BE471642A

BE471642A -

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Publication number: BE471642A
Authority: BE; Belgium
Prior art keywords: sep; water; reaction; salt; amine
Prior art date

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English (en)

French (fr)

Publication of BE471642A publication Critical patent/BE471642A/fr

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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 168
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 139
235000002639 sodium chloride Nutrition 0.000 description 103
150000003839 salts Chemical class 0.000 description 76
239000011541 reaction mixture Substances 0.000 description 75
239000000243 solution Substances 0.000 description 71
238000006243 chemical reaction Methods 0.000 description 68
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
QWJNFFYFEKXZBF-UHFFFAOYSA-N cyanocyanamide Chemical compound N#CNC#N QWJNFFYFEKXZBF-UHFFFAOYSA-N 0.000 description 53
-1 1-substituted 3-cyanoguanidines Chemical class 0.000 description 52
239000002253 acid Substances 0.000 description 51
150000001412 amines Chemical class 0.000 description 48
239000003153 chemical reaction reagent Substances 0.000 description 48
239000000203 mixture Substances 0.000 description 47
239000000047 product Substances 0.000 description 41
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 40
229910052708 sodium Inorganic materials 0.000 description 40
239000011734 sodium Substances 0.000 description 40
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
238000010438 heat treatment Methods 0.000 description 36
239000011575 calcium Substances 0.000 description 34
229910052791 calcium Inorganic materials 0.000 description 34
235000019441 ethanol Nutrition 0.000 description 34
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 33
239000000155 melt Substances 0.000 description 33
238000000034 method Methods 0.000 description 33
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 32
229940123208 Biguanide Drugs 0.000 description 30
238000002360 preparation method Methods 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
150000004283 biguanides Chemical class 0.000 description 23
239000007787 solid Substances 0.000 description 22
238000001816 cooling Methods 0.000 description 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
239000012458 free base Substances 0.000 description 17
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 15
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
230000008569 process Effects 0.000 description 13
235000011121 sodium hydroxide Nutrition 0.000 description 13
239000012265 solid product Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
150000007513 acids Chemical class 0.000 description 12
150000004982 aromatic amines Chemical class 0.000 description 11
239000013078 crystal Substances 0.000 description 11
238000001035 drying Methods 0.000 description 11
238000011084 recovery Methods 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
238000010992 reflux Methods 0.000 description 10
150000003335 secondary amines Chemical class 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 8
239000002585 base Substances 0.000 description 8
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 8
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
238000001914 filtration Methods 0.000 description 8
230000003287 optical effect Effects 0.000 description 8
239000002904 solvent Substances 0.000 description 8
229950000244 sulfanilic acid Drugs 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
125000003118 aryl group Chemical group 0.000 description 7
159000000007 calcium salts Chemical class 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
238000004821 distillation Methods 0.000 description 6
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 5
239000003513 alkali Substances 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical class NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000012258 stirred mixture Substances 0.000 description 5
229910021653 sulphate ion Inorganic materials 0.000 description 5
BSBNGAXSAIZPAV-UHFFFAOYSA-N 1-cyano-2-octadecylguanidine Chemical compound CCCCCCCCCCCCCCCCCCN=C(N)NC#N BSBNGAXSAIZPAV-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000011707 mineral Substances 0.000 description 4
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 4
239000002002 slurry Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000003518 caustics Substances 0.000 description 3
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000004753 textile Substances 0.000 description 3
FKPUYTAEIPNGRM-UHFFFAOYSA-N 1-(diaminomethylidene)guanidine;hydron;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=N FKPUYTAEIPNGRM-UHFFFAOYSA-N 0.000 description 2
DJYSROZOHXIMPW-UHFFFAOYSA-N 1-cyano-2-phenylguanidine Chemical compound N#CNC(N)=NC1=CC=CC=C1 DJYSROZOHXIMPW-UHFFFAOYSA-N 0.000 description 2
SRUGWSFEPMKUAK-UHFFFAOYSA-N 1-cyano-2-propan-2-ylguanidine Chemical compound CC(C)NC(N)=NC#N SRUGWSFEPMKUAK-UHFFFAOYSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
235000008733 Citrus aurantifolia Nutrition 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
235000011941 Tilia x europaea Nutrition 0.000 description 2
238000007605 air drying Methods 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
230000000078 anti-malarial effect Effects 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000036571 hydration Effects 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
229910017053 inorganic salt Inorganic materials 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000004571 lime Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000005060 rubber Substances 0.000 description 2
229960003080 taurine Drugs 0.000 description 2
NTTLKRPWPKPUAI-UHFFFAOYSA-N (1e)-1-[amino(anilino)methylidene]-2-phenylguanidine Chemical compound C=1C=CC=CC=1N=C(N)\N=C(/N)NC1=CC=CC=C1 NTTLKRPWPKPUAI-UHFFFAOYSA-N 0.000 description 1
XWFPIJRFFLYWRN-UHFFFAOYSA-N 1-(diaminomethylidene)-2-ethylguanidine Chemical compound CCN=C(N)N=C(N)N XWFPIJRFFLYWRN-UHFFFAOYSA-N 0.000 description 1
LKMYNXURMJNQBQ-UHFFFAOYSA-N 1-(n'-butylcarbamimidoyl)-2-octylguanidine Chemical compound CCCCCCCCN=C(N)NC(N)=NCCCC LKMYNXURMJNQBQ-UHFFFAOYSA-N 0.000 description 1
VSNAWQRNRYFNPM-UHFFFAOYSA-N 1-(n'-dodecylcarbamimidoyl)-2-ethylguanidine Chemical compound CCCCCCCCCCCCNC(=N)NC(=N)NCC VSNAWQRNRYFNPM-UHFFFAOYSA-N 0.000 description 1
MHRLRPGRERQKGS-UHFFFAOYSA-N 1-[amino(anilino)methylidene]-2-dodecylguanidine Chemical compound CCCCCCCCCCCCNC(=N)NC(=N)NC1=CC=CC=C1 MHRLRPGRERQKGS-UHFFFAOYSA-N 0.000 description 1
SARMGXPVOFNNNG-UHFFFAOYSA-N 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydron;chloride Chemical compound Cl.CC(C)N=C(N)N=C(N)NC1=CC=C(Cl)C=C1 SARMGXPVOFNNNG-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
JMEJOUCPQDFPFK-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-cyanoguanidine Chemical compound N#CNC(N)=NC1=CC=C(Cl)C=C1 JMEJOUCPQDFPFK-UHFFFAOYSA-N 0.000 description 1
ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical class NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 description 1
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
229940018563 3-aminophenol Drugs 0.000 description 1
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
RDVAGTCIMDGXFB-UHFFFAOYSA-N 4-[[N'-(N'-dodecylcarbamimidoyl)carbamimidoyl]amino]benzenesulfonic acid Chemical compound C(CCCCCCCCCCC)NC(=N)NC(=N)NC1=CC=C(C=C1)S(=O)(=O)O RDVAGTCIMDGXFB-UHFFFAOYSA-N 0.000 description 1
YEAICDDXRUOCKJ-UHFFFAOYSA-N 4-amino-n-pyrazin-2-ylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=CC=N1 YEAICDDXRUOCKJ-UHFFFAOYSA-N 0.000 description 1
DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
TWJPKRPAWOEANM-UHFFFAOYSA-N C[ClH]C Chemical compound C[ClH]C TWJPKRPAWOEANM-UHFFFAOYSA-N 0.000 description 1
101100489396 Caenorhabditis elegans zip-2 gene Proteins 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
240000004343 Indigofera suffruticosa Species 0.000 description 1
235000000177 Indigofera tinctoria Nutrition 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
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