307
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
• 239000004480 active ingredient Substances 0.000 description 63
• 241000196324 Embryophyta Species 0.000 description 36
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• 125000001246 bromo group Chemical group Br* 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 24
• 239000011572 manganese Substances 0.000 description 24
• 239000003921 oil Substances 0.000 description 24
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 23
• 239000013543 active substance Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 22
• 239000002904 solvent Substances 0.000 description 22
• 229920001223 polyethylene glycol Polymers 0.000 description 21
• 239000011347 resin Substances 0.000 description 21
• 229920005989 resin Polymers 0.000 description 21
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
• 235000014113 dietary fatty acids Nutrition 0.000 description 20
• 239000000194 fatty acid Substances 0.000 description 20
• 229930195729 fatty acid Natural products 0.000 description 20
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
• 239000002202 Polyethylene glycol Substances 0.000 description 16
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 15
• 239000007921 spray Substances 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 239000000126 substance Substances 0.000 description 14
• 229920002472 Starch Polymers 0.000 description 13
• 238000001816 cooling Methods 0.000 description 13
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 13
• 239000003826 tablet Substances 0.000 description 13
• 239000000454 talc Substances 0.000 description 13
• 229910052623 talc Inorganic materials 0.000 description 13
• 235000012222 talc Nutrition 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
• 239000008187 granular material Substances 0.000 description 12
• 229910052938 sodium sulfate Inorganic materials 0.000 description 12
• 235000011152 sodium sulphate Nutrition 0.000 description 12
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
• 239000000825 pharmaceutical preparation Substances 0.000 description 11
• 239000000741 silica gel Substances 0.000 description 11
• 229910002027 silica gel Inorganic materials 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 239000000839 emulsion Substances 0.000 description 10
• 238000001704 evaporation Methods 0.000 description 10
• 230000008020 evaporation Effects 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• 235000019698 starch Nutrition 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 9
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
• 239000006071 cream Substances 0.000 description 9
• 150000004665 fatty acids Chemical class 0.000 description 9
• 239000008101 lactose Substances 0.000 description 9
• BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 9
• 239000005995 Aluminium silicate Substances 0.000 description 8
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
• 235000012211 aluminium silicate Nutrition 0.000 description 8
• 230000015572 biosynthetic process Effects 0.000 description 8
• 238000009835 boiling Methods 0.000 description 8
• 239000013078 crystal Substances 0.000 description 8
• 239000003480 eluent Substances 0.000 description 8
• 239000003995 emulsifying agent Substances 0.000 description 8
• 235000019441 ethanol Nutrition 0.000 description 8
• 235000019359 magnesium stearate Nutrition 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 150000003254 radicals Chemical group 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
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• 238000003786 synthesis reaction Methods 0.000 description 8
• 230000009885 systemic effect Effects 0.000 description 8
• 239000008096 xylene Substances 0.000 description 8
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 7
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• 240000005979 Hordeum vulgare Species 0.000 description 7
• 239000005662 Paraffin oil Substances 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
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• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
• 150000002576 ketones Chemical class 0.000 description 7
• 239000002689 soil Substances 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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• 150000007513 acids Chemical class 0.000 description 6
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• 150000002009 diols Chemical class 0.000 description 6
• 150000002191 fatty alcohols Chemical class 0.000 description 6
• 235000011187 glycerol Nutrition 0.000 description 6
• IRHTZOCLLONTOC-UHFFFAOYSA-N hexacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 description 6
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• 238000002156 mixing Methods 0.000 description 6
• 239000002674 ointment Substances 0.000 description 6
• 239000003208 petroleum Substances 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 239000000047 product Substances 0.000 description 6
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• 238000003756 stirring Methods 0.000 description 6
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 5
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• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
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• 241000209140 Triticum Species 0.000 description 5
• 239000003513 alkali Substances 0.000 description 5
• 229910052783 alkali metal Inorganic materials 0.000 description 5
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• 239000012141 concentrate Substances 0.000 description 5
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• 150000002430 hydrocarbons Chemical class 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
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• FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 4
• HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
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• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
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• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
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• 150000007522 mineralic acids Chemical class 0.000 description 4
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• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
• 150000007524 organic acids Chemical class 0.000 description 4
• 235000005985 organic acids Nutrition 0.000 description 4
• 239000003755 preservative agent Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• 235000000346 sugar Nutrition 0.000 description 4
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