NO123346B - - Google Patents
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- Publication number
- NO123346B NO123346B NO162948A NO16294866A NO123346B NO 123346 B NO123346 B NO 123346B NO 162948 A NO162948 A NO 162948A NO 16294866 A NO16294866 A NO 16294866A NO 123346 B NO123346 B NO 123346B
- Authority
- NO
- Norway
- Prior art keywords
- found
- requires
- isothiocyanate
- mixture
- sulfone
- Prior art date
Links
- -1 isothiocyanate radical Chemical class 0.000 claims description 71
- 238000002360 preparation method Methods 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 40
- 230000000855 fungicidal effect Effects 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 32
- 150000002540 isothiocyanates Chemical class 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000013543 active substance Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000006185 dispersion Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229960001701 chloroform Drugs 0.000 description 13
- 239000000443 aerosol Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229920001817 Agar Polymers 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000779 smoke Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 6
- VSEGGIPVCHEXNW-UHFFFAOYSA-N 1-isothiocyanato-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(N=C=S)C=C1 VSEGGIPVCHEXNW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 241000227653 Lycopersicon Species 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 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 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 241000222291 Passalora fulva Species 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- RWIQBTLWENXMRJ-UHFFFAOYSA-N 1-chloro-4-[(4-chloro-3-nitrophenyl)methylsulfonylmethyl]-2-nitrobenzene Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(CS(=O)(=O)CC=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 RWIQBTLWENXMRJ-UHFFFAOYSA-N 0.000 description 3
- TXBIITITEGKVRG-UHFFFAOYSA-N 1-hexylsulfonyl-4-isothiocyanatobenzene Chemical compound C(CCCCC)S(=O)(=O)C1=CC=C(C=C1)N=C=S TXBIITITEGKVRG-UHFFFAOYSA-N 0.000 description 3
- YDQNDKBOOVXRTL-UHFFFAOYSA-N 4-acetamidobenzenesulfinic acid Chemical compound CC(=O)NC1=CC=C(S(O)=O)C=C1 YDQNDKBOOVXRTL-UHFFFAOYSA-N 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 241000282898 Sus scrofa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 239000000346 nonvolatile oil Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- WKDRVRBBKZEGFP-UHFFFAOYSA-N 1-isothiocyanato-4-(3-methylbutylsulfonyl)benzene Chemical compound CC(CCS(=O)(=O)C1=CC=C(C=C1)N=C=S)C WKDRVRBBKZEGFP-UHFFFAOYSA-N 0.000 description 2
- FMHBQVCLDGQWET-UHFFFAOYSA-N 1-isothiocyanato-4-propan-2-ylsulfonylbenzene Chemical compound CC(C)S(=O)(=O)C1=CC=C(N=C=S)C=C1 FMHBQVCLDGQWET-UHFFFAOYSA-N 0.000 description 2
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QSAPAXHVSIVXPH-UHFFFAOYSA-N 4-(chloromethylsulfonyl)aniline Chemical compound NC1=CC=C(S(=O)(=O)CCl)C=C1 QSAPAXHVSIVXPH-UHFFFAOYSA-N 0.000 description 2
- 240000007087 Apium graveolens Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241001337928 Podosphaera leucotricha Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000003898 horticulture Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 235000012976 tarts Nutrition 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- QTPNYNXBWBDLKT-UHFFFAOYSA-N 1-(dichloromethylsulfonyl)-4-isothiocyanatobenzene Chemical compound ClC(S(=O)(=O)C1=CC=C(C=C1)N=C=S)Cl QTPNYNXBWBDLKT-UHFFFAOYSA-N 0.000 description 1
- TUDDXKYVUMVQHR-UHFFFAOYSA-N 1-benzylsulfonyl-4-isothiocyanatobenzene Chemical compound C(C1=CC=CC=C1)S(=O)(=O)C1=CC=C(C=C1)N=C=S TUDDXKYVUMVQHR-UHFFFAOYSA-N 0.000 description 1
- FHPOZBBMKUGBCJ-UHFFFAOYSA-N 1-butylsulfanyl-4-chlorobenzene Chemical compound CCCCSC1=CC=C(Cl)C=C1 FHPOZBBMKUGBCJ-UHFFFAOYSA-N 0.000 description 1
- WHYOJLDOGJLLID-UHFFFAOYSA-N 1-butylsulfanyl-4-nitrobenzene Chemical compound CCCCSC1=CC=C([N+]([O-])=O)C=C1 WHYOJLDOGJLLID-UHFFFAOYSA-N 0.000 description 1
- BNTDSRCIGYVKEO-UHFFFAOYSA-N 1-butylsulfonyl-4-chlorobenzene Chemical compound CCCCS(=O)(=O)C1=CC=C(Cl)C=C1 BNTDSRCIGYVKEO-UHFFFAOYSA-N 0.000 description 1
- RUWLFSCBPCABKC-UHFFFAOYSA-N 1-chloro-2-nitro-4-propan-2-ylsulfonylbenzene Chemical compound CC(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 RUWLFSCBPCABKC-UHFFFAOYSA-N 0.000 description 1
- QISRMHPCKWPHDK-UHFFFAOYSA-N 1-chloro-4-(2-methylpropylsulfanyl)benzene Chemical compound CC(C)CSC1=CC=C(Cl)C=C1 QISRMHPCKWPHDK-UHFFFAOYSA-N 0.000 description 1
- WAFZLIUGPYJQIS-UHFFFAOYSA-N 1-chloro-4-(2-methylpropylsulfonyl)benzene Chemical compound CC(C)CS(=O)(=O)C1=CC=C(Cl)C=C1 WAFZLIUGPYJQIS-UHFFFAOYSA-N 0.000 description 1
- JEVYVLLSVHNREX-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)methylsulfonylmethyl]benzene Chemical compound C1=CC(Cl)=CC=C1CS(=O)(=O)CC1=CC=C(Cl)C=C1 JEVYVLLSVHNREX-UHFFFAOYSA-N 0.000 description 1
- JBWNSPWRWGJJHB-UHFFFAOYSA-N 1-chloro-4-[2-[2-(4-chlorophenyl)ethylsulfanyl]ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1CCSCCC1=CC=C(Cl)C=C1 JBWNSPWRWGJJHB-UHFFFAOYSA-N 0.000 description 1
- IPKMJXNLTCUQPW-UHFFFAOYSA-N 1-chloro-4-ethylsulfanylbenzene Chemical compound CCSC1=CC=C(Cl)C=C1 IPKMJXNLTCUQPW-UHFFFAOYSA-N 0.000 description 1
- FVSFDDWOQCUYKZ-UHFFFAOYSA-N 1-chloro-4-ethylsulfonylbenzene Chemical compound CCS(=O)(=O)C1=CC=C(Cl)C=C1 FVSFDDWOQCUYKZ-UHFFFAOYSA-N 0.000 description 1
- ZWKPKISWPZWKLB-UHFFFAOYSA-N 1-chloro-4-propan-2-ylsulfanylbenzene Chemical compound CC(C)SC1=CC=C(Cl)C=C1 ZWKPKISWPZWKLB-UHFFFAOYSA-N 0.000 description 1
- ZKVPUWNTECRZSQ-UHFFFAOYSA-N 1-chloro-4-propan-2-ylsulfonylbenzene Chemical compound CC(C)S(=O)(=O)C1=CC=C(Cl)C=C1 ZKVPUWNTECRZSQ-UHFFFAOYSA-N 0.000 description 1
- UIVFJAFRNBDAEM-UHFFFAOYSA-N 1-chloro-4-propylsulfanylbenzene Chemical compound CCCSC1=CC=C(Cl)C=C1 UIVFJAFRNBDAEM-UHFFFAOYSA-N 0.000 description 1
- JUTHAQSZBVIJPB-UHFFFAOYSA-N 1-chloro-4-propylsulfonylbenzene Chemical compound CCCS(=O)(=O)C1=CC=C(Cl)C=C1 JUTHAQSZBVIJPB-UHFFFAOYSA-N 0.000 description 1
- FNMHESQXCQHNJF-UHFFFAOYSA-N 1-isothiocyanato-3-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC(N=C=S)=C1 FNMHESQXCQHNJF-UHFFFAOYSA-N 0.000 description 1
- ZZNDQCACFUJAKJ-UHFFFAOYSA-N 1-phenyltridecan-1-one Chemical compound CCCCCCCCCCCCC(=O)C1=CC=CC=C1 ZZNDQCACFUJAKJ-UHFFFAOYSA-N 0.000 description 1
- XDUPGYBBARIWPQ-UHFFFAOYSA-N 1-tert-butylsulfanyl-4-nitrobenzene Chemical compound CC(C)(C)SC1=CC=C([N+]([O-])=O)C=C1 XDUPGYBBARIWPQ-UHFFFAOYSA-N 0.000 description 1
- DTAYWUPWXVSLJP-UHFFFAOYSA-N 1-tert-butylsulfonyl-4-nitrobenzene Chemical compound CC(C)(C)S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 DTAYWUPWXVSLJP-UHFFFAOYSA-N 0.000 description 1
- TYBSAXQGELBODE-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonyl-1-phenylethanone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)CC(=O)C1=CC=CC=C1 TYBSAXQGELBODE-UHFFFAOYSA-N 0.000 description 1
- LGAJYTCRJPCZRJ-UHFFFAOYSA-N 2-bromopentane Chemical compound CCCC(C)Br LGAJYTCRJPCZRJ-UHFFFAOYSA-N 0.000 description 1
- HMMCKNRGRBISIV-UHFFFAOYSA-N 2-chloro-5-(3-methylbutylsulfonyl)aniline Chemical compound CC(CCS(=O)(=O)C1=CC(=C(C=C1)Cl)N)C HMMCKNRGRBISIV-UHFFFAOYSA-N 0.000 description 1
- GUZUWSRUQYJVBV-UHFFFAOYSA-N 2-chloro-5-propylsulfonylaniline Chemical compound C(CC)S(=O)(=O)C1=CC(=C(C=C1)Cl)N GUZUWSRUQYJVBV-UHFFFAOYSA-N 0.000 description 1
- AIRCUKSSERIWCS-UHFFFAOYSA-N 2-isothiocyanato-1-methyl-4-methylsulfonylbenzene Chemical compound CC1=C(C=C(C=C1)S(=O)(=O)C)N=C=S AIRCUKSSERIWCS-UHFFFAOYSA-N 0.000 description 1
- QALKLBYSMSGFAY-UHFFFAOYSA-N 2-methyl-5-propylsulfonylaniline Chemical compound CCCS(=O)(=O)C1=CC=C(C)C(N)=C1 QALKLBYSMSGFAY-UHFFFAOYSA-N 0.000 description 1
- FBSPARWZQMEZEU-UHFFFAOYSA-N 3-methyl-1-(3-methylbutylsulfonyl)butane Chemical compound CC(C)CCS(=O)(=O)CCC(C)C FBSPARWZQMEZEU-UHFFFAOYSA-N 0.000 description 1
- JQJVGSXHBSTCRU-UHFFFAOYSA-N 4-(3-methylbutylsulfonyl)aniline Chemical compound CC(C)CCS(=O)(=O)C1=CC=C(N)C=C1 JQJVGSXHBSTCRU-UHFFFAOYSA-N 0.000 description 1
- WZDKMFBTWJYTTA-UHFFFAOYSA-N 4-(bromomethylsulfonyl)aniline Chemical compound NC1=CC=C(S(=O)(=O)CBr)C=C1 WZDKMFBTWJYTTA-UHFFFAOYSA-N 0.000 description 1
- VLHZKBJNAOSNIP-UHFFFAOYSA-N 4-butylsulfonyl-1-chloro-2-nitrobenzene Chemical compound ClC1=C(C=C(C=C1)S(=O)(=O)CCCC)[N+](=O)[O-] VLHZKBJNAOSNIP-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- SEZCFBLDUKGZKN-UHFFFAOYSA-N 4-ethylsulfonyl-1-methyl-2-nitrobenzene Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)S(=O)(=O)CC)C SEZCFBLDUKGZKN-UHFFFAOYSA-N 0.000 description 1
- XJEVFFNOMKXBLU-UHFFFAOYSA-N 4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C=C1 XJEVFFNOMKXBLU-UHFFFAOYSA-N 0.000 description 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
- DIHIFAYUBGSXGR-UHFFFAOYSA-N 4-propan-2-ylsulfonylaniline Chemical compound CC(C)S(=O)(=O)C1=CC=C(N)C=C1 DIHIFAYUBGSXGR-UHFFFAOYSA-N 0.000 description 1
- SXEJMVMJVOXEPE-UHFFFAOYSA-N 5-[2-[2-(3-amino-4-methylphenyl)ethylsulfonyl]ethyl]-2-methylaniline Chemical compound NC=1C=C(C=CC1C)CCS(=O)(=O)CCC1=CC(=C(C=C1)C)N SXEJMVMJVOXEPE-UHFFFAOYSA-N 0.000 description 1
- SONXETQQIUYXKT-UHFFFAOYSA-N 5-butylsulfonyl-2-chloroaniline Chemical compound CCCCS(=O)(=O)C1=CC(N)=C(Cl)C=C1 SONXETQQIUYXKT-UHFFFAOYSA-N 0.000 description 1
- KWQZWFQITGWDGV-UHFFFAOYSA-N 5-isothiocyanato-6-sulfonylcyclohexa-1,3-diene Chemical compound S(=O)(=O)=C1C(C=CC=C1)N=C=S KWQZWFQITGWDGV-UHFFFAOYSA-N 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 241001328752 Asplenium ceterach Species 0.000 description 1
- 241001529717 Corticium <basidiomycota> Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 241001518836 Monilinia fructigena Species 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000599030 Pythium debaryanum Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 241001597359 Septoria apiicola Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000722133 Tilletia Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VBQUDDWATQWCPP-UHFFFAOYSA-N ethylsulfonylbenzene Chemical compound CCS(=O)(=O)C1=CC=CC=C1 VBQUDDWATQWCPP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical class ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002917 insecticide Substances 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
- 229960004592 isopropanol Drugs 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- RIUACYYLCFNQNI-UHFFFAOYSA-N n-[4-(bromomethylsulfonyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(S(=O)(=O)CBr)C=C1 RIUACYYLCFNQNI-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Preliminary Treatment Of Fibers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH870962A CH416636A (de) | 1962-07-19 | 1962-07-19 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |
| CH870862A CH415627A (de) | 1962-07-19 | 1962-07-19 | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
| CH1240762 | 1962-10-23 | ||
| CH1240862 | 1962-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123346B true NO123346B (da) | 1971-11-01 |
Family
ID=27429170
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO149459A NO119637B (da) | 1962-07-19 | 1963-07-18 | |
| NO162948A NO123346B (da) | 1962-07-19 | 1966-05-10 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO149459A NO119637B (da) | 1962-07-19 | 1963-07-18 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3314948A (da) |
| BE (1) | BE635096A (da) |
| BR (1) | BR6350873D0 (da) |
| DE (2) | DE1246742B (da) |
| DK (2) | DK117771B (da) |
| ES (1) | ES290082A1 (da) |
| FI (1) | FI42086B (da) |
| FR (2) | FR1363683A (da) |
| GB (2) | GB1043852A (da) |
| LU (1) | LU44067A1 (da) |
| MY (1) | MY6900114A (da) |
| NL (3) | NL6608685A (da) |
| NO (2) | NO119637B (da) |
| OA (1) | OA00707A (da) |
| SE (2) | SE318568B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH452531A (de) * | 1964-10-09 | 1968-03-15 | Sandoz Ag | Verfahren zur Herstellung von neuen Thieno-benzothiazin-Derivaten |
| FR2497806A1 (fr) * | 1981-01-13 | 1982-07-16 | Pharmindustrie | Nouveau procede de preparation du n,n-dimethyl (aza-1 bicyclo (2,2,2) octyl-3)-10 10h-phenothiazinesulfonamide-2 |
| USD901671S1 (en) | 2018-11-28 | 2020-11-10 | Rpc Formatec Gmbh | Inhaler |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE556474A (fr) * | 1956-04-07 | 1960-02-26 | Rhone Poulenc Sa | Nouveaux derives de la phenothiazine et leur preparation. |
| NL97976C (da) * | 1956-04-07 | Krupp Ag | ||
| CH365379A (de) * | 1956-04-18 | 1962-11-15 | Sandoz Ag | Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen |
| NL123928C (da) * | 1960-03-10 | 1900-01-01 |
-
0
- BE BE635096D patent/BE635096A/xx unknown
- NL NL123137D patent/NL123137C/xx active
- NL NL295220D patent/NL295220A/xx unknown
-
1963
- 1963-07-01 GB GB25969/63A patent/GB1043852A/en not_active Expired
- 1963-07-01 GB GB54125/65A patent/GB1043853A/en not_active Expired
- 1963-07-16 LU LU44067D patent/LU44067A1/xx unknown
- 1963-07-17 SE SE7948/63A patent/SE318568B/xx unknown
- 1963-07-17 FR FR941800A patent/FR1363683A/fr not_active Expired
- 1963-07-17 US US295836A patent/US3314948A/en not_active Expired - Lifetime
- 1963-07-17 BR BR150873/63A patent/BR6350873D0/pt unknown
- 1963-07-17 ES ES290082A patent/ES290082A1/es not_active Expired
- 1963-07-18 NO NO149459A patent/NO119637B/no unknown
- 1963-07-18 DE DES86249A patent/DE1246742B/de active Pending
- 1963-07-18 FI FI1422/63A patent/FI42086B/fi active
- 1963-07-18 DK DK344263AA patent/DK117771B/da unknown
- 1963-10-16 FR FR950738A patent/FR3045M/fr not_active Expired
-
1964
- 1964-12-08 OA OA50787A patent/OA00707A/xx unknown
-
1965
- 1965-03-23 DK DK150565AA patent/DK111617B/da unknown
-
1966
- 1966-05-10 NO NO162948A patent/NO123346B/no unknown
- 1966-06-22 NL NL6608685A patent/NL6608685A/xx unknown
-
1967
- 1967-05-11 SE SE6609/67A patent/SE324770B/xx unknown
-
1968
- 1968-09-04 DE DE19681620242 patent/DE1620242A1/de active Pending
-
1969
- 1969-12-31 MY MY1969114A patent/MY6900114A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| OA00707A (fr) | 1967-07-15 |
| DE1246742B (de) | 1967-08-10 |
| BE635096A (da) | |
| NO119637B (da) | 1970-06-15 |
| DK111617B (da) | 1968-09-23 |
| ES290082A1 (es) | 1963-10-16 |
| SE324770B (da) | 1970-06-15 |
| BR6350873D0 (pt) | 1973-06-28 |
| GB1043853A (en) | 1966-09-28 |
| NL123137C (da) | |
| FR1363683A (fr) | 1964-06-12 |
| DK117771B (da) | 1970-06-01 |
| FR3045M (fr) | 1965-01-04 |
| DE1620242A1 (de) | 1970-06-04 |
| FI42086B (da) | 1970-02-02 |
| NL6608685A (da) | 1966-08-25 |
| MY6900114A (en) | 1969-12-31 |
| US3314948A (en) | 1967-04-18 |
| NL295220A (da) | |
| SE318568B (da) | 1969-12-15 |
| GB1043852A (en) | 1966-09-28 |
| LU44067A1 (da) | 1964-01-16 |
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